Structure via PubChem · Public domain (PubChem)
sirólimus
Sign in to saveAlso known as rapamycin, WY-090217, AY-22989, (-)-rapamycin
medicamento inmunosupresor usado para evitar el rechazo de órganos trasplantados
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
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
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
Sources (8)
via Wikidata · CC0
Article · Español
La rapamicina o sirólimus es una lactona macrocíclica aislada del , una bacteria que se encuentra en el suelo de Rapa Nui (isla de Pascua) que inhibe el crecimiento de hongos tales como Candida albicans, y . Es un medicamento inmunosupresor usado para evitar el rechazo de órganos trasplantados; se usa especialmente en el trasplante de riñón. Tiempo después, el medicamento mostró eficacia para combatir algunos cánceres, al frenar la proliferación celular y el crecimiento de los tumores. Por esta propiedad igualmente se usa para recubrir stents medicados de uso intracoronario y evitar su reestenosis. En julio de 2009, un artículo en la revista Nature demostraba que este medicamento prolongó hasta en un 38% la vida de unos ratones, hallazgo que abre expectativas sobre su uso en tratamientos para retrasar el envejecimiento humano. Se comercializa bajo el nombre comercial de Rapamune por Wyeth.
Abstract from DBpedia / Wikipedia · CC BY-SA