https://chemwiki.ch.ic.ac.uk/api.php?action=feedcontributions&feedformat=atom&user=Ywt05ChemWiki - User contributions [en]2026-04-20T12:20:28ZUser contributionsMediaWiki 1.43.0https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7577It:Sucralose2006-12-07T15:02:08Z<p>Ywt05: /* What is sucralose? */</p>
<hr />
<div>__toc__<br />
== What is sucralose?==<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
Sucralose is not used as a energy source in the body as it does not break down like other sugar(ie. sucrose). The majority of ingested sucralose is excreted unchanged in the feces and most of what is absorbed appears unchanged in the urine, with only minor amounts appearing as metabolites. Sucralose does not interfere with the utilization of sucrose in man.<br />
<br />
Sucralose is a disaccharide that is made from sucrose in a five-step process that<br />
selectively substitutes three atoms of chlorine for three hydroxyl<br />
groups in the sugar molecule. It is produced at an approximate purity<br />
of 98 percent. Sucralose is a free-flowing, white crystalline solid<br />
that is soluble in water and stable both in crystalline form and in<br />
most aqueous solutions.]<br />
<br />
Sucralose has been approved for use in 27 plus countries in addition to the US. It has been used commercially since 1991 in more than 400 different food products.<br />
<br />
Arguments for the use of sucralose:<br />
<br />
Hundreds of toxicity studies have shown sucralose to be a safer option than other low calorie sweeteners, such as saccharin, cyclamate, acesulfame-K and aspartame. <br />
Sucralose is heat stable.<br />
The chlorine element in sucralose is in a form that is safe and occurs naturally in other foods. (ie. salts)<br />
<br />
Arguments against the use of sucralose:<br />
Sucralose is an artificial substance that is not found in nature.<br />
It has a half life up to 23 hours, which is quite long.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html<br />
<br />
*http://www.wholefoods.com/healthinfo/sucralose.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7570It:Sucralose2006-12-07T14:56:11Z<p>Ywt05: /* References */</p>
<hr />
<div>__toc__<br />
== What is sucralose?==<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
Sucralose is not used as a energy source in the body as it does not break down like other sugar(ie. sucrose). The majority of ingested sucralose is excreted unchanged in the feces and most of what is absorbed appears unchanged in the urine, with only minor amounts appearing as metabolites. Sucralose does not interfere with the utilization of sucrose in man.<br />
<br />
Sucralose is a disaccharide that is made from sucrose in a five-step process that<br />
selectively substitutes three atoms of chlorine for three hydroxyl<br />
groups in the sugar molecule. It is produced at an approximate purity<br />
of 98 percent. Sucralose is a free-flowing, white crystalline solid<br />
that is soluble in water and stable both in crystalline form and in<br />
most aqueous solutions.]<br />
<br />
Sucralose has been approved for use in 27 plus countries in addition to the US. It has been used commercially since 1991 in more than 400 different food products.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html<br />
<br />
*http://www.wholefoods.com/healthinfo/sucralose.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7569It:Sucralose2006-12-07T14:55:18Z<p>Ywt05: /* What is sucralose? */</p>
<hr />
<div>__toc__<br />
== What is sucralose?==<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
Sucralose is not used as a energy source in the body as it does not break down like other sugar(ie. sucrose). The majority of ingested sucralose is excreted unchanged in the feces and most of what is absorbed appears unchanged in the urine, with only minor amounts appearing as metabolites. Sucralose does not interfere with the utilization of sucrose in man.<br />
<br />
Sucralose is a disaccharide that is made from sucrose in a five-step process that<br />
selectively substitutes three atoms of chlorine for three hydroxyl<br />
groups in the sugar molecule. It is produced at an approximate purity<br />
of 98 percent. Sucralose is a free-flowing, white crystalline solid<br />
that is soluble in water and stable both in crystalline form and in<br />
most aqueous solutions.]<br />
<br />
Sucralose has been approved for use in 27 plus countries in addition to the US. It has been used commercially since 1991 in more than 400 different food products.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7560It:Sucralose2006-12-07T14:46:28Z<p>Ywt05: /* What is sucralose */</p>
<hr />
<div>__toc__<br />
== What is sucralose?==<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7559It:Sucralose2006-12-07T14:46:19Z<p>Ywt05: </p>
<hr />
<div>__toc__<br />
== What is sucralose==<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7558It:Sucralose2006-12-07T14:45:41Z<p>Ywt05: /* What is sucralose? */</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== Sucralsoe in the body ==<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7556It:Sucralose2006-12-07T14:40:05Z<p>Ywt05: </p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
== What is sucralose? ==<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7554It:Sucralose2006-12-07T14:39:11Z<p>Ywt05: /* References */</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
*http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sucralose&diff=7553It:Sucralose2006-12-07T14:39:00Z<p>Ywt05: /* References */</p>
<hr />
<div>__toc__<br />
<br />
Sucralose is a sweetener that is produced from suger to act as a low-calorie substitute. It has a similar taste to sugar but is around 600 times sweeter. Sucralose's low-calorie characteristic originates from the inability of the body to metabolise most of the substance. Although this molecule is made from sugar, the human body does not recognise Sucralose as a carbohydrate, therefore the molecule is not broken down for energy and the Sucralose molecule(s) is passed through the body unchanged and is eliminated shortly after consumption.<br />
<br />
==Structure of Sucralose ==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|- align="center"<br />
| bgcolor="lt blue"|'''2D Image''' <br />
| bgcolor="lt blue"|'''3D Image''' <br />
|+ <br />
! [[Image:Sucralose5_stereochemistry.gif]]!!<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>350</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 -0.578 -2.553 0.472 0.00 0.00 Cl+0<br />
ATOM 2 C 0 -0.858 -1.025 1.386 0.00 0.00 C+0<br />
ATOM 3 C 0 -1.107 0.120 0.402 0.00 0.00 C+0<br />
ATOM 4 O 0 0.081 0.384 -0.346 0.00 0.00 O+0<br />
ATOM 5 C 0 1.104 0.700 0.600 0.00 0.00 C+0<br />
ATOM 6 H 0 0.650 1.121 1.497 0.00 0.00 H+0<br />
ATOM 7 C 0 2.066 1.721 -0.011 0.00 0.00 C+0<br />
ATOM 8 H 0 2.860 1.946 0.700 0.00 0.00 H+0<br />
ATOM 9 O 0 1.354 2.919 -0.327 0.00 0.00 O+0<br />
ATOM 10 C 0 2.674 1.132 -1.289 0.00 0.00 C+0<br />
ATOM 11 H 0 1.895 1.004 -2.040 0.00 0.00 H+0<br />
ATOM 12 O 0 3.683 2.012 -1.790 0.00 0.00 O+0<br />
ATOM 13 C 0 3.294 -0.229 -0.954 0.00 0.00 C+0<br />
ATOM 14 Cl 0 4.696 0.003 0.155 0.00 0.00 Cl+0<br />
ATOM 15 H 0 3.631 -0.712 -1.872 0.00 0.00 H+0<br />
ATOM 16 C 0 2.240 -1.103 -0.271 0.00 0.00 C+0<br />
ATOM 17 H 0 1.384 -1.223 -0.935 0.00 0.00 H+0<br />
ATOM 18 C 0 2.840 -2.476 0.038 0.00 0.00 C+0<br />
ATOM 19 O 0 1.835 -3.319 0.605 0.00 0.00 O+0<br />
ATOM 20 O 0 1.816 -0.488 0.942 0.00 0.00 O+0<br />
ATOM 21 C 0 -1.535 1.386 1.169 0.00 0.00 C+0<br />
ATOM 22 H 0 -1.546 1.197 2.242 0.00 0.00 H+0<br />
ATOM 23 O 0 -0.663 2.476 0.863 0.00 0.00 O+0<br />
ATOM 24 C 0 -2.967 1.674 0.656 0.00 0.00 C+0<br />
ATOM 25 H 0 -2.954 2.426 -0.134 0.00 0.00 H+0<br />
ATOM 26 O 0 -3.821 2.079 1.728 0.00 0.00 O+0<br />
ATOM 27 C 0 -3.396 0.293 0.097 0.00 0.00 C+0<br />
ATOM 28 H 0 -3.742 -0.355 0.902 0.00 0.00 H+0<br />
ATOM 29 C 0 -4.483 0.456 -0.966 0.00 0.00 C+0<br />
ATOM 30 Cl 0 -5.040 -1.170 -1.511 0.00 0.00 Cl+0<br />
ATOM 31 O 0 -2.180 -0.227 -0.490 0.00 0.00 O+0<br />
ATOM 32 H 0 -1.727 -1.143 2.034 0.00 0.00 H+0<br />
ATOM 33 H 0 0.019 -0.798 1.993 0.00 0.00 H+0<br />
ATOM 34 H 0 1.995 3.533 -0.709 0.00 0.00 H+0<br />
ATOM 35 H 0 4.037 1.603 -2.592 0.00 0.00 H+0<br />
ATOM 36 H 0 3.213 -2.925 -0.882 0.00 0.00 H+0<br />
ATOM 37 H 0 3.661 -2.363 0.746 0.00 0.00 H+0<br />
ATOM 38 H 0 2.253 -4.172 0.785 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.978 3.237 1.368 0.00 0.00 H+0<br />
ATOM 40 H 0 -4.694 2.242 1.344 0.00 0.00 H+0<br />
ATOM 41 H 0 -5.325 1.006 -0.544 0.00 0.00 H+0<br />
ATOM 42 H 0 -4.080 1.006 -1.817 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 47<br />
CONECT 2 1 3 32 33 NONE 48<br />
CONECT 3 2 31 4 21 NONE 49<br />
CONECT 4 3 5 0 0 NONE 50<br />
CONECT 5 4 20 6 7 NONE 51<br />
CONECT 7 5 8 9 10 NONE 52<br />
CONECT 9 7 34 0 0 NONE 53<br />
CONECT 10 7 11 12 13 NONE 54<br />
CONECT 12 10 35 0 0 NONE 55<br />
CONECT 13 10 14 15 16 NONE 56<br />
CONECT 14 13 0 0 0 NONE 57<br />
CONECT 16 13 17 18 20 NONE 58<br />
CONECT 18 16 19 36 37 NONE 59<br />
CONECT 19 18 38 0 0 NONE 60<br />
CONECT 20 16 5 0 0 NONE 61<br />
CONECT 21 3 22 23 24 NONE 62<br />
CONECT 23 21 39 0 0 NONE 63<br />
CONECT 24 21 25 26 27 NONE 64<br />
CONECT 26 24 40 0 0 NONE 65<br />
CONECT 27 24 28 29 31 NONE 66<br />
CONECT 29 27 30 41 42 NONE 67<br />
CONECT 30 29 0 0 0 NONE 68<br />
CONECT 31 27 3 0 0 NONE 69<br />
END NONE 70<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
| align="center" colspan="1" bgcolor="#ffffff|R and S represent the stereocentres of the molecule<br />
|}<br />
<br />
== Properties of Sucralose ==<br />
<br />
{|class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="3" bgcolor="Lt blue"|'''Table of properties'''<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''General properties''' <br />
|-<br />
| Chemical name<br />
| align="center"|2-[2,5-bis(chloromethyl)-3,4-dihydroxy-oxolan-2-yl]oxy-<br />
5-chloro-6-(hydroxymethyl)oxane-3,4-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub><br />
|-<br />
| Molecular weight<br />
| align="center"|398 g/mol<br />
|-<br />
| align="center" colspan="3" bgcolor="white"|'''Physical properties''' <br />
|-<br />
| Melting point<br />
| align="center"|130 °C<br />
|-<br />
| Boiling point<br />
| align="center"|... °C<br />
|-<br />
| Appearance<br />
| align="center"|White crystalline powder (40 times their natural size)<br />
[[Image:Sci-of-sucralose.jpg]]<br />
<br />
|-<br />
|align="center" colspan="3" bgcolor="white"|'''Miscellaneous ''' <br />
|-<br />
| SMILES<br />
| align="center"|ClC[C@]1(O[C@]2([H])[C@H](O)[C@@H](O)[C@](Cl)<br />
([H])[C@@H](CO)O2)[C@@H](O)[C@H](O)[C@@H](CCl)O1<br />
|-<br />
|+<br />
|-<br />
| align="center" colspan="3" bgcolor="lt blue" |'''Table of relative potency of artificial sweeteners''' <br />
|-<br />
| sugar<br />
| align="center"|1x<br />
|-<br />
| cyclamate <br />
| align="center"|45x <br />
|-<br />
| aspartame <br />
| align="center"|180x<br />
|-<br />
| saccharin<br />
| align="center"|300x<br />
|-<br />
| '''sucralose'''<br />
| align="center"|'''600x'''<br />
|-<br />
| neotame<br />
| align="center"|13,000x<br />
|}<br />
<br />
==Synthesis of Sucralose from Sucrose==<br />
<br />
Sucralose is synthesised from the readily available sugar sucrose:<br />
<br />
[[Image:Synthesis of sucralose from sucrose.gif]]<br />
<br />
The hydroxyl groups in sucrose are replaced by chlorine atoms. The halogenation with chlorine increases the stability of the molecule.<br />
<br />
==Sucralose facts==<br />
<br />
===History of Sucralose===<br />
Sucralose, C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>, low-calorie sweetener was discovered in 1976 by Tate & Lyle sugar company. A graduate student, Shashikant Phadnis, misunderstood “testing” for “tasting” and tasted the chlorinated sugars. He found that chlorinated sugars are many times sweeter than sucrose. Tate & Lyle collaborated with Johnson & Johnson to manufacture and sell sucralose in 1980.<br />
<br />
=== Is Sucralose safe? ===<br />
Safety of Sucralose use has been documented in more than 100 scientific studies over a 20-year period, which demonstrated that Sucralose is safe for Human consumption.<br />
<br />
*''"The data from the studies were independently evaluated by international experts in a variety of scientific disciplines, including toxicology, oncology, teratology, neurology, hematology, pediatrics and nutrition. Importantly, comprehensive toxicology studies, designed to meet the highest scientific standards, have clearly demonstrated that sucralose is not carcinogenic".'' IFIC Foundations<br />
<br />
Although the safety Sucralose itself has been tested in detail, one by product of sucralose which is formed when the molecule breaks down in the body, 1,6-dichlorofructose has not. There is some concern about the long term side effects of 1,6-dichlorofructose if any.<br />
<br />
== References ==<br />
<br />
*[http://www.ific.org/publications/brochures/sucralosebroch.cfm/ IFIC foundations] - Everthing you need to know about Sucralose<br />
<br />
*[http://www.people.virginia.edu/~jyj3b/sucralosesynthesis.htm] - Synthesis Of Sucralose<br />
<br />
*SciFinder - Lin, Daobing; Jia, Xudong; Liu, Deming. (Shanghai Desano Vitamins Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006)<br />
<br />
http://www.caloriecontrol.org/sucralos.html</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=5078It:Roaccutane2006-11-09T14:16:59Z<p>Ywt05: /* A picture of roaccutane pill */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==='''A picture of roaccutane pill'''===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=5077It:Roaccutane2006-11-09T14:16:30Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=5076It:Roaccutane2006-11-09T14:15:45Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4368It:Roaccutane2006-10-26T14:54:25Z<p>Ywt05: /* retinal */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4367It:Roaccutane2006-10-26T14:53:29Z<p>Ywt05: /* retinal */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.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>water.mol<br />
title1<br />
title2<br />
HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4364It:Roaccutane2006-10-26T14:52:17Z<p>Ywt05: /* retinal */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
[[Image:Retinal.bmp]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Retinal.bmp&diff=4363File:Retinal.bmp2006-10-26T14:52:01Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4357It:Roaccutane2006-10-26T14:48:37Z<p>Ywt05: /* retinal */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4355It:Roaccutane2006-10-26T14:47:57Z<p>Ywt05: /* retinoic acid molecule */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END NONE 75<br />
NONE 77<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4354It:Roaccutane2006-10-26T14:47:07Z<p>Ywt05: /* retinol */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinal===<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.884 -1.133 -1.894 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.286 -0.952 -0.429 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.193 -2.298 0.293 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.355 0.028 0.225 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.060 -0.420 0.589 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.960 0.214 0.102 0.00 0.00 C+0<br />
ATOM 7 C 0 0.323 -0.268 0.414 0.00 0.00 C+0<br />
ATOM 8 C 0 0.479 -1.486 1.286 0.00 0.00 C+0<br />
ATOM 9 C 0 1.428 0.369 -0.075 0.00 0.00 C+0<br />
ATOM 10 C 0 2.701 -0.179 0.133 0.00 0.00 C+0<br />
ATOM 11 C 0 3.823 0.516 -0.264 0.00 0.00 C+0<br />
ATOM 12 C 0 5.094 -0.031 -0.056 0.00 0.00 C+0<br />
ATOM 13 C 0 5.236 -1.379 0.602 0.00 0.00 C+0<br />
ATOM 14 C 0 6.216 0.664 -0.453 0.00 0.00 C+0<br />
ATOM 15 C 0 7.477 0.065 -0.367 0.00 0.00 C+0<br />
ATOM 16 H 0 7.563 -0.970 -0.070 0.00 0.00 H+0<br />
ATOM 17 O 0 8.475 0.709 -0.625 0.00 0.00 O+0<br />
ATOM 18 C 0 -3.675 1.286 0.479 0.00 0.00 C+0<br />
ATOM 19 C 0 -2.639 2.165 1.132 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.011 1.888 0.154 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.751 1.011 -0.857 0.00 0.00 C+0<br />
ATOM 22 C 0 -5.724 -0.435 -0.357 0.00 0.00 C+0<br />
ATOM 23 H 0 -4.556 -1.848 -2.369 0.00 0.00 H+0<br />
ATOM 24 H 0 -3.949 -0.175 -2.410 0.00 0.00 H+0<br />
ATOM 25 H 0 -2.861 -1.506 -1.947 0.00 0.00 H+0<br />
ATOM 26 H 0 -3.194 -2.713 0.161 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.390 -2.154 1.355 0.00 0.00 H+0<br />
ATOM 28 H 0 -4.930 -2.984 -0.123 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.948 -1.264 1.252 0.00 0.00 H+0<br />
ATOM 30 H 0 -1.072 1.087 -0.523 0.00 0.00 H+0<br />
ATOM 31 H 0 0.408 -2.384 0.672 0.00 0.00 H+0<br />
ATOM 32 H 0 1.452 -1.459 1.778 0.00 0.00 H+0<br />
ATOM 33 H 0 -0.308 -1.497 2.040 0.00 0.00 H+0<br />
ATOM 34 H 0 1.321 1.294 -0.621 0.00 0.00 H+0<br />
ATOM 35 H 0 2.803 -1.145 0.605 0.00 0.00 H+0<br />
ATOM 36 H 0 3.721 1.482 -0.735 0.00 0.00 H+0<br />
ATOM 37 H 0 6.292 -1.596 0.762 0.00 0.00 H+0<br />
ATOM 38 H 0 4.716 -1.373 1.560 0.00 0.00 H+0<br />
ATOM 39 H 0 4.802 -2.145 -0.042 0.00 0.00 H+0<br />
ATOM 40 H 0 6.122 1.672 -0.831 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.064 2.682 0.364 0.00 0.00 H+0<br />
ATOM 42 H 0 -3.134 2.897 1.770 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.970 1.551 1.735 0.00 0.00 H+0<br />
ATOM 44 H 0 -5.603 1.966 1.066 0.00 0.00 H+0<br />
ATOM 45 H 0 -4.866 2.883 -0.267 0.00 0.00 H+0<br />
ATOM 46 H 0 -6.784 1.349 -0.948 0.00 0.00 H+0<br />
ATOM 47 H 0 -5.256 1.073 -1.827 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.364 -1.053 -0.988 0.00 0.00 H+0<br />
ATOM 49 H 0 -6.075 -0.473 0.674 0.00 0.00 H+0<br />
CONECT 1 2 23 24 25 NONE 54<br />
CONECT 2 1 22 3 4 NONE 55<br />
CONECT 3 2 26 27 28 NONE 56<br />
CONECT 4 2 5 18 0 NONE 57<br />
CONECT 5 4 6 29 0 NONE 58<br />
CONECT 6 5 7 30 0 NONE 59<br />
CONECT 7 6 8 9 0 NONE 60<br />
CONECT 8 7 31 32 33 NONE 61<br />
CONECT 9 7 10 34 0 NONE 62<br />
CONECT 10 9 11 35 0 NONE 63<br />
CONECT 11 10 12 36 0 NONE 64<br />
CONECT 12 11 13 14 0 NONE 65<br />
CONECT 13 12 37 38 39 NONE 66<br />
CONECT 14 12 15 40 0 NONE 67<br />
CONECT 15 14 16 17 0 NONE 68<br />
CONECT 17 15 0 0 0 NONE 69<br />
CONECT 18 4 19 20 0 NONE 70<br />
CONECT 19 18 41 42 43 NONE 71<br />
CONECT 20 18 21 44 45 NONE 72<br />
CONECT 21 20 22 46 47 NONE 73<br />
CONECT 22 21 2 48 49 NONE 74<br />
END NONE 75<br />
NONE 77<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4343It:Roaccutane2006-10-26T14:41:55Z<p>Ywt05: /* retinoic acid molecule */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===retinol===<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 26-Oct-06 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 26-Oct-06 0 NONE 4<br />
ATOM 1 C 0 -3.911 -1.227 -1.887 0.00 0.00 C+0<br />
ATOM 2 C 0 -4.337 -1.005 -0.434 0.00 0.00 C+0<br />
ATOM 3 C 0 -4.226 -2.324 0.333 0.00 0.00 C+0<br />
ATOM 4 C 0 -3.436 0.015 0.198 0.00 0.00 C+0<br />
ATOM 5 C 0 -2.097 -0.405 0.607 0.00 0.00 C+0<br />
ATOM 6 C 0 -1.007 0.235 0.117 0.00 0.00 C+0<br />
ATOM 7 C 0 0.286 -0.199 0.476 0.00 0.00 C+0<br />
ATOM 8 C 0 0.455 -1.375 1.403 0.00 0.00 C+0<br />
ATOM 9 C 0 1.379 0.443 -0.014 0.00 0.00 C+0<br />
ATOM 10 C 0 2.669 -0.065 0.243 0.00 0.00 C+0<br />
ATOM 11 C 0 3.763 0.636 -0.146 0.00 0.00 C+0<br />
ATOM 12 C 0 5.100 0.110 0.121 0.00 0.00 C+0<br />
ATOM 13 C 0 5.263 -1.211 0.828 0.00 0.00 C+0<br />
ATOM 14 C 0 6.178 0.799 -0.262 0.00 0.00 C+0<br />
ATOM 15 C 0 7.551 0.198 -0.108 0.00 0.00 C+0<br />
ATOM 16 O 0 8.179 0.110 -1.388 0.00 0.00 O+0<br />
ATOM 17 C 0 -3.785 1.273 0.406 0.00 0.00 C+0<br />
ATOM 18 C 0 -2.776 2.194 1.042 0.00 0.00 C+0<br />
ATOM 19 C 0 -5.129 1.835 0.045 0.00 0.00 C+0<br />
ATOM 20 C 0 -5.838 0.910 -0.946 0.00 0.00 C+0<br />
ATOM 21 C 0 -5.787 -0.518 -0.399 0.00 0.00 C+0<br />
ATOM 22 H 0 -4.561 -1.971 -2.347 0.00 0.00 H+0<br />
ATOM 23 H 0 -3.989 -0.288 -2.435 0.00 0.00 H+0<br />
ATOM 24 H 0 -2.880 -1.578 -1.914 0.00 0.00 H+0<br />
ATOM 25 H 0 -3.218 -2.724 0.225 0.00 0.00 H+0<br />
ATOM 26 H 0 -4.436 -2.150 1.388 0.00 0.00 H+0<br />
ATOM 27 H 0 -4.946 -3.039 -0.067 0.00 0.00 H+0<br />
ATOM 28 H 0 -1.977 -1.226 1.298 0.00 0.00 H+0<br />
ATOM 29 H 0 -1.128 1.078 -0.547 0.00 0.00 H+0<br />
ATOM 30 H 0 0.426 -2.300 0.827 0.00 0.00 H+0<br />
ATOM 31 H 0 1.413 -1.297 1.918 0.00 0.00 H+0<br />
ATOM 32 H 0 -0.352 -1.379 2.136 0.00 0.00 H+0<br />
ATOM 33 H 0 1.260 1.341 -0.601 0.00 0.00 H+0<br />
ATOM 34 H 0 2.785 -1.011 0.750 0.00 0.00 H+0<br />
ATOM 35 H 0 3.646 1.582 -0.653 0.00 0.00 H+0<br />
ATOM 36 H 0 5.387 -2.005 0.091 0.00 0.00 H+0<br />
ATOM 37 H 0 6.142 -1.173 1.472 0.00 0.00 H+0<br />
ATOM 38 H 0 4.378 -1.411 1.432 0.00 0.00 H+0<br />
ATOM 39 H 0 6.065 1.788 -0.682 0.00 0.00 H+0<br />
ATOM 40 H 0 8.152 0.828 0.549 0.00 0.00 H+0<br />
ATOM 41 H 0 7.465 -0.799 0.324 0.00 0.00 H+0<br />
ATOM 42 H 0 9.053 -0.279 -1.245 0.00 0.00 H+0<br />
ATOM 43 H 0 -2.171 2.662 0.266 0.00 0.00 H+0<br />
ATOM 44 H 0 -3.296 2.965 1.611 0.00 0.00 H+0<br />
ATOM 45 H 0 -2.132 1.622 1.710 0.00 0.00 H+0<br />
ATOM 46 H 0 -5.735 1.931 0.946 0.00 0.00 H+0<br />
ATOM 47 H 0 -4.999 2.818 -0.408 0.00 0.00 H+0<br />
ATOM 48 H 0 -6.876 1.223 -1.061 0.00 0.00 H+0<br />
ATOM 49 H 0 -5.332 0.951 -1.911 0.00 0.00 H+0<br />
ATOM 50 H 0 -6.405 -1.169 -1.017 0.00 0.00 H+0<br />
ATOM 51 H 0 -6.151 -0.530 0.628 0.00 0.00 H+0<br />
CONECT 1 2 22 23 24 NONE 56<br />
CONECT 2 1 21 3 4 NONE 57<br />
CONECT 3 2 25 26 27 NONE 58<br />
CONECT 4 2 5 17 0 NONE 59<br />
CONECT 5 4 6 28 0 NONE 60<br />
CONECT 6 5 7 29 0 NONE 61<br />
CONECT 7 6 8 9 0 NONE 62<br />
CONECT 8 7 30 31 32 NONE 63<br />
CONECT 9 7 10 33 0 NONE 64<br />
CONECT 10 9 11 34 0 NONE 65<br />
CONECT 11 10 12 35 0 NONE 66<br />
CONECT 12 11 13 14 0 NONE 67<br />
CONECT 13 12 36 37 38 NONE 68<br />
CONECT 14 12 15 39 0 NONE 69<br />
CONECT 15 14 16 40 41 NONE 70<br />
CONECT 16 15 42 0 0 NONE 71<br />
CONECT 17 4 18 19 0 NONE 72<br />
CONECT 18 17 43 44 45 NONE 73<br />
CONECT 19 17 20 46 47 NONE 74<br />
CONECT 20 19 21 48 49 NONE 75<br />
CONECT 21 20 2 50 51 NONE 76<br />
END NONE 77<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4326It:Roaccutane2006-10-26T14:25:59Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria. Isotretinoin will cause the other retinoids, arachidonic acid release from macrophages to be inhibited. This may account for the anti-inflammatory effects of retinoids.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4322It:Roaccutane2006-10-26T14:23:16Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
The mechanisms are not well understood, but Roaccutane was found to decrease reduce the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
Isotretinoin's anti-acne effects can last for months to years following a twenty week course.<br />
Unlike antibiotic treatments, isotretinoin does not promote antibiotic-resistant bacteria.<br />
<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4314It:Roaccutane2006-10-26T14:18:30Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
isotretinoin is an isomer of tretinoin. The only structural difference between the two molecules lies in the spatial arrangement of the atoms around one carbon-carbon double bond.<br />
<br />
Roaccutane works by reducing the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
Isotretinoion has a half life of 18.7±6.2 hours in the body.<br />
<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4310It:Roaccutane2006-10-26T14:17:51Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
Roaccutane works by reducing the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, also known as retinol,we will find that it takes part in the metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers of retinoic acid:(retinoic acid and 1,3-cis- retinoic acid).<br />
<br />
While isotretinoin is converted into oxo-isotretinoin, it interconverts between retionoic acid from vitamin A. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4304It:Roaccutane2006-10-26T14:14:19Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
Roaccutane works by reducing the production of the sebum by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process of isotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4301It:Roaccutane2006-10-26T14:13:05Z<p>Ywt05: /* '''A little history of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4300It:Roaccutane2006-10-26T14:12:55Z<p>Ywt05: /* '''A little history of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4299It:Roaccutane2006-10-26T14:12:32Z<p>Ywt05: /* '''A little history of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4298It:Roaccutane2006-10-26T14:12:13Z<p>Ywt05: /* '''A little history of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4297It:Roaccutane2006-10-26T14:11:49Z<p>Ywt05: /* '''A little history of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982 and was approved by the Food and Drug Administration (FDA)for the treatment of severe acne problems that has not responded to antibiotics.<br />
<br />
Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy.<br />
<br />
Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4290It:Roaccutane2006-10-26T14:09:18Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane is taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4284It:Roaccutane2006-10-26T14:07:45Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane, also known as isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4253It:Roaccutane2006-10-26T13:54:52Z<p>Ywt05: /* retinol molecule */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinoic acid molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4004It:Roaccutane2006-10-24T16:57:02Z<p>Ywt05: /* '''reaction scheme''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
[[Image:Synthesis.GIF]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Synthesis.GIF&diff=4003File:Synthesis.GIF2006-10-24T16:56:44Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=4002It:Roaccutane2006-10-24T16:56:32Z<p>Ywt05: </p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''reaction scheme'''==<br />
<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3994It:Roaccutane2006-10-24T16:34:12Z<p>Ywt05: /* retinol molecule */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3993It:Roaccutane2006-10-24T16:33:47Z<p>Ywt05: /* '''A little histroy of isotretinoin and some properties''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little history of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
[[Image:Retinol.MOL]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:9133rtrt.pdb&diff=3988File:9133rtrt.pdb2006-10-24T16:29:36Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Retinol2.MOL&diff=3987File:Retinol2.MOL2006-10-24T16:29:16Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3981It:Roaccutane2006-10-24T16:23:29Z<p>Ywt05: /* retinol molecule */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
[[Image:Retinol.MOL]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Retinol.MOL&diff=3980File:Retinol.MOL2006-10-24T16:23:06Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3971It:Roaccutane2006-10-24T16:13:57Z<p>Ywt05: /* A picture of roaccutane pill */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
===A picture of roaccutane pill===<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3970It:Roaccutane2006-10-24T16:13:50Z<p>Ywt05: /* '''A picture of roaccutane pill''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
==A picture of roaccutane pill==<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3967It:Roaccutane2006-10-24T16:13:28Z<p>Ywt05: /* a picture of retinol */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===retinol molecule===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
=='''A picture of roaccutane pill'''==<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3966It:Roaccutane2006-10-24T16:12:44Z<p>Ywt05: /* a picture of retinol */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===a picture of retinol===<br />
[[Image:Untitledretinol.gif]]<br />
<br />
=='''A picture of roaccutane pill'''==<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:Untitledretinol.gif&diff=3965File:Untitledretinol.gif2006-10-24T16:12:30Z<p>Ywt05: </p>
<hr />
<div></div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3951It:Roaccutane2006-10-24T15:55:54Z<p>Ywt05: /* '''How does it work?''' */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
===a picture of retinol===<br />
[[Image:RetinolUntitled.gif]]<br />
<br />
=='''A picture of roaccutane pill'''==<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=File:RetinolUntitled.gif&diff=3949File:RetinolUntitled.gif2006-10-24T15:54:09Z<p>Ywt05: retinol</p>
<hr />
<div>retinol</div>Ywt05https://chemwiki.ch.ic.ac.uk/index.php?title=It:Roaccutane&diff=3946It:Roaccutane2006-10-24T15:39:23Z<p>Ywt05: /* References */</p>
<hr />
<div><jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>black</color><br />
<script>zoom 100; cpk off;frame 1; move 40 -20 20 0 0 0 0 0 3; delay 0.5;</script><br />
<inlineContents>roaccutane.pdb<br />
title1<br />
title2<br />
ATOM 1 C1 MOL 1 14.263 13.508 0.005 1.00 0.00 <br />
ATOM 2 C2 MOL 1 15.445 12.906 0.072 1.00 0.00 <br />
ATOM 3 C3 MOL 1 12.940 12.770 -0.027 1.00 0.00 <br />
ATOM 4 C4 MOL 1 16.692 13.626 0.034 1.00 0.00 <br />
ATOM 5 C5 MOL 1 12.825 11.196 -0.135 1.00 0.00 <br />
ATOM 6 C6 MOL 1 11.833 13.525 0.052 1.00 0.00 <br />
ATOM 7 C7 MOL 1 17.817 12.921 0.063 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.708 15.125 -0.058 1.00 0.00 <br />
ATOM 9 C9 MOL 1 13.847 10.514 -1.092 1.00 0.00 <br />
ATOM 10 C10 MOL 1 13.053 10.611 1.285 1.00 0.00 <br />
ATOM 11 C11 MOL 1 11.426 10.791 -0.613 1.00 0.00 <br />
ATOM 12 C12 MOL 1 11.973 15.022 0.150 1.00 0.00 <br />
ATOM 13 C13 MOL 1 10.425 12.944 0.039 1.00 0.00 <br />
ATOM 14 C14 MOL 1 19.122 13.553 0.008 1.00 0.00 <br />
ATOM 15 C15 MOL 1 10.413 11.431 0.300 1.00 0.00 <br />
ATOM 16 C16 MOL 1 20.200 12.776 0.050 1.00 0.00 <br />
ATOM 17 C17 MOL 1 21.537 13.348 -0.007 1.00 0.00 <br />
ATOM 18 C18 MOL 1 22.581 12.508 0.048 1.00 0.00 <br />
ATOM 19 C19 MOL 1 21.682 14.844 -0.126 1.00 0.00 <br />
ATOM 20 C20 MOL 1 24.024 12.882 0.002 1.00 0.00 <br />
ATOM 21 O21 MOL 1 24.869 11.984 0.071 1.00 0.00 <br />
ATOM 22 O22 MOL 1 24.460 14.200 -0.117 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol> <br />
<br />
[[Image:Roaccutane.gif|thumb|right|200|Roaccutane]]<br />
<br />
'''Roaccutane''' otherwise known as ''isoretinoin'', ''Tasmar'' or ''Teriosal''.<br />
{| border="1"<br />
|+ <br />
{| border="1"<br />
! Formula !! Molecular weight !! Melting Point<br />
|-<br />
! C<sub>20</sub>H<sub>28</sub>O<sub>2</sub> <br />
| 300.44 || 189-190C<br />
|-<br />
|}<br />
===Interesting Fact===<br />
'''Roaccutane''' is a form of Vitamin A prescribed by dermatologists for severe '''acne''', and it is only given to patients who have not responded to previous milder treatments. Roaccutane makes the sebaceous gland less productive, reduces the size of the sebaceous glands and the inflammation of the skin in acne.<br />
<br />
<br />
=='''A little histroy of isotretinoin and some properties'''==<br />
Oral isotretinoin was introduced in 1982. Today, it would still be one of the most effective antiacne drug for various reasons.<br />
Isotretinoin is a naturally occurring molecule in humans, found in every patient with acne and in women during pregnancy. Isotretinoin is a metabolic product, which is a derivative of vitamin A,commonly found primarily in liver, dairy products, and vegetables.<br />
It has a half life of 18.7±6.2 hours in the body.<br />
<br />
=='''How does it work?'''==<br />
<br />
Roaccutane ,isotretinoin, belongs to a group of medicines known as retinoids (a derivatives vitamin A),and has IUPAC name of 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid.<br />
Roaccutane taken into body through the mouth in tablet form. This medicine works by reducing the production of the skin’s natural oil (sebum) by decreacing the size and activity of the sebaceous glands in the skin, thus stops the glands from becoming blocked and infected by bacteria.<br />
If we follow the metabolic pathway of Vitamin A, retinol,we will find that it takes part in metabolising process ofisotretinoin. Vitamin A is absorbed from the in the body and converted into retinal, which is then oxidised into retinoic acids. Isomers present:(retinoic acid and 1,3-cis- retinoic acid) <br />
Isotretinoin is converted into oxo-isotretinoin and interconversion between retionoic acid. These metabolites are then stored in the adipose layer of tissues.<br />
<br />
=='''A picture of roaccutane pill'''==<br />
[[Image:Images.jpg]]<br />
<br />
=='''Side effect and some precaution'''==<br />
Isotretinoin causes birth defects if taken during pregnancy period. <br />
This medicine may cause depression but rarely causes suicide attempts<br />
Dry skin may be experienced. Dryness of the mucous membranes (lips and eyes).Disturbances in the composition of the blood may happen (increase plasma concentration).<br />
Isotretinoin is used in combination with tetracycline-type antibiotics increases the pressure within the skull. For this reason, tetracycline antibiotics must not be taken with isotretinoin. An overdose, may cause changes in the structure of the bone. Roaccutane has a simmilar structure to vitamin A, therefore vitamin A supplements should therefore be avoided.<br />
<br />
<br />
==References==<br />
*[http://linkinghub.elsevier.com/retrieve/pii/S0190962298704384 ]- Journal of the American Academy of Dermatology, Volume 39, Issue 2, Pages S8-S12 U. Wiegand, R. Chou<br />
<br />
<br />
===KIMCHI===<br />
<br />
Roaccutane contains the active ingredient isotretinoin. This is a vitamin A derivative. Roaccutane is used to treat severe forms of acne (such as nodular orconglobate acne, or acne at risk of permanent scarring) which has not got better after other anti-acnetreatments, including oral antibiotics. Roaccutane treatment must be supervised by a dermatologist (a doctor specialised in the treatment of skin problems). Roaccutane may increase the levels of fats such as triglycerides or cholesterol in your blood. Roaccutane is teratogenic. This means that it is likely to damage an unborn baby. There is also an increased risk of miscarriage</div>Ywt05