ChemWiki - User contributions [en]

It07:Sibutramine

2007-12-07T08:24:49Z

Jhl406: Further Studies -petition for a ban

{{Drug-Box |
| Box_Name = Sibutramine
| ImageFile = [[Image:Sibutramine.png|190px|Sibutramine.png]]
| IUPACName = 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
| OtherName = Meridia, Reductil
| CAS_No = 106650-56-0
| ATC_Code = A08AA10
| PubChem = 5210
| SMILES = surround in nowiki script code '<' nowiki'>' insert SMILE here'</'nowiki'>'
| Formula = C<sub>17</sub>H<sub>26</sub>ClN
| MolarMass = 279.84804g/mol
| Bioavailability = Resorption 77%, considerable first-pass metabolism
| Protein_binding
| Metabolism = Hepatic
| Half_life = sibutramine approx. 1 hour
Metabolite 1: 14 hours
Metabolite 2: 16 hours
| Excretion = Biliary (sibutramine and active metabolites), renal (inactive metabolites)
| Pregnancy_cat = X, no human data existing, teratogenic potential in animal studies
| Legal_status =
| Routes = Oral
}}

== 3D Model of Sibutramine ==

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== General Information ==
Sibutramine has been used as an appetite suppressant since it was approved by the FDA in the US in 1997. It is produced and marketed by Knoll Pharmaceuticals and is available in over 40 countries.
<br>
It was originally evaluated as an antidepressent due to its mechanism action being similar to the tricyclic group of antidepressents, such as [http://en.wikipedia.org/wiki/Amitriptyline Amitriptyline] without having the same negative side effects as Amitriptyline

Sibutramine is found in a class of medications called appetite suppressants. Sibutramine is commonly used in conjunction with a reduced calorie diet and exercise to help overweight people diminish their appetite. It primary mechanism involves acting on neurotransmitters that control appetite in the brain to decrease appetite.

==History==

Sibutramine was originally investigated as an anti-depressent due to its action as a serotonin uptake inhibitor. Seratonin (structure shown below) is a neurotransmitter, which is responsible for the feeling of ‘happiness’. The body controls the levels of seratonin very carefully and when levels get too high, it is reabsorbed. By inhibiting this reabsorption, the levels are able to get a little higher allowing the person a constant feeling of wellbeing. It showed real potential as a new drug as it did not seem to have any of the negative side effects usually associated with anti-depressents.

[[Image:Seratonin.png]] Seratonin

It was through the trials of sibutramine as an anti-depressent that it was discovered that patients also showed significant weight loss. It, therefore, started to become investigated as a possible anorexiant. Following this discovery, sibrutamine’s properties as an anti-depressent stopped being evaluated, perhaps due to a lack of positive or consistent results, and its properties as an anorexient became the subject of new research. Sibutramine is now marketed in its HCl monohydrate form as MeridiaTM and ReductilTM

<ref>Sibutramine History - http://www.chemsoc.org/ExemplarChem/entries/2003/imperial_Rowlands/web/history.html (Provided by Imperial College)</ref>

==How does it work?==

Sibutramine specifically blocks the reuptake of the neurotransmitters dopamine, norepinephrine, and serotonin. These are brain chemicals which influence feelings of hunger and fullness and taking sibutramine will induce the sensation of feeling full sooner when you eat and thus the patient will eat less.

[[Image:Sibutraminemechanismofaction.gif]]<ref>http://www.vaccine-edu.com/public/2006-201/slides/Slide34.gif</ref>

==Pharmacokinetics==

Sibutramine is absorbed (77% of a single dose) in the gastro-intestinal tract and, first, is metabolised in the liver by the cytochrome P450(3A4) to DMS and DDMS (structures shown below). The half life of this is just over 1 hour, and peak plasma concentrations of the metabolites are then reached after 3 to 4 hours. DMS and DDMS are then further metabolised in the liver by hydroxylation to pharmacologically inactive forms, with elimination half lives of 16 and 14 hours respectively. Sibutramine is excreted over approximately 15 days (85% of a dose), 77% of which is excreted in the urine.

[[Image:DMS2.png]]

<ref>Sibutramine Clinical - http://www.chemsoc.org/ExemplarChem/entries/2003/imperial_Rowlands/web/pharmacology.html (Provided by Imperial College)</ref>

==Side effects==

The most common side effects that occur whilst a patient is taking sibutramine are as follows; dry mouth, headache, constipation and insomnia. The drug has also shown to cause a significant increase in heart rate and diastolic blood pressure and, in some cases, persistent increases. Please see 'Further Studies'.

== Reaction Mechanism for the Synthesis of Sibutramine ==

[[Image:Subutraminereactionpicture.gif|centre|300|4-step Synthesis of Sibutramine]]<ref>[http://www.rsc.org/publishing/journals/article.asp?doi=p19960002583 Jeffery, J. E. J. E. (1996). "Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites." Journal of the Chemical Society. Perkin transactions 1(21): 2583-2589.]</ref>

==Further Studies==

In 2002 a petition was submitted to the FDA declaring the use of sibutramine to be banned. http://www.citizen.org/publications/print_release.cfm?ID=7160 It was reported that the use of sibutramine had been associated with 29 deaths including 19 from cardiovascular adverse effects in people using this drug. Previously its use was even suspended in Italy because of two cardiovascular deaths. The petition refers to clinical trials where it was shown that taking the drug resulted in a significant increase in blood pressure and heart rate.

Other research, http://www.rxlist.com/cgi/generic/sibutramine_ad.htm, indicated that Convulsions were reported as an adverse event in three of 2068 (0.1%) sibutramine treated patients. There were also abnormal liver function tests. Cases of depression, suicidal ideation and suicide have been reported rarely in patients on sibutramine treatment. However, a relationship has not been established between the occurrence of depression and/or suicidal ideation and the use of sibutramine.

== References==
<references/>
http://www.fda.gov/bbs/topics/ANSWERS/ANS00835.html

It07:Azadirachtin

2007-12-07T07:57:13Z

Jhl406: Uses

== Azadirachtin ==

{| class="toccolours" border="1" width="150px" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''{{PAGENAME}}''' 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Azadirachtin.png|300px|It07-Azadirachtin]] 
|-
| [[IUPAC nomenclature|Systematic name]]
| {{dimethyl (2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-acetoxy-
3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-
6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-
2,7-methanofuro[2,3-b]oxireno[e]oxepin-
1a(2H)-yl]-4-methyl-8-
{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-
1H-naphtho[1,8a-c:4,5-b'c']difuran-
5,10a(8H)-dicarboxylate}} 
|-
| [[Chemical formula]]
| C<sub>35</sub>H<sub>44</sub>O<sub>16</sub>
|-
| [[Molar mass]]
| 720.63 g/mol
|-
| [[Density]]
| 1.51 ± 0.1 g/cm³
|-
| [[Solubility]]
| 0.015 g/dm<sup>3</sup>
|-
| [[Boiling point]]
| 792.4 ± 60.0 °C
|-
| [[CAS registry number|CAS number]]
| 11141-17-6
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>C\C=C(/C)\C(=O)O[C@H]1C[C@H]
([C@]2(CO[C@@H]3[C@@H]2[C@]14CO[C@@]
([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]
7C[C@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)
(C(=O)OC)O)C(=O)OC)OC(=O)C</small>
|-
| [[Hazards]]
| Possible irritant, toxicological properties have not been investigated.
|-
| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
|-
|}<noinclude>
[[Category:WikiProject Chemistry Templates|Chembox simple organic]]
</noinclude>

'''Azadirachtin''' is a triterpenoid compound extracted from the Neem tree (''Azadirachta indica''). The molecular structure is highly complex, with 16 stereogenic centers - seven of which are tetrasubstituted. Complete synthesis was first achieved by Steven Ley in 2007, 22 years after the structure was established (also by Ley and co-workers) in 1985.<ref name="synthesis">S. V. Ley, A. A. Denholm and A. Wood, Nat. Prod. Rep., 1993, 10,
109. http://www.rsc.org/ejarchive/NP/1993/NP9931000109.pdf (accessed 25 October 2007)</ref> It is a yellow-green powder, with a strong garlic-sulfur odor.<ref>Farm Chemicals Handbook. 1995. Meister Publishing Co. Willoughby, OH.</ref><ref>Thomson, W.T. Agricultural Chemicals. Book I: Insecticides. 1992. Thomson Publications, Fresno, CA.</ref>

=== Mode of Action ===
The process of moulting (shedding of exoskeleton) and metamorphosis (final transformation where insect makes transition from pupal stage to become fully adult) is triggered by prothoracicotropic hormone (PTTH) as well as ecdysone.<ref>Kimball, J. W. (9 February 2002) 'Insect Hormones', http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/I/InsectHormones.html (accessed 23 October 2007)</ref> Azadirachtin blocks the action of ecdysone and hence stops moulting and subsequent growth of insects. As such, it is a good antifeedant - a substance that inhibits the insect from feeding but does not kill it directly.<ref>K. Munakata, Pure Appl. Chem., 1975, 42, 57.</ref>

=== 3d Structure ===
To zoom in/out, click on molecule and use scroll wheel on mouse.
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ATOM 1 C 0 -0.415 6.019 -1.839 0.00 0.00 C+0
ATOM 2 C 0 0.229 4.734 -2.293 0.00 0.00 C+0
ATOM 3 C 0 0.349 3.715 -1.447 0.00 0.00 C+0
ATOM 4 C 0 -0.159 3.845 -0.034 0.00 0.00 C+0
ATOM 5 C 0 0.977 2.462 -1.889 0.00 0.00 C+0
ATOM 6 O 0 1.387 2.357 -3.029 0.00 0.00 O+0
ATOM 7 O 0 1.098 1.429 -1.032 0.00 0.00 O+0
ATOM 8 C 0 1.715 0.199 -1.467 0.00 0.00 C+0
ATOM 9 C 0 3.222 0.270 -1.199 0.00 0.00 C+0
ATOM 10 C 0 3.406 0.496 0.303 0.00 0.00 C+0
ATOM 11 C 0 2.893 -0.685 1.082 0.00 0.00 C+0
ATOM 12 C 0 2.537 -0.280 2.535 0.00 0.00 C+0
ATOM 13 O 0 1.085 -0.249 2.561 0.00 0.00 O+0
ATOM 14 C 0 0.707 -1.383 1.759 0.00 0.00 C+0
ATOM 15 C 0 1.631 -1.350 0.562 0.00 0.00 C+0
ATOM 16 C 0 1.123 -1.036 -0.789 0.00 0.00 C+0
ATOM 17 C 0 1.530 -2.235 -1.720 0.00 0.00 C+0
ATOM 18 O 0 0.437 -3.158 -1.560 0.00 0.00 O+0
ATOM 19 C 0 -0.757 -2.339 -1.642 0.00 0.00 C+0
ATOM 20 C 0 -0.408 -1.020 -0.954 0.00 0.00 C+0
ATOM 21 C 0 -1.181 -0.668 0.283 0.00 0.00 C+0
ATOM 22 C 0 -0.762 -1.503 1.489 0.00 0.00 C+0
ATOM 23 O 0 -1.114 -2.873 1.319 0.00 0.00 O+0
ATOM 24 C 0 -0.965 0.818 0.643 0.00 0.00 C+0
ATOM 25 C 0 -2.688 -0.808 0.062 0.00 0.00 C+0
ATOM 26 C 0 -3.420 0.335 -0.683 0.00 0.00 C+0
ATOM 27 C 0 -4.914 0.008 -0.432 0.00 0.00 C+0
ATOM 28 C 0 -4.907 -0.407 1.077 0.00 0.00 C+0
ATOM 29 C 0 -3.641 -1.295 1.169 0.00 0.00 C+0
ATOM 30 O 0 -3.285 -2.108 0.017 0.00 0.00 O+0
ATOM 31 C 0 -3.133 -1.665 2.564 0.00 0.00 C+0
ATOM 32 C 0 -4.574 0.908 1.789 0.00 0.00 C+0
ATOM 33 C 0 -4.371 0.829 3.277 0.00 0.00 C+0
ATOM 34 C 0 -3.294 1.573 3.533 0.00 0.00 C+0
ATOM 35 O 0 -2.752 2.121 2.393 0.00 0.00 O+0
ATOM 36 C 0 -3.106 1.218 1.360 0.00 0.00 C+0
ATOM 37 O 0 -3.088 1.564 0.007 0.00 0.00 O+0
ATOM 38 O 0 -5.486 1.948 1.431 0.00 0.00 O+0
ATOM 39 C 0 -1.074 -2.085 -3.100 0.00 0.00 C+0
ATOM 40 O 0 -0.407 -2.604 -3.963 0.00 0.00 O+0
ATOM 41 O 0 -2.098 -1.283 -3.434 0.00 0.00 O+0
ATOM 42 C 0 -2.472 -1.126 -4.828 0.00 0.00 C+0
ATOM 43 O 0 -1.827 -3.065 -1.054 0.00 0.00 O+0
ATOM 44 C 0 3.984 -1.724 1.149 0.00 0.00 C+0
ATOM 45 O 0 3.794 -2.829 0.699 0.00 0.00 O+0
ATOM 46 O 0 5.165 -1.421 1.710 0.00 0.00 O+0
ATOM 47 C 0 6.216 -2.422 1.775 0.00 0.00 C+0
ATOM 48 O 0 4.819 0.678 0.587 0.00 0.00 O+0
ATOM 49 C 0 5.356 1.908 0.560 0.00 0.00 C+0
ATOM 50 O 0 4.664 2.864 0.299 0.00 0.00 O+0
ATOM 51 C 0 6.822 2.097 0.855 0.00 0.00 C+0
ATOM 52 H 0 -0.423 6.732 -2.663 0.00 0.00 H+0
ATOM 53 H 0 -1.438 5.820 -1.521 0.00 0.00 H+0
ATOM 54 H 0 0.151 6.434 -1.005 0.00 0.00 H+0
ATOM 55 H 0 0.594 4.641 -3.306 0.00 0.00 H+0
ATOM 56 H 0 -0.589 4.836 0.108 0.00 0.00 H+0
ATOM 57 H 0 -0.923 3.089 0.149 0.00 0.00 H+0
ATOM 58 H 0 0.666 3.703 0.664 0.00 0.00 H+0
ATOM 59 H 0 1.568 0.100 -2.552 0.00 0.00 H+0
ATOM 60 H 0 3.701 -0.658 -1.507 0.00 0.00 H+0
ATOM 61 H 0 3.653 1.107 -1.753 0.00 0.00 H+0
ATOM 62 H 0 2.864 1.390 0.605 0.00 0.00 H+0
ATOM 63 H 0 2.907 -1.026 3.235 0.00 0.00 H+0
ATOM 64 H 0 2.941 0.703 2.768 0.00 0.00 H+0
ATOM 65 H 0 0.991 -2.265 2.340 0.00 0.00 H+0
ATOM 66 H 0 1.941 -2.394 0.482 0.00 0.00 H+0
ATOM 67 H 0 1.631 -1.901 -2.750 0.00 0.00 H+0
ATOM 68 H 0 2.467 -2.676 -1.376 0.00 0.00 H+0
ATOM 69 H 0 -0.627 -0.221 -1.697 0.00 0.00 H+0
ATOM 70 H 0 -1.302 -1.121 2.371 0.00 0.00 H+0
ATOM 71 H 0 -0.821 -3.337 2.115 0.00 0.00 H+0
ATOM 72 H 0 -1.507 1.446 -0.064 0.00 0.00 H+0
ATOM 73 H 0 -1.333 1.005 1.652 0.00 0.00 H+0
ATOM 74 H 0 0.099 1.052 0.596 0.00 0.00 H+0
ATOM 75 H 0 -3.174 0.367 -1.745 0.00 0.00 H+0
ATOM 76 H 0 -5.537 0.888 -0.590 0.00 0.00 H+0
ATOM 77 H 0 -5.243 -0.818 -1.062 0.00 0.00 H+0
ATOM 78 H 0 -5.822 -0.893 1.418 0.00 0.00 H+0
ATOM 79 H 0 -3.972 -1.977 3.185 0.00 0.00 H+0
ATOM 80 H 0 -2.416 -2.482 2.485 0.00 0.00 H+0
ATOM 81 H 0 -2.649 -0.799 3.016 0.00 0.00 H+0
ATOM 82 H 0 -4.972 0.284 3.990 0.00 0.00 H+0
ATOM 83 H 0 -2.892 1.728 4.524 0.00 0.00 H+0
ATOM 84 H 0 -2.519 0.307 1.483 0.00 0.00 H+0
ATOM 85 H 0 -5.165 2.758 1.853 0.00 0.00 H+0
ATOM 86 H 0 -2.835 -2.078 -5.216 0.00 0.00 H+0
ATOM 87 H 0 -3.259 -0.377 -4.911 0.00 0.00 H+0
ATOM 88 H 0 -1.603 -0.807 -5.404 0.00 0.00 H+0
ATOM 89 H 0 -1.886 -3.908 -1.525 0.00 0.00 H+0
ATOM 90 H 0 7.094 -1.996 2.260 0.00 0.00 H+0
ATOM 91 H 0 5.865 -3.280 2.347 0.00 0.00 H+0
ATOM 92 H 0 6.477 -2.741 0.766 0.00 0.00 H+0
ATOM 93 H 0 7.391 2.026 -0.072 0.00 0.00 H+0
ATOM 94 H 0 6.979 3.078 1.303 0.00 0.00 H+0
ATOM 95 H 0 7.156 1.323 1.546 0.00 0.00 H+0
CONECT 1 2 52 53 54 NONE 100
CONECT 2 1 3 55 0 NONE 101
CONECT 3 2 4 5 0 NONE 102
CONECT 4 3 56 57 58 NONE 103
CONECT 5 3 6 7 0 NONE 104
CONECT 6 5 0 0 0 NONE 105
CONECT 7 5 8 0 0 NONE 106
CONECT 8 7 16 9 59 NONE 107
CONECT 9 8 10 60 61 NONE 108
CONECT 10 9 11 48 62 NONE 109
CONECT 11 10 15 12 44 NONE 110
CONECT 12 11 13 63 64 NONE 111
CONECT 13 12 14 0 0 NONE 112
CONECT 14 13 22 15 65 NONE 113
CONECT 15 14 11 16 66 NONE 114
CONECT 16 15 8 20 17 NONE 115
CONECT 17 16 18 67 68 NONE 116
CONECT 18 17 19 0 0 NONE 117
CONECT 19 18 20 39 43 NONE 118
CONECT 20 19 16 21 69 NONE 119
CONECT 21 20 22 24 25 NONE 120
CONECT 22 21 14 23 70 NONE 121
CONECT 23 22 71 0 0 NONE 122
CONECT 24 21 72 73 74 NONE 123
CONECT 25 21 29 30 26 NONE 124
CONECT 26 25 37 27 75 NONE 125
CONECT 27 26 28 76 77 NONE 126
CONECT 28 27 29 32 78 NONE 127
CONECT 29 28 25 30 31 NONE 128
CONECT 30 29 25 0 0 NONE 129
CONECT 31 29 79 80 81 NONE 130
CONECT 32 28 36 33 38 NONE 131
CONECT 33 32 34 82 0 NONE 132
CONECT 34 33 35 83 0 NONE 133
CONECT 35 34 36 0 0 NONE 134
CONECT 36 35 32 37 84 NONE 135
CONECT 37 36 26 0 0 NONE 136
CONECT 38 32 85 0 0 NONE 137
CONECT 39 19 40 41 0 NONE 138
CONECT 40 39 0 0 0 NONE 139
CONECT 41 39 42 0 0 NONE 140
CONECT 42 41 86 87 88 NONE 141
CONECT 43 19 89 0 0 NONE 142
CONECT 44 11 45 46 0 NONE 143
CONECT 45 44 0 0 0 NONE 144
CONECT 46 44 47 0 0 NONE 145
CONECT 47 46 90 91 92 NONE 146
CONECT 48 10 49 0 0 NONE 147
CONECT 49 48 50 51 0 NONE 148
CONECT 50 49 0 0 0 NONE 149
CONECT 51 49 93 94 95 NONE 150
END NONE 151
70
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=== Sources and Synthesis ===
The Azadirachtin molecule has a complex molecular structure which is mainly the reason why it has taken so long for a successful synthesis path to be found. There are 16 continuous stereogenic centres, seven of which are tetrasubstituted carbons. It is sensitive to both acid and base and is unstable in light. The C8-C14 bond is of particular importance as it was the hardest bond to create given the highly hindered environment around it. There are also intra-molecular hydrogen-bonds which impose even more conformational considerations when considering a synthetic path.

[[Image:C18-c14.jpg]]

The synthetic path can be summarised as the fusing of a pyran and decalin fragment by selective O-coupling. The crucial C8-C14 bond is then formed under thermal or gold(I)-catalysed conditions via a Claisen rearrangement. The tricyclic system is then formed by a radical cyclization. The final step involves a selective epoxidation. This was also a challenge to the acheive synthetically, but on prolonged heating with magnesium monoperoxyphthalate in the presence of a radical inhibitor, complete synthesis of Azadirachtin was achieved.

Azadirachtin can also be easily extracted from the seeds of the Neem tree. A polar solvent such as water, ethanol or methanol will suffice. In fact, Indian villagers have been known to crush the seeds and soak them in cold water. After soaking overnight, the emulsion at the top is applied directly to plants.

The exact biosynthesis of Azadirachtin is unknown but most certainly proceeds via a steroid modification.
<ref>Synthesis of Azadirachtin: A Long but Successful Journey Gemma E. Veitch, Edith Beckmann, Brenda J. Burke, Alistair Boyer, Sarah L. Maslen, and
Steven V. Ley</ref>

=== Uses ===
Azadirachtin works as an insect growth regulator. It prevents the larval stage molting into an adult. It works by disturbing or inhibiting the development of the eggs, larvae, or pupae, disturbing mating and sexual communication, repelling larvae and adults, and deterring females from laying eggs.

There has been much research into this pesticide and it has been shown that the spray solution of neem oil helps to control common pests like white flies, aphids, scales, mealy bugs, spider mites, locusts, thrips, and Japanese beetles. There are no reported adverse effects to humans, wildlife, or the environment.

==References==
<references/>

It07:Capreomycin

2007-10-29T15:37:56Z

Jhl406: /* Advancements */ detail added about the findings of the report

== '''Capreomycin''' ==

Capreomycin is used in the treatment of Tuberculosis (TB) but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. It has a molecular formula of C25H44N14O8.

=== Structure ===

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ATOM 1 N 0 -1.440 5.168 0.918 0.00 0.00 N+0
ATOM 2 C 0 -1.593 3.761 0.527 0.00 0.00 C+0
ATOM 3 C 0 -0.732 2.897 1.412 0.00 0.00 C+0
ATOM 4 N 0 0.622 3.097 1.398 0.00 0.00 N+0
ATOM 5 C 0 1.384 2.207 2.311 0.00 0.00 C+0
ATOM 6 C 0 1.337 0.808 1.753 0.00 0.00 C+0
ATOM 7 N 0 1.591 -0.248 2.577 0.00 0.00 N+0
ATOM 8 C 0 1.492 -1.592 1.962 0.00 0.00 C+0
ATOM 9 C 0 0.033 -1.889 1.714 0.00 0.00 C+0
ATOM 10 O 0 -0.501 -2.861 2.207 0.00 0.00 O+0
ATOM 11 C 0 2.256 -1.612 0.637 0.00 0.00 C+0
ATOM 12 N 0 3.627 -1.146 0.857 0.00 0.00 N+0
ATOM 13 C 0 4.490 -1.079 -0.177 0.00 0.00 C+0
ATOM 14 C 0 5.901 -0.600 0.050 0.00 0.00 C+0
ATOM 15 C 0 6.665 -0.620 -1.276 0.00 0.00 C+0
ATOM 16 N 0 6.067 0.353 -2.200 0.00 0.00 N+0
ATOM 17 C 0 8.129 -0.254 -1.026 0.00 0.00 C+0
ATOM 18 C 0 8.919 -0.394 -2.329 0.00 0.00 C+0
ATOM 19 C 0 10.384 -0.028 -2.079 0.00 0.00 C+0
ATOM 20 N 0 11.142 -0.163 -3.329 0.00 0.00 N+0
ATOM 21 O 0 4.131 -1.404 -1.288 0.00 0.00 O+0
ATOM 22 O 0 1.075 0.623 0.583 0.00 0.00 O+0
ATOM 23 C 0 2.836 2.679 2.399 0.00 0.00 C+0
ATOM 24 O 0 2.881 3.970 3.009 0.00 0.00 O+0
ATOM 25 O 0 -1.227 2.046 2.120 0.00 0.00 O+0
ATOM 26 C 0 -3.058 3.346 0.680 0.00 0.00 C+0
ATOM 27 N 0 -3.330 2.178 -0.167 0.00 0.00 N+0
ATOM 28 C 0 -4.764 1.884 -0.039 0.00 0.00 C+0
ATOM 29 C 0 -5.048 0.497 -0.620 0.00 0.00 C+0
ATOM 30 C 0 -4.640 0.467 -2.095 0.00 0.00 C+0
ATOM 31 N 0 -4.881 -0.872 -2.653 0.00 0.00 N+0
ATOM 32 C 0 -4.946 -1.017 -4.018 0.00 0.00 C+0
ATOM 33 N 0 -4.902 -2.282 -4.555 0.00 0.00 N+0
ATOM 34 N 0 -5.047 -0.005 -4.816 0.00 0.00 N+0
ATOM 35 C 0 -5.083 1.382 -4.365 0.00 0.00 C+0
ATOM 36 C 0 -5.498 1.459 -2.894 0.00 0.00 C+0
ATOM 37 N 0 -4.267 -0.508 0.129 0.00 0.00 N+0
ATOM 38 C 0 -2.915 -0.341 0.118 0.00 0.00 C+0
ATOM 39 C 0 -2.074 -1.277 0.868 0.00 0.00 C+0
ATOM 40 N 0 -0.668 -1.027 0.915 0.00 0.00 N+0
ATOM 41 C 0 -2.611 -2.343 1.497 0.00 0.00 C+0
ATOM 42 N 0 -2.055 -3.592 1.332 0.00 0.00 N+0
ATOM 43 C 0 -2.517 -4.636 2.049 0.00 0.00 C+0
ATOM 44 N 0 -1.972 -5.858 1.888 0.00 0.00 N+0
ATOM 45 O 0 -3.426 -4.475 2.841 0.00 0.00 O+0
ATOM 46 O 0 -2.412 0.574 -0.508 0.00 0.00 O+0
ATOM 47 O 0 -5.134 1.908 1.341 0.00 0.00 O+0
ATOM 48 H 0 -0.464 5.397 0.802 0.00 0.00 H+0
ATOM 49 H 0 -1.948 5.715 0.239 0.00 0.00 H+0
ATOM 50 H 0 -1.287 3.636 -0.511 0.00 0.00 H+0
ATOM 51 H 0 1.048 3.764 0.838 0.00 0.00 H+0
ATOM 52 H 0 0.931 2.223 3.302 0.00 0.00 H+0
ATOM 53 H 0 1.823 -0.127 3.510 0.00 0.00 H+0
ATOM 54 H 0 1.909 -2.338 2.639 0.00 0.00 H+0
ATOM 55 H 0 2.276 -2.628 0.244 0.00 0.00 H+0
ATOM 56 H 0 1.759 -0.956 -0.078 0.00 0.00 H+0
ATOM 57 H 0 3.914 -0.886 1.746 0.00 0.00 H+0
ATOM 58 H 0 5.881 0.416 0.442 0.00 0.00 H+0
ATOM 59 H 0 6.397 -1.257 0.765 0.00 0.00 H+0
ATOM 60 H 0 6.609 -1.617 -1.713 0.00 0.00 H+0
ATOM 61 H 0 6.141 1.257 -1.757 0.00 0.00 H+0
ATOM 62 H 0 6.661 0.381 -3.015 0.00 0.00 H+0
ATOM 63 H 0 8.191 0.775 -0.673 0.00 0.00 H+0
ATOM 64 H 0 8.547 -0.922 -0.273 0.00 0.00 H+0
ATOM 65 H 0 8.857 -1.424 -2.682 0.00 0.00 H+0
ATOM 66 H 0 8.501 0.274 -3.081 0.00 0.00 H+0
ATOM 67 H 0 10.446 1.001 -1.725 0.00 0.00 H+0
ATOM 68 H 0 10.802 -0.696 -1.326 0.00 0.00 H+0
ATOM 69 H 0 10.791 0.542 -3.959 0.00 0.00 H+0
ATOM 70 H 0 12.097 0.087 -3.118 0.00 0.00 H+0
ATOM 71 H 0 3.412 1.973 2.998 0.00 0.00 H+0
ATOM 72 H 0 3.261 2.736 1.397 0.00 0.00 H+0
ATOM 73 H 0 3.812 4.230 3.045 0.00 0.00 H+0
ATOM 74 H 0 -3.257 3.094 1.721 0.00 0.00 H+0
ATOM 75 H 0 -3.702 4.172 0.377 0.00 0.00 H+0
ATOM 76 H 0 -3.178 2.470 -1.121 0.00 0.00 H+0
ATOM 77 H 0 -5.339 2.632 -0.584 0.00 0.00 H+0
ATOM 78 H 0 -6.111 0.276 -0.532 0.00 0.00 H+0
ATOM 79 H 0 -3.585 0.725 -2.192 0.00 0.00 H+0
ATOM 80 H 0 -4.992 -1.639 -2.069 0.00 0.00 H+0
ATOM 81 H 0 -4.827 -3.054 -3.971 0.00 0.00 H+0
ATOM 82 H 0 -4.947 -2.404 -5.516 0.00 0.00 H+0
ATOM 83 H 0 -4.093 1.823 -4.483 0.00 0.00 H+0
ATOM 84 H 0 -5.799 1.938 -4.970 0.00 0.00 H+0
ATOM 85 H 0 -6.551 1.195 -2.796 0.00 0.00 H+0
ATOM 86 H 0 -5.334 2.470 -2.520 0.00 0.00 H+0
ATOM 87 H 0 -4.691 -1.242 0.601 0.00 0.00 H+0
ATOM 88 H 0 -0.246 -0.306 0.422 0.00 0.00 H+0
ATOM 89 H 0 -3.478 -2.217 2.129 0.00 0.00 H+0
ATOM 90 H 0 -1.330 -3.721 0.701 0.00 0.00 H+0
ATOM 91 H 0 -1.247 -5.987 1.257 0.00 0.00 H+0
ATOM 92 H 0 -2.305 -6.609 2.404 0.00 0.00 H+0
ATOM 93 H 0 -4.936 2.796 1.668 0.00 0.00 H+0
CONECT 1 2 48 49 0 NONE 98
CONECT 2 1 3 26 50 NONE 99
CONECT 3 2 4 25 0 NONE 100
CONECT 4 3 5 51 0 NONE 101
CONECT 5 4 6 23 52 NONE 102
CONECT 6 5 7 22 0 NONE 103
CONECT 7 6 8 53 0 NONE 104
CONECT 8 7 9 11 54 NONE 105
CONECT 9 8 40 10 0 NONE 106
CONECT 10 9 0 0 0 NONE 107
CONECT 11 8 12 55 56 NONE 108
CONECT 12 11 13 57 0 NONE 109
CONECT 13 12 14 21 0 NONE 110
CONECT 14 13 15 58 59 NONE 111
CONECT 15 14 16 17 60 NONE 112
CONECT 16 15 61 62 0 NONE 113
CONECT 17 15 18 63 64 NONE 114
CONECT 18 17 19 65 66 NONE 115
CONECT 19 18 20 67 68 NONE 116
CONECT 20 19 69 70 0 NONE 117
CONECT 21 13 0 0 0 NONE 118
CONECT 22 6 0 0 0 NONE 119
CONECT 23 5 24 71 72 NONE 120
CONECT 24 23 73 0 0 NONE 121
CONECT 25 3 0 0 0 NONE 122
CONECT 26 2 27 74 75 NONE 123
CONECT 27 26 28 76 0 NONE 124
CONECT 28 27 29 47 77 NONE 125
CONECT 29 28 30 37 78 NONE 126
CONECT 30 29 36 31 79 NONE 127
CONECT 31 30 32 80 0 NONE 128
CONECT 32 31 33 34 0 NONE 129
CONECT 33 32 81 82 0 NONE 130
CONECT 34 32 35 0 0 NONE 131
CONECT 35 34 36 83 84 NONE 132
CONECT 36 35 30 85 86 NONE 133
CONECT 37 29 38 87 0 NONE 134
CONECT 38 37 39 46 0 NONE 135
CONECT 39 38 40 41 0 NONE 136
CONECT 40 39 9 88 0 NONE 137
CONECT 41 39 42 89 0 NONE 138
CONECT 42 41 43 90 0 NONE 139
CONECT 43 42 44 45 0 NONE 140
CONECT 44 43 91 92 0 NONE 141
CONECT 45 43 0 0 0 NONE 142
CONECT 46 38 0 0 0 NONE 143
CONECT 47 28 93 0 0 NONE 144
END NONE 145
M END</inlineContents>
</jmolApplet>

<jmolMenu>
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<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Capreomycin.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| Other names
| Capreomycin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>25</sub>H<sub>44</sub>N<sub>14</sub>O<sub>8
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| NC(CC(NCC2NC(C(CO)NC
(C(N)CNC(C(NC(/C(NC2=O)
=C\CC(N)=O)=O)C1N=C(N)
NCC1)=O)=O)=O)=O)CCCN
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 668.71
|-
! {{chembox header}} | Properties
|-
| Storage Temperature
| -20<sup>0</sup>
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C4142 Sigma Aldrich Safety Data
|-
| Main [[Worker safety and health|hazard]]s
| May cause damage to an the unborn child,
May be harmful 
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Overview ==

Capreomycin has the ability to kill a wide variety of bacteria. It does this by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for TB is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Although other medications are used with capreomycin these must be carefully chosen: if used in conjunction with other injectable TB treatments (streptomycin and viomycin) there is an increased risk of hearing and kidney damage in the patient. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

== Adverse Effects ==

The following are some of the side effects that are known to be associated with this medicine.

• Skin irritation and itching (pruritus)

• Allergy to active ingredients (hypersensitivity)

• Rash (allergic reaction)

• Loss of hearing

• Damage to the kidneys

• Alteration in results of liver function tests

• Disruption to the chemical components balance of electrolytes in the blood

== Further Studies ==

Capreomycin is an important drug used for TB which has developed resistance to many drugs. This is a characteristic of TB drugs and is termed multi-drug resistance (MDR). Capreomycin displays a unique bactericidal effect on non-replicating TB bacilli among known anti-TB drugs.

In a 2005 journal by L. Heifets, J. Simon and V. Pham it showed that only capreomycin is active against non-replicating M. tuberculosis bacilli at the same level as metronidazole in an in vitro model of persistence that monitors the curve of decline in bacterial counts. This confirms the conclusion made in a 1996 journal by N. Rastogi, V. Labrousse and K.S. Goh that stated that capreomycin was effective against MDR and intracellular TB bacilli.

== Synthesis ==

The synthesis of tuberculostatic macrocyclic peptide antibiotic capreomycin IB is composed of 27 complex steps and was determined in 2003 and outlined in a journal written by Duane E. DeMong and Robert M. Williams of Colorado State UniVersity. An enolate-aldimine condensation takes place between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal. This produces the cyclic guanidine amino acid (2S,3R)-capreomycidine. Finally there is a Hofmann rearrangement on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic
acid residue.

== Advancements ==

The August 2007 issue of 'Antimicrobial Agents and Chemotherapy' http://aac.asm.org/ reported a new novel way of treating TB. The findings, also reported by Reuters http://www.medscape.com/viewarticle/562095, presents treatment by inhalation of large porous particles of capreomycin following studies using a guinea pig model. Dr. Anthony J. Hickey and his research team at the University of North Carolina introduced this new concept as a way of the drug being adminstered so that it can directly act at the site of origin thereby hopefully reducing the severe side effects.

In the report the guinea pigs were tested using different methods. The effects of these methods were measured by looking at lung histopathologies for a reduction of the bacteria present in the lungs and by wet tissue weights. It was found that the lungs of animals receiving capreomycin particles by passive inhalation showed significantly, by histopathology, a smaller degree of inflammation and bacterial burdens than the animals treated by other methods.

As a result of this study, it was concluded that treating TB by means of inhaled capreomycin is feasable and safe.

== References ==

1. L. Heifets, J. Simon and V. Pham, Capreomycin is active against non-replicating M. tuberculosis, Ann Clin Microbiol Antimicrob 4 (2005) (1), p. 6. http://www.ann-clinmicrob.com/content/4/1/6

2. N. Rastogi, V. Labrousse and K.S. Goh, In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain in human macrophages, Curr Microbiol 33 (1996) (3), pp. 167–175 http://www.springerlink.com/content/rhkdjf3lngt1tnnd/

3. Synthesis D. E. DeMong, Journal of the American Chemical Society, 2003, 125, 8561-8565. http://pubs.acs.org/cgi-bin/article.cgi/jacsat/2003/125/i28/pdf/ja0351241.pdf

4. Inhaled Large Porous Particles of Capreomycin for Treatment of Tuberculosis in a Guinea Pig Model Garcia-Contreras L, Fiegel J, Telko MJ, Elbert K, Hawi A, Thomas M, VerBerkmoes J, Germishuizen WA, Fourie PB, Hickey AJ, Edwards D.
University of North Carolina, Chapel Hill, NC 27599-7360, USA.
http://aac.asm.org/cgi/content/full/51/8/2830?view=long&pmid=17517845

It07:Capreomycin

2007-10-22T15:06:40Z

Jhl406: added spinning menu

== '''Capreomycin''' ==

Capreomycin is used in the treatment of Tuberculosis (TB) but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. It has a molecular formula of C25H44N14O8.

=== Structure ===

<jmol>
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<inlineContents>water.mol
title1
title2
ATOM 1 N 0 -1.440 5.168 0.918 0.00 0.00 N+0
ATOM 2 C 0 -1.593 3.761 0.527 0.00 0.00 C+0
ATOM 3 C 0 -0.732 2.897 1.412 0.00 0.00 C+0
ATOM 4 N 0 0.622 3.097 1.398 0.00 0.00 N+0
ATOM 5 C 0 1.384 2.207 2.311 0.00 0.00 C+0
ATOM 6 C 0 1.337 0.808 1.753 0.00 0.00 C+0
ATOM 7 N 0 1.591 -0.248 2.577 0.00 0.00 N+0
ATOM 8 C 0 1.492 -1.592 1.962 0.00 0.00 C+0
ATOM 9 C 0 0.033 -1.889 1.714 0.00 0.00 C+0
ATOM 10 O 0 -0.501 -2.861 2.207 0.00 0.00 O+0
ATOM 11 C 0 2.256 -1.612 0.637 0.00 0.00 C+0
ATOM 12 N 0 3.627 -1.146 0.857 0.00 0.00 N+0
ATOM 13 C 0 4.490 -1.079 -0.177 0.00 0.00 C+0
ATOM 14 C 0 5.901 -0.600 0.050 0.00 0.00 C+0
ATOM 15 C 0 6.665 -0.620 -1.276 0.00 0.00 C+0
ATOM 16 N 0 6.067 0.353 -2.200 0.00 0.00 N+0
ATOM 17 C 0 8.129 -0.254 -1.026 0.00 0.00 C+0
ATOM 18 C 0 8.919 -0.394 -2.329 0.00 0.00 C+0
ATOM 19 C 0 10.384 -0.028 -2.079 0.00 0.00 C+0
ATOM 20 N 0 11.142 -0.163 -3.329 0.00 0.00 N+0
ATOM 21 O 0 4.131 -1.404 -1.288 0.00 0.00 O+0
ATOM 22 O 0 1.075 0.623 0.583 0.00 0.00 O+0
ATOM 23 C 0 2.836 2.679 2.399 0.00 0.00 C+0
ATOM 24 O 0 2.881 3.970 3.009 0.00 0.00 O+0
ATOM 25 O 0 -1.227 2.046 2.120 0.00 0.00 O+0
ATOM 26 C 0 -3.058 3.346 0.680 0.00 0.00 C+0
ATOM 27 N 0 -3.330 2.178 -0.167 0.00 0.00 N+0
ATOM 28 C 0 -4.764 1.884 -0.039 0.00 0.00 C+0
ATOM 29 C 0 -5.048 0.497 -0.620 0.00 0.00 C+0
ATOM 30 C 0 -4.640 0.467 -2.095 0.00 0.00 C+0
ATOM 31 N 0 -4.881 -0.872 -2.653 0.00 0.00 N+0
ATOM 32 C 0 -4.946 -1.017 -4.018 0.00 0.00 C+0
ATOM 33 N 0 -4.902 -2.282 -4.555 0.00 0.00 N+0
ATOM 34 N 0 -5.047 -0.005 -4.816 0.00 0.00 N+0
ATOM 35 C 0 -5.083 1.382 -4.365 0.00 0.00 C+0
ATOM 36 C 0 -5.498 1.459 -2.894 0.00 0.00 C+0
ATOM 37 N 0 -4.267 -0.508 0.129 0.00 0.00 N+0
ATOM 38 C 0 -2.915 -0.341 0.118 0.00 0.00 C+0
ATOM 39 C 0 -2.074 -1.277 0.868 0.00 0.00 C+0
ATOM 40 N 0 -0.668 -1.027 0.915 0.00 0.00 N+0
ATOM 41 C 0 -2.611 -2.343 1.497 0.00 0.00 C+0
ATOM 42 N 0 -2.055 -3.592 1.332 0.00 0.00 N+0
ATOM 43 C 0 -2.517 -4.636 2.049 0.00 0.00 C+0
ATOM 44 N 0 -1.972 -5.858 1.888 0.00 0.00 N+0
ATOM 45 O 0 -3.426 -4.475 2.841 0.00 0.00 O+0
ATOM 46 O 0 -2.412 0.574 -0.508 0.00 0.00 O+0
ATOM 47 O 0 -5.134 1.908 1.341 0.00 0.00 O+0
ATOM 48 H 0 -0.464 5.397 0.802 0.00 0.00 H+0
ATOM 49 H 0 -1.948 5.715 0.239 0.00 0.00 H+0
ATOM 50 H 0 -1.287 3.636 -0.511 0.00 0.00 H+0
ATOM 51 H 0 1.048 3.764 0.838 0.00 0.00 H+0
ATOM 52 H 0 0.931 2.223 3.302 0.00 0.00 H+0
ATOM 53 H 0 1.823 -0.127 3.510 0.00 0.00 H+0
ATOM 54 H 0 1.909 -2.338 2.639 0.00 0.00 H+0
ATOM 55 H 0 2.276 -2.628 0.244 0.00 0.00 H+0
ATOM 56 H 0 1.759 -0.956 -0.078 0.00 0.00 H+0
ATOM 57 H 0 3.914 -0.886 1.746 0.00 0.00 H+0
ATOM 58 H 0 5.881 0.416 0.442 0.00 0.00 H+0
ATOM 59 H 0 6.397 -1.257 0.765 0.00 0.00 H+0
ATOM 60 H 0 6.609 -1.617 -1.713 0.00 0.00 H+0
ATOM 61 H 0 6.141 1.257 -1.757 0.00 0.00 H+0
ATOM 62 H 0 6.661 0.381 -3.015 0.00 0.00 H+0
ATOM 63 H 0 8.191 0.775 -0.673 0.00 0.00 H+0
ATOM 64 H 0 8.547 -0.922 -0.273 0.00 0.00 H+0
ATOM 65 H 0 8.857 -1.424 -2.682 0.00 0.00 H+0
ATOM 66 H 0 8.501 0.274 -3.081 0.00 0.00 H+0
ATOM 67 H 0 10.446 1.001 -1.725 0.00 0.00 H+0
ATOM 68 H 0 10.802 -0.696 -1.326 0.00 0.00 H+0
ATOM 69 H 0 10.791 0.542 -3.959 0.00 0.00 H+0
ATOM 70 H 0 12.097 0.087 -3.118 0.00 0.00 H+0
ATOM 71 H 0 3.412 1.973 2.998 0.00 0.00 H+0
ATOM 72 H 0 3.261 2.736 1.397 0.00 0.00 H+0
ATOM 73 H 0 3.812 4.230 3.045 0.00 0.00 H+0
ATOM 74 H 0 -3.257 3.094 1.721 0.00 0.00 H+0
ATOM 75 H 0 -3.702 4.172 0.377 0.00 0.00 H+0
ATOM 76 H 0 -3.178 2.470 -1.121 0.00 0.00 H+0
ATOM 77 H 0 -5.339 2.632 -0.584 0.00 0.00 H+0
ATOM 78 H 0 -6.111 0.276 -0.532 0.00 0.00 H+0
ATOM 79 H 0 -3.585 0.725 -2.192 0.00 0.00 H+0
ATOM 80 H 0 -4.992 -1.639 -2.069 0.00 0.00 H+0
ATOM 81 H 0 -4.827 -3.054 -3.971 0.00 0.00 H+0
ATOM 82 H 0 -4.947 -2.404 -5.516 0.00 0.00 H+0
ATOM 83 H 0 -4.093 1.823 -4.483 0.00 0.00 H+0
ATOM 84 H 0 -5.799 1.938 -4.970 0.00 0.00 H+0
ATOM 85 H 0 -6.551 1.195 -2.796 0.00 0.00 H+0
ATOM 86 H 0 -5.334 2.470 -2.520 0.00 0.00 H+0
ATOM 87 H 0 -4.691 -1.242 0.601 0.00 0.00 H+0
ATOM 88 H 0 -0.246 -0.306 0.422 0.00 0.00 H+0
ATOM 89 H 0 -3.478 -2.217 2.129 0.00 0.00 H+0
ATOM 90 H 0 -1.330 -3.721 0.701 0.00 0.00 H+0
ATOM 91 H 0 -1.247 -5.987 1.257 0.00 0.00 H+0
ATOM 92 H 0 -2.305 -6.609 2.404 0.00 0.00 H+0
ATOM 93 H 0 -4.936 2.796 1.668 0.00 0.00 H+0
CONECT 1 2 48 49 0 NONE 98
CONECT 2 1 3 26 50 NONE 99
CONECT 3 2 4 25 0 NONE 100
CONECT 4 3 5 51 0 NONE 101
CONECT 5 4 6 23 52 NONE 102
CONECT 6 5 7 22 0 NONE 103
CONECT 7 6 8 53 0 NONE 104
CONECT 8 7 9 11 54 NONE 105
CONECT 9 8 40 10 0 NONE 106
CONECT 10 9 0 0 0 NONE 107
CONECT 11 8 12 55 56 NONE 108
CONECT 12 11 13 57 0 NONE 109
CONECT 13 12 14 21 0 NONE 110
CONECT 14 13 15 58 59 NONE 111
CONECT 15 14 16 17 60 NONE 112
CONECT 16 15 61 62 0 NONE 113
CONECT 17 15 18 63 64 NONE 114
CONECT 18 17 19 65 66 NONE 115
CONECT 19 18 20 67 68 NONE 116
CONECT 20 19 69 70 0 NONE 117
CONECT 21 13 0 0 0 NONE 118
CONECT 22 6 0 0 0 NONE 119
CONECT 23 5 24 71 72 NONE 120
CONECT 24 23 73 0 0 NONE 121
CONECT 25 3 0 0 0 NONE 122
CONECT 26 2 27 74 75 NONE 123
CONECT 27 26 28 76 0 NONE 124
CONECT 28 27 29 47 77 NONE 125
CONECT 29 28 30 37 78 NONE 126
CONECT 30 29 36 31 79 NONE 127
CONECT 31 30 32 80 0 NONE 128
CONECT 32 31 33 34 0 NONE 129
CONECT 33 32 81 82 0 NONE 130
CONECT 34 32 35 0 0 NONE 131
CONECT 35 34 36 83 84 NONE 132
CONECT 36 35 30 85 86 NONE 133
CONECT 37 29 38 87 0 NONE 134
CONECT 38 37 39 46 0 NONE 135
CONECT 39 38 40 41 0 NONE 136
CONECT 40 39 9 88 0 NONE 137
CONECT 41 39 42 89 0 NONE 138
CONECT 42 41 43 90 0 NONE 139
CONECT 43 42 44 45 0 NONE 140
CONECT 44 43 91 92 0 NONE 141
CONECT 45 43 0 0 0 NONE 142
CONECT 46 38 0 0 0 NONE 143
CONECT 47 28 93 0 0 NONE 144
END NONE 145
M END</inlineContents>
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<jmolMenu>
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<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Capreomycin.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| Other names
| Capreomycin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>25</sub>H<sub>44</sub>N<sub>14</sub>O<sub>8
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| NC(CC(NCC2NC(C(CO)NC
(C(N)CNC(C(NC(/C(NC2=O)
=C\CC(N)=O)=O)C1N=C(N)
NCC1)=O)=O)=O)=O)CCCN
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 668.71
|-
! {{chembox header}} | Properties
|-
| Storage Temperature
| -20<sup>0</sup>
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C4142 Sigma Aldrich Safety Data
|-
| Main [[Worker safety and health|hazard]]s
| May cause damage to an the unborn child,
May be harmful 
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Overview ==

Capreomycin has the ability to kill a wide variety of bacteria. It does this by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for TB is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Although other medications are used with capreomycin these must be carefully chosen: if used in conjunction with other injectable TB treatments (streptomycin and viomycin) there is an increased risk of hearing and kidney damage in the patient. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

== Adverse Effects ==

The following are some of the side effects that are known to be associated with this medicine.

• Skin irritation and itching (pruritus)

• Allergy to active ingredients (hypersensitivity)

• Rash (allergic reaction)

• Loss of hearing

• Damage to the kidneys

• Alteration in results of liver function tests

• Disruption to the chemical components balance of electrolytes in the blood

== Further Studies ==

Capreomycin is an important drug used for TB which has developed resistance to many drugs. This is a characteristic of TB drugs and is termed multi-drug resistance (MDR). Capreomycin displays a unique bactericidal effect on non-replicating TB bacilli among known anti-TB drugs.

In a 2005 journal by L. Heifets, J. Simon and V. Pham it showed that only capreomycin is active against non-replicating M. tuberculosis bacilli at the same level as metronidazole in an in vitro model of persistence that monitors the curve of decline in bacterial counts. This confirms the conclusion made in a 1996 journal by N. Rastogi, V. Labrousse and K.S. Goh that stated that capreomycin was effective against MDR and intracellular TB bacilli.

== Synthesis ==

The synthesis of tuberculostatic macrocyclic peptide antibiotic capreomycin IB is composed of 27 complex steps and was determined in 2003 and outlined in a journal written by Duane E. DeMong and Robert M. Williams of Colorado State UniVersity. An enolate-aldimine condensation takes place between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal. This produces the cyclic guanidine amino acid (2S,3R)-capreomycidine. Finally there is a Hofmann rearrangement on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic
acid residue.

== Advancements ==

The August 2007 issue of 'Antimicrobial Agents and Chemotherapy' http://aac.asm.org/ reported a new novel way of treating TB. The findings, also reported by Reuters http://www.medscape.com/viewarticle/562095, presents treatment by inhalation of large porous particles of capreomycin following studies using a guinea pig model. Dr. Anthony J. Hickey and his research team at the University of North Carolina introduced this new concept as a way of the drug being adminstered so that it can directly act at the site of origin thereby hopefully reducing the severe side effects.

== References ==

1. L. Heifets, J. Simon and V. Pham, Capreomycin is active against non-replicating M. tuberculosis, Ann Clin Microbiol Antimicrob 4 (2005) (1), p. 6. http://www.ann-clinmicrob.com/content/4/1/6

2. N. Rastogi, V. Labrousse and K.S. Goh, In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain in human macrophages, Curr Microbiol 33 (1996) (3), pp. 167–175 http://www.springerlink.com/content/rhkdjf3lngt1tnnd/

3. Synthesis D. E. DeMong, Journal of the American Chemical Society, 2003, 125, 8561-8565. http://pubs.acs.org/cgi-bin/article.cgi/jacsat/2003/125/i28/pdf/ja0351241.pdf

4. Inhaled Large Porous Particles of Capreomycin for Treatment of Tuberculosis in a Guinea Pig Model Garcia-Contreras L, Fiegel J, Telko MJ, Elbert K, Hawi A, Thomas M, VerBerkmoes J, Germishuizen WA, Fourie PB, Hickey AJ, Edwards D.
University of North Carolina, Chapel Hill, NC 27599-7360, USA.
http://aac.asm.org/cgi/content/full/51/8/2830?view=long&pmid=17517845

It07:Azadirachtin

2007-10-22T14:36:58Z

Jhl406: How it works

== Azadirachtin ==

=== Structure ===

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ATOM 1 C 0 -0.415 6.019 -1.839 0.00 0.00 C+0
ATOM 2 C 0 0.229 4.734 -2.293 0.00 0.00 C+0
ATOM 3 C 0 0.349 3.715 -1.447 0.00 0.00 C+0
ATOM 4 C 0 -0.159 3.845 -0.034 0.00 0.00 C+0
ATOM 5 C 0 0.977 2.462 -1.889 0.00 0.00 C+0
ATOM 6 O 0 1.387 2.357 -3.029 0.00 0.00 O+0
ATOM 7 O 0 1.098 1.429 -1.032 0.00 0.00 O+0
ATOM 8 C 0 1.715 0.199 -1.467 0.00 0.00 C+0
ATOM 9 C 0 3.222 0.270 -1.199 0.00 0.00 C+0
ATOM 10 C 0 3.406 0.496 0.303 0.00 0.00 C+0
ATOM 11 C 0 2.893 -0.685 1.082 0.00 0.00 C+0
ATOM 12 C 0 2.537 -0.280 2.535 0.00 0.00 C+0
ATOM 13 O 0 1.085 -0.249 2.561 0.00 0.00 O+0
ATOM 14 C 0 0.707 -1.383 1.759 0.00 0.00 C+0
ATOM 15 C 0 1.631 -1.350 0.562 0.00 0.00 C+0
ATOM 16 C 0 1.123 -1.036 -0.789 0.00 0.00 C+0
ATOM 17 C 0 1.530 -2.235 -1.720 0.00 0.00 C+0
ATOM 18 O 0 0.437 -3.158 -1.560 0.00 0.00 O+0
ATOM 19 C 0 -0.757 -2.339 -1.642 0.00 0.00 C+0
ATOM 20 C 0 -0.408 -1.020 -0.954 0.00 0.00 C+0
ATOM 21 C 0 -1.181 -0.668 0.283 0.00 0.00 C+0
ATOM 22 C 0 -0.762 -1.503 1.489 0.00 0.00 C+0
ATOM 23 O 0 -1.114 -2.873 1.319 0.00 0.00 O+0
ATOM 24 C 0 -0.965 0.818 0.643 0.00 0.00 C+0
ATOM 25 C 0 -2.688 -0.808 0.062 0.00 0.00 C+0
ATOM 26 C 0 -3.420 0.335 -0.683 0.00 0.00 C+0
ATOM 27 C 0 -4.914 0.008 -0.432 0.00 0.00 C+0
ATOM 28 C 0 -4.907 -0.407 1.077 0.00 0.00 C+0
ATOM 29 C 0 -3.641 -1.295 1.169 0.00 0.00 C+0
ATOM 30 O 0 -3.285 -2.108 0.017 0.00 0.00 O+0
ATOM 31 C 0 -3.133 -1.665 2.564 0.00 0.00 C+0
ATOM 32 C 0 -4.574 0.908 1.789 0.00 0.00 C+0
ATOM 33 C 0 -4.371 0.829 3.277 0.00 0.00 C+0
ATOM 34 C 0 -3.294 1.573 3.533 0.00 0.00 C+0
ATOM 35 O 0 -2.752 2.121 2.393 0.00 0.00 O+0
ATOM 36 C 0 -3.106 1.218 1.360 0.00 0.00 C+0
ATOM 37 O 0 -3.088 1.564 0.007 0.00 0.00 O+0
ATOM 38 O 0 -5.486 1.948 1.431 0.00 0.00 O+0
ATOM 39 C 0 -1.074 -2.085 -3.100 0.00 0.00 C+0
ATOM 40 O 0 -0.407 -2.604 -3.963 0.00 0.00 O+0
ATOM 41 O 0 -2.098 -1.283 -3.434 0.00 0.00 O+0
ATOM 42 C 0 -2.472 -1.126 -4.828 0.00 0.00 C+0
ATOM 43 O 0 -1.827 -3.065 -1.054 0.00 0.00 O+0
ATOM 44 C 0 3.984 -1.724 1.149 0.00 0.00 C+0
ATOM 45 O 0 3.794 -2.829 0.699 0.00 0.00 O+0
ATOM 46 O 0 5.165 -1.421 1.710 0.00 0.00 O+0
ATOM 47 C 0 6.216 -2.422 1.775 0.00 0.00 C+0
ATOM 48 O 0 4.819 0.678 0.587 0.00 0.00 O+0
ATOM 49 C 0 5.356 1.908 0.560 0.00 0.00 C+0
ATOM 50 O 0 4.664 2.864 0.299 0.00 0.00 O+0
ATOM 51 C 0 6.822 2.097 0.855 0.00 0.00 C+0
ATOM 52 H 0 -0.423 6.732 -2.663 0.00 0.00 H+0
ATOM 53 H 0 -1.438 5.820 -1.521 0.00 0.00 H+0
ATOM 54 H 0 0.151 6.434 -1.005 0.00 0.00 H+0
ATOM 55 H 0 0.594 4.641 -3.306 0.00 0.00 H+0
ATOM 56 H 0 -0.589 4.836 0.108 0.00 0.00 H+0
ATOM 57 H 0 -0.923 3.089 0.149 0.00 0.00 H+0
ATOM 58 H 0 0.666 3.703 0.664 0.00 0.00 H+0
ATOM 59 H 0 1.568 0.100 -2.552 0.00 0.00 H+0
ATOM 60 H 0 3.701 -0.658 -1.507 0.00 0.00 H+0
ATOM 61 H 0 3.653 1.107 -1.753 0.00 0.00 H+0
ATOM 62 H 0 2.864 1.390 0.605 0.00 0.00 H+0
ATOM 63 H 0 2.907 -1.026 3.235 0.00 0.00 H+0
ATOM 64 H 0 2.941 0.703 2.768 0.00 0.00 H+0
ATOM 65 H 0 0.991 -2.265 2.340 0.00 0.00 H+0
ATOM 66 H 0 1.941 -2.394 0.482 0.00 0.00 H+0
ATOM 67 H 0 1.631 -1.901 -2.750 0.00 0.00 H+0
ATOM 68 H 0 2.467 -2.676 -1.376 0.00 0.00 H+0
ATOM 69 H 0 -0.627 -0.221 -1.697 0.00 0.00 H+0
ATOM 70 H 0 -1.302 -1.121 2.371 0.00 0.00 H+0
ATOM 71 H 0 -0.821 -3.337 2.115 0.00 0.00 H+0
ATOM 72 H 0 -1.507 1.446 -0.064 0.00 0.00 H+0
ATOM 73 H 0 -1.333 1.005 1.652 0.00 0.00 H+0
ATOM 74 H 0 0.099 1.052 0.596 0.00 0.00 H+0
ATOM 75 H 0 -3.174 0.367 -1.745 0.00 0.00 H+0
ATOM 76 H 0 -5.537 0.888 -0.590 0.00 0.00 H+0
ATOM 77 H 0 -5.243 -0.818 -1.062 0.00 0.00 H+0
ATOM 78 H 0 -5.822 -0.893 1.418 0.00 0.00 H+0
ATOM 79 H 0 -3.972 -1.977 3.185 0.00 0.00 H+0
ATOM 80 H 0 -2.416 -2.482 2.485 0.00 0.00 H+0
ATOM 81 H 0 -2.649 -0.799 3.016 0.00 0.00 H+0
ATOM 82 H 0 -4.972 0.284 3.990 0.00 0.00 H+0
ATOM 83 H 0 -2.892 1.728 4.524 0.00 0.00 H+0
ATOM 84 H 0 -2.519 0.307 1.483 0.00 0.00 H+0
ATOM 85 H 0 -5.165 2.758 1.853 0.00 0.00 H+0
ATOM 86 H 0 -2.835 -2.078 -5.216 0.00 0.00 H+0
ATOM 87 H 0 -3.259 -0.377 -4.911 0.00 0.00 H+0
ATOM 88 H 0 -1.603 -0.807 -5.404 0.00 0.00 H+0
ATOM 89 H 0 -1.886 -3.908 -1.525 0.00 0.00 H+0
ATOM 90 H 0 7.094 -1.996 2.260 0.00 0.00 H+0
ATOM 91 H 0 5.865 -3.280 2.347 0.00 0.00 H+0
ATOM 92 H 0 6.477 -2.741 0.766 0.00 0.00 H+0
ATOM 93 H 0 7.391 2.026 -0.072 0.00 0.00 H+0
ATOM 94 H 0 6.979 3.078 1.303 0.00 0.00 H+0
ATOM 95 H 0 7.156 1.323 1.546 0.00 0.00 H+0
CONECT 1 2 52 53 54 NONE 100
CONECT 2 1 3 55 0 NONE 101
CONECT 3 2 4 5 0 NONE 102
CONECT 4 3 56 57 58 NONE 103
CONECT 5 3 6 7 0 NONE 104
CONECT 6 5 0 0 0 NONE 105
CONECT 7 5 8 0 0 NONE 106
CONECT 8 7 16 9 59 NONE 107
CONECT 9 8 10 60 61 NONE 108
CONECT 10 9 11 48 62 NONE 109
CONECT 11 10 15 12 44 NONE 110
CONECT 12 11 13 63 64 NONE 111
CONECT 13 12 14 0 0 NONE 112
CONECT 14 13 22 15 65 NONE 113
CONECT 15 14 11 16 66 NONE 114
CONECT 16 15 8 20 17 NONE 115
CONECT 17 16 18 67 68 NONE 116
CONECT 18 17 19 0 0 NONE 117
CONECT 19 18 20 39 43 NONE 118
CONECT 20 19 16 21 69 NONE 119
CONECT 21 20 22 24 25 NONE 120
CONECT 22 21 14 23 70 NONE 121
CONECT 23 22 71 0 0 NONE 122
CONECT 24 21 72 73 74 NONE 123
CONECT 25 21 29 30 26 NONE 124
CONECT 26 25 37 27 75 NONE 125
CONECT 27 26 28 76 77 NONE 126
CONECT 28 27 29 32 78 NONE 127
CONECT 29 28 25 30 31 NONE 128
CONECT 30 29 25 0 0 NONE 129
CONECT 31 29 79 80 81 NONE 130
CONECT 32 28 36 33 38 NONE 131
CONECT 33 32 34 82 0 NONE 132
CONECT 34 33 35 83 0 NONE 133
CONECT 35 34 36 0 0 NONE 134
CONECT 36 35 32 37 84 NONE 135
CONECT 37 36 26 0 0 NONE 136
CONECT 38 32 85 0 0 NONE 137
CONECT 39 19 40 41 0 NONE 138
CONECT 40 39 0 0 0 NONE 139
CONECT 41 39 42 0 0 NONE 140
CONECT 42 41 86 87 88 NONE 141
CONECT 43 19 89 0 0 NONE 142
CONECT 44 11 45 46 0 NONE 143
CONECT 45 44 0 0 0 NONE 144
CONECT 46 44 47 0 0 NONE 145
CONECT 47 46 90 91 92 NONE 146
CONECT 48 10 49 0 0 NONE 147
CONECT 49 48 50 51 0 NONE 148
CONECT 50 49 0 0 0 NONE 149
CONECT 51 49 93 94 95 NONE 150
END NONE 151
70
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== Overview ==

Azadirachtin is a compound extracted from the from the neem tree (Azadirachta indica). Tests have indicated that neem extract based insecticides are extremely effective. The structure is highly complex and thus the synthesis itself has taken well over 20 years. Azadirachtin has 16 stereogenic centers, -seven of which are tetrasubstituted. It has a molecular formula of C35H44O16. It is a yellow-green powder, with a strong garlic-sulfur odor.

Azadirachtin works as an "ecdysone blocker". Ecdysone are important hormones which control the process of metamorphosis as the insects pass from larva to pupa to adult. By blocking these hormones the insect will die.

=== Sources/Synthesis ===

=== Uses/Related products ===

It07:Azadirachtin

2007-10-22T14:30:07Z

Jhl406:

== Azadirachtin ==

=== Structure ===

<jmol>
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title1
title2
ATOM 1 C 0 -0.415 6.019 -1.839 0.00 0.00 C+0
ATOM 2 C 0 0.229 4.734 -2.293 0.00 0.00 C+0
ATOM 3 C 0 0.349 3.715 -1.447 0.00 0.00 C+0
ATOM 4 C 0 -0.159 3.845 -0.034 0.00 0.00 C+0
ATOM 5 C 0 0.977 2.462 -1.889 0.00 0.00 C+0
ATOM 6 O 0 1.387 2.357 -3.029 0.00 0.00 O+0
ATOM 7 O 0 1.098 1.429 -1.032 0.00 0.00 O+0
ATOM 8 C 0 1.715 0.199 -1.467 0.00 0.00 C+0
ATOM 9 C 0 3.222 0.270 -1.199 0.00 0.00 C+0
ATOM 10 C 0 3.406 0.496 0.303 0.00 0.00 C+0
ATOM 11 C 0 2.893 -0.685 1.082 0.00 0.00 C+0
ATOM 12 C 0 2.537 -0.280 2.535 0.00 0.00 C+0
ATOM 13 O 0 1.085 -0.249 2.561 0.00 0.00 O+0
ATOM 14 C 0 0.707 -1.383 1.759 0.00 0.00 C+0
ATOM 15 C 0 1.631 -1.350 0.562 0.00 0.00 C+0
ATOM 16 C 0 1.123 -1.036 -0.789 0.00 0.00 C+0
ATOM 17 C 0 1.530 -2.235 -1.720 0.00 0.00 C+0
ATOM 18 O 0 0.437 -3.158 -1.560 0.00 0.00 O+0
ATOM 19 C 0 -0.757 -2.339 -1.642 0.00 0.00 C+0
ATOM 20 C 0 -0.408 -1.020 -0.954 0.00 0.00 C+0
ATOM 21 C 0 -1.181 -0.668 0.283 0.00 0.00 C+0
ATOM 22 C 0 -0.762 -1.503 1.489 0.00 0.00 C+0
ATOM 23 O 0 -1.114 -2.873 1.319 0.00 0.00 O+0
ATOM 24 C 0 -0.965 0.818 0.643 0.00 0.00 C+0
ATOM 25 C 0 -2.688 -0.808 0.062 0.00 0.00 C+0
ATOM 26 C 0 -3.420 0.335 -0.683 0.00 0.00 C+0
ATOM 27 C 0 -4.914 0.008 -0.432 0.00 0.00 C+0
ATOM 28 C 0 -4.907 -0.407 1.077 0.00 0.00 C+0
ATOM 29 C 0 -3.641 -1.295 1.169 0.00 0.00 C+0
ATOM 30 O 0 -3.285 -2.108 0.017 0.00 0.00 O+0
ATOM 31 C 0 -3.133 -1.665 2.564 0.00 0.00 C+0
ATOM 32 C 0 -4.574 0.908 1.789 0.00 0.00 C+0
ATOM 33 C 0 -4.371 0.829 3.277 0.00 0.00 C+0
ATOM 34 C 0 -3.294 1.573 3.533 0.00 0.00 C+0
ATOM 35 O 0 -2.752 2.121 2.393 0.00 0.00 O+0
ATOM 36 C 0 -3.106 1.218 1.360 0.00 0.00 C+0
ATOM 37 O 0 -3.088 1.564 0.007 0.00 0.00 O+0
ATOM 38 O 0 -5.486 1.948 1.431 0.00 0.00 O+0
ATOM 39 C 0 -1.074 -2.085 -3.100 0.00 0.00 C+0
ATOM 40 O 0 -0.407 -2.604 -3.963 0.00 0.00 O+0
ATOM 41 O 0 -2.098 -1.283 -3.434 0.00 0.00 O+0
ATOM 42 C 0 -2.472 -1.126 -4.828 0.00 0.00 C+0
ATOM 43 O 0 -1.827 -3.065 -1.054 0.00 0.00 O+0
ATOM 44 C 0 3.984 -1.724 1.149 0.00 0.00 C+0
ATOM 45 O 0 3.794 -2.829 0.699 0.00 0.00 O+0
ATOM 46 O 0 5.165 -1.421 1.710 0.00 0.00 O+0
ATOM 47 C 0 6.216 -2.422 1.775 0.00 0.00 C+0
ATOM 48 O 0 4.819 0.678 0.587 0.00 0.00 O+0
ATOM 49 C 0 5.356 1.908 0.560 0.00 0.00 C+0
ATOM 50 O 0 4.664 2.864 0.299 0.00 0.00 O+0
ATOM 51 C 0 6.822 2.097 0.855 0.00 0.00 C+0
ATOM 52 H 0 -0.423 6.732 -2.663 0.00 0.00 H+0
ATOM 53 H 0 -1.438 5.820 -1.521 0.00 0.00 H+0
ATOM 54 H 0 0.151 6.434 -1.005 0.00 0.00 H+0
ATOM 55 H 0 0.594 4.641 -3.306 0.00 0.00 H+0
ATOM 56 H 0 -0.589 4.836 0.108 0.00 0.00 H+0
ATOM 57 H 0 -0.923 3.089 0.149 0.00 0.00 H+0
ATOM 58 H 0 0.666 3.703 0.664 0.00 0.00 H+0
ATOM 59 H 0 1.568 0.100 -2.552 0.00 0.00 H+0
ATOM 60 H 0 3.701 -0.658 -1.507 0.00 0.00 H+0
ATOM 61 H 0 3.653 1.107 -1.753 0.00 0.00 H+0
ATOM 62 H 0 2.864 1.390 0.605 0.00 0.00 H+0
ATOM 63 H 0 2.907 -1.026 3.235 0.00 0.00 H+0
ATOM 64 H 0 2.941 0.703 2.768 0.00 0.00 H+0
ATOM 65 H 0 0.991 -2.265 2.340 0.00 0.00 H+0
ATOM 66 H 0 1.941 -2.394 0.482 0.00 0.00 H+0
ATOM 67 H 0 1.631 -1.901 -2.750 0.00 0.00 H+0
ATOM 68 H 0 2.467 -2.676 -1.376 0.00 0.00 H+0
ATOM 69 H 0 -0.627 -0.221 -1.697 0.00 0.00 H+0
ATOM 70 H 0 -1.302 -1.121 2.371 0.00 0.00 H+0
ATOM 71 H 0 -0.821 -3.337 2.115 0.00 0.00 H+0
ATOM 72 H 0 -1.507 1.446 -0.064 0.00 0.00 H+0
ATOM 73 H 0 -1.333 1.005 1.652 0.00 0.00 H+0
ATOM 74 H 0 0.099 1.052 0.596 0.00 0.00 H+0
ATOM 75 H 0 -3.174 0.367 -1.745 0.00 0.00 H+0
ATOM 76 H 0 -5.537 0.888 -0.590 0.00 0.00 H+0
ATOM 77 H 0 -5.243 -0.818 -1.062 0.00 0.00 H+0
ATOM 78 H 0 -5.822 -0.893 1.418 0.00 0.00 H+0
ATOM 79 H 0 -3.972 -1.977 3.185 0.00 0.00 H+0
ATOM 80 H 0 -2.416 -2.482 2.485 0.00 0.00 H+0
ATOM 81 H 0 -2.649 -0.799 3.016 0.00 0.00 H+0
ATOM 82 H 0 -4.972 0.284 3.990 0.00 0.00 H+0
ATOM 83 H 0 -2.892 1.728 4.524 0.00 0.00 H+0
ATOM 84 H 0 -2.519 0.307 1.483 0.00 0.00 H+0
ATOM 85 H 0 -5.165 2.758 1.853 0.00 0.00 H+0
ATOM 86 H 0 -2.835 -2.078 -5.216 0.00 0.00 H+0
ATOM 87 H 0 -3.259 -0.377 -4.911 0.00 0.00 H+0
ATOM 88 H 0 -1.603 -0.807 -5.404 0.00 0.00 H+0
ATOM 89 H 0 -1.886 -3.908 -1.525 0.00 0.00 H+0
ATOM 90 H 0 7.094 -1.996 2.260 0.00 0.00 H+0
ATOM 91 H 0 5.865 -3.280 2.347 0.00 0.00 H+0
ATOM 92 H 0 6.477 -2.741 0.766 0.00 0.00 H+0
ATOM 93 H 0 7.391 2.026 -0.072 0.00 0.00 H+0
ATOM 94 H 0 6.979 3.078 1.303 0.00 0.00 H+0
ATOM 95 H 0 7.156 1.323 1.546 0.00 0.00 H+0
CONECT 1 2 52 53 54 NONE 100
CONECT 2 1 3 55 0 NONE 101
CONECT 3 2 4 5 0 NONE 102
CONECT 4 3 56 57 58 NONE 103
CONECT 5 3 6 7 0 NONE 104
CONECT 6 5 0 0 0 NONE 105
CONECT 7 5 8 0 0 NONE 106
CONECT 8 7 16 9 59 NONE 107
CONECT 9 8 10 60 61 NONE 108
CONECT 10 9 11 48 62 NONE 109
CONECT 11 10 15 12 44 NONE 110
CONECT 12 11 13 63 64 NONE 111
CONECT 13 12 14 0 0 NONE 112
CONECT 14 13 22 15 65 NONE 113
CONECT 15 14 11 16 66 NONE 114
CONECT 16 15 8 20 17 NONE 115
CONECT 17 16 18 67 68 NONE 116
CONECT 18 17 19 0 0 NONE 117
CONECT 19 18 20 39 43 NONE 118
CONECT 20 19 16 21 69 NONE 119
CONECT 21 20 22 24 25 NONE 120
CONECT 22 21 14 23 70 NONE 121
CONECT 23 22 71 0 0 NONE 122
CONECT 24 21 72 73 74 NONE 123
CONECT 25 21 29 30 26 NONE 124
CONECT 26 25 37 27 75 NONE 125
CONECT 27 26 28 76 77 NONE 126
CONECT 28 27 29 32 78 NONE 127
CONECT 29 28 25 30 31 NONE 128
CONECT 30 29 25 0 0 NONE 129
CONECT 31 29 79 80 81 NONE 130
CONECT 32 28 36 33 38 NONE 131
CONECT 33 32 34 82 0 NONE 132
CONECT 34 33 35 83 0 NONE 133
CONECT 35 34 36 0 0 NONE 134
CONECT 36 35 32 37 84 NONE 135
CONECT 37 36 26 0 0 NONE 136
CONECT 38 32 85 0 0 NONE 137
CONECT 39 19 40 41 0 NONE 138
CONECT 40 39 0 0 0 NONE 139
CONECT 41 39 42 0 0 NONE 140
CONECT 42 41 86 87 88 NONE 141
CONECT 43 19 89 0 0 NONE 142
CONECT 44 11 45 46 0 NONE 143
CONECT 45 44 0 0 0 NONE 144
CONECT 46 44 47 0 0 NONE 145
CONECT 47 46 90 91 92 NONE 146
CONECT 48 10 49 0 0 NONE 147
CONECT 49 48 50 51 0 NONE 148
CONECT 50 49 0 0 0 NONE 149
CONECT 51 49 93 94 95 NONE 150
END NONE 151
70
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== Overview ==

Azadirachtin is a compound extracted from the from the neem tree (Azadirachta indica). Tests have indicated that neem extract based insecticides are extremely effective. The structure is highly complex and thus the synthesis itself has taken well over 20 years. Azadirachtin has 16 stereogenic centers, -seven of which are tetrasubstituted. It has a molecular formula of C35H44O16

=== Sources/Synthesis ===

=== Uses/Related products ===

It07:Capreomycin

2007-10-22T14:29:22Z

Jhl406: Changed layout

== '''Capreomycin''' ==

Capreomycin is used in the treatment of Tuberculosis (TB) but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. It has a molecular formula of C25H44N14O8.

=== Structure ===

<jmol>
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<size>200</size>
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<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
ATOM 1 N 0 -1.440 5.168 0.918 0.00 0.00 N+0
ATOM 2 C 0 -1.593 3.761 0.527 0.00 0.00 C+0
ATOM 3 C 0 -0.732 2.897 1.412 0.00 0.00 C+0
ATOM 4 N 0 0.622 3.097 1.398 0.00 0.00 N+0
ATOM 5 C 0 1.384 2.207 2.311 0.00 0.00 C+0
ATOM 6 C 0 1.337 0.808 1.753 0.00 0.00 C+0
ATOM 7 N 0 1.591 -0.248 2.577 0.00 0.00 N+0
ATOM 8 C 0 1.492 -1.592 1.962 0.00 0.00 C+0
ATOM 9 C 0 0.033 -1.889 1.714 0.00 0.00 C+0
ATOM 10 O 0 -0.501 -2.861 2.207 0.00 0.00 O+0
ATOM 11 C 0 2.256 -1.612 0.637 0.00 0.00 C+0
ATOM 12 N 0 3.627 -1.146 0.857 0.00 0.00 N+0
ATOM 13 C 0 4.490 -1.079 -0.177 0.00 0.00 C+0
ATOM 14 C 0 5.901 -0.600 0.050 0.00 0.00 C+0
ATOM 15 C 0 6.665 -0.620 -1.276 0.00 0.00 C+0
ATOM 16 N 0 6.067 0.353 -2.200 0.00 0.00 N+0
ATOM 17 C 0 8.129 -0.254 -1.026 0.00 0.00 C+0
ATOM 18 C 0 8.919 -0.394 -2.329 0.00 0.00 C+0
ATOM 19 C 0 10.384 -0.028 -2.079 0.00 0.00 C+0
ATOM 20 N 0 11.142 -0.163 -3.329 0.00 0.00 N+0
ATOM 21 O 0 4.131 -1.404 -1.288 0.00 0.00 O+0
ATOM 22 O 0 1.075 0.623 0.583 0.00 0.00 O+0
ATOM 23 C 0 2.836 2.679 2.399 0.00 0.00 C+0
ATOM 24 O 0 2.881 3.970 3.009 0.00 0.00 O+0
ATOM 25 O 0 -1.227 2.046 2.120 0.00 0.00 O+0
ATOM 26 C 0 -3.058 3.346 0.680 0.00 0.00 C+0
ATOM 27 N 0 -3.330 2.178 -0.167 0.00 0.00 N+0
ATOM 28 C 0 -4.764 1.884 -0.039 0.00 0.00 C+0
ATOM 29 C 0 -5.048 0.497 -0.620 0.00 0.00 C+0
ATOM 30 C 0 -4.640 0.467 -2.095 0.00 0.00 C+0
ATOM 31 N 0 -4.881 -0.872 -2.653 0.00 0.00 N+0
ATOM 32 C 0 -4.946 -1.017 -4.018 0.00 0.00 C+0
ATOM 33 N 0 -4.902 -2.282 -4.555 0.00 0.00 N+0
ATOM 34 N 0 -5.047 -0.005 -4.816 0.00 0.00 N+0
ATOM 35 C 0 -5.083 1.382 -4.365 0.00 0.00 C+0
ATOM 36 C 0 -5.498 1.459 -2.894 0.00 0.00 C+0
ATOM 37 N 0 -4.267 -0.508 0.129 0.00 0.00 N+0
ATOM 38 C 0 -2.915 -0.341 0.118 0.00 0.00 C+0
ATOM 39 C 0 -2.074 -1.277 0.868 0.00 0.00 C+0
ATOM 40 N 0 -0.668 -1.027 0.915 0.00 0.00 N+0
ATOM 41 C 0 -2.611 -2.343 1.497 0.00 0.00 C+0
ATOM 42 N 0 -2.055 -3.592 1.332 0.00 0.00 N+0
ATOM 43 C 0 -2.517 -4.636 2.049 0.00 0.00 C+0
ATOM 44 N 0 -1.972 -5.858 1.888 0.00 0.00 N+0
ATOM 45 O 0 -3.426 -4.475 2.841 0.00 0.00 O+0
ATOM 46 O 0 -2.412 0.574 -0.508 0.00 0.00 O+0
ATOM 47 O 0 -5.134 1.908 1.341 0.00 0.00 O+0
ATOM 48 H 0 -0.464 5.397 0.802 0.00 0.00 H+0
ATOM 49 H 0 -1.948 5.715 0.239 0.00 0.00 H+0
ATOM 50 H 0 -1.287 3.636 -0.511 0.00 0.00 H+0
ATOM 51 H 0 1.048 3.764 0.838 0.00 0.00 H+0
ATOM 52 H 0 0.931 2.223 3.302 0.00 0.00 H+0
ATOM 53 H 0 1.823 -0.127 3.510 0.00 0.00 H+0
ATOM 54 H 0 1.909 -2.338 2.639 0.00 0.00 H+0
ATOM 55 H 0 2.276 -2.628 0.244 0.00 0.00 H+0
ATOM 56 H 0 1.759 -0.956 -0.078 0.00 0.00 H+0
ATOM 57 H 0 3.914 -0.886 1.746 0.00 0.00 H+0
ATOM 58 H 0 5.881 0.416 0.442 0.00 0.00 H+0
ATOM 59 H 0 6.397 -1.257 0.765 0.00 0.00 H+0
ATOM 60 H 0 6.609 -1.617 -1.713 0.00 0.00 H+0
ATOM 61 H 0 6.141 1.257 -1.757 0.00 0.00 H+0
ATOM 62 H 0 6.661 0.381 -3.015 0.00 0.00 H+0
ATOM 63 H 0 8.191 0.775 -0.673 0.00 0.00 H+0
ATOM 64 H 0 8.547 -0.922 -0.273 0.00 0.00 H+0
ATOM 65 H 0 8.857 -1.424 -2.682 0.00 0.00 H+0
ATOM 66 H 0 8.501 0.274 -3.081 0.00 0.00 H+0
ATOM 67 H 0 10.446 1.001 -1.725 0.00 0.00 H+0
ATOM 68 H 0 10.802 -0.696 -1.326 0.00 0.00 H+0
ATOM 69 H 0 10.791 0.542 -3.959 0.00 0.00 H+0
ATOM 70 H 0 12.097 0.087 -3.118 0.00 0.00 H+0
ATOM 71 H 0 3.412 1.973 2.998 0.00 0.00 H+0
ATOM 72 H 0 3.261 2.736 1.397 0.00 0.00 H+0
ATOM 73 H 0 3.812 4.230 3.045 0.00 0.00 H+0
ATOM 74 H 0 -3.257 3.094 1.721 0.00 0.00 H+0
ATOM 75 H 0 -3.702 4.172 0.377 0.00 0.00 H+0
ATOM 76 H 0 -3.178 2.470 -1.121 0.00 0.00 H+0
ATOM 77 H 0 -5.339 2.632 -0.584 0.00 0.00 H+0
ATOM 78 H 0 -6.111 0.276 -0.532 0.00 0.00 H+0
ATOM 79 H 0 -3.585 0.725 -2.192 0.00 0.00 H+0
ATOM 80 H 0 -4.992 -1.639 -2.069 0.00 0.00 H+0
ATOM 81 H 0 -4.827 -3.054 -3.971 0.00 0.00 H+0
ATOM 82 H 0 -4.947 -2.404 -5.516 0.00 0.00 H+0
ATOM 83 H 0 -4.093 1.823 -4.483 0.00 0.00 H+0
ATOM 84 H 0 -5.799 1.938 -4.970 0.00 0.00 H+0
ATOM 85 H 0 -6.551 1.195 -2.796 0.00 0.00 H+0
ATOM 86 H 0 -5.334 2.470 -2.520 0.00 0.00 H+0
ATOM 87 H 0 -4.691 -1.242 0.601 0.00 0.00 H+0
ATOM 88 H 0 -0.246 -0.306 0.422 0.00 0.00 H+0
ATOM 89 H 0 -3.478 -2.217 2.129 0.00 0.00 H+0
ATOM 90 H 0 -1.330 -3.721 0.701 0.00 0.00 H+0
ATOM 91 H 0 -1.247 -5.987 1.257 0.00 0.00 H+0
ATOM 92 H 0 -2.305 -6.609 2.404 0.00 0.00 H+0
ATOM 93 H 0 -4.936 2.796 1.668 0.00 0.00 H+0
CONECT 1 2 48 49 0 NONE 98
CONECT 2 1 3 26 50 NONE 99
CONECT 3 2 4 25 0 NONE 100
CONECT 4 3 5 51 0 NONE 101
CONECT 5 4 6 23 52 NONE 102
CONECT 6 5 7 22 0 NONE 103
CONECT 7 6 8 53 0 NONE 104
CONECT 8 7 9 11 54 NONE 105
CONECT 9 8 40 10 0 NONE 106
CONECT 10 9 0 0 0 NONE 107
CONECT 11 8 12 55 56 NONE 108
CONECT 12 11 13 57 0 NONE 109
CONECT 13 12 14 21 0 NONE 110
CONECT 14 13 15 58 59 NONE 111
CONECT 15 14 16 17 60 NONE 112
CONECT 16 15 61 62 0 NONE 113
CONECT 17 15 18 63 64 NONE 114
CONECT 18 17 19 65 66 NONE 115
CONECT 19 18 20 67 68 NONE 116
CONECT 20 19 69 70 0 NONE 117
CONECT 21 13 0 0 0 NONE 118
CONECT 22 6 0 0 0 NONE 119
CONECT 23 5 24 71 72 NONE 120
CONECT 24 23 73 0 0 NONE 121
CONECT 25 3 0 0 0 NONE 122
CONECT 26 2 27 74 75 NONE 123
CONECT 27 26 28 76 0 NONE 124
CONECT 28 27 29 47 77 NONE 125
CONECT 29 28 30 37 78 NONE 126
CONECT 30 29 36 31 79 NONE 127
CONECT 31 30 32 80 0 NONE 128
CONECT 32 31 33 34 0 NONE 129
CONECT 33 32 81 82 0 NONE 130
CONECT 34 32 35 0 0 NONE 131
CONECT 35 34 36 83 84 NONE 132
CONECT 36 35 30 85 86 NONE 133
CONECT 37 29 38 87 0 NONE 134
CONECT 38 37 39 46 0 NONE 135
CONECT 39 38 40 41 0 NONE 136
CONECT 40 39 9 88 0 NONE 137
CONECT 41 39 42 89 0 NONE 138
CONECT 42 41 43 90 0 NONE 139
CONECT 43 42 44 45 0 NONE 140
CONECT 44 43 91 92 0 NONE 141
CONECT 45 43 0 0 0 NONE 142
CONECT 46 38 0 0 0 NONE 143
CONECT 47 28 93 0 0 NONE 144
END NONE 145
M END</inlineContents>
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<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Capreomycin.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| Other names
| Capreomycin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>25</sub>H<sub>44</sub>N<sub>14</sub>O<sub>8
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| NC(CC(NCC2NC(C(CO)NC
(C(N)CNC(C(NC(/C(NC2=O)
=C\CC(N)=O)=O)C1N=C(N)
NCC1)=O)=O)=O)=O)CCCN
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 668.71
|-
! {{chembox header}} | Properties
|-
| Storage Temperature
| -20<sup>0</sup>
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C4142 Sigma Aldrich Safety Data
|-
| Main [[Worker safety and health|hazard]]s
| May cause damage to an the unborn child,
May be harmful 
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

== Overview ==

Capreomycin has the ability to kill a wide variety of bacteria. It does this by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for TB is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Although other medications are used with capreomycin these must be carefully chosen: if used in conjunction with other injectable TB treatments (streptomycin and viomycin) there is an increased risk of hearing and kidney damage in the patient. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

== Adverse Effects ==

The following are some of the side effects that are known to be associated with this medicine.

• Skin irritation and itching (pruritus)

• Allergy to active ingredients (hypersensitivity)

• Rash (allergic reaction)

• Loss of hearing

• Damage to the kidneys

• Alteration in results of liver function tests

• Disruption to the chemical components balance of electrolytes in the blood

== Further Studies ==

Capreomycin is an important drug used for TB which has developed resistance to many drugs. This is a characteristic of TB drugs and is termed multi-drug resistance (MDR). Capreomycin displays a unique bactericidal effect on non-replicating TB bacilli among known anti-TB drugs.

In a 2005 journal by L. Heifets, J. Simon and V. Pham it showed that only capreomycin is active against non-replicating M. tuberculosis bacilli at the same level as metronidazole in an in vitro model of persistence that monitors the curve of decline in bacterial counts. This confirms the conclusion made in a 1996 journal by N. Rastogi, V. Labrousse and K.S. Goh that stated that capreomycin was effective against MDR and intracellular TB bacilli.

== Synthesis ==

The synthesis of tuberculostatic macrocyclic peptide antibiotic capreomycin IB is composed of 27 complex steps and was determined in 2003 and outlined in a journal written by Duane E. DeMong and Robert M. Williams of Colorado State UniVersity. An enolate-aldimine condensation takes place between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal. This produces the cyclic guanidine amino acid (2S,3R)-capreomycidine. Finally there is a Hofmann rearrangement on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic
acid residue.

== Advancements ==

The August 2007 issue of 'Antimicrobial Agents and Chemotherapy' http://aac.asm.org/ reported a new novel way of treating TB. The findings, also reported by Reuters http://www.medscape.com/viewarticle/562095, presents treatment by inhalation of large porous particles of capreomycin following studies using a guinea pig model. Dr. Anthony J. Hickey and his research team at the University of North Carolina introduced this new concept as a way of the drug being adminstered so that it can directly act at the site of origin thereby hopefully reducing the severe side effects.

== References ==

1. L. Heifets, J. Simon and V. Pham, Capreomycin is active against non-replicating M. tuberculosis, Ann Clin Microbiol Antimicrob 4 (2005) (1), p. 6. http://www.ann-clinmicrob.com/content/4/1/6

2. N. Rastogi, V. Labrousse and K.S. Goh, In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain in human macrophages, Curr Microbiol 33 (1996) (3), pp. 167–175 http://www.springerlink.com/content/rhkdjf3lngt1tnnd/

3. Synthesis D. E. DeMong, Journal of the American Chemical Society, 2003, 125, 8561-8565. http://pubs.acs.org/cgi-bin/article.cgi/jacsat/2003/125/i28/pdf/ja0351241.pdf

4. Inhaled Large Porous Particles of Capreomycin for Treatment of Tuberculosis in a Guinea Pig Model Garcia-Contreras L, Fiegel J, Telko MJ, Elbert K, Hawi A, Thomas M, VerBerkmoes J, Germishuizen WA, Fourie PB, Hickey AJ, Edwards D.
University of North Carolina, Chapel Hill, NC 27599-7360, USA.
http://aac.asm.org/cgi/content/full/51/8/2830?view=long&pmid=17517845

It07:Azadirachtin

2007-10-22T14:25:24Z

Jhl406: Brief Intro

== Azadirachtin ==

=== Structure ===

<jmol>
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title1
title2
ATOM 1 C 0 -0.415 6.019 -1.839 0.00 0.00 C+0
ATOM 2 C 0 0.229 4.734 -2.293 0.00 0.00 C+0
ATOM 3 C 0 0.349 3.715 -1.447 0.00 0.00 C+0
ATOM 4 C 0 -0.159 3.845 -0.034 0.00 0.00 C+0
ATOM 5 C 0 0.977 2.462 -1.889 0.00 0.00 C+0
ATOM 6 O 0 1.387 2.357 -3.029 0.00 0.00 O+0
ATOM 7 O 0 1.098 1.429 -1.032 0.00 0.00 O+0
ATOM 8 C 0 1.715 0.199 -1.467 0.00 0.00 C+0
ATOM 9 C 0 3.222 0.270 -1.199 0.00 0.00 C+0
ATOM 10 C 0 3.406 0.496 0.303 0.00 0.00 C+0
ATOM 11 C 0 2.893 -0.685 1.082 0.00 0.00 C+0
ATOM 12 C 0 2.537 -0.280 2.535 0.00 0.00 C+0
ATOM 13 O 0 1.085 -0.249 2.561 0.00 0.00 O+0
ATOM 14 C 0 0.707 -1.383 1.759 0.00 0.00 C+0
ATOM 15 C 0 1.631 -1.350 0.562 0.00 0.00 C+0
ATOM 16 C 0 1.123 -1.036 -0.789 0.00 0.00 C+0
ATOM 17 C 0 1.530 -2.235 -1.720 0.00 0.00 C+0
ATOM 18 O 0 0.437 -3.158 -1.560 0.00 0.00 O+0
ATOM 19 C 0 -0.757 -2.339 -1.642 0.00 0.00 C+0
ATOM 20 C 0 -0.408 -1.020 -0.954 0.00 0.00 C+0
ATOM 21 C 0 -1.181 -0.668 0.283 0.00 0.00 C+0
ATOM 22 C 0 -0.762 -1.503 1.489 0.00 0.00 C+0
ATOM 23 O 0 -1.114 -2.873 1.319 0.00 0.00 O+0
ATOM 24 C 0 -0.965 0.818 0.643 0.00 0.00 C+0
ATOM 25 C 0 -2.688 -0.808 0.062 0.00 0.00 C+0
ATOM 26 C 0 -3.420 0.335 -0.683 0.00 0.00 C+0
ATOM 27 C 0 -4.914 0.008 -0.432 0.00 0.00 C+0
ATOM 28 C 0 -4.907 -0.407 1.077 0.00 0.00 C+0
ATOM 29 C 0 -3.641 -1.295 1.169 0.00 0.00 C+0
ATOM 30 O 0 -3.285 -2.108 0.017 0.00 0.00 O+0
ATOM 31 C 0 -3.133 -1.665 2.564 0.00 0.00 C+0
ATOM 32 C 0 -4.574 0.908 1.789 0.00 0.00 C+0
ATOM 33 C 0 -4.371 0.829 3.277 0.00 0.00 C+0
ATOM 34 C 0 -3.294 1.573 3.533 0.00 0.00 C+0
ATOM 35 O 0 -2.752 2.121 2.393 0.00 0.00 O+0
ATOM 36 C 0 -3.106 1.218 1.360 0.00 0.00 C+0
ATOM 37 O 0 -3.088 1.564 0.007 0.00 0.00 O+0
ATOM 38 O 0 -5.486 1.948 1.431 0.00 0.00 O+0
ATOM 39 C 0 -1.074 -2.085 -3.100 0.00 0.00 C+0
ATOM 40 O 0 -0.407 -2.604 -3.963 0.00 0.00 O+0
ATOM 41 O 0 -2.098 -1.283 -3.434 0.00 0.00 O+0
ATOM 42 C 0 -2.472 -1.126 -4.828 0.00 0.00 C+0
ATOM 43 O 0 -1.827 -3.065 -1.054 0.00 0.00 O+0
ATOM 44 C 0 3.984 -1.724 1.149 0.00 0.00 C+0
ATOM 45 O 0 3.794 -2.829 0.699 0.00 0.00 O+0
ATOM 46 O 0 5.165 -1.421 1.710 0.00 0.00 O+0
ATOM 47 C 0 6.216 -2.422 1.775 0.00 0.00 C+0
ATOM 48 O 0 4.819 0.678 0.587 0.00 0.00 O+0
ATOM 49 C 0 5.356 1.908 0.560 0.00 0.00 C+0
ATOM 50 O 0 4.664 2.864 0.299 0.00 0.00 O+0
ATOM 51 C 0 6.822 2.097 0.855 0.00 0.00 C+0
ATOM 52 H 0 -0.423 6.732 -2.663 0.00 0.00 H+0
ATOM 53 H 0 -1.438 5.820 -1.521 0.00 0.00 H+0
ATOM 54 H 0 0.151 6.434 -1.005 0.00 0.00 H+0
ATOM 55 H 0 0.594 4.641 -3.306 0.00 0.00 H+0
ATOM 56 H 0 -0.589 4.836 0.108 0.00 0.00 H+0
ATOM 57 H 0 -0.923 3.089 0.149 0.00 0.00 H+0
ATOM 58 H 0 0.666 3.703 0.664 0.00 0.00 H+0
ATOM 59 H 0 1.568 0.100 -2.552 0.00 0.00 H+0
ATOM 60 H 0 3.701 -0.658 -1.507 0.00 0.00 H+0
ATOM 61 H 0 3.653 1.107 -1.753 0.00 0.00 H+0
ATOM 62 H 0 2.864 1.390 0.605 0.00 0.00 H+0
ATOM 63 H 0 2.907 -1.026 3.235 0.00 0.00 H+0
ATOM 64 H 0 2.941 0.703 2.768 0.00 0.00 H+0
ATOM 65 H 0 0.991 -2.265 2.340 0.00 0.00 H+0
ATOM 66 H 0 1.941 -2.394 0.482 0.00 0.00 H+0
ATOM 67 H 0 1.631 -1.901 -2.750 0.00 0.00 H+0
ATOM 68 H 0 2.467 -2.676 -1.376 0.00 0.00 H+0
ATOM 69 H 0 -0.627 -0.221 -1.697 0.00 0.00 H+0
ATOM 70 H 0 -1.302 -1.121 2.371 0.00 0.00 H+0
ATOM 71 H 0 -0.821 -3.337 2.115 0.00 0.00 H+0
ATOM 72 H 0 -1.507 1.446 -0.064 0.00 0.00 H+0
ATOM 73 H 0 -1.333 1.005 1.652 0.00 0.00 H+0
ATOM 74 H 0 0.099 1.052 0.596 0.00 0.00 H+0
ATOM 75 H 0 -3.174 0.367 -1.745 0.00 0.00 H+0
ATOM 76 H 0 -5.537 0.888 -0.590 0.00 0.00 H+0
ATOM 77 H 0 -5.243 -0.818 -1.062 0.00 0.00 H+0
ATOM 78 H 0 -5.822 -0.893 1.418 0.00 0.00 H+0
ATOM 79 H 0 -3.972 -1.977 3.185 0.00 0.00 H+0
ATOM 80 H 0 -2.416 -2.482 2.485 0.00 0.00 H+0
ATOM 81 H 0 -2.649 -0.799 3.016 0.00 0.00 H+0
ATOM 82 H 0 -4.972 0.284 3.990 0.00 0.00 H+0
ATOM 83 H 0 -2.892 1.728 4.524 0.00 0.00 H+0
ATOM 84 H 0 -2.519 0.307 1.483 0.00 0.00 H+0
ATOM 85 H 0 -5.165 2.758 1.853 0.00 0.00 H+0
ATOM 86 H 0 -2.835 -2.078 -5.216 0.00 0.00 H+0
ATOM 87 H 0 -3.259 -0.377 -4.911 0.00 0.00 H+0
ATOM 88 H 0 -1.603 -0.807 -5.404 0.00 0.00 H+0
ATOM 89 H 0 -1.886 -3.908 -1.525 0.00 0.00 H+0
ATOM 90 H 0 7.094 -1.996 2.260 0.00 0.00 H+0
ATOM 91 H 0 5.865 -3.280 2.347 0.00 0.00 H+0
ATOM 92 H 0 6.477 -2.741 0.766 0.00 0.00 H+0
ATOM 93 H 0 7.391 2.026 -0.072 0.00 0.00 H+0
ATOM 94 H 0 6.979 3.078 1.303 0.00 0.00 H+0
ATOM 95 H 0 7.156 1.323 1.546 0.00 0.00 H+0
CONECT 1 2 52 53 54 NONE 100
CONECT 2 1 3 55 0 NONE 101
CONECT 3 2 4 5 0 NONE 102
CONECT 4 3 56 57 58 NONE 103
CONECT 5 3 6 7 0 NONE 104
CONECT 6 5 0 0 0 NONE 105
CONECT 7 5 8 0 0 NONE 106
CONECT 8 7 16 9 59 NONE 107
CONECT 9 8 10 60 61 NONE 108
CONECT 10 9 11 48 62 NONE 109
CONECT 11 10 15 12 44 NONE 110
CONECT 12 11 13 63 64 NONE 111
CONECT 13 12 14 0 0 NONE 112
CONECT 14 13 22 15 65 NONE 113
CONECT 15 14 11 16 66 NONE 114
CONECT 16 15 8 20 17 NONE 115
CONECT 17 16 18 67 68 NONE 116
CONECT 18 17 19 0 0 NONE 117
CONECT 19 18 20 39 43 NONE 118
CONECT 20 19 16 21 69 NONE 119
CONECT 21 20 22 24 25 NONE 120
CONECT 22 21 14 23 70 NONE 121
CONECT 23 22 71 0 0 NONE 122
CONECT 24 21 72 73 74 NONE 123
CONECT 25 21 29 30 26 NONE 124
CONECT 26 25 37 27 75 NONE 125
CONECT 27 26 28 76 77 NONE 126
CONECT 28 27 29 32 78 NONE 127
CONECT 29 28 25 30 31 NONE 128
CONECT 30 29 25 0 0 NONE 129
CONECT 31 29 79 80 81 NONE 130
CONECT 32 28 36 33 38 NONE 131
CONECT 33 32 34 82 0 NONE 132
CONECT 34 33 35 83 0 NONE 133
CONECT 35 34 36 0 0 NONE 134
CONECT 36 35 32 37 84 NONE 135
CONECT 37 36 26 0 0 NONE 136
CONECT 38 32 85 0 0 NONE 137
CONECT 39 19 40 41 0 NONE 138
CONECT 40 39 0 0 0 NONE 139
CONECT 41 39 42 0 0 NONE 140
CONECT 42 41 86 87 88 NONE 141
CONECT 43 19 89 0 0 NONE 142
CONECT 44 11 45 46 0 NONE 143
CONECT 45 44 0 0 0 NONE 144
CONECT 46 44 47 0 0 NONE 145
CONECT 47 46 90 91 92 NONE 146
CONECT 48 10 49 0 0 NONE 147
CONECT 49 48 50 51 0 NONE 148
CONECT 50 49 0 0 0 NONE 149
CONECT 51 49 93 94 95 NONE 150
END NONE 151
70
</inlineContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
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</jmol>
==== Overview ====

Azadirachtin is a compound extracted from the from the neem tree (Azadirachta indica). Tests have indicated that neem extract based insecticides are extremely effective. The structure is highly complex and thus the synthesis itself has taken well over 20 years. Azadirachtin has 16 stereogenic centers, -seven of which are tetrasubstituted. It has a molecular formula of C35H44O16

=== Sources/Synthesis ===

=== Uses/Related products ===

It07:Azadirachtin

2007-10-22T13:56:50Z

Jhl406: /* Structure */

It07:Azadirachtin

2007-10-22T13:56:07Z

Jhl406: Added Structure

It07:sitagliptin page

2007-10-22T13:53:43Z

Jhl406: Replacing page with '== '''Azadirachtin''' =='

== '''Azadirachtin''' ==

It07:sitagliptin page

2007-10-22T13:46:35Z

Jhl406: Structure

== '''Azadirachtin''' ==

=== Structure ===

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
ATOM 1 C 0 -0.415 6.019 -1.839 0.00 0.00 C+0
ATOM 2 C 0 0.229 4.734 -2.293 0.00 0.00 C+0
ATOM 3 C 0 0.349 3.715 -1.447 0.00 0.00 C+0
ATOM 4 C 0 -0.159 3.845 -0.034 0.00 0.00 C+0
ATOM 5 C 0 0.977 2.462 -1.889 0.00 0.00 C+0
ATOM 6 O 0 1.387 2.357 -3.029 0.00 0.00 O+0
ATOM 7 O 0 1.098 1.429 -1.032 0.00 0.00 O+0
ATOM 8 C 0 1.715 0.199 -1.467 0.00 0.00 C+0
ATOM 9 C 0 3.222 0.270 -1.199 0.00 0.00 C+0
ATOM 10 C 0 3.406 0.496 0.303 0.00 0.00 C+0
ATOM 11 C 0 2.893 -0.685 1.082 0.00 0.00 C+0
ATOM 12 C 0 2.537 -0.280 2.535 0.00 0.00 C+0
ATOM 13 O 0 1.085 -0.249 2.561 0.00 0.00 O+0
ATOM 14 C 0 0.707 -1.383 1.759 0.00 0.00 C+0
ATOM 15 C 0 1.631 -1.350 0.562 0.00 0.00 C+0
ATOM 16 C 0 1.123 -1.036 -0.789 0.00 0.00 C+0
ATOM 17 C 0 1.530 -2.235 -1.720 0.00 0.00 C+0
ATOM 18 O 0 0.437 -3.158 -1.560 0.00 0.00 O+0
ATOM 19 C 0 -0.757 -2.339 -1.642 0.00 0.00 C+0
ATOM 20 C 0 -0.408 -1.020 -0.954 0.00 0.00 C+0
ATOM 21 C 0 -1.181 -0.668 0.283 0.00 0.00 C+0
ATOM 22 C 0 -0.762 -1.503 1.489 0.00 0.00 C+0
ATOM 23 O 0 -1.114 -2.873 1.319 0.00 0.00 O+0
ATOM 24 C 0 -0.965 0.818 0.643 0.00 0.00 C+0
ATOM 25 C 0 -2.688 -0.808 0.062 0.00 0.00 C+0
ATOM 26 C 0 -3.420 0.335 -0.683 0.00 0.00 C+0
ATOM 27 C 0 -4.914 0.008 -0.432 0.00 0.00 C+0
ATOM 28 C 0 -4.907 -0.407 1.077 0.00 0.00 C+0
ATOM 29 C 0 -3.641 -1.295 1.169 0.00 0.00 C+0
ATOM 30 O 0 -3.285 -2.108 0.017 0.00 0.00 O+0
ATOM 31 C 0 -3.133 -1.665 2.564 0.00 0.00 C+0
ATOM 32 C 0 -4.574 0.908 1.789 0.00 0.00 C+0
ATOM 33 C 0 -4.371 0.829 3.277 0.00 0.00 C+0
ATOM 34 C 0 -3.294 1.573 3.533 0.00 0.00 C+0
ATOM 35 O 0 -2.752 2.121 2.393 0.00 0.00 O+0
ATOM 36 C 0 -3.106 1.218 1.360 0.00 0.00 C+0
ATOM 37 O 0 -3.088 1.564 0.007 0.00 0.00 O+0
ATOM 38 O 0 -5.486 1.948 1.431 0.00 0.00 O+0
ATOM 39 C 0 -1.074 -2.085 -3.100 0.00 0.00 C+0
ATOM 40 O 0 -0.407 -2.604 -3.963 0.00 0.00 O+0
ATOM 41 O 0 -2.098 -1.283 -3.434 0.00 0.00 O+0
ATOM 42 C 0 -2.472 -1.126 -4.828 0.00 0.00 C+0
ATOM 43 O 0 -1.827 -3.065 -1.054 0.00 0.00 O+0
ATOM 44 C 0 3.984 -1.724 1.149 0.00 0.00 C+0
ATOM 45 O 0 3.794 -2.829 0.699 0.00 0.00 O+0
ATOM 46 O 0 5.165 -1.421 1.710 0.00 0.00 O+0
ATOM 47 C 0 6.216 -2.422 1.775 0.00 0.00 C+0
ATOM 48 O 0 4.819 0.678 0.587 0.00 0.00 O+0
ATOM 49 C 0 5.356 1.908 0.560 0.00 0.00 C+0
ATOM 50 O 0 4.664 2.864 0.299 0.00 0.00 O+0
ATOM 51 C 0 6.822 2.097 0.855 0.00 0.00 C+0
ATOM 52 H 0 -0.423 6.732 -2.663 0.00 0.00 H+0
ATOM 53 H 0 -1.438 5.820 -1.521 0.00 0.00 H+0
ATOM 54 H 0 0.151 6.434 -1.005 0.00 0.00 H+0
ATOM 55 H 0 0.594 4.641 -3.306 0.00 0.00 H+0
ATOM 56 H 0 -0.589 4.836 0.108 0.00 0.00 H+0
ATOM 57 H 0 -0.923 3.089 0.149 0.00 0.00 H+0
ATOM 58 H 0 0.666 3.703 0.664 0.00 0.00 H+0
ATOM 59 H 0 1.568 0.100 -2.552 0.00 0.00 H+0
ATOM 60 H 0 3.701 -0.658 -1.507 0.00 0.00 H+0
ATOM 61 H 0 3.653 1.107 -1.753 0.00 0.00 H+0
ATOM 62 H 0 2.864 1.390 0.605 0.00 0.00 H+0
ATOM 63 H 0 2.907 -1.026 3.235 0.00 0.00 H+0
ATOM 64 H 0 2.941 0.703 2.768 0.00 0.00 H+0
ATOM 65 H 0 0.991 -2.265 2.340 0.00 0.00 H+0
ATOM 66 H 0 1.941 -2.394 0.482 0.00 0.00 H+0
ATOM 67 H 0 1.631 -1.901 -2.750 0.00 0.00 H+0
ATOM 68 H 0 2.467 -2.676 -1.376 0.00 0.00 H+0
ATOM 69 H 0 -0.627 -0.221 -1.697 0.00 0.00 H+0
ATOM 70 H 0 -1.302 -1.121 2.371 0.00 0.00 H+0
ATOM 71 H 0 -0.821 -3.337 2.115 0.00 0.00 H+0
ATOM 72 H 0 -1.507 1.446 -0.064 0.00 0.00 H+0
ATOM 73 H 0 -1.333 1.005 1.652 0.00 0.00 H+0
ATOM 74 H 0 0.099 1.052 0.596 0.00 0.00 H+0
ATOM 75 H 0 -3.174 0.367 -1.745 0.00 0.00 H+0
ATOM 76 H 0 -5.537 0.888 -0.590 0.00 0.00 H+0
ATOM 77 H 0 -5.243 -0.818 -1.062 0.00 0.00 H+0
ATOM 78 H 0 -5.822 -0.893 1.418 0.00 0.00 H+0
ATOM 79 H 0 -3.972 -1.977 3.185 0.00 0.00 H+0
ATOM 80 H 0 -2.416 -2.482 2.485 0.00 0.00 H+0
ATOM 81 H 0 -2.649 -0.799 3.016 0.00 0.00 H+0
ATOM 82 H 0 -4.972 0.284 3.990 0.00 0.00 H+0
ATOM 83 H 0 -2.892 1.728 4.524 0.00 0.00 H+0
ATOM 84 H 0 -2.519 0.307 1.483 0.00 0.00 H+0
ATOM 85 H 0 -5.165 2.758 1.853 0.00 0.00 H+0
ATOM 86 H 0 -2.835 -2.078 -5.216 0.00 0.00 H+0
ATOM 87 H 0 -3.259 -0.377 -4.911 0.00 0.00 H+0
ATOM 88 H 0 -1.603 -0.807 -5.404 0.00 0.00 H+0
ATOM 89 H 0 -1.886 -3.908 -1.525 0.00 0.00 H+0
ATOM 90 H 0 7.094 -1.996 2.260 0.00 0.00 H+0
ATOM 91 H 0 5.865 -3.280 2.347 0.00 0.00 H+0
ATOM 92 H 0 6.477 -2.741 0.766 0.00 0.00 H+0
ATOM 93 H 0 7.391 2.026 -0.072 0.00 0.00 H+0
ATOM 94 H 0 6.979 3.078 1.303 0.00 0.00 H+0
ATOM 95 H 0 7.156 1.323 1.546 0.00 0.00 H+0
CONECT 1 2 52 53 54 NONE 100
CONECT 2 1 3 55 0 NONE 101
CONECT 3 2 4 5 0 NONE 102
CONECT 4 3 56 57 58 NONE 103
CONECT 5 3 6 7 0 NONE 104
CONECT 6 5 0 0 0 NONE 105
CONECT 7 5 8 0 0 NONE 106
CONECT 8 7 16 9 59 NONE 107
CONECT 9 8 10 60 61 NONE 108
CONECT 10 9 11 48 62 NONE 109
CONECT 11 10 15 12 44 NONE 110
CONECT 12 11 13 63 64 NONE 111
CONECT 13 12 14 0 0 NONE 112
CONECT 14 13 22 15 65 NONE 113
CONECT 15 14 11 16 66 NONE 114
CONECT 16 15 8 20 17 NONE 115
CONECT 17 16 18 67 68 NONE 116
CONECT 18 17 19 0 0 NONE 117
CONECT 19 18 20 39 43 NONE 118
CONECT 20 19 16 21 69 NONE 119
CONECT 21 20 22 24 25 NONE 120
CONECT 22 21 14 23 70 NONE 121
CONECT 23 22 71 0 0 NONE 122
CONECT 24 21 72 73 74 NONE 123
CONECT 25 21 29 30 26 NONE 124
CONECT 26 25 37 27 75 NONE 125
CONECT 27 26 28 76 77 NONE 126
CONECT 28 27 29 32 78 NONE 127
CONECT 29 28 25 30 31 NONE 128
CONECT 30 29 25 0 0 NONE 129
CONECT 31 29 79 80 81 NONE 130
CONECT 32 28 36 33 38 NONE 131
CONECT 33 32 34 82 0 NONE 132
CONECT 34 33 35 83 0 NONE 133
CONECT 35 34 36 0 0 NONE 134
CONECT 36 35 32 37 84 NONE 135
CONECT 37 36 26 0 0 NONE 136
CONECT 38 32 85 0 0 NONE 137
CONECT 39 19 40 41 0 NONE 138
CONECT 40 39 0 0 0 NONE 139
CONECT 41 39 42 0 0 NONE 140
CONECT 42 41 86 87 88 NONE 141
CONECT 43 19 89 0 0 NONE 142
CONECT 44 11 45 46 0 NONE 143
CONECT 45 44 0 0 0 NONE 144
CONECT 46 44 47 0 0 NONE 145
CONECT 47 46 90 91 92 NONE 146
CONECT 48 10 49 0 0 NONE 147
CONECT 49 48 50 51 0 NONE 148
CONECT 50 49 0 0 0 NONE 149
CONECT 51 49 93 94 95 NONE 150
END NONE 151
70
</inlineContents>
</jmolApplet>
</jmol>

It07:Capreomycin

2007-10-22T12:50:36Z

Jhl406: Advancements in TB treatment -guinea pig model findings

== '''Capreomycin''' ==

Capreomycin is used in the treatment of Tuberculosis (TB) but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. It has a molecular formula of C25H44N14O8.

=== Structure ===

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
ATOM 1 N 0 -1.440 5.168 0.918 0.00 0.00 N+0
ATOM 2 C 0 -1.593 3.761 0.527 0.00 0.00 C+0
ATOM 3 C 0 -0.732 2.897 1.412 0.00 0.00 C+0
ATOM 4 N 0 0.622 3.097 1.398 0.00 0.00 N+0
ATOM 5 C 0 1.384 2.207 2.311 0.00 0.00 C+0
ATOM 6 C 0 1.337 0.808 1.753 0.00 0.00 C+0
ATOM 7 N 0 1.591 -0.248 2.577 0.00 0.00 N+0
ATOM 8 C 0 1.492 -1.592 1.962 0.00 0.00 C+0
ATOM 9 C 0 0.033 -1.889 1.714 0.00 0.00 C+0
ATOM 10 O 0 -0.501 -2.861 2.207 0.00 0.00 O+0
ATOM 11 C 0 2.256 -1.612 0.637 0.00 0.00 C+0
ATOM 12 N 0 3.627 -1.146 0.857 0.00 0.00 N+0
ATOM 13 C 0 4.490 -1.079 -0.177 0.00 0.00 C+0
ATOM 14 C 0 5.901 -0.600 0.050 0.00 0.00 C+0
ATOM 15 C 0 6.665 -0.620 -1.276 0.00 0.00 C+0
ATOM 16 N 0 6.067 0.353 -2.200 0.00 0.00 N+0
ATOM 17 C 0 8.129 -0.254 -1.026 0.00 0.00 C+0
ATOM 18 C 0 8.919 -0.394 -2.329 0.00 0.00 C+0
ATOM 19 C 0 10.384 -0.028 -2.079 0.00 0.00 C+0
ATOM 20 N 0 11.142 -0.163 -3.329 0.00 0.00 N+0
ATOM 21 O 0 4.131 -1.404 -1.288 0.00 0.00 O+0
ATOM 22 O 0 1.075 0.623 0.583 0.00 0.00 O+0
ATOM 23 C 0 2.836 2.679 2.399 0.00 0.00 C+0
ATOM 24 O 0 2.881 3.970 3.009 0.00 0.00 O+0
ATOM 25 O 0 -1.227 2.046 2.120 0.00 0.00 O+0
ATOM 26 C 0 -3.058 3.346 0.680 0.00 0.00 C+0
ATOM 27 N 0 -3.330 2.178 -0.167 0.00 0.00 N+0
ATOM 28 C 0 -4.764 1.884 -0.039 0.00 0.00 C+0
ATOM 29 C 0 -5.048 0.497 -0.620 0.00 0.00 C+0
ATOM 30 C 0 -4.640 0.467 -2.095 0.00 0.00 C+0
ATOM 31 N 0 -4.881 -0.872 -2.653 0.00 0.00 N+0
ATOM 32 C 0 -4.946 -1.017 -4.018 0.00 0.00 C+0
ATOM 33 N 0 -4.902 -2.282 -4.555 0.00 0.00 N+0
ATOM 34 N 0 -5.047 -0.005 -4.816 0.00 0.00 N+0
ATOM 35 C 0 -5.083 1.382 -4.365 0.00 0.00 C+0
ATOM 36 C 0 -5.498 1.459 -2.894 0.00 0.00 C+0
ATOM 37 N 0 -4.267 -0.508 0.129 0.00 0.00 N+0
ATOM 38 C 0 -2.915 -0.341 0.118 0.00 0.00 C+0
ATOM 39 C 0 -2.074 -1.277 0.868 0.00 0.00 C+0
ATOM 40 N 0 -0.668 -1.027 0.915 0.00 0.00 N+0
ATOM 41 C 0 -2.611 -2.343 1.497 0.00 0.00 C+0
ATOM 42 N 0 -2.055 -3.592 1.332 0.00 0.00 N+0
ATOM 43 C 0 -2.517 -4.636 2.049 0.00 0.00 C+0
ATOM 44 N 0 -1.972 -5.858 1.888 0.00 0.00 N+0
ATOM 45 O 0 -3.426 -4.475 2.841 0.00 0.00 O+0
ATOM 46 O 0 -2.412 0.574 -0.508 0.00 0.00 O+0
ATOM 47 O 0 -5.134 1.908 1.341 0.00 0.00 O+0
ATOM 48 H 0 -0.464 5.397 0.802 0.00 0.00 H+0
ATOM 49 H 0 -1.948 5.715 0.239 0.00 0.00 H+0
ATOM 50 H 0 -1.287 3.636 -0.511 0.00 0.00 H+0
ATOM 51 H 0 1.048 3.764 0.838 0.00 0.00 H+0
ATOM 52 H 0 0.931 2.223 3.302 0.00 0.00 H+0
ATOM 53 H 0 1.823 -0.127 3.510 0.00 0.00 H+0
ATOM 54 H 0 1.909 -2.338 2.639 0.00 0.00 H+0
ATOM 55 H 0 2.276 -2.628 0.244 0.00 0.00 H+0
ATOM 56 H 0 1.759 -0.956 -0.078 0.00 0.00 H+0
ATOM 57 H 0 3.914 -0.886 1.746 0.00 0.00 H+0
ATOM 58 H 0 5.881 0.416 0.442 0.00 0.00 H+0
ATOM 59 H 0 6.397 -1.257 0.765 0.00 0.00 H+0
ATOM 60 H 0 6.609 -1.617 -1.713 0.00 0.00 H+0
ATOM 61 H 0 6.141 1.257 -1.757 0.00 0.00 H+0
ATOM 62 H 0 6.661 0.381 -3.015 0.00 0.00 H+0
ATOM 63 H 0 8.191 0.775 -0.673 0.00 0.00 H+0
ATOM 64 H 0 8.547 -0.922 -0.273 0.00 0.00 H+0
ATOM 65 H 0 8.857 -1.424 -2.682 0.00 0.00 H+0
ATOM 66 H 0 8.501 0.274 -3.081 0.00 0.00 H+0
ATOM 67 H 0 10.446 1.001 -1.725 0.00 0.00 H+0
ATOM 68 H 0 10.802 -0.696 -1.326 0.00 0.00 H+0
ATOM 69 H 0 10.791 0.542 -3.959 0.00 0.00 H+0
ATOM 70 H 0 12.097 0.087 -3.118 0.00 0.00 H+0
ATOM 71 H 0 3.412 1.973 2.998 0.00 0.00 H+0
ATOM 72 H 0 3.261 2.736 1.397 0.00 0.00 H+0
ATOM 73 H 0 3.812 4.230 3.045 0.00 0.00 H+0
ATOM 74 H 0 -3.257 3.094 1.721 0.00 0.00 H+0
ATOM 75 H 0 -3.702 4.172 0.377 0.00 0.00 H+0
ATOM 76 H 0 -3.178 2.470 -1.121 0.00 0.00 H+0
ATOM 77 H 0 -5.339 2.632 -0.584 0.00 0.00 H+0
ATOM 78 H 0 -6.111 0.276 -0.532 0.00 0.00 H+0
ATOM 79 H 0 -3.585 0.725 -2.192 0.00 0.00 H+0
ATOM 80 H 0 -4.992 -1.639 -2.069 0.00 0.00 H+0
ATOM 81 H 0 -4.827 -3.054 -3.971 0.00 0.00 H+0
ATOM 82 H 0 -4.947 -2.404 -5.516 0.00 0.00 H+0
ATOM 83 H 0 -4.093 1.823 -4.483 0.00 0.00 H+0
ATOM 84 H 0 -5.799 1.938 -4.970 0.00 0.00 H+0
ATOM 85 H 0 -6.551 1.195 -2.796 0.00 0.00 H+0
ATOM 86 H 0 -5.334 2.470 -2.520 0.00 0.00 H+0
ATOM 87 H 0 -4.691 -1.242 0.601 0.00 0.00 H+0
ATOM 88 H 0 -0.246 -0.306 0.422 0.00 0.00 H+0
ATOM 89 H 0 -3.478 -2.217 2.129 0.00 0.00 H+0
ATOM 90 H 0 -1.330 -3.721 0.701 0.00 0.00 H+0
ATOM 91 H 0 -1.247 -5.987 1.257 0.00 0.00 H+0
ATOM 92 H 0 -2.305 -6.609 2.404 0.00 0.00 H+0
ATOM 93 H 0 -4.936 2.796 1.668 0.00 0.00 H+0
CONECT 1 2 48 49 0 NONE 98
CONECT 2 1 3 26 50 NONE 99
CONECT 3 2 4 25 0 NONE 100
CONECT 4 3 5 51 0 NONE 101
CONECT 5 4 6 23 52 NONE 102
CONECT 6 5 7 22 0 NONE 103
CONECT 7 6 8 53 0 NONE 104
CONECT 8 7 9 11 54 NONE 105
CONECT 9 8 40 10 0 NONE 106
CONECT 10 9 0 0 0 NONE 107
CONECT 11 8 12 55 56 NONE 108
CONECT 12 11 13 57 0 NONE 109
CONECT 13 12 14 21 0 NONE 110
CONECT 14 13 15 58 59 NONE 111
CONECT 15 14 16 17 60 NONE 112
CONECT 16 15 61 62 0 NONE 113
CONECT 17 15 18 63 64 NONE 114
CONECT 18 17 19 65 66 NONE 115
CONECT 19 18 20 67 68 NONE 116
CONECT 20 19 69 70 0 NONE 117
CONECT 21 13 0 0 0 NONE 118
CONECT 22 6 0 0 0 NONE 119
CONECT 23 5 24 71 72 NONE 120
CONECT 24 23 73 0 0 NONE 121
CONECT 25 3 0 0 0 NONE 122
CONECT 26 2 27 74 75 NONE 123
CONECT 27 26 28 76 0 NONE 124
CONECT 28 27 29 47 77 NONE 125
CONECT 29 28 30 37 78 NONE 126
CONECT 30 29 36 31 79 NONE 127
CONECT 31 30 32 80 0 NONE 128
CONECT 32 31 33 34 0 NONE 129
CONECT 33 32 81 82 0 NONE 130
CONECT 34 32 35 0 0 NONE 131
CONECT 35 34 36 83 84 NONE 132
CONECT 36 35 30 85 86 NONE 133
CONECT 37 29 38 87 0 NONE 134
CONECT 38 37 39 46 0 NONE 135
CONECT 39 38 40 41 0 NONE 136
CONECT 40 39 9 88 0 NONE 137
CONECT 41 39 42 89 0 NONE 138
CONECT 42 41 43 90 0 NONE 139
CONECT 43 42 44 45 0 NONE 140
CONECT 44 43 91 92 0 NONE 141
CONECT 45 43 0 0 0 NONE 142
CONECT 46 38 0 0 0 NONE 143
CONECT 47 28 93 0 0 NONE 144
END NONE 145
M END</inlineContents>
</jmolApplet>
</jmol>

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Capreomycin.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| Other names
| Capreomycin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>25</sub>H<sub>44</sub>N<sub>14</sub>O<sub>8
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| NC(CC(NCC2NC(C(CO)NC(C(N)CNC(C(NC(/C(NC2=O)=C\CC(N)=O)=O)C1N=C(N)NCC1)=O)=O)=O)=O)CCCN
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 668.71
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| {{{Mp}}} K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''<sub>a</sub>) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''<sub>b</sub>) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination<br />geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant ε<sub>r</sub>], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
{{Chem-Data_Structure}}

=== Overview ===

Capreomycin has the ability to kill a wide variety of bacteria. It does this by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for TB is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

=== Adverse Effects ===

The following are some of the side effects that are known to be associated with this medicine.

• Skin irritation and itching (pruritus)

• Allergy to active ingredients (hypersensitivity)

• Rash (allergic reaction)

• Loss of hearing

• Damage to the kidneys

• Alteration in results of liver function tests

• Disruption to the chemical components balance of electrolytes in the blood

=== Further Studies ===

Capreomycin is an important drug used for TB which has developed resistance to many drugs. This is a characteristic of TB drugs and is termed multi-drug resistance (MDR). Capreomycin displays a unique bactericidal effect on non-replicating TB bacilli among known anti-TB drugs.

In a 2005 journal by L. Heifets, J. Simon and V. Pham it showed that only capreomycin is active against non-replicating M. tuberculosis bacilli at the same level as metronidazole in an in vitro model of persistence that monitors the curve of decline in bacterial counts. This confirms the conclusion made in a 1996 journal by N. Rastogi, V. Labrousse and K.S. Goh that stated that capreomycin was effective against MDR and intracellular TB bacilli.

=== Synthesis ===

The synthesis of tuberculostatic macrocyclic peptide antibiotic capreomycin IB is composed of 27 complex steps and was determined in 2003 and outlined in a journal written by Duane E. DeMong and Robert M. Williams of Colorado State UniVersity. An enolate-aldimine condensation takes place between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal. This produces the cyclic guanidine amino acid (2S,3R)-capreomycidine. Finally there is a Hofmann rearrangement on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic
acid residue.

=== Advancements ===

The August 2007 issue of 'Antimicrobial Agents and Chemotherapy' http://aac.asm.org/ reported a new novel way of treating TB. The findings, also reported by Reuters http://www.medscape.com/viewarticle/562095, presents treatment by inhalation of large porous particles of capreomycin following studies using a guinea pig model. Dr. Anthony J. Hickey and his research team at the University of North Carolina introduced this new concept as a way of the drug being adminstered so that it can directly act at the site of origin thereby hopefully reducing the severe side effects.

=== References ===

1. L. Heifets, J. Simon and V. Pham, Capreomycin is active against non-replicating M. tuberculosis, Ann Clin Microbiol Antimicrob 4 (2005) (1), p. 6. http://www.ann-clinmicrob.com/content/4/1/6

2. N. Rastogi, V. Labrousse and K.S. Goh, In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain in human macrophages, Curr Microbiol 33 (1996) (3), pp. 167–175 http://www.springerlink.com/content/rhkdjf3lngt1tnnd/

3. Synthesis D. E. DeMong, Journal of the American Chemical Society, 2003, 125, 8561-8565. http://pubs.acs.org/cgi-bin/article.cgi/jacsat/2003/125/i28/pdf/ja0351241.pdf

4. Inhaled Large Porous Particles of Capreomycin for Treatment of Tuberculosis in a Guinea Pig Model Garcia-Contreras L, Fiegel J, Telko MJ, Elbert K, Hawi A, Thomas M, VerBerkmoes J, Germishuizen WA, Fourie PB, Hickey AJ, Edwards D.
University of North Carolina, Chapel Hill, NC 27599-7360, USA.
http://aac.asm.org/cgi/content/full/51/8/2830?view=long&pmid=17517845

It07:Capreomycin

2007-10-22T12:26:36Z

Jhl406: /* Adverse Effects */ -side effects

It07:Capreomycin

2007-10-22T12:25:13Z

Jhl406:

It07:Capreomycin

2007-10-22T11:51:45Z

Jhl406: Further studies+journal references

It07:Capreomycin

2007-10-22T10:49:16Z

Jhl406: /* Synthesis */ +update

It07:Capreomycin

2007-10-22T10:48:09Z

Jhl406: Synthesis and Reference to a journal added

It07:Gossypol

2007-10-22T10:20:27Z

Jhl406:

{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem =
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Legal_status =
| Routes =
}}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a male contraceptive.

Whilst Gossypol is the common name by which the molecule is known its IUPAC name is 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), rather a mouthful.

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

= History =

Gossypol is a chemical which is produced in cotton plants. In 1929, there was a study in China of couples, who cooked with crude cottonseed oil, in relation to their smaller than average families. This study concluded that it was this oil that affected male fertlilty and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception.

= References =

http://www.emolecules.com/cgi-bin/more?vid=538892#

It07:Gossypol

2007-10-22T10:20:05Z

Jhl406:

{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem =
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Legal_status =
| Routes =
}}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a male contraceptive.

Whilst Gossypol is the common name by which the molecule is known its IUPAC name is 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), rather a mouthful.

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

=== History ===

Gossypol is a chemical which is produced in cotton plants. In 1929, there was a study in China of couples, who cooked with crude cottonseed oil, in relation to their smaller than average families. This study concluded that it was this oil that affected male fertlilty and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception.

= References =

http://www.emolecules.com/cgi-bin/more?vid=538892#

It07:Gossypol

2007-10-22T10:19:39Z

Jhl406: history of gossypol

{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem =
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Legal_status =
| Routes =
}}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a male contraceptive.

Whilst Gossypol is the common name by which the molecule is known its IUPAC name is 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene), rather a mouthful.

<jmol>
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<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

= References =

http://www.emolecules.com/cgi-bin/more?vid=538892#

=== History ===

Gossypol is a chemical which is produced in cotton plants. In 1929, there was a study in China of couples, who cooked with crude cottonseed oil, in relation to their smaller than average families. This study concluded that it was this oil that affected male fertlilty and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception.

It07:Sibutramine

2007-10-22T09:54:21Z

Jhl406: How sibutramine works

== General Information ==
'''Name''':Sibutramine
<br>'''IUPAC Systematic Name:''' 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
<br>'''Molecular Formula:'''C<sub>17</sub>H<sub>26</sub>ClN
<br>'''Molecular Weight:'''279.84804g/mol

== 3D Model of Sibutramine ==

<jmol>
<jmolApplet>
<size>400</size>
<title>Sibutramine</title><color>white</color>
<uploadedFileContents>Sibutramine.MOL</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>

</jmol>

== General Information ==
Sibutramine has been used as an appetite suppressant since it was approved by the FDA in the US in 1997. It is produced and marketed by Knoll Pharmaceuticals and is available in over 40 countries.
<br>
It was originally evaluated as an antidepressent due to its mechanism action being similar to the tricyclic group of antidepressents, such as [http://en.wikipedia.org/wiki/Amitriptyline Amitriptyline] without having the same negative side effects as Amitriptyline

Sibutramine is found in a class of medications called appetite suppressants. Sibutramine is commonly used in conjunction with a reduced calorie diet and exercise to help overweight people diminish their appetite. It primary mechanism involves acting on neurotransmitters that control appetite in the brain to decrease appetite.

Sibutramine specifically blocks the reuptake of the neurotransmitters dopamine, norepinephrine, and serotonin. These are brain chemicals which influence feelings of hunger and fullness and taking sibutramine will induce the sensation of feeling full sooner when you eat and thus the patient will eat less.

== Reaction Mechanism for the Synthesis of Sibutramine ==

[[Image:Subutraminereactionpicture.gif|centre|300|4-step Synthesis of Sibutramine]]<ref>[http://www.rsc.org/publishing/journals/article.asp?doi=p19960002583 Jeffery, J. E. J. E. (1996). "Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites." Journal of the Chemical Society. Perkin transactions 1(21): 2583-2589.]</ref>

== References==
<references/>

It07:Capreomycin

2007-10-22T09:51:03Z

Jhl406:

It07:Capreomycin

2007-10-22T09:49:46Z

Jhl406: /* Structure */

It07:Capreomycin

2007-10-22T09:48:51Z

Jhl406: /* Capreomycin */

It07:Capreomycin

2007-10-22T09:40:44Z

Jhl406: Brief Insight with Jmol

== Capreomycin ==
Capreomycin is used in the treatment of Tuberculosis (TB) but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. They have the ability to kill a wide variety of bacteria by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for TB is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
ATOM 1 N 0 -1.440 5.168 0.918 0.00 0.00 N+0
ATOM 2 C 0 -1.593 3.761 0.527 0.00 0.00 C+0
ATOM 3 C 0 -0.732 2.897 1.412 0.00 0.00 C+0
ATOM 4 N 0 0.622 3.097 1.398 0.00 0.00 N+0
ATOM 5 C 0 1.384 2.207 2.311 0.00 0.00 C+0
ATOM 6 C 0 1.337 0.808 1.753 0.00 0.00 C+0
ATOM 7 N 0 1.591 -0.248 2.577 0.00 0.00 N+0
ATOM 8 C 0 1.492 -1.592 1.962 0.00 0.00 C+0
ATOM 9 C 0 0.033 -1.889 1.714 0.00 0.00 C+0
ATOM 10 O 0 -0.501 -2.861 2.207 0.00 0.00 O+0
ATOM 11 C 0 2.256 -1.612 0.637 0.00 0.00 C+0
ATOM 12 N 0 3.627 -1.146 0.857 0.00 0.00 N+0
ATOM 13 C 0 4.490 -1.079 -0.177 0.00 0.00 C+0
ATOM 14 C 0 5.901 -0.600 0.050 0.00 0.00 C+0
ATOM 15 C 0 6.665 -0.620 -1.276 0.00 0.00 C+0
ATOM 16 N 0 6.067 0.353 -2.200 0.00 0.00 N+0
ATOM 17 C 0 8.129 -0.254 -1.026 0.00 0.00 C+0
ATOM 18 C 0 8.919 -0.394 -2.329 0.00 0.00 C+0
ATOM 19 C 0 10.384 -0.028 -2.079 0.00 0.00 C+0
ATOM 20 N 0 11.142 -0.163 -3.329 0.00 0.00 N+0
ATOM 21 O 0 4.131 -1.404 -1.288 0.00 0.00 O+0
ATOM 22 O 0 1.075 0.623 0.583 0.00 0.00 O+0
ATOM 23 C 0 2.836 2.679 2.399 0.00 0.00 C+0
ATOM 24 O 0 2.881 3.970 3.009 0.00 0.00 O+0
ATOM 25 O 0 -1.227 2.046 2.120 0.00 0.00 O+0
ATOM 26 C 0 -3.058 3.346 0.680 0.00 0.00 C+0
ATOM 27 N 0 -3.330 2.178 -0.167 0.00 0.00 N+0
ATOM 28 C 0 -4.764 1.884 -0.039 0.00 0.00 C+0
ATOM 29 C 0 -5.048 0.497 -0.620 0.00 0.00 C+0
ATOM 30 C 0 -4.640 0.467 -2.095 0.00 0.00 C+0
ATOM 31 N 0 -4.881 -0.872 -2.653 0.00 0.00 N+0
ATOM 32 C 0 -4.946 -1.017 -4.018 0.00 0.00 C+0
ATOM 33 N 0 -4.902 -2.282 -4.555 0.00 0.00 N+0
ATOM 34 N 0 -5.047 -0.005 -4.816 0.00 0.00 N+0
ATOM 35 C 0 -5.083 1.382 -4.365 0.00 0.00 C+0
ATOM 36 C 0 -5.498 1.459 -2.894 0.00 0.00 C+0
ATOM 37 N 0 -4.267 -0.508 0.129 0.00 0.00 N+0
ATOM 38 C 0 -2.915 -0.341 0.118 0.00 0.00 C+0
ATOM 39 C 0 -2.074 -1.277 0.868 0.00 0.00 C+0
ATOM 40 N 0 -0.668 -1.027 0.915 0.00 0.00 N+0
ATOM 41 C 0 -2.611 -2.343 1.497 0.00 0.00 C+0
ATOM 42 N 0 -2.055 -3.592 1.332 0.00 0.00 N+0
ATOM 43 C 0 -2.517 -4.636 2.049 0.00 0.00 C+0
ATOM 44 N 0 -1.972 -5.858 1.888 0.00 0.00 N+0
ATOM 45 O 0 -3.426 -4.475 2.841 0.00 0.00 O+0
ATOM 46 O 0 -2.412 0.574 -0.508 0.00 0.00 O+0
ATOM 47 O 0 -5.134 1.908 1.341 0.00 0.00 O+0
ATOM 48 H 0 -0.464 5.397 0.802 0.00 0.00 H+0
ATOM 49 H 0 -1.948 5.715 0.239 0.00 0.00 H+0
ATOM 50 H 0 -1.287 3.636 -0.511 0.00 0.00 H+0
ATOM 51 H 0 1.048 3.764 0.838 0.00 0.00 H+0
ATOM 52 H 0 0.931 2.223 3.302 0.00 0.00 H+0
ATOM 53 H 0 1.823 -0.127 3.510 0.00 0.00 H+0
ATOM 54 H 0 1.909 -2.338 2.639 0.00 0.00 H+0
ATOM 55 H 0 2.276 -2.628 0.244 0.00 0.00 H+0
ATOM 56 H 0 1.759 -0.956 -0.078 0.00 0.00 H+0
ATOM 57 H 0 3.914 -0.886 1.746 0.00 0.00 H+0
ATOM 58 H 0 5.881 0.416 0.442 0.00 0.00 H+0
ATOM 59 H 0 6.397 -1.257 0.765 0.00 0.00 H+0
ATOM 60 H 0 6.609 -1.617 -1.713 0.00 0.00 H+0
ATOM 61 H 0 6.141 1.257 -1.757 0.00 0.00 H+0
ATOM 62 H 0 6.661 0.381 -3.015 0.00 0.00 H+0
ATOM 63 H 0 8.191 0.775 -0.673 0.00 0.00 H+0
ATOM 64 H 0 8.547 -0.922 -0.273 0.00 0.00 H+0
ATOM 65 H 0 8.857 -1.424 -2.682 0.00 0.00 H+0
ATOM 66 H 0 8.501 0.274 -3.081 0.00 0.00 H+0
ATOM 67 H 0 10.446 1.001 -1.725 0.00 0.00 H+0
ATOM 68 H 0 10.802 -0.696 -1.326 0.00 0.00 H+0
ATOM 69 H 0 10.791 0.542 -3.959 0.00 0.00 H+0
ATOM 70 H 0 12.097 0.087 -3.118 0.00 0.00 H+0
ATOM 71 H 0 3.412 1.973 2.998 0.00 0.00 H+0
ATOM 72 H 0 3.261 2.736 1.397 0.00 0.00 H+0
ATOM 73 H 0 3.812 4.230 3.045 0.00 0.00 H+0
ATOM 74 H 0 -3.257 3.094 1.721 0.00 0.00 H+0
ATOM 75 H 0 -3.702 4.172 0.377 0.00 0.00 H+0
ATOM 76 H 0 -3.178 2.470 -1.121 0.00 0.00 H+0
ATOM 77 H 0 -5.339 2.632 -0.584 0.00 0.00 H+0
ATOM 78 H 0 -6.111 0.276 -0.532 0.00 0.00 H+0
ATOM 79 H 0 -3.585 0.725 -2.192 0.00 0.00 H+0
ATOM 80 H 0 -4.992 -1.639 -2.069 0.00 0.00 H+0
ATOM 81 H 0 -4.827 -3.054 -3.971 0.00 0.00 H+0
ATOM 82 H 0 -4.947 -2.404 -5.516 0.00 0.00 H+0
ATOM 83 H 0 -4.093 1.823 -4.483 0.00 0.00 H+0
ATOM 84 H 0 -5.799 1.938 -4.970 0.00 0.00 H+0
ATOM 85 H 0 -6.551 1.195 -2.796 0.00 0.00 H+0
ATOM 86 H 0 -5.334 2.470 -2.520 0.00 0.00 H+0
ATOM 87 H 0 -4.691 -1.242 0.601 0.00 0.00 H+0
ATOM 88 H 0 -0.246 -0.306 0.422 0.00 0.00 H+0
ATOM 89 H 0 -3.478 -2.217 2.129 0.00 0.00 H+0
ATOM 90 H 0 -1.330 -3.721 0.701 0.00 0.00 H+0
ATOM 91 H 0 -1.247 -5.987 1.257 0.00 0.00 H+0
ATOM 92 H 0 -2.305 -6.609 2.404 0.00 0.00 H+0
ATOM 93 H 0 -4.936 2.796 1.668 0.00 0.00 H+0
CONECT 1 2 48 49 0 NONE 98
CONECT 2 1 3 26 50 NONE 99
CONECT 3 2 4 25 0 NONE 100
CONECT 4 3 5 51 0 NONE 101
CONECT 5 4 6 23 52 NONE 102
CONECT 6 5 7 22 0 NONE 103
CONECT 7 6 8 53 0 NONE 104
CONECT 8 7 9 11 54 NONE 105
CONECT 9 8 40 10 0 NONE 106
CONECT 10 9 0 0 0 NONE 107
CONECT 11 8 12 55 56 NONE 108
CONECT 12 11 13 57 0 NONE 109
CONECT 13 12 14 21 0 NONE 110
CONECT 14 13 15 58 59 NONE 111
CONECT 15 14 16 17 60 NONE 112
CONECT 16 15 61 62 0 NONE 113
CONECT 17 15 18 63 64 NONE 114
CONECT 18 17 19 65 66 NONE 115
CONECT 19 18 20 67 68 NONE 116
CONECT 20 19 69 70 0 NONE 117
CONECT 21 13 0 0 0 NONE 118
CONECT 22 6 0 0 0 NONE 119
CONECT 23 5 24 71 72 NONE 120
CONECT 24 23 73 0 0 NONE 121
CONECT 25 3 0 0 0 NONE 122
CONECT 26 2 27 74 75 NONE 123
CONECT 27 26 28 76 0 NONE 124
CONECT 28 27 29 47 77 NONE 125
CONECT 29 28 30 37 78 NONE 126
CONECT 30 29 36 31 79 NONE 127
CONECT 31 30 32 80 0 NONE 128
CONECT 32 31 33 34 0 NONE 129
CONECT 33 32 81 82 0 NONE 130
CONECT 34 32 35 0 0 NONE 131
CONECT 35 34 36 83 84 NONE 132
CONECT 36 35 30 85 86 NONE 133
CONECT 37 29 38 87 0 NONE 134
CONECT 38 37 39 46 0 NONE 135
CONECT 39 38 40 41 0 NONE 136
CONECT 40 39 9 88 0 NONE 137
CONECT 41 39 42 89 0 NONE 138
CONECT 42 41 43 90 0 NONE 139
CONECT 43 42 44 45 0 NONE 140
CONECT 44 43 91 92 0 NONE 141
CONECT 45 43 0 0 0 NONE 142
CONECT 46 38 0 0 0 NONE 143
CONECT 47 28 93 0 0 NONE 144
END NONE 145
M END</inlineContents>
</jmolApplet>
</jmol>

It07:Capreomycin

2007-10-22T07:51:37Z

Jhl406: /* Capreomycin */

It07:Capreomycin

2007-10-22T07:51:08Z

Jhl406: /* Capreomycin */

== Capreomycin ==
Capreomycin is used in the treatment of Tuberculosis, TB, but its use is limited due to harmful side effects. Capreomycin is found in the aminoglycoside family of antibiotics. They have the ability to kill a wide variety of bacteria by binding to the bacterial cell which results in the formation of abnormal proteins. Proteins are necessary for the bacteria's survival and thus the abnormal proteins will kill the bacteria. The bacteria responsible for tuberculosis (TB) is difficult to kill and so capreomycin is prescribed in combination with other medications that target the bacteria in different ways. It is risky to treat TB using capreomycin alone as the bacteria can develop resistance. Capreomycin is only used when the bacteria are resistant to the drugs that are usually prescribed to treat TB.

It07:Sibutramine

2007-10-22T07:42:53Z

Jhl406: /* General Information */

== General Information ==
'''Name''':Sibutramine
<br>'''IUPAC Systematic Name:''' 1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
<br>'''Molecular Formula:'''C<sub>17</sub>H<sub>26</sub>ClN
<br>'''Molecular Weight:'''279.84804g/mol

== 3D Model of Sibutramine ==

<jmol>
<jmolApplet>
<size>400</size>
<title>Sibutramine</title><color>white</color>
<uploadedFileContents>Sibutramine.MOL</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>

</jmol>

== General Information ==
Sibutramine has been used as an appetite suppressant since it was approved by the FDA in the US in 1997. It is produced and marketed by Knoll Pharmaceuticals and is available in over 40 countries.
<br>
It was originally evaluated as an antidepressent due to its mechanism action being similar to the tricyclic group of antidepressents, such as [http://en.wikipedia.org/wiki/Amitriptyline Amitriptyline] without having the same negative side effects as Amitriptyline

Sibutramine is found in a class of medications called appetite suppressants. Sibutramine is commonly used in conjunction with a reduced calorie diet and exercise to help overweight people diminish their appetite. It primary mechanism involves acting on neurotransmitters that control appetite in the brain to decrease appetite.

Sibutramine specifically blocks the reuptake of the neurotransmitters dopamine, norepinephrine, and serotonin. These brain chemicals influence feelings of hunger and fullness and taking sibutramine will induce the sensation of feeling full sooner when you eat and thus the patient will eat less.

== Reaction Mechanism for the Synthesis of Sibutramine ==

[[Image:Subutraminereactionpicture.gif|centre|300|4-step Synthesis of Sibutramine]]<ref>[http://www.rsc.org/publishing/journals/article.asp?doi=p19960002583 Jeffery, J. E. J. E. (1996). "Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites." Journal of the Chemical Society. Perkin transactions 1(21): 2583-2589.]</ref>

== References==
<references/>