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Rapamycin
- Sirolimus
- Optical Purity: Optically pure
- Soluble in DMSO
- MF: C51H79NO13
- MW: 914.17
Description
Specific inhibitor of mTOR (mammalian target of Rapamycin); it binds the cytosolic protein FKBP12 and inhibits mTOR pathway by directly binding the mTORC1. Rapamycin selectively inhibits interleukin-2 (IL-2) activation of p70 S6 kinase. It prevents activation of T cells and B cells by inhibiting their response to IL-2. An immunosuppressant drug used to prevent rejection in organ transplantation, especially useful in kidney transplants; also used as a coronary stent coating.
More Information
| Parent CAS No. | 53123-88-9 |
|---|---|
| Chemical Name | (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 |
| extra_info | . |
| SMILES | O=C1C([C@]2([C@@H](CC[C@@]([H])(C[C@@H](C(=CC=CC=C[C@H](C[C@@H](C)C(=O)[C@H](OC)[C@H](O)C(C)=C[C@@H](C)C(=O)C[C@@]([H])([C@H](C)C[C@@H]3CC[C@@H](O)[C@H](OC)C3)OC(=O)[C@]3([H])CCCCN13)C)C)OC)O2)C)O)=O |t:11,13,15,29,&1:3,4,7,10,17,19,23,26,31,36,38,41,44,46,53,r| |
| MFCD | N.A. |
| 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 |
| InChiKey | QFJCIRLUMZQUOT-HPLJOQBZSA-N |
| CID | 5284616 |
| Short Description | mTOR inhibitor |
References
- CJ Kuo et al. Rapamycin selectively inhibits interleukin-2 activation of p70 S6 kinase. Nature 1992, 358(6381), 70-73.
- EJ Brown et al. A mammalian protein targeted by G1-arresting rapamycin-receptor complex. Nature 1994, 369(6483) 756-758.
- S Kobayashi et al. Rapamycin, a specific inhibitor of the mammalian target of rapamycin, suppresses lymphangiogenesis and lymphatic metastasis. Cancer Sci. 2007, 98(5), 726-33.
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