Sirolimus

Also known as rapamycin, WY-090217, AY-22989, (-)-rapamycin

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 tumour (PEComa). It has immunosuppressant functions in humans and is especially useful in preventing the rejection of kidney transplants. It is a mammalian target of rapamycin (mTOR) kinase inhibitor that reduces the sensitivity of T cells and B cells to interleukin-2 (IL-2), inhibiting their activity.

Key facts

Drug.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[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
Drug.C: 51
Drug.H: 79
Drug.N: 1
Drug.O: 13
Drug.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
Drug.StdInChI: 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
Drug.StdInChIKey: QFJCIRLUMZQUOT-HPLJOQBZSA-N
Drug.solubility: 0.0026
Drug.Watchedfields: changed
Drug.verifiedrevid: 732542693
Drug.image: Sirolimus structure.svg
Drug.image_class: skin-invert-image
Drug.width: 250
Drug.image2: Sirolimus-from-1C9H-3D-sticks.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Rapamune, others

via Wikipedia infobox

Chemical data

Formula: C51H79NO13
Molecular weight: 914.2 g/mol
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]propan-2-yl]-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
SMILES: C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC
InChIKey: QFJCIRLUMZQUOT-HPLJOQBZSA-N
XLogP: 6
Polar surface area: 195 Å²
H-bond donors: 3
H-bond acceptors: 13
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1999
Admin. routes: oral, parenteral, topical
Indications: acute lymphoblastic leukemia, kidney disease, Abnormality of the cardiovascular system, acute graft vs. host disease

via ChEMBL · EBI

Research

28,544 papers

Sirolimus: its discovery, biological properties, and mechanism of action.Transplantation proceedings · 2003
Topical sirolimus in dermatology: a systematic review.Clinical and experimental dermatology · 2024
Sirolimus for Venous Malformations: A Systematic Review of Efficacy and Safety.Lymphatic research and biology · 2025
Sirolimus--challenging current perspectives.Therapeutic drug monitoring · 2006
Sirolimus for vascular anomalies in the first year of life: a systematic review.Journal of perinatology : official journal of the California Perinatal Association · 2024

via PubMed

Described at

newscientist.com →

Link to a page describing this subject · not written by Vinony

Wikidata facts

Has part: carbon
Mass: 913.555142

Show 14 more facts

Commons category: Sirolimus
chemical formula: C₅₁H₇₉NO₁₃
NCI Thesaurus ID: C1212
World Health Organisation international non-proprietary name: sirolimusum
canonical SMILES: CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
isomeric SMILES: CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=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](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O
medical condition treated: graft-versus-host disease
route of administration: intravenous infusion and defusion
defined daily dose: 3
subject has role: bactericide
found in taxon: Ophiocordyceps
legal status (medicine): boxed warning
significant drug interaction: ketoconazole
described at URL: www.newscientist.com/article/2516893-rapamycin-can-add-years-to-your-life-or-none-at-all-its-a-lottery

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