ChemWiki - User contributions [en]

It07:Rapamycin

2007-10-22T22:56:19Z

Jlj06: /* Rapamycin */

==Rapamycin==
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(C<br>C(C(=O)C(C(C(=CC(C(=O)<br>CC(OC(=O)C3CCCCN3C(=<br>
O)C(=O)C1(O2)O)C(C)<br>CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui

[[Image:Rap_cell.png|350px]]
<br>
The above shows how rapamycin blocks T-cell activation by inserting itself between two proteins in the body.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

===Alternative Treatments===

The most commonly used immunosuppressives are currently cyclosporin and FK506. Both of these work in a different way to rapamycin by inhibitng calcineurin in the T-cells. Although it works in a very different way, FK506 binds to FKBP in exactly the same way rapamycin does and shows strucural similarities to it.

The main disadvantages of alternative drugs are that they must be taken for the rest of the patient's life and do not guarantee long term survival of the organ as 55% of transplanted kidneys fail within ten years. Because of the suppression of the entire immune system they also make patients susceptible to viruses, bacteria and cancer.

===How to Take Rapamycin===

Rapamycin (Sirolimus) comes as a tablet and a solution (liquid) to take by mouth. It is usually taken once a day, either always with food or always without food. To help you remember to take sirolimus, take it around the same time every day. Follow the directions on your prescription label carefully, and ask your doctor or pharmacist to explain any part you do not understand. Take sirolimus exactly as directed. Do not take more or less of it or take it more often than prescribed by your doctor.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>
7. http://www.ch.ic.ac.uk/local/projects/russell/index.html<Br>

It07:Rapamycin

2007-10-22T22:54:53Z

Jlj06: /* Rapamycin */

==Rapamycin==
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(C<br>C(C(=O)C(C(C(=CC(C(=O)<br>CC(OC(=O)C3CCCCN3C(=<br>
O)C(=O)C1(O2)O)C(C)<br>CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui

[[Image:Rap_cell.png|350px]]
<br>
The above shows how rapamycin blocks T-cell activation by inserting itself between two proteins in the body.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

===Alternative Treatments===

The most commonly used immunosuppressives are currently cyclosporin and FK506. Both of these work in a different way to rapamycin by inhibitng calcineurin in the T-cells. Although it works in a very different way, FK506 binds to FKBP in exactly the same way rapamycin does and shows strucural similarities to it.

The main disadvantages of alternative drugs are that they must be taken for the rest of the patient's life and do not guarantee long term survival of the organ as 55% of transplanted kidneys fail within ten years. Because of the suppression of the entire immune system they also make patients susceptible to viruses, bacteria and cancer.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>
7. http://www.ch.ic.ac.uk/local/projects/russell/index.html<Br>

It07:Rapamycin

2007-10-22T22:52:37Z

Jlj06: /* References */

==Rapamycin==
<jmol>
<jmolApplet>
<title>Rapamycin</title>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Rapamycin.pdb</uploadedFileContents>
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(C<br>C(C(=O)C(C(C(=CC(C(=O)<br>CC(OC(=O)C3CCCCN3C(=<br>
O)C(=O)C1(O2)O)C(C)<br>CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui

[[Image:Rap_cell.png|350px]]
<br>
The above shows how rapamycin blocks T-cell activation by inserting itself between two proteins in the body.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>
7. http://www.ch.ic.ac.uk/local/projects/russell/index.html<Br>

It07:Rapamycin

2007-10-22T22:52:08Z

Jlj06: /* Overview */

==Rapamycin==
<jmol>
<jmolApplet>
<title>Rapamycin</title>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Rapamycin.pdb</uploadedFileContents>
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<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(C<br>C(C(=O)C(C(C(=CC(C(=O)<br>CC(OC(=O)C3CCCCN3C(=<br>
O)C(=O)C1(O2)O)C(C)<br>CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui

[[Image:Rap_cell.png|350px]]
<br>
The above shows how rapamycin blocks T-cell activation by inserting itself between two proteins in the body.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>

File:Rap cell.png

2007-10-22T22:50:22Z

Jlj06:

It07:Rapamycin

2007-10-22T22:47:27Z

Jlj06: /* Rapamycin */

==Rapamycin==
<jmol>
<jmolApplet>
<title>Rapamycin</title>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Rapamycin.pdb</uploadedFileContents>
</jmolApplet>

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

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(C<br>C(C(=O)C(C(C(=CC(C(=O)<br>CC(OC(=O)C3CCCCN3C(=<br>
O)C(=O)C1(O2)O)C(C)<br>CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>

It07:Piperine

2007-10-22T22:45:59Z

Jlj06: /* Piperine */

== Piperine ==

<jmol>
<jmolApplet>
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<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 O 0 -3.501 -2.058 -0.092 0.00 0.00 O+0
ATOM 2 C 0 -3.433 -0.864 0.133 0.00 0.00 C+0
ATOM 3 C 0 -2.172 -0.221 0.173 0.00 0.00 C+0
ATOM 4 C 0 -1.034 -0.953 0.060 0.00 0.00 C+0
ATOM 5 C 0 0.223 -0.313 0.100 0.00 0.00 C+0
ATOM 6 C 0 1.358 -1.043 -0.012 0.00 0.00 C+0
ATOM 7 C 0 2.666 -0.376 0.029 0.00 0.00 C+0
ATOM 8 C 0 3.841 -1.128 -0.087 0.00 0.00 C+0
ATOM 9 C 0 5.069 -0.497 -0.048 0.00 0.00 C+0
ATOM 10 C 0 5.136 0.889 0.108 0.00 0.00 C+0
ATOM 11 O 0 6.449 1.261 0.115 0.00 0.00 O+0
ATOM 12 C 0 7.169 0.148 -0.446 0.00 0.00 C+0
ATOM 13 O 0 6.340 -0.988 -0.137 0.00 0.00 O+0
ATOM 14 C 0 3.971 1.635 0.223 0.00 0.00 C+0
ATOM 15 C 0 2.742 1.014 0.179 0.00 0.00 C+0
ATOM 16 N 0 -4.559 -0.151 0.339 0.00 0.00 N+0
ATOM 17 C 0 -4.504 1.309 0.490 0.00 0.00 C+0
ATOM 18 C 0 -5.471 1.945 -0.513 0.00 0.00 C+0
ATOM 19 C 0 -6.866 1.345 -0.320 0.00 0.00 C+0
ATOM 20 C 0 -6.817 -0.161 -0.585 0.00 0.00 C+0
ATOM 21 C 0 -5.865 -0.820 0.411 0.00 0.00 C+0
ATOM 22 H 0 -2.116 0.850 0.293 0.00 0.00 H+0
ATOM 23 H 0 -1.090 -2.025 -0.060 0.00 0.00 H+0
ATOM 24 H 0 0.279 0.759 0.220 0.00 0.00 H+0
ATOM 25 H 0 1.301 -2.115 -0.132 0.00 0.00 H+0
ATOM 26 H 0 3.788 -2.200 -0.206 0.00 0.00 H+0
ATOM 27 H 0 7.272 0.264 -1.525 0.00 0.00 H+0
ATOM 28 H 0 8.147 0.048 0.024 0.00 0.00 H+0
ATOM 29 H 0 4.027 2.706 0.343 0.00 0.00 H+0
ATOM 30 H 0 1.838 1.598 0.269 0.00 0.00 H+0
ATOM 31 H 0 -4.796 1.583 1.504 0.00 0.00 H+0
ATOM 32 H 0 -3.490 1.659 0.292 0.00 0.00 H+0
ATOM 33 H 0 -5.512 3.021 -0.347 0.00 0.00 H+0
ATOM 34 H 0 -5.127 1.746 -1.528 0.00 0.00 H+0
ATOM 35 H 0 -7.200 1.523 0.702 0.00 0.00 H+0
ATOM 36 H 0 -7.562 1.814 -1.016 0.00 0.00 H+0
ATOM 37 H 0 -7.815 -0.583 -0.471 0.00 0.00 H+0
ATOM 38 H 0 -6.460 -0.340 -1.600 0.00 0.00 H+0
ATOM 39 H 0 -5.751 -1.876 0.163 0.00 0.00 H+0
ATOM 40 H 0 -6.265 -0.721 1.420 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 16 0 NONE 46
CONECT 3 2 4 22 0 NONE 47
CONECT 4 3 5 23 0 NONE 48
CONECT 5 4 6 24 0 NONE 49
CONECT 6 5 7 25 0 NONE 50
CONECT 7 6 15 8 0 NONE 51
CONECT 8 7 9 26 0 NONE 52
CONECT 9 8 13 10 0 NONE 53
CONECT 10 9 11 14 0 NONE 54
CONECT 11 10 12 0 0 NONE 55
CONECT 12 11 13 27 28 NONE 56
CONECT 13 12 9 0 0 NONE 57
CONECT 14 10 15 29 0 NONE 58
CONECT 15 14 7 30 0 NONE 59
CONECT 16 2 21 17 0 NONE 60
CONECT 17 16 18 31 32 NONE 61
CONECT 18 17 19 33 34 NONE 62
CONECT 19 18 20 35 36 NONE 63
CONECT 20 19 21 37 38 NONE 64
CONECT 21 20 16 39 40 NONE 65
END NONE 66
</inlineContents>
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</jmol>

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 120; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
HEADER NONAME 22-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 22-Oct-07 0 NONE 4
ATOM 1 O 0 3.512 -2.114 -0.138 0.00 0.00 O+0
ATOM 2 C 0 3.450 -0.905 -0.266 0.00 0.00 C+0
ATOM 3 N 0 4.581 -0.179 -0.363 0.00 0.00 N+0
ATOM 4 C 0 4.523 1.265 -0.631 0.00 0.00 C+0
ATOM 5 C 0 5.326 1.999 0.448 0.00 0.00 C+0
ATOM 6 C 0 6.744 1.426 0.502 0.00 0.00 C+0
ATOM 7 C 0 6.683 -0.058 0.871 0.00 0.00 C+0
ATOM 8 C 0 5.895 -0.814 -0.198 0.00 0.00 C+0
ATOM 9 C 0 2.190 -0.262 -0.320 0.00 0.00 C+0
ATOM 10 C 0 1.053 -0.978 -0.119 0.00 0.00 C+0
ATOM 11 C 0 -0.202 -0.338 -0.172 0.00 0.00 C+0
ATOM 12 C 0 -1.335 -1.052 0.029 0.00 0.00 C+0
ATOM 13 C 0 -2.643 -0.385 -0.027 0.00 0.00 C+0
ATOM 14 C 0 -2.721 0.988 -0.287 0.00 0.00 C+0
ATOM 15 C 0 -3.948 1.610 -0.338 0.00 0.00 C+0
ATOM 16 C 0 -5.112 0.881 -0.133 0.00 0.00 C+0
ATOM 17 O 0 -6.423 1.257 -0.133 0.00 0.00 O+0
ATOM 18 C 0 -7.129 0.193 0.532 0.00 0.00 C+0
ATOM 19 O 0 -6.311 -0.967 0.289 0.00 0.00 O+0
ATOM 20 C 0 -5.042 -0.490 0.127 0.00 0.00 C+0
ATOM 21 C 0 -3.816 -1.122 0.175 0.00 0.00 C+0
ATOM 22 H 0 4.954 1.473 -1.610 0.00 0.00 H+0
ATOM 23 H 0 3.486 1.600 -0.606 0.00 0.00 H+0
ATOM 24 H 0 5.372 3.061 0.209 0.00 0.00 H+0
ATOM 25 H 0 4.842 1.864 1.416 0.00 0.00 H+0
ATOM 26 H 0 7.218 1.538 -0.473 0.00 0.00 H+0
ATOM 27 H 0 7.324 1.963 1.252 0.00 0.00 H+0
ATOM 28 H 0 7.694 -0.460 0.932 0.00 0.00 H+0
ATOM 29 H 0 6.186 -0.173 1.835 0.00 0.00 H+0
ATOM 30 H 0 5.764 -1.852 0.110 0.00 0.00 H+0
ATOM 31 H 0 6.435 -0.777 -1.144 0.00 0.00 H+0
ATOM 32 H 0 2.132 0.797 -0.521 0.00 0.00 H+0
ATOM 33 H 0 1.111 -2.038 0.082 0.00 0.00 H+0
ATOM 34 H 0 -0.260 0.722 -0.373 0.00 0.00 H+0
ATOM 35 H 0 -1.277 -2.111 0.229 0.00 0.00 H+0
ATOM 36 H 0 -1.818 1.560 -0.447 0.00 0.00 H+0
ATOM 37 H 0 -4.007 2.670 -0.539 0.00 0.00 H+0
ATOM 38 H 0 -7.202 0.393 1.602 0.00 0.00 H+0
ATOM 39 H 0 -8.120 0.061 0.098 0.00 0.00 H+0
ATOM 40 H 0 -3.762 -2.182 0.376 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 45
CONECT 2 1 3 9 0 NONE 46
CONECT 3 2 8 4 0 NONE 47
CONECT 4 3 5 22 23 NONE 48
CONECT 5 4 6 24 25 NONE 49
CONECT 6 5 7 26 27 NONE 50
CONECT 7 6 8 28 29 NONE 51
CONECT 8 7 3 30 31 NONE 52
CONECT 9 2 10 32 0 NONE 53
CONECT 10 9 11 33 0 NONE 54
CONECT 11 10 12 34 0 NONE 55
CONECT 12 11 13 35 0 NONE 56
CONECT 13 12 21 14 0 NONE 57
CONECT 14 13 15 36 0 NONE 58
CONECT 15 14 16 37 0 NONE 59
CONECT 16 15 17 20 0 NONE 60
CONECT 17 16 18 0 0 NONE 61
CONECT 18 17 19 38 39 NONE 62
CONECT 19 18 20 0 0 NONE 63
CONECT 20 16 19 21 0 NONE 64
CONECT 21 20 13 40 0 NONE 65
END NONE 66
</inlineContents>
</jmolApplet>
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Right Click the mouse on the above 3D molecule to explore more about this molecular structure

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | {{Piperine}}
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Piperine.png|300px]]
|-

|-
| [[IUPAC nomenclature|Systematic name]]
| 1-(5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoyl)-piperidine 
|-
| [[Chemical formula|Molecular formula]]
| C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub> 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| O=C(/C=C/C=C/C2=CC3=C(OCO3)C=C2)N1CCCCC1
|-
| [[Molar mass]]
| 285.34 g/mol
|-
! {{chembox header}} | Properties
|-
| [[Density]]
| 1.193 g/cm³
|-
| [[Melting point]]
| 129-130°C

|-

! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [http://www.sciencelab.com/xMSDS-Piperine-9926579 Piperine MSDS]
|-
| Main [[Worker safety and health|hazard]]s
| Irritant of eyes and skin 
|-
| [[RTECS]] number
| TN2321500
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

=== Overview ===

Piperine is an alkaloid found naturally in plants belonging to the Piperaceae family, such as Piper nigrum L, commonly known as black pepper, and Piper longum L, commonly known as long pepper. Piperine is the major pungent substance in these plants and is isolated from the fruit of the black pepper and long pepper plants. Piperine comprises 1 to 99% of these plants. The term black pepper is used both for the plant Piper nigrum and the spice that is mainly in the fruit of the plant. Piperine is a solid substance essentially insoluble in water. It is a weak base that is tasteless at first, but leaves a burning aftertaste. Piperine belongs to the vanilloid family of compounds, a family that also includes capsaicin, the pungent substance in hot chili peppers.

It is a naturally occuring heterocyclic compound found in the [http://en.wikipedia.org/wiki/Oleoresin oleoresin] of [http://en.wikipedia.org/wiki/Black_pepper black pepper] and is responsible for the pungency of the spice and for the way the spice induces sneezing.

Apart from adding to the aroma and flavour your favourite dish piperine has long been used for its medicinal properties in India. It has antiasthmatic, antifertility, [http://en.wikipedia.org/wiki/Central_nervous_system CNS] depressant and anti-inflammatory properites. It also inhibits the enzyme hepatic monooxygenase and UDP–glucoronyl transeferase.
<br>[[Image:Black_Pepper.jpg|300px]]

===Little History of Piperine===
Piperine has had a great influence on food storage all over the world for thousand of years. Before the processed foods and fridges were invented the only few possible ways to keep food was to dry them or use a lot of salt all over the food (e.g meat) to prevent them from going bad. However, if these did not work then the food would begin to go bad and smelly. Thanks to the tangy and spicy taste of the piperine, pepper was then used as the perfect additive for most foods to mask the taste.
Piperine was discovered in 1820 and identified by Hans Christian Orsted first who was the Danish physicist, chemist and professor at the University of Copenhagen. And In 1882 and 1894, the isolation of chemical makeup of piperine was successfully synthesized in the lab.
Today the popularity of pepper and piperine is still very high and they are still heavily used overall the world.

===Substance Identification===
*Chemical Name: 1-(5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoyl)-piperidine; 1-piperinoyl-piperidin; piperine
*Autoname: 5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-penta-2,4-dien-1-one
*Molecular Formula: C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
*Molecular Weight: 285.34g/mol
*Type of Substance: Heterocyclic
*Type of Bonding: Piperine has predominantly covalent bonds. However, with its large amount of hydrogen atoms it has been hydrogen bonds as well.
*Melting Point
<table cellspacing=0 border=1>
<tr><th>VALUE(MP)</th>
<th>Solvent (.SOL)</th>
<th>Entry Date</th>
<th>Notes</th><th>Refs.</th></tr>
<tr><th> C</th>
<th><br></th><th><br></th><th><br></th><th><br></th></tr>
<tr><td>129.2 - 130.5</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>1</td>
</tr>
<tr><td>129</td>
<td>diethyl ether</td>
<td><br></td>
<td><br></td>
<td>2-3</td>
</tr>
<tr><td>128</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>4</td>
</tr>
<tr><td>128 - 129.5</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>5-6</td>
</tr>
<tr><td>129 - 130</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>7</td>
</tr>
<tr><td>128 - 129</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>8</td>
</tr>
<tr><td>127 - 129</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>9</td>
</tr>
<tr><td>128 - 129</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>10</td>
</tr>
<tr><td>120 - 129</td>
<td><br></td>
<td><br></td>
<td><br></td>
<td>11</td>
</tr>
</table>

*Purity in Nature: 98% in piper nigrum. Can only be attained in 100% purity through processing in the laboratory
*Percent Composition by mass: C= 71% O= 17% H=6% N=5%
*Molecualr Structure of piperine:
[[Image:piperine1.jpg|frame|left|200px]]
<br>

===Chemical Property===
Piperine is more yellowish power in nature and turns to a stronger green tint after synthesis.
Piperine is soluble in the following solvents: alcohol, chloroform, ether, benzene and water. It is reactive only when in a solution.
<br>
Piperine does not have any taste unless it is in a solution. Its flavour comes from the reaction between the oil in the peppercorns and itself. The transformation of piperine into Chavicine associates with the loose of the piperine’s characteristic flavour ( pungency). In a boiled alcoholic caustic potash piperic acid can be produced from the piperine.
<br>
Piperine has the same molecular formula as the following substance: chavicine, morphine and volatile oil.

=== Synthesis ===

Piperine is a component of black pepper which causes sneezing. Its presence in pepper was discovered many years ago, and its structure was elucidated near the beginning of the century. The synthesis starts with an allylic, radical halogenation to introduce a bromine atom. An Arbuzov reaction with triethyl phosphite displaces the bromine and produces a phosphonate that is then coupled to piperonal using a modified Wittig reaction. Hydrolysis of the ester, formation of the acid chloride using oxalyl chloride, and coupling to piperidine completes the synthesis.

[[Image:Pip_Synthesis.png|500px]]

===Uses of Piperine===
Piperine is not only used to season food but also very useful in the medical field. Piperine has been used by people for thousands of years to cure many small ailments. In recent years the use of piperine has gone into a profound stage as assistant to the medications which save many lives each year. From the recent medical studies piperine was found to be very helpful to increase the absorption of certain vitamins (e.g. Selenium, Beta-Carotene and Vitamin B). What is more, piperine also has the ability to increase the thermo genesis of a body and create a demand for nutrients for metabolism as a consequence. This has a significant positive effect on sick or aged with defective intestinal lining patients.
<br>
Country Use
Mexico Anti-inflammatory
Anti-malarial Treatment
Cure for Stomach Ache
Morocco Weight Loss Treatment
Anti-leukemia Treatment
Indonesia Fever prevention/reducer
Treatment for Snake Venom Poisoning
Anti-epileptic Treatment
<br>
However, piperine can also act as a deadly killer of the common housefly and it can be found in most insecticides.

===Hazards Identification===
Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation (lung irritant)
<br>
Piperine may be combustible at high tempertature
<br>
Products of its combustion are potentially harmful as they contain CO, CO<sub>2</sub>, NO, NO<sub>2</sub>

===Precaution===
Keep away from heat. Keep away from sources of ignition. Empty containers pose a fire risk, evaporate the residue under a fume hood. Do not ingest or breathe dust. Avoid contact with skin and eyes.

===Storage===
Keep container dry. Keep in a cool place, well-ventilated palce. Keep container tightly closed.

== References ==

1. Sloop, J.C. J. Chem. Ed. 1995, 72, A25-A27 (Synthesis)
<br>
2. http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml
<br>
3. Substance Identification: Beilstein Reference 5-20-03-00469, 6-20
<br>
4. Melting Point 1-9 (Beilstein(2007/03): http://localhost:16001/x_BS070300AE_S90739.html
<br>
5. Little History of Piperine: http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_history_page.htm
<br>
6.http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_properties_page.htm
<br>
7.http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2000/Piperine/piperin_uses_page.htm

It07:Rapamycin

2007-10-22T22:41:24Z

Jlj06: /* References */

==Rapamycin==
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C<br>(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=
O)C(=O)<br>C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm<br>
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.<br>
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74<br>

It07:Rapamycin

2007-10-22T22:39:20Z

Jlj06:

==Rapamycin==
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! Rapamycin | General
|-
| [[IUPAC nomenclature|Systematic name]]
| (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,<br>
26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,<br>
27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-<br>
[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-<br>
1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-<br>
hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]-<br>
oxaazacyclohentriacontine-1,5,11,28,29<br>
(4H,6H,31H)-pentone
|-
| Other names
| Sirolimus, Antibiotic AY 22989, Rapamune, RAPA, RPM
|-
| [[Chemical formula|Molecular formula]]
| C<sub>51</sub>H<sub>79</sub>NO<sub>13 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C<br>(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=
O)C(=O)<br>C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

|-
| [[CAS registry number|CAS number]]
| 53123-88-9
|-
| [[Merck Index]]
| 12, 8288
|-
! {{chembox header}} | Properties
|-
| [[Molar mass]]
| 914.17 g/mol
|-
| [[Melting point]]
| 183°C-185°C (456K-458K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Optical Rotary Power (ORP)]]
| -58.2° at 589nm and 25°C
|-
| [[Solubility]]
| Soluble in Methanol, DMSO (Dimethyl sulfoxide)
|-
| [[Appearance]]
| White/Yellow powder
|-
| [[Safety]]
| Harmful if swallowed
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants. Sirolimus is used in combination with other medications to prevent rejection of kidney transplants. Sirolimus is in a class of medications called immunosuppressants. It works by suppressing the body's immune system. More specifically, it inhibits cytokine production by disrupting the transcriptional activation of cytokines. Rapamycin is a triene macrolide antibiotic, which demonstrates anti-fungal, anti-inflammatory, anti-tumor, anti-neoplastic and immunosuppressive properties. Rapamycin has been shown to block T-cell activation and proliferation, as well as, the activation of p70 S6 kinase and exhibits strong binding to FK-506 binding proteins. Rapamycin also inhibits the activity of the protein, mTOR, (mammalian target of rapamycin) which functions in a signaling pathway to promote tumor growth. Rapamycin binds to a receptor protein (FKBP12) and the rapamycin/FKB12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway. However, Rapamycin will only do this if it is bound to immunophilins. Rapamycin’s name is derived from the native word for Easter Island, Rapi Nui
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

===Uses===

Rapamycin's main use is currently to help prevent rejection of organ transplants by suprresing the body's immune system. It is also non toxic towards organs. It is also in testing stages as a treatment for cancer. Rapamycin potently inhibits downstream signaling from the mammalian target of rapamycin (mTOR) proteins which functions in a signaling pathway to promote tumor growth. These evolutionarily conserved protein kinases coordinate the balance between protein synthesis and protein degradation in response to nutrient quality and quantity. Rapamycin binds to the FK-506 binding protein (FKBP12, Kd = 0.2 nM) and the rapamycin/FKBP12 complex then binds to mTOR and prevents interaction of mTOR with target proteins in this signaling pathway.

==References==
1. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602026.html<br>
2. http://www.agscientific.com/Item/R1018.htm<br>
3. http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm<br>
4. http://www.fermentek.co.il/rapamycin.htm
5. Journal; Seghal et al.; JANTAJ; J. Antibiot.; 28; 1975; 727,729.
6. http://www.proteinkinase.biz/Shop/page.php?modul=GoShopping&op=show_article&aid=361&cid=74

2007-10-21T23:51:41Z

Jlj06: /* Rapamycin */

2007-10-21T23:35:15Z

Jlj06: /* Rapamycin */

It07:Rapamycin

2007-10-21T23:33:11Z

Jlj06: /* Rapamycin */

==Rapamycin==
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<title>Rapamycin</title>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Rapamycin.pdb</uploadedFileContents>
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Rapamycin
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Rapamycin.png|200px|]]
|-
! {{chembox header}} | General
|-
| [[IUPAC nomenclature|Systematic name]]
| ? 
|-
| Other names
| ? 
|-
| [[Chemical formula|Molecular formula]]
| ? 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| ?
|-
| [[Molar mass]]
| ?.?? g/mol
|-
| Appearance
| ? 
|-
| [[CAS registry number|CAS number]]
| [?-?-?]
|-
! {{chembox header}} | Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| ? g/cm³, ? 
|-
| [[Solubility]] in [[Water_(molecule)|water]]
| ? g/100 ml (?°C) 
|-



| [[Melting point]]
| ?°C (? K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Acid dissociation constant|Acidity]] (p''K''<sub>a</sub>) 
| ?
|-
| [[Acid dissociation constant|Basicity]] (p''K''<sub>b</sub>) 
| ?
|-
| [[Specific rotation|Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>]] 
| ?°
|-
| [[Viscosity]]
| ? [[Poise|cP]] at ?°C 
|-
! {{chembox header}} | Structure
|-
| [[Orbital_hybridisation#Molecule_shape|Molecular shape]] 
| ? 
|-
| [[Coordination geometry|Coordination<br />geometry]] 
| ? 
|-
| [[Crystal structure]] 
| ? 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| ? [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| ? 
|-
| [[NFPA 704]]
| 
|-
| [[Flash point]]
| ?°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: ? <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| ?
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [[Refractive index|''n'']], [[Dielectric constant|ε<sub>r</sub>]], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| ? 
|-
| Other [[Ion|cation]]s 
| ? 
|-
| Related [[?]] 
| ? 
|-
| Related compounds

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

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

==References==
#http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm

It07:Rapamycin

2007-10-21T23:30:41Z

Jlj06: /* Rapamycin */

==Rapamycin==
<jmol>
<jmolApplet>
<title>Rapamycin</title>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Rapamycin.pdb</uploadedFileContents>
</jmolApplet>

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

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:{{PAGENAME}}.jpg|200px|{{PAGENAME}}]] 
|-
! {{chembox header}} | General
|-
| [[IUPAC nomenclature|Systematic name]]
| ? 
|-
| Other names
| ? 
|-
| [[Chemical formula|Molecular formula]]
| ? 
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| ?
|-
| [[Molar mass]]
| ?.?? g/mol
|-
| Appearance
| ? 
|-
| [[CAS registry number|CAS number]]
| [?-?-?]
|-
! {{chembox header}} | Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| ? g/cm³, ? 
|-
| [[Solubility]] in [[Water_(molecule)|water]]
| ? g/100 ml (?°C) 
|-



| [[Melting point]]
| ?°C (? K) 
|-
| [[Boiling point]]
| ?°C (? K)
|-
| [[Acid dissociation constant|Acidity]] (p''K''<sub>a</sub>) 
| ?
|-
| [[Acid dissociation constant|Basicity]] (p''K''<sub>b</sub>) 
| ?
|-
| [[Specific rotation|Chiral rotation <nowiki>[α]</nowiki><sub>D</sub>]] 
| ?°
|-
| [[Viscosity]]
| ? [[Poise|cP]] at ?°C 
|-
! {{chembox header}} | Structure
|-
| [[Orbital_hybridisation#Molecule_shape|Molecular shape]] 
| ? 
|-
| [[Coordination geometry|Coordination<br />geometry]] 
| ? 
|-
| [[Crystal structure]] 
| ? 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| ? [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| ? 
|-
| [[NFPA 704]]
| 
|-
| [[Flash point]]
| ?°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: ? <br /> [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| ?
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and<br />properties]]
| [[Refractive index|''n'']], [[Dielectric constant|ε<sub>r</sub>]], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic<br />data]]
| Phase behaviour<br />Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| ? 
|-
| Other [[Ion|cation]]s 
| ? 
|-
| Related [[?]] 
| ? 
|-
| Related compounds

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

===Overview===

Also known as '''Sirolimus''' it helps to prevent organ rejection in transplants.
[[Image:Kidneytransplant.jpeg|thumb|Kidney transplant [http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm]]]

==References==
#http://www.thompsonsurgical.com/surgical_specialties/transplant/index.htm

File:Rapamycin.png

2007-10-21T23:28:13Z

Jlj06:

2007-10-21T19:41:27Z

Jlj06:

It07:Rapamycin

2007-10-19T00:24:34Z

Jlj06: /* Piperine */