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Pfizer Europe Ma Eeig (ES)
Source
CIMA_ES
USDailyMed:Sirolimus
AU:C
L04AH01(WHO)L01EG04(WHO),S01XA23(WHO),QC01EB90(WHO)
US:℞-onlyEU:Rx-only
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-((1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-2-propanyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
53123–88–9Y
5284616
DB00877Y
10482078Y
W36ZG6FT64
D00753Y
CHEBI:9168Y
ChEMBL413Y
RAP (PDBe,RCSB PDB)
DTXSID5023582
Interactive image
O[C@@H]1CC[C@H](C[C@H]1OC)C[C@@H](C)[C@@H]4CC(=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(/C)[C@@H](OC)C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N3CCCC[C@H]3C(=O)O4
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/s1YKey:QFJCIRLUMZQUOT-HPLJOQBZSA-NY
Sirolimus, also known asrapamycinand sold under the brand nameRapamuneamong others, is amacrolidecompound that is used to coatcoronary stents, preventorgan transplant rejection, treat a rare lung disease calledlymphangioleiomyomatosis, and treatperivascular epithelioid cell tumour(PEComa).It hasimmunosuppressantfunctions in humans and is especially useful in preventing the rejection ofkidneytransplants. It is amammalian target of rapamycin(mTOR) kinase inhibitorthat reduces the sensitivity ofT cellsandB cellstointerleukin-2(IL-2), inhibiting their activity.
This compound also has a use in cardiovasculardrug-eluting stenttechnologies to inhibitrestenosis.
It is produced by thebacteriumStreptomyces hygroscopicusand was isolated for the first time in 1972, from samples ofS. hygroscopicusfound onEaster Island.The compound was originally named rapamycin after the native name of the island, Rapa Nui.Sirolimus was initially developed as anantifungalagent. However, this use was abandoned when it was discovered to have potent immunosuppressive andantiproliferativeproperties due to itsability to inhibit mTOR. It was approved by the USFood and Drug Administration(FDA) in 1999.Hyftor (sirolimus gel) was authorized for topical treatment of facialangiofibromain the European Union in May 2023.