ChemWiki - User contributions [en]

It:Bufotoxin

2006-11-15T16:57:49Z

Yp305: /* Citations */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Synthesis of Bufotoxin===

Completion of a formal total synthetic route to the toad venom constituents bufotalin, cinobufagin, bufalitoxin, and bufotoxin has been accomplished. Bufalin was employed as relay and converted to 14-dehydrobufalin 3-acetate. Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin and thence to cinobufagin.

Condensation of bufalin with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin, and an analogous route from bufotalin led to bufotoxin.

In a classic investigation of toad venom constituents, Wieland and colleagues isolated bufotoxin in 1922 from the European toad Bufo vulgaris (Bufo bufo bufo LinnB), and some 20 years later they were able to propose a tentative structure. Meanwhile, Kondo and co-workers succeeded in isolating bufotoxin and the parent steroid bufotalin from the Japanese toad venom preparation Senso (the Chinese Ch'an SU). The same substance was reisolated from Bufo bufo bufo L, and named vulgarobufotoxin. In 1955, the isolation of bufotoxin from Bufo bufo bufo L was reconfirmed by the Reichstein group 7 and more recently the correct structure proposed by Y.K. It was confirmed by Meyeraour which states that the partial synthesis of bufotoxin from bufotalin2 is part of Steroids and Related Natural Produds and series number 36 of Bufadienolides.

In this remarkable study the average yield of crude bufotoxin from Bufo vulgaris (800 males and 400 females) was found to be 1.34 mg/toad, while the female was found to yield 1.23 mg on the average of bufotalin. The male provided only 0.55 mg of bufotalin. In the same investigation, arenobufotoxin was isolated from the South American toad Bufo arenarum and purified by column chromatography on aluminum oxide.

Until 1974 the only known bufotoxin-type toad venom constituents were suberylarginine esters of a 30-hydroxybufadienolide. Investigation of the venom from Bufo vulgaris formosus. Boulenger has led to the isolation of bufotoxins with succinic, glutaric, pimelic, or adipic acid replacing suberic acid.

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

===Safety issues===

Bufotoxin is toxic, which has a function similar to digitalis glycosides. Although it is used in patentpreparations, is traditionally known for its toxicity and is seldom used in decoctions. Toxicity is often due to over dosage of the patents, such as Liushenwan and Houzhengwan. After administration one and a half to two hours, symptoms similar to digitalis toxicity appear, such as nausea, which is often the first indicator of toxicity, anorexia, vomiting, visual disturbances relating to colour vision, headache, weakness, psychosis, arrythmias, slowing of heart rate, AV block, and asystole.Severe cardiac damage is the major cause of death. It has also been known to promote contraction of the uterus; therefore it should not be used in pregnant women

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.

2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947

3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.

4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.

5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.

6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

7. J. Org. Chem. 1987,52, 3573-3578 3573

8. Registry No. 9, 5307-05-1; 12,4603-89-8; 13,42775-84-8; 14,
108512-22-7; 15, 108590-49-4; 16, 108590-50-7; 17, 108512-23-8;
18,108512-24-9; 20,108512-25-0; 21,108512-26-1; 23,108512-27-2;
24,108512-29-4; 25,108512-31-8; 26,108512-32-9; 27,108512-33-0;
28,108512-34-1; 29,108512-35-2; 30,108512-36-3; 31,108512-28-3;
32,108512-30-7; 33,108512-37-4; 35,108512-38-5; 36,108512-39-6;
38,108512-41-0; 40,108512-40-9; 41,108512-43-2; 42,108512-42-1;
43, 108512-44-3; N-(ethoxycarbonyl)phthalimide, 22509-74-6; 3,5-dimethoxyphenol, 500-99-2.

9. (a) The present contribution is part 104 of Steroids and Related Natural Produds and series number 36 of Bufadienolides; for parts 103 and 35 refer to, respectively: ''Pettit, G. R''; ''Herald, D. L''; ''Herald, C. L''; ''Kokke, W. C. M. C''; Djerassi, C. Steroids 1986, 47, 321. ''Green, B''; ''Snatzke, F''; ''Snatzke, G''; ''Pettit, G. R''; ''Kamano, Y''; ''Niven, M. L. Croat''. Chim. Acta 1985, 58, 371. (b) On leave from the ''Institute of Organic Chemistry and Biochemistry'', Czechoslovak Academy of Sciences, 166 10 Prague, Czechoslovakia.

10. A portion of the present study was summarized in a preliminary report by: ''Pettit, G. R''; ''Kamano, Y''. Chem. Commun. 1972, 45.

11. ''Wieland, H''; ''Alles, R''. Chem. Ber. 1922,55, 1789.

12. ''Wieland, H''; ''Behringer, H. Ann''. 1941,549,209.

13. ''Kondo. H'': ''Ikawa. S. J''. Pharm. Soc,. Jpn. 1933. 53. 23; Chem.Abstr.1933,27,1887. ''Kondo, H''; ''Ono, S. J''. Pharm. Soc.,Jpn. 1938,58, 37; Chem. Abstr. 1939, 32, 3765.

14. ''Chen, K. K''; ''Jensen, H''; ''Chen, A. L. J''. Pharmacol. 1933,47,307.

15. ''Urscheler, H. R''; ''Tamm, C''; ''Reichstein, T''. Helv. Chim. Acta 1955, 3,883.

16 ''Meyer, K''; ''Linde, H''. In Venomous Animals and Their Venoms; ''Bucherl, W'', ''Buckley, E. E'', Eds.; 1971; Vol. 2, p 521. For more recent advances in the chemistry of naturally occurring bufadienolides, refer to: ''Ode, H''; ''Kamano, Y''; ''Pettit, G. R''. MTP ''International Review of Science'', Organic Chemistry Series One; ''Johns, W. F'', Butterworths: London, 1975; Vol. 8, Chapter 6, pp 145-177. ''Nassimbeni, L. R''; ''Niven, M. L''; ''Sheldrick, G. M''; ''Pettit, G. R''; ''Inoue, M''; Kamano, Y. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1983, C39, 801 and ref la.

17 (a) ''Shimada, K''; ''Fujii, Y''; ''Mitsuishi, E''; ''Nambara, T''. Tetrahedron Lett. 1974, 467. ''Shimada, K''; ''Fujii, Y''; ''Niizaki, Y''; Nambara, T. Tetrahedron Lett. 1975, 653. ''Shimada, K''; ''Sato, Y''; ''Fujii, Y''; Nambara, T. Chem. Pharm. Bull. 1976,24, 1120. ''Shimada, K''; ''Ro, J. S''; Ohishi, K.; Nambara, T. Chem. Pharm. Bull. 1985,33,2767. (b) Shimada, K.; Fujii, ''Yamashita, E''; ''Niizaki, Y''; ''Sato, Y''; Nambara, T. Chem. Pharm. Bull 1977, 25, 714. See also: ''Shimada, K''; ''Ohishi, K''; Nambara, T. Tetrahedron Lett. 1984,24,551. ''Shimada, K''; ''Ohishi, K''; ''Nambara, T''. Chem. Pharm. Bull. 1984,32,4396. (c) ''Shimada, K''; ''Nambara, T''. Tetrahedron Lett. 1979,163. ''Shimada, K''; Nambara, T. Chem. Pharm. Bull. 1980,28,1559.

It:Gentamycin

2006-11-15T16:47:16Z

Yp305: /* Gentamycin A */

== Gentamycin A ==

[[image:image8.JPG]] [[image:image7.JPG]]

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image2.jpg]]

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines.

[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

[[image:image3.jpg]]

RNA−gentamicin C1a contacts observed in the solution structure. (A) Stereo view of specific contacts made between rings I and II of gentamicin C1a and A-site RNA. The RNA is in beige, gentamicin C1a is red, and the view is looking into the major groove of the RNA. Important chemical groups are shown explicitly. The nitrogen atoms are highlighted in blue. Possible hydrogen bonding contacts are indicated by dashed lines. (B) Stereo view of specific contacts made between ring III of gentamicin C1a and A-site RNA. Possible hydrogen bonding contacts are indicated by dashed lines.

[[image:image4.jpg]]

Best-fit superposition of the paromomycin−RNA and gentamicin C1a−RNA complexes, viewed from the major groove side of the RNA. The heavy atoms of the core (nucleotides U1406 to A1410, and U1490 to U1495) of the RNA are superimposed. Only the core is represented. For the paromomycin−RNA complex, the RNA is represented in brown and the antibiotic in yellow. For the gentamicin C1a−RNA complex, the RNA is in tan and the gentamicin in red.

[[image:image5.jpg]]

(A) View of specific contacts made between ring III of gentamicin C1a and A-site RNA. The RNA is in tan, gentamicin C1a is red, and the view is into the major groove of the RNA. Possible hydrogen bonding contacts between G1405/C1496 base pair and ring III of gentamicin C1a are indicated by dashed lines. (B) Autoradiograph of DMS probing reactions on the 3' end labeled 27 nucleotide RNA with G1405C/C1496G substitutions. In all reactions, the oligonucleotide is present at a concentration of 5 nM. Lanes 1 and 9 are control reactions with no DMS added. Lanes 3 and 10 are DMS probing reaction in the absence of antibiotics. DMS probing reactions were carried out at 25°C. Lanes 3−8 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM gentamicin C1a, respectively. Lanes 11−16 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM paromomycin, respectively.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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68 70 0 0 0 0 0 0 0 0999 V2000
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1
-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
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14 48 1 0 0 0
17 16 1 0 0 0
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17 53 1 0 0 0
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24 59 1 0 0 0
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29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
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2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
4 37 1 0 0 0
4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image8.JPG

2006-11-15T16:46:50Z

Yp305: product of gentamysin

product of gentamysin

It:Gentamycin

2006-11-15T16:45:26Z

Yp305: /* Gentamycin A */

== Gentamycin A ==

[[image:image6.JPG]] [[image:image7.JPG]]

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image2.jpg]]

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines.

[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

[[image:image3.jpg]]

RNA−gentamicin C1a contacts observed in the solution structure. (A) Stereo view of specific contacts made between rings I and II of gentamicin C1a and A-site RNA. The RNA is in beige, gentamicin C1a is red, and the view is looking into the major groove of the RNA. Important chemical groups are shown explicitly. The nitrogen atoms are highlighted in blue. Possible hydrogen bonding contacts are indicated by dashed lines. (B) Stereo view of specific contacts made between ring III of gentamicin C1a and A-site RNA. Possible hydrogen bonding contacts are indicated by dashed lines.

[[image:image4.jpg]]

Best-fit superposition of the paromomycin−RNA and gentamicin C1a−RNA complexes, viewed from the major groove side of the RNA. The heavy atoms of the core (nucleotides U1406 to A1410, and U1490 to U1495) of the RNA are superimposed. Only the core is represented. For the paromomycin−RNA complex, the RNA is represented in brown and the antibiotic in yellow. For the gentamicin C1a−RNA complex, the RNA is in tan and the gentamicin in red.

[[image:image5.jpg]]

(A) View of specific contacts made between ring III of gentamicin C1a and A-site RNA. The RNA is in tan, gentamicin C1a is red, and the view is into the major groove of the RNA. Possible hydrogen bonding contacts between G1405/C1496 base pair and ring III of gentamicin C1a are indicated by dashed lines. (B) Autoradiograph of DMS probing reactions on the 3' end labeled 27 nucleotide RNA with G1405C/C1496G substitutions. In all reactions, the oligonucleotide is present at a concentration of 5 nM. Lanes 1 and 9 are control reactions with no DMS added. Lanes 3 and 10 are DMS probing reaction in the absence of antibiotics. DMS probing reactions were carried out at 25°C. Lanes 3−8 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM gentamicin C1a, respectively. Lanes 11−16 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM paromomycin, respectively.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
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-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
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-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
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-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
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17 16 1 0 0 0
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17 53 1 0 0 0
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31 68 1 0 0 0
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3 4 1 0 0 0
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4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
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8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image7.JPG

2006-11-15T16:43:51Z

Yp305: gentamysin product

gentamysin product

File:Image6.JPG

2006-11-15T16:40:01Z

Yp305: gentamysin eye drops

gentamysin eye drops

It:Gentamycin

2006-11-15T16:33:10Z

Yp305: /* Structural origins of gentamicin antibiotic action */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image2.jpg]]

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines.

[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

[[image:image3.jpg]]

RNA−gentamicin C1a contacts observed in the solution structure. (A) Stereo view of specific contacts made between rings I and II of gentamicin C1a and A-site RNA. The RNA is in beige, gentamicin C1a is red, and the view is looking into the major groove of the RNA. Important chemical groups are shown explicitly. The nitrogen atoms are highlighted in blue. Possible hydrogen bonding contacts are indicated by dashed lines. (B) Stereo view of specific contacts made between ring III of gentamicin C1a and A-site RNA. Possible hydrogen bonding contacts are indicated by dashed lines.

[[image:image4.jpg]]

Best-fit superposition of the paromomycin−RNA and gentamicin C1a−RNA complexes, viewed from the major groove side of the RNA. The heavy atoms of the core (nucleotides U1406 to A1410, and U1490 to U1495) of the RNA are superimposed. Only the core is represented. For the paromomycin−RNA complex, the RNA is represented in brown and the antibiotic in yellow. For the gentamicin C1a−RNA complex, the RNA is in tan and the gentamicin in red.

[[image:image5.jpg]]

(A) View of specific contacts made between ring III of gentamicin C1a and A-site RNA. The RNA is in tan, gentamicin C1a is red, and the view is into the major groove of the RNA. Possible hydrogen bonding contacts between G1405/C1496 base pair and ring III of gentamicin C1a are indicated by dashed lines. (B) Autoradiograph of DMS probing reactions on the 3' end labeled 27 nucleotide RNA with G1405C/C1496G substitutions. In all reactions, the oligonucleotide is present at a concentration of 5 nM. Lanes 1 and 9 are control reactions with no DMS added. Lanes 3 and 10 are DMS probing reaction in the absence of antibiotics. DMS probing reactions were carried out at 25°C. Lanes 3−8 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM gentamicin C1a, respectively. Lanes 11−16 are reactions in the presence of 0.25, 0.5, 1, 5, 10 and 100 muM paromomycin, respectively.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
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4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
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-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
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-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
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0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
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2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
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22 57 1 0 0 0
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24 59 1 0 0 0
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31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
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3 4 1 0 0 0
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4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
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13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
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16 51 1 0 0 0
16 18 1 0 0 0
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20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image5.jpg

2006-11-15T16:30:24Z

Yp305: structure of gentamysin action

structure of gentamysin action

File:Image4.jpg

2006-11-15T16:30:02Z

Yp305: structure of gentamysin action

structure of gentamysin action

It:Gentamycin

2006-11-15T16:28:30Z

Yp305: /* Structural origins of gentamicin antibiotic action */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image2.jpg]]

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines.

[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

[[image:image3.jpg]]

RNA−gentamicin C1a contacts observed in the solution structure. (A) Stereo view of specific contacts made between rings I and II of gentamicin C1a and A-site RNA. The RNA is in beige, gentamicin C1a is red, and the view is looking into the major groove of the RNA. Important chemical groups are shown explicitly. The nitrogen atoms are highlighted in blue. Possible hydrogen bonding contacts are indicated by dashed lines. (B) Stereo view of specific contacts made between ring III of gentamicin C1a and A-site RNA. Possible hydrogen bonding contacts are indicated by dashed lines.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
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-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
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-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
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0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
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3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
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9 43 1 0 0 0
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14 48 1 0 0 0
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29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
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2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
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4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
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23 58 1 0 0 0
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image3.jpg

2006-11-15T16:26:33Z

Yp305: structure of gentamysin action

structure of gentamysin action

It:Gentamycin

2006-11-15T16:26:07Z

Yp305: /* Structural origins of gentamicin antibiotic action */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image2.jpg]]

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines.

[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image2.jpg

2006-11-15T16:22:01Z

Yp305: structure of gentamysin action

structure of gentamysin action

It:Gentamycin

2006-11-15T16:21:21Z

Yp305: /* Gentamycin A */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Structural origins of gentamicin antibiotic action==
[[image:image1.jpg]]

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The three rings of gentamicin C1a are numbered as in Figure 1. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
<jmol>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32
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-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
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5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
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9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
17 52 1 0 0 0
17 53 1 0 0 0
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24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
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31 30 1 0 0 0
31 68 1 0 0 0
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32 3 1 0 0 0
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2 34 1 0 0 0
2 3 1 0 0 0
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6 39 1 0 0 0
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8 41 1 0 0 0
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25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

File:Image1.jpg

2006-11-15T16:17:53Z

Yp305: Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The three rings of gentamicin C1a are numbered as in Figure 1. The bas

Binding pocket of gentamicin in the A-site RNA. The Connolly surface of the RNA is represented by blue dots and the gentamicin C1a is red. The view is from the major groove of the RNA. The three rings of gentamicin C1a are numbered as in Figure 1. The base moiety of residue G1491 which is creating a platform for ring I binding is highlighted in yellow.

File:7591334f5a.jpg

2006-11-15T16:10:56Z

Yp305: (A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. The RNA is shown in beige and gentamicin C1a is red. Th

(A) Best-fit superposition of 38 final simulated annealing structures of the A-site RNA−gentamicin C1a complex, viewed from the major groove side of the RNA. The heavy atoms have been superimposed. The RNA is shown in beige and gentamicin C1a is red. The three rings of gentamicin C1a are numbered as in Figure 1. (B) Single representative structure of A-site RNA−gentamicin C1a complex. All heavy atoms are displayed. The same colors as in (A) are used except that RNA phosphate groups are highlighted. (C) Best-fit superposition of gentamicin C1a of the 38 final structures of the A-site RNA−gentamicin C1a complex. Gentamicin C1a is in red and nitrogen atoms are highlighted in blue. Inter-ring hydrogen bonds are represented by dashed lines. Gentamicin C1a rings are labeled as in Figure 1.

It:Gentamycin

2006-11-15T15:47:52Z

Yp305: /* Interactions of Gentamysin with Dietary Supplements */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

'''Vitamin K'''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

ChemWiki:Help

2006-11-06T13:59:38Z

Yp305:

*http://www.vitacost.com/science/hn/Supp/Multi_Vitamin.htm*

It:Gentamycin

2006-11-06T13:54:06Z

Yp305: /* Gentamycin A */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

''Vitamin K''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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M END

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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

It:Gentamycin

2006-11-06T13:53:48Z

Yp305: /* Interactions of Gentamysin with Dietary Supplements */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin Injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

'''Calcium'''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.''(1)'' In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.''(2)'' The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

'''Magnesium'''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.''(3)(4)''

'''Potassium'''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.''(5)''

'''Probiotics'''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.''(6)''

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii''(7)'' or Saccharomyces cerevisiae (baker’s or brewer’s yeast),''(8)'' helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.''(9)'' Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.''(10)''

'''Vitamin B6'''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.''(11)'' The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

''Vitamin K''

Several cases of excessive bleeding have been reported in people who take antibiotics.''(12) (13) (14) (15)'' This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.''(16)'' Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.''(17)'' No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.''(18)''

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

It:Gentamycin

2006-11-06T13:44:13Z

Yp305: /* References */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin Injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

''Calcium''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.1 In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.2 The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

''Magnesium''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.3 4

''Potassium''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.5

''Probiotics''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.6

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii7 or Saccharomyces cerevisiae (baker’s or brewer’s yeast),8 helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.9 Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.10

''Vitamin B6''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.11 The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

''Vitamin K''

Several cases of excessive bleeding have been reported in people who take antibiotics.12 13 14 15 This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.16 Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.17 No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.18

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00
TER
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M END

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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

1. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

2. ''Humes HD'', ''Sastrasingh M'', ''Weinberg, JM''. Calcium is a competitive inhibitor of gentamicin-renal membrane binding interactions and dietary calcium supplementation protects against gentamicin nephrotoxicity. J Clin Invest 1984;73:134.

3. ''McLean R''. Magnesium and its therapeutic uses: A review. Am J Med 1994;96:63–76.

4. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

5. ''Kes P'', ''Reiner Z''. Symptomatic hypomagnesemia associated with gentamicin therapy. Magnes Trace Elem 1990;9:54–60.

6. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

7. ''Elmer GW'', ''Surawicz CM'', McFarland LV. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

8. ''Schellenberg D'', ''Bonington A'', ''Champion CM'', et al. Treatment of Clostridium difficile diarrhoea with brewer’s yeast. Lancet 1994;343:171–2.

9. ''Surawicz CM'', ''Elmer GW'', ''Speelman P'', et al. Prevention of antibiotic-associated diarrhea by Saccharomyces boulardii: A prospective study. Gastroenterol 1989;96:981–8.

10. ''Elmer GW'', ''Surawicz CM'', ''McFarland LV''. Biotherapeutic agents. A neglected modality for the treatment and prevention of selected intestinal and vaginal infections. JAMA 1996;275:870–6 [review].

11. ''Weir MR'', ''Keniston RC'', ''Enriquez JI Sr'', ''McNamee GA''. Depression of vitamin B6 levels due to gentamicin. Vet Hum Toxicol 1990;32:235–8.

12. ''Suzuki K'', ''Fukushima T'', ''Meguro K'', et al. Intracranial hemorrhage in an infant owing to vitamin K deficiency despite prophylaxis. Childs Nerv Syst 1999;15:292–4.

13. ''Huilgol VR'', ''Markus SL'', ''Vakil NB''. Antibiotic-induced iatrogenic hemobilia. Am J Gastroenterol 1997;92:706–7.

14. ''Bandrowsky T'', ''Vorono AA'', ''Borris TJ'', ''Marcantoni HW''. Amoxicllin-related postextraction bleeding in an anticoagulated patient with tranexamic acid rinses. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 1996;82:610–2.

15. ''Kaiser CW'', ''McAuliffe JD'', ''Barth RJ'', ''Lynch JA''. Hypoprothrombinemia and hemorrhage in a surgical patient treated with cefotetan. Arch Surg 1991;126:524–5.

16. ''Conly J'', ''Stein K''. Reduction of vitamin K2 concentration in human liver associated with the use of broad spectrum antimicrobials. Clin Invest Med 1994;17:531–9.

17. ''Jin X'', ''Jin X'', ''Sheng X''. Methylcobalamin as antagonist to transient ototoxic action of gentamicin. Acta Otolaryngol 2001;121:351–4.

18. ''Mazzon E'', ''Britti D'', ''De Sarro A'', et al. Effect of N-acetylcysteine on gentamicin-mediated nephropathy in rats. Eur J Pharmacol 2001;424:75–83.

It:Gentamycin

2006-11-06T13:37:17Z

Yp305: /* Gentamycin A */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

Gentamicin Injection will be stored in the pharmacy or on the ward. The injection is kept in a cool dry place, protected from light, where the temperature stays below 25 degrees C.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

''Calcium''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.1 In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.2 The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

''Magnesium''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.3 4

''Potassium''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.5

''Probiotics''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.6

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii7 or Saccharomyces cerevisiae (baker’s or brewer’s yeast),8 helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.9 Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.10

''Vitamin B6''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.11 The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

''Vitamin K''

Several cases of excessive bleeding have been reported in people who take antibiotics.12 13 14 15 This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.16 Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.17 No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.18

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00
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== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

It:Gentamycin

2006-11-06T13:36:46Z

Yp305: /* Storage of Gentamysin injection */

== Gentamycin A ==

'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.

It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed.

Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.

Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

==Taking Gentamycin with care==

Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.

Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin

There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.

Making sure you don't overdose the rat on gentamicin is also an easy way to ensure no toxic results from using gentamicin. The recommended dose for rats is 1 to 2 mg per pound twice daily, injected subcutaneously for 7 to 14 days. Although the book Veterinary Pharmaceuticals and Biologicals doesn't give us any treatment suggestions for rats, it does give us the results of a toxicity study using gentamicin in rats. It is as follows: "No toxic effects were observed in rats given gentamicin sulfate 20 mg/kg/ day for twenty-four days". Translated from kilograms to pounds that is 9.09 mg per pound! That is far more than double the highest dose we recommend and a full 10 days beyond recommended treatment length. No comparison and still NOT toxic according to this study.

[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]

==Side Effects==
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).

In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:
*deafness

The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.

*loss of equilibrium

The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.

In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.

==Symptoms of overdose ==

*damage to the kidneys

*hearing loss

*dizziness

*numbness

*skin tingling

*muscle twitching

*seizures (which may be signs of nerve damage)

*Trouble walking or balancing

*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.

==Interactions of Gentamysin with Dietary Supplements==

''Calcium''

Gentamicin has been associated with hypocalcemia (low calcium levels) in humans.1 In a study using rats, authors reported oral calcium supplementation reduced gentamicin-induced kidney damage.2 The implications of this report for humans are unclear. People receiving gentamicin should ask their doctor about monitoring calcium levels and calcium supplementation.

''Magnesium''

Gentamicin has been associated with urinary loss of magnesium, resulting in hypomagnesemia (low magnesium levels) in humans.3 4

''Potassium''

Gentamicin has been associated with hypokalemia (low potassium levels) in humans.5

''Probiotics''

A common side effect of antibiotics is diarrhea, which may be caused by the elimination of beneficial bacteria normally found in the colon. Controlled studies have shown that taking probiotic microorganisms—such as Lactobacillus casei, Lactobacillus acidophilus, Bifidobacterium longum, or Saccharomyces boulardii—helps prevent antibiotic-induced diarrhea.6

The diarrhea experienced by some people who take antibiotics also might be due to an overgrowth of the bacterium Clostridium difficile, which causes a disease known as pseudomembranous colitis. Controlled studies have shown that supplementation with harmless yeast, such as Saccharomyces boulardii7 or Saccharomyces cerevisiae (baker’s or brewer’s yeast),8 helps prevent recurrence of this infection. In one study, taking 500 mg of Saccharomyces boulardii twice daily enhanced the effectiveness of the antibiotic vancomycin in preventing recurrent clostridium infection.9 Therefore, people taking antibiotics who later develop diarrhea might benefit from supplementing with saccharomyces organisms.

Treatment with antibiotics also commonly leads to an overgrowth of yeast (Candida albicans) in the vagina (candida vaginitis) and the intestines (sometimes referred to as “dysbiosis”). Controlled studies have shown that Lactobacillus acidophilus might prevent candida vaginitis.10

''Vitamin B6''

Gentamicin administration has been associated with vitamin B6 depletion in rabbits.11 The authors of this study mention early evidence that vitamin B6 administration may protect against gentamicin-induced kidney damage.

''Vitamin K''

Several cases of excessive bleeding have been reported in people who take antibiotics.12 13 14 15 This side effect may be the result of reduced vitamin K activity and/or reduced vitamin K production by bacteria in the colon. One study showed that people who had taken broad-spectrum antibiotics had lower liver concentrations of vitamin K2 (menaquinone), though vitamin K1 (phylloquinone) levels remained normal.16 Several antibiotics appear to exert a strong effect on vitamin K activity, while others may not have any effect. Therefore, one should refer to a specific antibiotic for information on whether it interacts with vitamin K. Doctors of natural medicine sometimes recommend vitamin K supplementation to people taking antibiotics. Additional research is needed to determine whether the amount of vitamin K1found in some multivitamins is sufficient to prevent antibiotic-induced bleeding. Moreover, most multivitamins do not contain vitamin K.

In a study of guinea pigs, a single intramuscular injection of methylcobalamin (a form of vitamin B12), in the amount of 125 mg per 2.2 pounds of body weight, given immediately after administration of gentamicin, prevented damage to the inner ear, which is a common side effect of gentamicin therapy.17 No studies have been done to determine whether the same protective effect would occur in humans.

In another animal study, injections of N-Acetyl cysteine (10 mg per 2.2 pounds of body weight per day for five days) reduced the severity of kidney damage resulting from administration of gentamicin.18

== Structure of Gentamycin ==

[[Image:gentamycinA1.gif]] <br>
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REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00
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ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00
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TER
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1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68
1 2 1 0 0 0
1 33 1 0 0 0
5 4 1 0 0 0
5 38 1 0 0 0
7 6 1 0 0 0
7 40 1 0 0 0
9 8 1 0 0 0
9 42 1 0 0 0
9 43 1 0 0 0
11 10 1 0 0 0
11 12 1 0 0 0
14 13 1 0 0 0
14 47 1 0 0 0
14 48 1 0 0 0
17 16 1 0 0 0
17 52 1 0 0 0
17 53 1 0 0 0
19 18 1 0 0 0
19 20 1 0 0 0
22 21 1 0 0 0
22 57 1 0 0 0
24 23 1 0 0 0
24 25 1 0 0 0
24 59 1 0 0 0
27 26 1 0 0 0
27 64 1 0 0 0
29 28 1 0 0 0
29 20 1 0 0 0
31 30 1 0 0 0
31 68 1 0 0 0
32 10 1 0 0 0
32 3 1 0 0 0
2 35 1 0 0 0
2 34 1 0 0 0
2 3 1 0 0 0
3 36 1 0 0 0
3 4 1 0 0 0
4 37 1 0 0 0
4 6 1 0 0 0
6 8 1 0 0 0
6 39 1 0 0 0
8 10 1 0 0 0
8 41 1 0 0 0
10 44 1 0 0 0
12 30 1 0 0 0
12 45 1 0 0 0
12 13 1 0 0 0
13 15 1 0 0 0
13 46 1 0 0 0
15 16 1 0 0 0
15 50 1 0 0 0
15 49 1 0 0 0
16 51 1 0 0 0
16 18 1 0 0 0
18 30 1 0 0 0
18 54 1 0 0 0
20 55 1 0 0 0
20 21 1 0 0 0
21 56 1 0 0 0
21 23 1 0 0 0
23 58 1 0 0 0
23 26 1 0 0 0
25 60 1 0 0 0
25 61 1 0 0 0
25 62 1 0 0 0
26 63 1 0 0 0
26 28 1 0 0 0
28 66 1 0 0 0
28 65 1 0 0 0
30 67 1 0 0 0
M END

</inlineContents>
</jmolApplet>
</jmol>

== Properties of Gentamycin ==

'''Physical propertites'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|'''General'''
|-
| Impirical Forumla
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
|-
| Molecular Weight
| align="center"|468.50g/mol
|-
| Molecular Volume
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr)
|-
| Melting point
| align="center"| 105°C (218-237°C as sulfate salt)
|-
| solubility in water
| align="center"| 100mg/mL
|-
|align="left" colspan="3" bgcolor="white"|'''Other'''
|-
| Smiles String
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1
|-
| CA Index Name
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)

|-
|CAS Registry Number
| align="center"| 13291-74-2
|-
|}
'''Pharmacokinetic properties'''

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| Toxicity
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
|-
| Protein bonding
| align="left"|Low (between 0 and 30%)
|-
| Half life
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
|-
| Dosage form
| align="left"|Cream Drops Liquid Ointment Solution
|-
|}

==Reaction scheme of Gentamysin==

Gentamicin sample +PBD+Ab–› PBD-Ab Aggregates +Gentamicin sample -Ab

== References ==

*Sci Finder, Registry Number: 13291-74-2
*http://en.wikipedia.org/wiki/Gentamicin
*http://www.appco.com.au/appguide/drug.asp?drug_id=00200278&t=cmi

It:Gentamycin

2006-11-06T13:28:20Z

Yp305: /* storage of Gentamysin injection */

It:Bufotoxin

2006-11-06T12:43:09Z

Yp305: /* Synthesis of Bufotoxin */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Synthesis of Bufotoxin===

Completion of a formal total synthetic route to the toad venom constituents bufotalin, cinobufagin, bufalitoxin, and bufotoxin has been accomplished. Bufalin was employed as relay and converted to 14-dehydrobufalin 3-acetate. Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin and thence to cinobufagin.

Condensation of bufalin with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin, and an analogous route from bufotalin led to bufotoxin.

In a classic investigation of toad venom constituents, Wieland and colleagues isolated bufotoxin in 1922 from the European toad Bufo vulgaris (Bufo bufo bufo LinnB), and some 20 years later they were able to propose a tentative structure. Meanwhile, Kondo and co-workers succeeded in isolating bufotoxin and the parent steroid bufotalin from the Japanese toad venom preparation Senso (the Chinese Ch'an SU). The same substance was reisolated from Bufo bufo bufo L, and named vulgarobufotoxin. In 1955, the isolation of bufotoxin from Bufo bufo bufo L was reconfirmed by the Reichstein group 7 and more recently the correct structure proposed by Y.K. It was confirmed by Meyeraour which states that the partial synthesis of bufotoxin from bufotalin2 is part of Steroids and Related Natural Produds and series number 36 of Bufadienolides.

In this remarkable study the average yield of crude bufotoxin from Bufo vulgaris (800 males and 400 females) was found to be 1.34 mg/toad, while the female was found to yield 1.23 mg on the average of bufotalin. The male provided only 0.55 mg of bufotalin. In the same investigation, arenobufotoxin was isolated from the South American toad Bufo arenarum and purified by column chromatography on aluminum oxide.

Until 1974 the only known bufotoxin-type toad venom constituents were suberylarginine esters of a 30-hydroxybufadienolide. Investigation of the venom from Bufo vulgaris formosus. Boulenger has led to the isolation of bufotoxins with succinic, glutaric, pimelic, or adipic acid replacing suberic acid.

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

===Safety issues===

Bufotoxin is toxic, which has a function similar to digitalis glycosides. Although it is used in patentpreparations, is traditionally known for its toxicity and is seldom used in decoctions. Toxicity is often due to over dosage of the patents, such as Liushenwan and Houzhengwan. After administration one and a half to two hours, symptoms similar to digitalis toxicity appear, such as nausea, which is often the first indicator of toxicity, anorexia, vomiting, visual disturbances relating to colour vision, headache, weakness, psychosis, arrythmias, slowing of heart rate, AV block, and asystole.Severe cardiac damage is the major cause of death. It has also been known to promote contraction of the uterus; therefore it should not be used in pregnant women

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

7. J. Org. Chem. 1987,52, 3573-3578 3573
<div align="left"><br>
8. Registry No. 9, 5307-05-1; 12,4603-89-8; 13,42775-84-8; 14,
108512-22-7; 15, 108590-49-4; 16, 108590-50-7; 17, 108512-23-8;
18,108512-24-9; 20,108512-25-0; 21,108512-26-1; 23,108512-27-2;
24,108512-29-4; 25,108512-31-8; 26,108512-32-9; 27,108512-33-0;
28,108512-34-1; 29,108512-35-2; 30,108512-36-3; 31,108512-28-3;
32,108512-30-7; 33,108512-37-4; 35,108512-38-5; 36,108512-39-6;
38,108512-41-0; 40,108512-40-9; 41,108512-43-2; 42,108512-42-1;
43, 108512-44-3; N-(ethoxycarbonyl)phthalimide, 22509-74-6; 3,5-dimethoxyphenol, 500-99-2.
<div align="left"><br>
9. (a) The present contribution is part 104 of Steroids and Related Natural Produds and series number 36 of Bufadienolides; for parts 103 and 35 refer to, respectively: ''Pettit, G. R''; ''Herald, D. L''; ''Herald, C. L''; ''Kokke, W. C. M. C''; Djerassi, C. Steroids 1986, 47, 321. ''Green, B''; ''Snatzke, F''; ''Snatzke, G''; ''Pettit, G. R''; ''Kamano, Y''; ''Niven, M. L. Croat''. Chim. Acta 1985, 58, 371. (b) On leave from the ''Institute of Organic Chemistry and Biochemistry'', Czechoslovak Academy of Sciences, 166 10 Prague, Czechoslovakia.
<div align="left"><br>
10. A portion of the present study was summarized in a preliminary report by: ''Pettit, G. R''; ''Kamano, Y''. Chem. Commun. 1972, 45.
<div align="left"><br>
11. ''Wieland, H''; ''Alles, R''. Chem. Ber. 1922,55, 1789.
<div align="left"><br>
12. ''Wieland, H''; ''Behringer, H. Ann''. 1941,549,209.
<div align="left"><br>
13. ''Kondo. H'': ''Ikawa. S. J''. Pharm. Soc,. Jpn. 1933. 53. 23; Chem.Abstr.1933,27,1887. ''Kondo, H''; ''Ono, S. J''. Pharm. Soc.,Jpn. 1938,58, 37; Chem. Abstr. 1939, 32, 3765.
<div align="left"><br>
14. ''Chen, K. K''; ''Jensen, H''; ''Chen, A. L. J''. Pharmacol. 1933,47,307.
<div align="left"><br>
15. ''Urscheler, H. R''; ''Tamm, C''; ''Reichstein, T''. Helv. Chim. Acta 1955, 3,883.
<div align="left"><br>
16 ''Meyer, K''; ''Linde, H''. In Venomous Animals and Their Venoms; ''Bucherl, W'', ''Buckley, E. E'', Eds.; 1971; Vol. 2, p 521. For more recent advances in the chemistry of naturally occurring bufadienolides, refer to: ''Ode, H''; ''Kamano, Y''; ''Pettit, G. R''. MTP ''International Review of Science'', Organic Chemistry Series One; ''Johns, W. F'', Butterworths: London, 1975; Vol. 8, Chapter 6, pp 145-177. ''Nassimbeni, L. R''; ''Niven, M. L''; ''Sheldrick, G. M''; ''Pettit, G. R''; ''Inoue, M''; Kamano, Y. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1983, C39, 801 and ref la.
<div align="left"><br>
17 (a) ''Shimada, K''; ''Fujii, Y''; ''Mitsuishi, E''; ''Nambara, T''. Tetrahedron Lett. 1974, 467. ''Shimada, K''; ''Fujii, Y''; ''Niizaki, Y''; Nambara, T. Tetrahedron Lett. 1975, 653. ''Shimada, K''; ''Sato, Y''; ''Fujii, Y''; Nambara, T. Chem. Pharm. Bull. 1976,24, 1120. ''Shimada, K''; ''Ro, J. S''; Ohishi, K.; Nambara, T. Chem. Pharm. Bull. 1985,33,2767. (b) Shimada, K.; Fujii, ''Yamashita, E''; ''Niizaki, Y''; ''Sato, Y''; Nambara, T. Chem. Pharm. Bull 1977, 25, 714. See also: ''Shimada, K''; ''Ohishi, K''; Nambara, T. Tetrahedron Lett. 1984,24,551. ''Shimada, K''; ''Ohishi, K''; ''Nambara, T''. Chem. Pharm. Bull. 1984,32,4396. (c) ''Shimada, K''; ''Nambara, T''. Tetrahedron Lett. 1979,163. ''Shimada, K''; Nambara, T. Chem. Pharm. Bull. 1980,28,1559.

It:Bufotoxin

2006-11-02T15:32:09Z

Yp305: /* Citations */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Synthesis of Bufotoxin===

Completion of a formal total synthetic route to the toad venom constituents bufotalin, cinobufagin, bufalitoxin, and bufotoxin has been accomplished. Bufalin was employed as relay and converted to 14-dehydrobufalin 3-acetate. Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin and thence to cinobufagin.

Condensation of bufalin with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin, and an analogous route from bufotalin led to bufotoxin.

In a classic investigation of toad venom constituents, Wieland and colleagues isolated bufotoxin in 1922 from the European toad Bufo vulgaris (Bufo bufo bufo LinnB), and some 20 years later they were able to propose a tentative structure. Meanwhile, Kondo and co-workers succeeded in isolating bufotoxin and the parent steroid bufotalin from the Japanese toad venom preparation Senso (the Chinese Ch'an SU). The same substance was reisolated from Bufo bufo bufo L, and named vulgarobufotoxin. In 1955, the isolation of bufotoxin from Bufo bufo bufo L was reconfirmed by the Reichstein group 7 and more recently the correct structure proposed by Y.K. It was confirmed by Meyeraour which states that the partial synthesis of bufotoxin from bufotalin2 is part of Steroids and Related Natural Produds and series number 36 of Bufadienolides.

In this remarkable study the average yield of crude bufotoxin from Bufo vulgaris (800 males and 400 females) was found to be 1.34 mg/toad, while the female was found to yield 1.23 mg on the average of bufotalin. The male provided only 0.55 mg of bufotalin. In the same investigation, arenobufotoxin was isolated from the South American toad Bufo arenarum and purified by column chromatography on aluminum oxide.

Until 1974 the only known bufotoxin-type toad venom constituents were suberylarginine esters of a 30-hydroxybufadienolide. Investigation of the venom from Bufo vulgaris formosus. Boulenger has led to the isolation of bufotoxins with succinic, glutaric, pimelic, or adipic acid replacing suberic acid.

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

===Safety issues===

Bufotoxin is toxic, which has a function similar to digitalis glycosides. Although it is used in patentpreparations, is traditionally known for its toxicity and is seldom used in decoctions. Toxicity is often due to over dosage of the patents, such as Liushenwan and Houzhengwan. After administration one and a half to two hours, symptoms similar to digitalis toxicity appear, such as nausea, which is often the first indicator of toxicity, anorexia, vomiting, visual disturbances relating to colour vision, headache, weakness, psychosis, arrythmias, slowing of heart rate, AV block, and asystole.Severe cardiac damage is the major cause of death. It has also been known to promote contraction of the uterus; therefore it should not be used in pregnant women

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

7. J. Org. Chem. 1987,52, 3573-3578 3573
<div align="left"><br>
8. Registry No. 9, 5307-05-1; 12,4603-89-8; 13,42775-84-8; 14,
108512-22-7; 15, 108590-49-4; 16, 108590-50-7; 17, 108512-23-8;
18,108512-24-9; 20,108512-25-0; 21,108512-26-1; 23,108512-27-2;
24,108512-29-4; 25,108512-31-8; 26,108512-32-9; 27,108512-33-0;
28,108512-34-1; 29,108512-35-2; 30,108512-36-3; 31,108512-28-3;
32,108512-30-7; 33,108512-37-4; 35,108512-38-5; 36,108512-39-6;
38,108512-41-0; 40,108512-40-9; 41,108512-43-2; 42,108512-42-1;
43, 108512-44-3; N-(ethoxycarbonyl)phthalimide, 22509-74-6; 3,5-dimethoxyphenol, 500-99-2.
<div align="left"><br>
9. (a) The present contribution is part 104 of Steroids and Related Natural Produds and series number 36 of Bufadienolides; for parts 103 and 35 refer to, respectively: ''Pettit, G. R''; ''Herald, D. L''; ''Herald, C. L''; ''Kokke, W. C. M. C''; Djerassi, C. Steroids 1986, 47, 321. ''Green, B''; ''Snatzke, F''; ''Snatzke, G''; ''Pettit, G. R''; ''Kamano, Y''; ''Niven, M. L. Croat''. Chim. Acta 1985, 58, 371. (b) On leave from the ''Institute of Organic Chemistry and Biochemistry'', Czechoslovak Academy of Sciences, 166 10 Prague, Czechoslovakia.
<div align="left"><br>
10. A portion of the present study was summarized in a preliminary report by: ''Pettit, G. R''; ''Kamano, Y''. Chem. Commun. 1972, 45.
<div align="left"><br>
11. ''Wieland, H''; ''Alles, R''. Chem. Ber. 1922,55, 1789.
<div align="left"><br>
12. ''Wieland, H''; ''Behringer, H. Ann''. 1941,549,209.
<div align="left"><br>
13. ''Kondo. H'': ''Ikawa. S. J''. Pharm. Soc,. Jpn. 1933. 53. 23; Chem.Abstr.1933,27,1887. ''Kondo, H''; ''Ono, S. J''. Pharm. Soc.,Jpn. 1938,58, 37; Chem. Abstr. 1939, 32, 3765.
<div align="left"><br>
14. ''Chen, K. K''; ''Jensen, H''; ''Chen, A. L. J''. Pharmacol. 1933,47,307.
<div align="left"><br>
15. ''Urscheler, H. R''; ''Tamm, C''; ''Reichstein, T''. Helv. Chim. Acta 1955, 3,883.
<div align="left"><br>
16 ''Meyer, K''; ''Linde, H''. In Venomous Animals and Their Venoms; ''Bucherl, W'', ''Buckley, E. E'', Eds.; 1971; Vol. 2, p 521. For more recent advances in the chemistry of naturally occurring bufadienolides, refer to: ''Ode, H''; ''Kamano, Y''; ''Pettit, G. R''. MTP ''International Review of Science'', Organic Chemistry Series One; ''Johns, W. F'', Butterworths: London, 1975; Vol. 8, Chapter 6, pp 145-177. ''Nassimbeni, L. R''; ''Niven, M. L''; ''Sheldrick, G. M''; ''Pettit, G. R''; ''Inoue, M''; Kamano, Y. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1983, C39, 801 and ref la.
<div align="left"><br>
17 (a) ''Shimada, K''; ''Fujii, Y''; ''Mitsuishi, E''; ''Nambara, T''. Tetrahedron Lett. 1974, 467. ''Shimada, K''; ''Fujii, Y''; ''Niizaki, Y''; Nambara, T. Tetrahedron Lett. 1975, 653. ''Shimada, K''; ''Sato, Y''; ''Fujii, Y''; Nambara, T. Chem. Pharm. Bull. 1976,24, 1120. ''Shimada, K''; ''Ro, J. S''; Ohishi, K.; Nambara, T. Chem. Pharm. Bull. 1985,33,2767. (b) Shimada, K.; Fujii, ''Yamashita, E''; ''Niizaki, Y''; ''Sato, Y''; Nambara, T. Chem. Pharm. Bull 1977, 25, 714. See also: ''Shimada, K''; ''Ohishi, K''; Nambara, T. Tetrahedron Lett. 1984,24,551. ''Shimada, K''; ''Ohishi, K''; ''Nambara, T''. Chem. Pharm. Bull. 1984,32,4396. (c) ''Shimada, K''; ''Nambara, T''. Tetrahedron Lett. 1979,163. ''Shimada, K''; Nambara, T. Chem. Pharm. Bull. 1980,28,1559.

It:Bufotoxin

2006-11-02T14:43:55Z

Yp305: /* Bufotoxin and the toad, ''Bufo vulgaris'' */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Synthesis of Bufotoxin===

Completion of a formal total synthetic route to the toad venom constituents bufotalin, cinobufagin, bufalitoxin, and bufotoxin has been accomplished. Bufalin was employed as relay and converted to 14-dehydrobufalin 3-acetate. Selective oxidation of olefin 4 with a chromium trioxide-pyridine reagent afforded 16-ketone 5, which we had previously transformed to bufotalin and thence to cinobufagin.

Condensation of bufalin with suberic anhydride followed by a mixed carbonic anhydride reaction sequence using arginine monohydrochloride yielded bufalitoxin, and an analogous route from bufotalin led to bufotoxin.

In a classic investigation of toad venom constituents, Wieland and colleagues isolated bufotoxin in 1922 from the European toad Bufo vulgaris (Bufo bufo bufo LinnB), and some 20 years later they were able to propose a tentative structure. Meanwhile, Kondo and co-workers succeeded in isolating bufotoxin and the parent steroid bufotalin from the Japanese toad venom preparation Senso (the Chinese Ch'an SU). The same substance was reisolated from Bufo bufo bufo L, and named vulgarobufotoxin. In 1955, the isolation of bufotoxin from Bufo bufo bufo L was reconfirmed by the Reichstein group 7 and more recently the correct structure proposed by Y.K. It was confirmed by Meyeraour which states that the partial synthesis of bufotoxin from bufotalin2 is part of Steroids and Related Natural Produds and series number 36 of Bufadienolides.

In this remarkable study the average yield of crude bufotoxin from Bufo vulgaris (800 males and 400 females) was found to be 1.34 mg/toad, while the female was found to yield 1.23 mg on the average of bufotalin. The male provided only 0.55 mg of bufotalin. In the same investigation, arenobufotoxin was isolated from the South American toad Bufo arenarum and purified by column chromatography on aluminum oxide.

Until 1974 the only known bufotoxin-type toad venom constituents were suberylarginine esters of a 30-hydroxybufadienolide. Investigation of the venom from Bufo vulgaris formosus. Boulenger has led to the isolation of bufotoxins with succinic, glutaric, pimelic, or adipic acid replacing suberic acid.

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

===Safety issues===

Bufotoxin is toxic, which has a function similar to digitalis glycosides. Although it is used in patentpreparations, is traditionally known for its toxicity and is seldom used in decoctions. Toxicity is often due to over dosage of the patents, such as Liushenwan and Houzhengwan. After administration one and a half to two hours, symptoms similar to digitalis toxicity appear, such as nausea, which is often the first indicator of toxicity, anorexia, vomiting, visual disturbances relating to colour vision, headache, weakness, psychosis, arrythmias, slowing of heart rate, AV block, and asystole.Severe cardiac damage is the major cause of death. It has also been known to promote contraction of the uterus; therefore it should not be used in pregnant women

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-11-02T14:19:42Z

Yp305: /* Use of Bufotoxin */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

===Safety issues===

Bufotoxin is toxic, which has a function similar to digitalis glycosides. Although it is used in patentpreparations, is traditionally known for its toxicity and is seldom used in decoctions. Toxicity is often due to over dosage of the patents, such as Liushenwan and Houzhengwan. After administration one and a half to two hours, symptoms similar to digitalis toxicity appear, such as nausea, which is often the first indicator of toxicity, anorexia, vomiting, visual disturbances relating to colour vision, headache, weakness, psychosis, arrythmias, slowing of heart rate, AV block, and asystole.Severe cardiac damage is the major cause of death. It has also been known to promote contraction of the uterus; therefore it should not be used in pregnant women

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-30T16:11:50Z

Yp305: /* Use of Bufotoxin */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

According to the World Health Organization, more than 350 million people have the chronic form of hepatitis B, and about 75% of those live in Asia. Fortunately, researchers found the combination of Chinese herbal medicine and interferon was up to two times more effective at reducing the level of the hepatitis B virus to nearly undetectable levels. In particular, researcher Michael McCulloch says in a news release, herbs with the active ingredients bufotoxin or kurorinone showed the most promise and merit more study.

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-30T16:04:28Z

Yp305: /* Bufotoxin and the toad, ''Bufo vulgaris'' */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

===Use of Bufotoxin===

Bufotoxin and kurorinone have been singled out as having the best potential for being investigated for drugs. However, it works together with other herbal as a group, That is know as the herbal treatments in chinese medical studies, are particular mixtures in a distillation of centuries of clinical use."

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-30T15:17:56Z

Yp305: /* Bufotoxin and the toad, ''Bufo vulgaris'' */

== Abstruct ==

The occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known bufotoxin, in the skin of the North American toad, B. americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were sepd. by column chromatog. on silica gel, high-performance liq. chromatog. and gel chromatog. on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>

==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-30T15:12:34Z

Yp305: /* '''Properties of Vulgarobutotoxin''' */

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
| '''Melting point'''
| 218-225
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Gentamycin

2006-10-27T12:37:24Z

Yp305: /* Properties of Gentamycin */

It:Gentamycin

2006-10-27T12:25:28Z

Yp305: /* References */

It:Gentamycin

2006-10-27T12:23:23Z

Yp305: /* Symptoms of overdose */

It:Gentamycin

2006-10-27T12:20:25Z

Yp305: /* Before taking Gentamycin */

It:Gentamycin

2006-10-27T12:18:29Z

Yp305: /* Before taking Gentamycin, */

It:Gentamycin

2006-10-26T12:11:31Z

Yp305: /* Side Effects */

It:Gentamycin

2006-10-26T12:09:09Z

Yp305: /* Symptoms of overdose */

It:Gentamycin

2006-10-26T12:06:18Z

Yp305: /* Symptoms of overdose */

It:Gentamycin

2006-10-26T12:04:46Z

Yp305: /* Side Effects */

It:Gentamycin

2006-10-26T11:00:06Z

Yp305: /* Gentamycin A */

Ribosome

2006-10-26T10:58:37Z

Yp305:

[[http://en.wikipedia.org/wiki/Ribosome]]

It:Gentamycin

2006-10-26T10:40:40Z

Yp305: /* Gentamycin A */

It:Gentamycin

2006-10-26T10:39:28Z

Yp305: /* Gentamycin A */

Gram

2006-10-26T10:39:11Z

Yp305:

[[http://en.wikipedia.org/wiki/Gram]]

Gram negative

2006-10-26T10:38:12Z

Yp305:

[[http://en.wikipedia.org/wiki/Gram]]

It:Gentamycin

2006-10-23T15:37:20Z

Yp305: /* Properties of Gentacymin */

It:Gentamycin

2006-10-23T15:26:25Z

Yp305: /* Properties of Gentacymin */

It:Gentamycin

2006-10-23T15:00:28Z

Yp305: /* Properties of Gentacymin */