Sirolimus

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 Ų

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

• 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

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

Wikidata facts

Has part

carbon

Mass

913.555142

via Wikidata · CC0