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
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.