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ChemWiki - User contributions [en]
2026-04-03T18:03:57Z
User contributions
MediaWiki 1.43.0
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7684
It:TNT
2006-12-07T18:35:40Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure and properties==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
<br />
It has a melting point of 80.35°C.<br />
<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
It has a molar mass of 227.131 g/mol.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Synthesis of TNT==<br />
<br />
Trinitrotoluene can be synthesised by the stepwise nitration of toluene involving a primary, secondary and tertiary nitration.<br />
<br />
[[Image:TNTSYNTHESIS.bmp]]</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=File:TNTSYNTHESIS.bmp&diff=7682
File:TNTSYNTHESIS.bmp
2006-12-07T18:31:42Z
<p>Yf205: </p>
<hr />
<div></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7673
It:TNT
2006-12-07T18:22:44Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure and properties==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
<br />
It has a melting point of 80.35°C.<br />
<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
It has a molar mass of 227.131 g/mol.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Synthesis of TNT==</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7670
It:TNT
2006-12-07T18:20:03Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure and properties==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
<br />
It has a melting point of 80.35°C.<br />
<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
It has a molar mass of 227.131 g/mol.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7668
It:TNT
2006-12-07T18:19:38Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
<br />
It has a melting point of 80.35°C.<br />
<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
It has a molar mass of 227.131 g/mol.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7647
It:TNT
2006-12-07T17:58:08Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
<br />
It has a melting point of 80.35°C.<br />
<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7646
It:TNT
2006-12-07T17:57:50Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Structure==<br />
<br />
Trinitrotoluene is in the form of long yellow crystals.<br />
It has a melting point of 80.35°C.<br />
It has a density of 1.654g/cm<sup>3</sup>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7644
It:TNT
2006-12-07T17:50:02Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and also as weaponry.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. The nitration of toluene is a simple method of synthesising trinitrotoluene in the laboratory.<br />
<br />
==Physical structure==<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7639
It:TNT
2006-12-07T17:36:32Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
Trinitrotoluene is a high explosive that is immune to ordinary shocks and so it must be set off by a detonator. This makes it relatively safe and so it is commonly used in construction and arms.<br />
<br />
Trinitrotoluene was invented by Joseph Wilbrand in 1863. <br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7634
It:TNT
2006-12-07T17:29:17Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
The big explosion picture is from http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7632
It:TNT
2006-12-07T17:28:51Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]From http://www.hnd.usace.army.mil/pao/CEAInfo/<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7631
It:TNT
2006-12-07T17:28:28Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]From http://www.hnd.usace.army.mil/pao/CEAInfo/Explosion%20Photo.JPG<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7629
It:TNT
2006-12-07T17:27:48Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
[[Image:TNT.bmp]][[Image:bang.jpg]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Bang.jpg&diff=7628
File:Bang.jpg
2006-12-07T17:27:13Z
<p>Yf205: </p>
<hr />
<div></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=File:TNT.bmp&diff=7626
File:TNT.bmp
2006-12-07T17:19:54Z
<p>Yf205: </p>
<hr />
<div></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7625
It:TNT
2006-12-07T17:19:33Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.<br />
<br />
[[Image:TNT.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 07-Dec-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 07-Dec-06 0 NONE 4<br />
ATOM 1 C 0 2.704 -0.001 -0.016 0.00 0.00 C+0<br />
ATOM 2 C 0 1.197 -0.001 -0.006 0.00 0.00 C+0<br />
ATOM 3 C 0 0.507 1.197 -0.002 0.00 0.00 C+0<br />
ATOM 4 N 0 1.247 2.478 -0.007 0.00 0.00 N+1<br />
ATOM 5 O 0 0.645 3.529 -0.136 0.00 0.00 O-1<br />
ATOM 6 O 0 2.459 2.482 0.117 0.00 0.00 O+0<br />
ATOM 7 C 0 -0.876 1.198 0.006 0.00 0.00 C+0<br />
ATOM 8 C 0 -1.567 0.001 0.011 0.00 0.00 C+0<br />
ATOM 9 N 0 -3.048 0.002 0.021 0.00 0.00 N+1<br />
ATOM 10 O 0 -3.656 1.057 0.024 0.00 0.00 O-1<br />
ATOM 11 O 0 -3.657 -1.053 0.025 0.00 0.00 O+0<br />
ATOM 12 C 0 -0.877 -1.197 0.007 0.00 0.00 C+0<br />
ATOM 13 C 0 0.505 -1.197 -0.007 0.00 0.00 C+0<br />
ATOM 14 N 0 1.245 -2.480 -0.011 0.00 0.00 N+1<br />
ATOM 15 O 0 0.639 -3.532 -0.108 0.00 0.00 O-1<br />
ATOM 16 O 0 2.459 -2.483 0.081 0.00 0.00 O+0<br />
ATOM 17 H 0 3.074 -0.062 1.008 0.00 0.00 H+0<br />
ATOM 18 H 0 3.063 -0.860 -0.583 0.00 0.00 H+0<br />
ATOM 19 H 0 3.065 0.917 -0.478 0.00 0.00 H+0<br />
ATOM 20 H 0 -1.415 2.133 0.009 0.00 0.00 H+0<br />
ATOM 21 H 0 -1.417 -2.132 0.011 0.00 0.00 H+0<br />
CONECT 1 2 17 18 19 NONE 26<br />
CONECT 2 1 13 3 0 NONE 27<br />
CONECT 3 2 4 7 0 NONE 28<br />
CONECT 4 3 5 6 0 NONE 29<br />
CONECT 5 4 0 0 0 NONE 30<br />
CONECT 6 4 0 0 0 NONE 31<br />
CONECT 7 3 8 20 0 NONE 32<br />
CONECT 8 7 9 12 0 NONE 33<br />
CONECT 9 8 10 11 0 NONE 34<br />
CONECT 10 9 0 0 0 NONE 35<br />
CONECT 11 9 0 0 0 NONE 36<br />
CONECT 12 8 13 21 0 NONE 37<br />
CONECT 13 12 2 14 0 NONE 38<br />
CONECT 14 13 15 16 0 NONE 39<br />
CONECT 15 14 0 0 0 NONE 40<br />
CONECT 16 14 0 0 0 NONE 41<br />
END NONE 42<br />
</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=File:TNT.cdx&diff=7619
File:TNT.cdx
2006-12-07T17:04:30Z
<p>Yf205: Stucture of TNT</p>
<hr />
<div>Stucture of TNT</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:TNT&diff=7606
It:TNT
2006-12-07T16:46:24Z
<p>Yf205: </p>
<hr />
<div>TNT is the acronym for the explosive chemical with the common name trinitrotoluene. Its IUPAC name is 2-methyl-1,3,5-trinitrobenzene and it has the chemical formula C<sub>7</sub>H<sub>5</sub>N<sub>3</sub>O<sub>6</sub>.</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5737
It:Vioxx
2006-11-20T17:13:28Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| Melting point<br />
| 204.7 [http://lfp.mimas.ac.uk/lfp/LinkFinderPlus/Display?&PAG=1778+-+1779&CNR=6311904&AU=Therien,+Michel%3b+Gauthier,+Jacques+Yves%3b+Leblanc,+Yves%3b+Leger,+Serge%3b+Perrier,+Helene%3b+Prasit,+Petpiboon%3b+Wang,+Zhaoyin&NB=12&LA=EN&PY=2001&JT=Synthesis&CO=SYNTBF&CED=2002%2f03%2f31&DT=Journal&_Origin=Beilstein]<br />
|-<br />
| And here is a 3D picture:<br />
| <br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl<sub>3</sub><br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects. Most NSAIDs act as non-selective inhibitors of the enzyme cyclooxygenase, inhibiting both the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes. Rofecoxib is an NSAID that selectively acts only on the cyclooxygenase-2 (COX-2) isoenzyme. This selectivity was thought to be beneficial because COX-2 is responsible for pain and inflammation and COX-1 is responsible for the protection of the stomach lining. Therefore, the drug developers were aiming for an NSAID without the side effects to the gastrointestinal system.[http://www.medinfo.co.uk/drugs/nsaids.html 2]<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
==Legal status==<br />
<br />
Rofecoxib was initially FDA-approved on 21st May 1999.<br />
<br />
== 3D Structure ==<br />
<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5730
It:Vioxx
2006-11-20T16:56:52Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| Melting point<br />
| 204.7 [http://lfp.mimas.ac.uk/lfp/LinkFinderPlus/Display?&PAG=1778+-+1779&CNR=6311904&AU=Therien,+Michel%3b+Gauthier,+Jacques+Yves%3b+Leblanc,+Yves%3b+Leger,+Serge%3b+Perrier,+Helene%3b+Prasit,+Petpiboon%3b+Wang,+Zhaoyin&NB=12&LA=EN&PY=2001&JT=Synthesis&CO=SYNTBF&CED=2002%2f03%2f31&DT=Journal&_Origin=Beilstein]<br />
|-<br />
| And here is a 3D picture:<br />
| <br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl<sub>3</sub><br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects. Most NSAIDs act as non-selective inhibitors of the enzyme cyclooxygenase, inhibiting both the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes. Rofecoxib is an NSAID that selectively acts only on the cyclooxygenase-2 (COX-2) isoenzyme. This selectivity was thought to be beneficial because COX-2 is responsible for pain and inflammation and COX-1 is responsible for the protection of the stomach lining. Therefore, the drug developers were aiming for an NSAID without the side effects to the gastrointestinal system.[http://www.medinfo.co.uk/drugs/nsaids.html 2]<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5729
It:Vioxx
2006-11-20T16:55:05Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| Melting point<br />
| 204.7 [http://lfp.mimas.ac.uk/lfp/LinkFinderPlus/Display?&PAG=1778+-+1779&CNR=6311904&AU=Therien,+Michel%3b+Gauthier,+Jacques+Yves%3b+Leblanc,+Yves%3b+Leger,+Serge%3b+Perrier,+Helene%3b+Prasit,+Petpiboon%3b+Wang,+Zhaoyin&NB=12&LA=EN&PY=2001&JT=Synthesis&CO=SYNTBF&CED=2002%2f03%2f31&DT=Journal&_Origin=Beilstein]<br />
|-<br />
| And here is a 3D picture:<br />
| <br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl<sub>3</sub><br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects. Most NSAIDs act as non-selective inhibitors of the enzyme cyclooxygenase, inhibiting both the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes. Rofecoxib is an NSAID that selectively acts only on the cyclooxygenase-2 (COX-2) isoenzyme. This selectivity was thought to be beneficial because COX-2 is responsible for pain and inflammation and COX-1 is responsible for the protection of the stomach lining. Therefore, the drug developers were aiming for an NSAID without the side effects to the gastrointestinal system.<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5725
It:Vioxx
2006-11-20T16:44:54Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| Melting point<br />
| 204.7 [http://lfp.mimas.ac.uk/lfp/LinkFinderPlus/Display?&PAG=1778+-+1779&CNR=6311904&AU=Therien,+Michel%3b+Gauthier,+Jacques+Yves%3b+Leblanc,+Yves%3b+Leger,+Serge%3b+Perrier,+Helene%3b+Prasit,+Petpiboon%3b+Wang,+Zhaoyin&NB=12&LA=EN&PY=2001&JT=Synthesis&CO=SYNTBF&CED=2002%2f03%2f31&DT=Journal&_Origin=Beilstein]<br />
|-<br />
| And here is a 3D picture:<br />
| <br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl<sub>3</sub><br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects. Most NSAIDs act as non-selective inhibitors of the enzyme cyclooxygenase, inhibiting both the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes. Rofecoxib is an NSAID that selectively acts only on the cyclooxygenase-2 (COX-2) isoenzyme.<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5716
It:Vioxx
2006-11-20T16:33:25Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl<sub>3</sub><br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects.<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5714
It:Vioxx
2006-11-20T16:31:19Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects.<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5713
It:Vioxx
2006-11-20T16:30:21Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
Rofecoxib belongs to a group of drugs called the nonsteroidal anti-inflammatory drugs (NSAID). They are drugs with analgesic (reduce pain), antipyretic (reduce fever) and anti-inflammatory (reduce inflammation) effects.<br />
<br />
==Side effects of Vioxx==<br />
<br />
Allergic reaction (difficulty breathing; closing of your throat; swelling of your lips, tongue, or face; or hives),<br />
<br />
Abdominal pain,<br />
<br />
Tenderness,<br />
<br />
Discomfort; <br />
<br />
Nausea;<br />
<br />
Blood in your vomit; <br />
<br />
Bloody,<br />
<br />
Black, <br />
<br />
Tarry stools; <br />
<br />
Unexplained weight gain; <br />
<br />
Swelling or water retention;<br />
<br />
Fatigue or lethargy; a skin rash; <br />
<br />
Itching; <br />
<br />
Yellowing of your skin or eyes;<br />
<br />
"Flu-like" symptoms; <br />
<br />
Unusual bruising or bleeding.<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5693
It:Vioxx
2006-11-20T16:05:39Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Mechanism of action==<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5692
It:Vioxx
2006-11-20T16:03:57Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
[[Image:SYNTHESIS DIAG.bmp]][http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf Diagram of the synthesis of rofecoxib]<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5683
It:Vioxx
2006-11-20T15:59:14Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. ''Rofecoxib''<br />
<br />
'''2'''. ''Thioanisole''<br />
<br />
'''3'''. ''Acetophenone'' - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. ''Sulfone'' - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. ''Bromoketone'' - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
'''1'''. ''Rofecoxib'' - bromoketone ('''5''') coupled and cyclized in a two step, one pot procedure with phenylacetic acid<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5681
It:Vioxx
2006-11-20T15:56:56Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. Rofecoxib<br />
<br />
'''2'''. Thioanisole<br />
<br />
'''3'''. Acetophenone - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
'''4'''. Sulfone - prepared by the oxidation of acetophenone ('''3''') with MMPP, magnesium monoperoxyphthalate hexahydrate<br />
<br />
'''5'''. Bromoketone - prepared by the reaction of the sulfone ('''4''') with bromine in chloroform at -5°C in the presence of a trace amount of AlCl3<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5675
It:Vioxx
2006-11-20T15:53:25Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. Rofecoxib<br />
<br />
'''2'''. Thioanisole<br />
<br />
'''3'''. Acetophenone - prepared by the Friedel-Crafts acylation of thioanysole ('''2''')<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5671
It:Vioxx
2006-11-20T15:52:34Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
'''1'''. Rofecoxib<br />
<br />
'''2'''. Thioanisole<br />
<br />
<br />
<br />
==Side effects of Vioxx==<br />
<br />
abdominal pain<br />
<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5650
It:Vioxx
2006-11-20T15:37:38Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]==<br />
<br />
==Side effects of rofecoxib==<br />
abdominal pain<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5648
It:Vioxx
2006-11-20T15:36:15Z
<p>Yf205: /* Synthesis of rofecoxib */</p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
4 7 1 0 0 0<br />
5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==[http://www.thieme-connect.com/ejournals/pdf/synthesis/doi/10.1055/s-2001-17519.pdf 2]<br />
<br />
==Side effects of rofecoxib==<br />
abdominal pain<br />
tenderness<br />
<br />
== 3D Structure ==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>water.mol<br />
title1<br />
title2<br />
<br />
ATOM 1 O 0 -4.931 1.018 -0.011 0.00 0.00 O+0<br />
ATOM 2 C 0 -3.796 1.451 0.018 0.00 0.00 C+0<br />
ATOM 3 O 0 -3.469 2.755 0.080 0.00 0.00 O+0<br />
ATOM 4 C 0 -2.019 2.859 0.098 0.00 0.00 C+0<br />
ATOM 5 C 0 -1.493 1.444 0.038 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.084 1.030 0.032 0.00 0.00 C+0<br />
ATOM 7 C 0 0.746 1.371 -1.043 0.00 0.00 C+0<br />
ATOM 8 C 0 2.067 0.979 -1.041 0.00 0.00 C+0<br />
ATOM 9 C 0 2.574 0.249 0.020 0.00 0.00 C+0<br />
ATOM 10 S 0 4.265 -0.247 0.013 0.00 0.00 S+0<br />
ATOM 11 C 0 5.105 1.137 0.831 0.00 0.00 C+0<br />
ATOM 12 O 0 4.255 -1.410 0.830 0.00 0.00 O+0<br />
ATOM 13 O 0 4.572 -0.300 -1.373 0.00 0.00 O+0<br />
ATOM 14 C 0 1.761 -0.093 1.087 0.00 0.00 C+0<br />
ATOM 15 C 0 0.439 0.297 1.103 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.582 0.628 -0.003 0.00 0.00 C+0<br />
ATOM 17 C 0 -2.547 -0.852 -0.067 0.00 0.00 C+0<br />
ATOM 18 C 0 -3.045 -1.610 0.993 0.00 0.00 C+0<br />
ATOM 19 C 0 -3.010 -2.988 0.927 0.00 0.00 C+0<br />
ATOM 20 C 0 -2.482 -3.617 -0.186 0.00 0.00 C+0<br />
ATOM 21 C 0 -1.987 -2.870 -1.240 0.00 0.00 C+0<br />
ATOM 22 C 0 -2.021 -1.492 -1.189 0.00 0.00 C+0<br />
ATOM 23 H 0 -1.674 3.424 -0.768 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.689 3.343 1.017 0.00 0.00 H+0<br />
ATOM 25 H 0 0.351 1.940 -1.872 0.00 0.00 H+0<br />
ATOM 26 H 0 2.708 1.241 -1.869 0.00 0.00 H+0<br />
ATOM 27 H 0 4.710 1.257 1.840 0.00 0.00 H+0<br />
ATOM 28 H 0 6.175 0.933 0.883 0.00 0.00 H+0<br />
ATOM 29 H 0 4.936 2.051 0.263 0.00 0.00 H+0<br />
ATOM 30 H 0 2.165 -0.663 1.911 0.00 0.00 H+0<br />
ATOM 31 H 0 -0.194 0.030 1.937 0.00 0.00 H+0<br />
ATOM 32 H 0 -3.457 -1.121 1.863 0.00 0.00 H+0<br />
ATOM 33 H 0 -3.394 -3.577 1.747 0.00 0.00 H+0<br />
ATOM 34 H 0 -2.456 -4.696 -0.233 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.576 -3.367 -2.107 0.00 0.00 H+0<br />
ATOM 36 H 0 -1.634 -0.910 -2.012 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 41<br />
CONECT 2 1 16 3 0 NONE 42<br />
CONECT 3 2 4 0 0 NONE 43<br />
CONECT 4 3 5 23 24 NONE 44<br />
CONECT 5 4 6 16 0 NONE 45<br />
CONECT 6 5 15 7 0 NONE 46<br />
CONECT 7 6 8 25 0 NONE 47<br />
CONECT 8 7 9 26 0 NONE 48<br />
CONECT 9 8 10 14 0 NONE 49<br />
CONECT 10 9 11 12 13 NONE 50<br />
CONECT 11 10 27 28 29 NONE 51<br />
CONECT 12 10 0 0 0 NONE 52<br />
CONECT 13 10 0 0 0 NONE 53<br />
CONECT 14 9 15 30 0 NONE 54<br />
CONECT 15 14 6 31 0 NONE 55<br />
CONECT 16 5 2 17 0 NONE 56<br />
CONECT 17 16 22 18 0 NONE 57<br />
CONECT 18 17 19 32 0 NONE 58<br />
CONECT 19 18 20 33 0 NONE 59<br />
CONECT 20 19 21 34 0 NONE 60<br />
CONECT 21 20 22 35 0 NONE 61<br />
CONECT 22 21 17 36 0 NONE 62<br />
END NONE 63</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=File:SYNTHESIS_DIAG.bmp&diff=5640
File:SYNTHESIS DIAG.bmp
2006-11-20T15:32:17Z
<p>Yf205: Common synthesis of rofecoxib</p>
<hr />
<div>Common synthesis of rofecoxib</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5628
It:Vioxx
2006-11-20T15:21:50Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
3 6 1 0 0 0<br />
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5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
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11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
16 32 1 0 0 0<br />
17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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]<br />
<br />
==Synthesis of rofecoxib==</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5623
It:Vioxx
2006-11-20T15:13:12Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
3 5 2 0 0 0<br />
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5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
9 13 1 0 0 0<br />
10 14 2 0 0 0<br />
11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
14 17 1 0 0 0<br />
15 18 2 0 0 0<br />
16 18 1 0 0 0<br />
18 19 1 0 0 0<br />
19 20 1 0 0 0<br />
19 21 2 0 0 0<br />
19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
7 24 1 0 0 0<br />
9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
15 31 1 0 0 0<br />
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17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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.<br />
<br />
==Synthesis of rofecoxib==</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5618
It:Vioxx
2006-11-20T15:08:41Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
16.4138 16.1875 -0.8276 H 0 0 0 0 0 0 0 0 0 0<br />
16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
15.4148 11.7925 -0.0326 H 0 0 0 0 0 0 0 0 0 0<br />
17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
9.6840 13.0235 -0.0192 H 0 0 0 0 0 0 0 0 0 0<br />
12.5974 10.0778 0.0261 H 0 0 0 0 0 0 0 0 0 0<br />
17.4080 10.3082 -0.0210 H 0 0 0 0 0 0 0 0 0 0<br />
19.8265 13.6638 0.0160 H 0 0 0 0 0 0 0 0 0 0<br />
10.2316 10.7555 0.0074 H 0 0 0 0 0 0 0 0 0 0<br />
22.4874 11.3178 0.1654 H 0 0 0 0 0 0 0 0 0 0<br />
21.6135 12.4141 1.0020 H 0 0 0 0 0 0 0 0 0 0<br />
21.6980 12.5078 -0.6259 H 0 0 0 0 0 0 0 0 0 0<br />
1 2 2 0 0 0<br />
2 3 1 0 0 0<br />
2 4 1 0 0 0<br />
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5 7 1 0 0 0<br />
5 8 1 0 0 0<br />
6 9 2 0 0 0<br />
6 10 1 0 0 0<br />
8 11 2 0 0 0<br />
8 12 1 0 0 0<br />
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11 15 1 0 0 0<br />
12 16 2 0 0 0<br />
13 17 2 0 0 0<br />
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16 18 1 0 0 0<br />
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19 20 1 0 0 0<br />
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19 22 2 0 0 0<br />
7 23 1 0 0 0<br />
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9 25 1 0 0 0<br />
10 26 1 0 0 0<br />
11 27 1 0 0 0<br />
12 28 1 0 0 0<br />
13 29 1 0 0 0<br />
14 30 1 0 0 0<br />
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17 33 1 0 0 0<br />
20 34 1 0 0 0<br />
20 35 1 0 0 0<br />
20 36 1 0 0 0<br />
<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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.<br />
<br />
==Synthesis of rofecoxib==</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5614
It:Vioxx
2006-11-20T15:01:41Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
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18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
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21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
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<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.<br />
<br />
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.</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5608
It:Vioxx
2006-11-20T14:54:03Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
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10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
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<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
'''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.</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5607
It:Vioxx
2006-11-20T14:53:27Z
<p>Yf205: </p>
<hr />
<div>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
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10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
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<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br />
<br />
'''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.<br />
What's up boy???</div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5601
It:Vioxx
2006-11-20T14:46:52Z
<p>Yf205: </p>
<hr />
<div>'''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.<br />
<br />
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Sertraline.mol<br />
title1<br />
title2<br />
36 38 0 0 0 0 0 0 0 0999 V2000<br />
12.4420 16.3191 -0.0067 O 0 0 0 0 0 0 0 0 0 1<br />
13.6151 15.9319 -0.0101 C 0 0 0 0 0 0 0 0 0 2<br />
14.0389 14.5359 -0.0088 C 0 0 0 0 0 0 0 0 0 3<br />
14.6700 16.8331 -0.0096 O 0 0 0 0 0 0 0 0 0 4<br />
15.3895 14.5634 -0.0109 C 0 0 0 0 0 0 0 0 0 5<br />
12.9962 13.3986 -0.0058 C 0 0 0 0 0 0 0 0 0 6<br />
15.8670 16.0043 -0.0107 C 0 0 0 0 0 0 0 0 0 7<br />
16.4856 13.5135 -0.0112 C 0 0 0 0 0 0 0 0 0 8<br />
11.7036 13.7387 -0.0153 C 0 0 0 0 0 0 0 0 0 9<br />
13.3193 11.9710 0.0098 C 0 0 0 0 0 0 0 0 0 10<br />
16.3328 12.1889 -0.0208 C 0 0 0 0 0 0 0 0 0 11<br />
17.8463 14.0562 0.0008 C 0 0 0 0 0 0 0 0 0 12<br />
10.6424 12.7383 -0.0110 C 0 0 0 0 0 0 0 0 0 13<br />
12.3565 11.0483 0.0148 C 0 0 0 0 0 0 0 0 0 14<br />
17.5233 11.3015 -0.0142 C 0 0 0 0 0 0 0 0 0 15<br />
18.9093 13.2656 0.0070 C 0 0 0 0 0 0 0 0 0 16<br />
10.9531 11.4479 0.0038 C 0 0 0 0 0 0 0 0 0 17<br />
18.7479 11.8328 0.0009 C 0 0 0 0 0 0 0 0 0 18<br />
20.2008 10.8229 0.0181 S 0 0 0 0 0 0 0 0 0 19<br />
21.6636 11.8844 0.1552 C 0 0 0 0 0 0 0 0 0 20<br />
20.2701 10.0133 -1.2622 O 0 0 0 0 0 0 0 0 0 21<br />
20.1395 9.8623 1.1899 O 0 0 0 0 0 0 0 0 0 22<br />
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16.4149 16.1869 0.8056 H 0 0 0 0 0 0 0 0 0 0<br />
11.4569 14.7077 -0.0256 H 0 0 0 0 0 0 0 0 0 0<br />
14.2769 11.6831 0.0168 H 0 0 0 0 0 0 0 0 0 0<br />
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17.9759 15.0478 0.0045 H 0 0 0 0 0 0 0 0 0 0<br />
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<br />
<br />
M END</inlineContents><br />
</jmolApplet><br />
</jmol></div>
Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5598
It:Vioxx
2006-11-20T14:42:41Z
<p>Yf205: </p>
<hr />
<div>==Vioxx==<br />
<br />
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.<br />
<br />
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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Yf205
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Vioxx&diff=5597
It:Vioxx
2006-11-20T14:37:50Z
<p>Yf205: </p>
<hr />
<div>==Vioxx==<br />
<br />
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.<br />
<br />
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
! {{chembox header}}| '''Vioxx (treatment of osteoarthritis symptoms and pain)''' <br />
<br />
<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Vioxx1.png]] <br />
|-<br />
| [[IUPAC nomenclature|Chemical name]]<br />
| ''12(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- (9CI)''<br />
|-<br />
| [[CAS nummber]]<br />
| 162011-90-7<br />
|-<br />
| [[Chemical formula]]<br />
| C17 H14 O4 S<br />
|-<br />
| [[Molecular mass]]<br />
| {{{mol_mass|314.355768 g/mol<br />
|-<br />
| And here is a 3D picture:<br />
| <jmol><br />
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Yf205