ChemWiki - User contributions [en]

It:Astemizole

2006-12-08T13:22:41Z

Jc905: /* Useful Links */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Astemizole [http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00585.txt]
|-
! {{chembox header}} colspan="3" |Structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Astemizole.gif|200px|Ceftriaxone]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
ATOM 1 F 0 -5.273 -4.650 -1.822 0.00 0.00 F+0
ATOM 2 C 0 -5.140 -3.573 -1.018 0.00 0.00 C+0
ATOM 3 C 0 -4.018 -3.440 -0.218 0.00 0.00 C+0
ATOM 4 C 0 -3.883 -2.338 0.605 0.00 0.00 C+0
ATOM 5 C 0 -4.868 -1.368 0.629 0.00 0.00 C+0
ATOM 6 C 0 -4.719 -0.166 1.526 0.00 0.00 C+0
ATOM 7 N 0 -4.028 0.902 0.801 0.00 0.00 N+0
ATOM 8 C 0 -4.620 1.892 0.034 0.00 0.00 C+0
ATOM 9 C 0 -5.932 2.199 -0.292 0.00 0.00 C+0
ATOM 10 C 0 -6.203 3.283 -1.102 0.00 0.00 C+0
ATOM 11 C 0 -5.171 4.068 -1.594 0.00 0.00 C+0
ATOM 12 C 0 -3.861 3.777 -1.281 0.00 0.00 C+0
ATOM 13 C 0 -3.571 2.683 -0.462 0.00 0.00 C+0
ATOM 14 N 0 -2.412 2.154 0.013 0.00 0.00 N+0
ATOM 15 C 0 -2.679 1.111 0.760 0.00 0.00 C+0
ATOM 16 N 0 -1.737 0.335 1.401 0.00 0.00 N+0
ATOM 17 C 0 -0.313 0.655 1.272 0.00 0.00 C+0
ATOM 18 C 0 0.446 0.112 2.487 0.00 0.00 C+0
ATOM 19 C 0 1.945 0.349 2.291 0.00 0.00 C+0
ATOM 20 N 0 2.409 -0.368 1.098 0.00 0.00 N+0
ATOM 21 C 0 3.846 -0.090 0.970 0.00 0.00 C+0
ATOM 22 C 0 4.378 -0.733 -0.312 0.00 0.00 C+0
ATOM 23 C 0 5.874 -0.563 -0.376 0.00 0.00 C+0
ATOM 24 C 0 6.701 -1.524 0.175 0.00 0.00 C+0
ATOM 25 C 0 8.073 -1.370 0.118 0.00 0.00 C+0
ATOM 26 C 0 8.620 -0.251 -0.493 0.00 0.00 C+0
ATOM 27 O 0 9.969 -0.098 -0.550 0.00 0.00 O+0
ATOM 28 C 0 10.216 1.135 -1.230 0.00 0.00 C+0
ATOM 29 C 0 7.787 0.712 -1.045 0.00 0.00 C+0
ATOM 30 C 0 6.416 0.551 -0.990 0.00 0.00 C+0
ATOM 31 C 0 1.756 0.246 -0.063 0.00 0.00 C+0
ATOM 32 C 0 0.246 0.003 0.004 0.00 0.00 C+0
ATOM 33 C 0 -5.988 -1.500 -0.170 0.00 0.00 C+0
ATOM 34 C 0 -6.123 -2.599 -0.997 0.00 0.00 C+0
ATOM 35 H 0 -3.248 -4.198 -0.236 0.00 0.00 H+0
ATOM 36 H 0 -3.008 -2.234 1.229 0.00 0.00 H+0
ATOM 37 H 0 -5.706 0.182 1.832 0.00 0.00 H+0
ATOM 38 H 0 -4.141 -0.441 2.408 0.00 0.00 H+0
ATOM 39 H 0 -6.741 1.592 0.087 0.00 0.00 H+0
ATOM 40 H 0 -7.225 3.522 -1.356 0.00 0.00 H+0
ATOM 41 H 0 -5.395 4.913 -2.227 0.00 0.00 H+0
ATOM 42 H 0 -3.062 4.391 -1.668 0.00 0.00 H+0
ATOM 43 H 0 -2.017 -0.423 1.937 0.00 0.00 H+0
ATOM 44 H 0 -0.186 1.736 1.216 0.00 0.00 H+0
ATOM 45 H 0 0.111 0.628 3.387 0.00 0.00 H+0
ATOM 46 H 0 0.257 -0.957 2.587 0.00 0.00 H+0
ATOM 47 H 0 2.130 1.416 2.166 0.00 0.00 H+0
ATOM 48 H 0 2.487 -0.012 3.165 0.00 0.00 H+0
ATOM 49 H 0 4.005 0.988 0.930 0.00 0.00 H+0
ATOM 50 H 0 4.374 -0.502 1.830 0.00 0.00 H+0
ATOM 51 H 0 4.132 -1.794 -0.315 0.00 0.00 H+0
ATOM 52 H 0 3.920 -0.251 -1.176 0.00 0.00 H+0
ATOM 53 H 0 6.275 -2.395 0.650 0.00 0.00 H+0
ATOM 54 H 0 8.719 -2.121 0.549 0.00 0.00 H+0
ATOM 55 H 0 9.789 1.089 -2.231 0.00 0.00 H+0
ATOM 56 H 0 9.757 1.953 -0.676 0.00 0.00 H+0
ATOM 57 H 0 11.291 1.301 -1.300 0.00 0.00 H+0
ATOM 58 H 0 8.211 1.584 -1.520 0.00 0.00 H+0
ATOM 59 H 0 5.768 1.300 -1.420 0.00 0.00 H+0
ATOM 60 H 0 1.950 1.318 -0.063 0.00 0.00 H+0
ATOM 61 H 0 2.153 -0.194 -0.977 0.00 0.00 H+0
ATOM 62 H 0 0.051 -1.069 0.029 0.00 0.00 H+0
ATOM 63 H 0 -0.232 0.441 -0.872 0.00 0.00 H+0
ATOM 64 H 0 -6.757 -0.741 -0.150 0.00 0.00 H+0
ATOM 65 H 0 -6.999 -2.701 -1.621 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 70
CONECT 2 1 34 3 0 NONE 71
CONECT 3 2 4 35 0 NONE 72
CONECT 4 3 5 36 0 NONE 73
CONECT 5 4 6 33 0 NONE 74
CONECT 6 5 7 37 38 NONE 75
CONECT 7 6 15 8 0 NONE 76
CONECT 8 7 13 9 0 NONE 77
CONECT 9 8 10 39 0 NONE 78
CONECT 10 9 11 40 0 NONE 79
CONECT 11 10 12 41 0 NONE 80
CONECT 12 11 13 42 0 NONE 81
CONECT 13 12 8 14 0 NONE 82
CONECT 14 13 15 0 0 NONE 83
CONECT 15 14 7 16 0 NONE 84
CONECT 16 15 17 43 0 NONE 85
CONECT 17 16 32 18 44 NONE 86
CONECT 18 17 19 45 46 NONE 87
CONECT 19 18 20 47 48 NONE 88
CONECT 20 19 21 31 0 NONE 89
CONECT 21 20 22 49 50 NONE 90
CONECT 22 21 23 51 52 NONE 91
CONECT 23 22 30 24 0 NONE 92
CONECT 24 23 25 53 0 NONE 93
CONECT 25 24 26 54 0 NONE 94
CONECT 26 25 27 29 0 NONE 95
CONECT 27 26 28 0 0 NONE 96
CONECT 28 27 55 56 57 NONE 97
CONECT 29 26 30 58 0 NONE 98
CONECT 30 29 23 59 0 NONE 99
CONECT 31 20 32 60 61 NONE 100
CONECT 32 31 17 62 63 NONE 101
CONECT 33 5 34 64 0 NONE 102
CONECT 34 33 2 65 0 NONE 103
END NONE 104
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]
-4-piperidyl]benzoimidazol-2-amine
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>28</sub>H<sub>31</sub>FN<sub>4</sub>O<sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |FC1=CC=C(CN3C2=CC=CC=C2N=C3NC4CCN
(CCC5=CC=C(OC)C=C5)CC4)C=C1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |458.571 g/mol
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 Water]
| colspan="2" | 432 mg/L
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" | 149.1°C
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

== Overview ==

'''Astemizole''' (brand name Hismanal) is an antihistamine that provides relief from seasonal allergies such as rash, hives, watery eyes, runny nose, itching eyes and sneezing. Only avaialbale on prescription (although withdrawn from the US market) the 10mg tablets should be taken on an emty stomach with a full glass of water.

== Medical Advice [http://www.personalmd.com/drgdb/5012.htm] ==

*'''Side Effects''' - may cause headache, increased appetite, stomach upset, nervousness, dry mouth although these should lesson as ones body adjusts to the drug (''notify doctor immediately'' if effects worsen or if one experiences dizziness, fainting, fast/irregular heartbeat)
*'''Precautions''' - advise doctor if one has pre-existing heart, kidney or liver disease, asthma or breathing problems, allergies or a history of drug dependence. Limit alcohol intaken and avoid use during pregnancy and during breast feeding
*'''Drug Interaction''' - advise doctor if one is taking sleeping pills, sedatives, tranquilizers, quinine, muscle relaxants, medication for depression. Also do not eat grapefruit or drink grapefruit juice!
*'''Overdose''' - Contact your doctor immediately if overdose is suspected. Symptoms of overdose may include dizziness, irregular or fast heartbeat, fainting, loss of consciousness, and seizures

== Synthesis ==
[[Image:synthesis of astemizole.jpg|centre|300|Reaction scheme showing Sibutramine synthesis]]

The above synthesis and reaction details below have been taken from Beilstein:

*Yield=48 percent
*Reagent=Na2CO3
*Solvent=dimethylformamide
*Temperature=70 C

Reference: ''5803865;Original Document via LinkFinderPlus; Journal; Janssens, Frans; Torremans, Joseph; Janssen, Marcel; Stokbroekx, Raymond A.; Luyckx, Marcel; Janssen, Paul A. J.; JMCMAR; J. Med. Chem.; EN; 28; 12; 1985; 1934-1943.''

== References ==
1-data taken from [http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00585.txt]

2-information summerised from [http://www.personalmd.com/drgdb/5012.htm]

== Useful Links ==

*Personal MD [http://www.personalmd.com/drgdb/5012.htm]
*Yahoo Health [http://health.yahoo.com/drug/d00794a1]
*Drug Bank [http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00585.txt]
*3DChem [http://www.3dchem.com/molecules.asp?ID=20]

It:Astemizole

2006-12-08T13:20:00Z

Jc905: /* References */

2006-11-20T15:34:26Z

Jc905: /* Side effects of rofecoxib */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)'''

|-
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]]
|-
| [[IUPAC nomenclature|Chemical name]]
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''
|-
| [[CAS nummber]]
| 162011-90-7
|-
| [[Chemical formula]]
| C17 H14 O4 S
|-
| [[Molecular mass]]
| {{{mol_mass|314.355768 g/mol
|-
| And here is a 3D picture:
| <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>Sertraline.mol
title1
title2
36 38 0 0 0 0 0 0 0 0999 V2000
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0
1 2 2 0 0 0
2 3 1 0 0 0
2 4 1 0 0 0
3 5 2 0 0 0
3 6 1 0 0 0
4 7 1 0 0 0
5 7 1 0 0 0
5 8 1 0 0 0
6 9 2 0 0 0
6 10 1 0 0 0
8 11 2 0 0 0
8 12 1 0 0 0
9 13 1 0 0 0
10 14 2 0 0 0
11 15 1 0 0 0
12 16 2 0 0 0
13 17 2 0 0 0
14 17 1 0 0 0
15 18 2 0 0 0
16 18 1 0 0 0
18 19 1 0 0 0
19 20 1 0 0 0
19 21 2 0 0 0
19 22 2 0 0 0
7 23 1 0 0 0
7 24 1 0 0 0
9 25 1 0 0 0
10 26 1 0 0 0
11 27 1 0 0 0
12 28 1 0 0 0
13 29 1 0 0 0
14 30 1 0 0 0
15 31 1 0 0 0
16 32 1 0 0 0
17 33 1 0 0 0
20 34 1 0 0 0
20 35 1 0 0 0
20 36 1 0 0 0

M END</inlineContents>
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|-
|}
'''Vioxx''', also known as Rofecoxib, is a nonsteroidal anti-inflammatory drug (NSAID) with the IUPAC systematic name of 4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one. It was developed by Merck & Co. to relieve the pain, tenderness, inflammation and stiffness caused by arthritis and to treat painful menstrual periods. Rofecoxib is a selective and orally active inhibitor of Cyclooxygenase-2.

Merck & Co. have announced the voluntary worldwide withdrawal of rofecoxib on 30th September 2004 after concerns of an increased risk of cardiovascular events such as heart attack and stroke was discovered in patients taking rofecoxib.[http://www.vioxx.com/rofecoxib/vioxx/consumer/index.jsp 1]

==Synthesis of rofecoxib==

==Side effects of rofecoxib==
abdominal pain
tenderness

== 3D Structure ==

<jmol>
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<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 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 41
CONECT 2 1 16 3 0 NONE 42
CONECT 3 2 4 0 0 NONE 43
CONECT 4 3 5 23 24 NONE 44
CONECT 5 4 6 16 0 NONE 45
CONECT 6 5 15 7 0 NONE 46
CONECT 7 6 8 25 0 NONE 47
CONECT 8 7 9 26 0 NONE 48
CONECT 9 8 10 14 0 NONE 49
CONECT 10 9 11 12 13 NONE 50
CONECT 11 10 27 28 29 NONE 51
CONECT 12 10 0 0 0 NONE 52
CONECT 13 10 0 0 0 NONE 53
CONECT 14 9 15 30 0 NONE 54
CONECT 15 14 6 31 0 NONE 55
CONECT 16 5 2 17 0 NONE 56
CONECT 17 16 22 18 0 NONE 57
CONECT 18 17 19 32 0 NONE 58
CONECT 19 18 20 33 0 NONE 59
CONECT 20 19 21 34 0 NONE 60
CONECT 21 20 22 35 0 NONE 61
CONECT 22 21 17 36 0 NONE 62
END NONE 63</inlineContents>
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</jmol>