Structure via PubChem · Public domain (PubChem)
sirolimus
Sign in to saveAlso 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 Ų
- H-bond donors
- 3
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
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
Rapamycin can add years to your life, or none at all – it’s a lottery | New Scientist
The drug rapamycin has been held up for its life-extending properties, but whether this treatment – or fasting – actually adds years to your life isn't guaranteed
newscientist.com →Link to a page describing this subject · 4,298 chars · not written by Vinony
Wikidata facts
- Mass
- 913.555142
Show 8 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
- defined daily dose
- 3
Sources (8)
via Wikidata · CC0
~29 min read
Article
37 sectionsContents
- Medical uses
- Prevention of transplant rejection
- Lymphangioleiomyomatosis
- Coronary stent coating
- Vascular malformations
- Angiofibromas
- Adverse effects
- Diabetes-like symptoms
- Lung toxicity
- Lowered effectiveness of immune system
- Cancer risk
- Impaired wound healing
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Biosynthesis
- Society and culture
- Legal status
- Research
- Cancer
- Tuberous sclerosis complex
- Effects on longevity
- Topical administration
- SARS-CoV-2
- Atherosclerosis
- Lupus
- Lymphatic malformation (LM)
- Graft-versus-host disease
- Applications in biology research
- Neurodegenerative disorders
- Veterinary uses
- See also
- References
- Further reading
- External links
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.
This compound also has a use in cardiovascular drug-eluting stent technologies to inhibit restenosis.