Sirolimus

Sirolimus
Clinical data
Trade names	Rapamune, Fyarro, Hyftor
Other names	Rapamycin, ABI-009
License data	EU EMA: by INN; US DailyMed: Sirolimus; US FDA: Sirolimus;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, intravenous, topical
ATC code	L04AH01 (WHO) L01EG04 (WHO), S01XA23 (WHO), QC01EB90 (WHO);
Legal status
Legal status	US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	14% (oral solution), lower with high-fat meals; 18% (tablet), higher with high-fat meals
Protein binding	92%
Metabolism	Liver
Elimination half-life	57–63 hours
Excretion	Mostly fecal
Identifiers
	IUPAC name (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[30.3.1.0~4,9~]hexatria; conta-16,24,26,28-tetraene-2,3,10,14,20-pentone;
CAS Number	53123-88-9 ;
PubChem CID	5284616;
DrugBank	DB00877 ;
ChemSpider	10482078 ;
UNII	W36ZG6FT64;
KEGG	D00753 ;
ChEBI	CHEBI:9168 ;
ChEMBL	ChEMBL413 ;
PDB ligand	RAP (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5023582 ;
ECHA InfoCard	100.107.147
Chemical and physical data
Formula	C51H79NO13
Molar mass	914.187 g·mol−1
3D model (JSmol)	Interactive image;
Solubility in water	0.0026
	SMILES 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 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 ; Key:QFJCIRLUMZQUOT-HPLJOQBZSA-N ;
	(verify)

Sirolimus, also known as rapamycin and sold under the brand name Rapamune among others, is a macrolide compound that is used to coat coronary stents, prevent organ transplant rejection, treat a rare lung disease called lymphangioleiomyomatosis, and treat perivascular epithelioid cell tumor (PEComa). It has immunosuppressant functions in humans and is especially useful in preventing the rejection of kidney transplants. It is a mechanistic target of rapamycin (mTOR) kinase inhibitor that reduces the sensitivity of T cells and B cells to interleukin-2 (IL-2), inhibiting their activity.

This compound also has a use in cardiovascular drug-eluting stent technologies to inhibit restenosis.

It is produced by the bacterium Streptomyces hygroscopicus and was isolated for the first time in 1972, from samples of Streptomyces hygroscopicus found on Easter Island. The compound was originally named rapamycin after the native name of the island, Rapa Nui. Sirolimus was initially developed as an antifungal agent. However, this use was abandoned when it was discovered to have potent immunosuppressive and antiproliferative properties due to its ability to inhibit mTOR. It was approved by the U.S. Food and Drug Administration (FDA) in September 1999. Hyftor was approved for treatment of facial angiofibroma in the European Union in May 2023.

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