Rapamycin (>85%)

CAS: 53123-88-9

Ref. TR-R124000

Product Information

• Name: Rapamycin (>85%)
• Synonyms: (-)-Rapamycin, AY 22989, Antibiotic AY 22989, Cypher, NSC 226080, RAPA, RPM, Rapammune, Rapamune, SIIA 9268A, Sirolimus, Wy 090217, (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-, (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, (3S,6R,7E,9R,10R,12R,14S,15Z,17E,19E,21S,26R,27R,34aS)-9,27-dihydroxy-3-{(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, 14S-Rapamycin, 23,27-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, 9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-(3-(4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-, (3S-(3R*S*1R*,3S*,4S*)),6S*,7E,9S*,10S*,12S*,14R*,15E,17E,19E,21R*,23R*,26S*,27S*,34aR*))-, 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine, rapamycin deriv., 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, 9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-, [3S-[3R*[S*(1R*,3S*,4S*)],6S*,7E,9S*,10S*,12S*,14R*,15E,17E,19E,21R*,23R*,26S*,27S*,34aR*]]-, 6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone, Ay 22989, Cypher Bx Velocity, De 109, Hexadecahydro-9,27-dihydroxy-3-((1R)-2-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylethyl)-10,21-imethoxy-, Ms-Ro01, Ms-Ro02, Ms-Ro03, Nab rapamycin, Nsc 226080, PNP-sirolimus, Perceiva, Rapa, Rapamycin, Rapamysin, Siia 9268A, Supralimus, Svp-R, [3S-[3R*[S*(1R*,3S*,4S*)],6S*,7E,9S*,10S*,12S*,14R*,15E,17E,19E,21R*,23R*,26S*,27S*,34aR*]]-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-Hexadecahydro-9,27-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone

Description

Applications A triene macrolide antibiotic isolated from Streptomyces hygroscopicus. Name derived from the native word for Easter Island, Rapa’Nui. Used as an immunosuppressant; antirestenotic. Sirolimus (INN/USAN), also known as rapamycin, is an immunosuppressant drug used to prevent rejection in organ transplantation; it is especially useful in kidney transplants. It has shown its efficacy against neurodegenerative diseases including Alzheimer's and Parkinson's.
References Martel, P.R., et al.: Can. J. Physiol. Pharmacol., 55, 48 (1977), Carlson, R.P., et al.: J. Pharmacol. Exp. Ther., 266, 1125 (1993), Kahan, B.D., et al.: Lancet, 356, 194 (2000), Holmes, D.R., et al.: Circulation, 109, 634 (2004),

• Brand: TRC

Chemical properties

• Molecular weight: 914.17
• Formula: C₅₁H₇₉NO₁₃
• Purity: >85%
• Color/Form: Neat
• InChI: InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11-,16-12-,31-17-,35-25-/t30-,32-,33-,34-,36-,37?,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
• InChI key: InChIKey=QFJCIRLUMZQUOT-AZVSMJNQSA-N
• SMILES: CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)CC2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C