Chemicals and Drugs

Sirolimus

A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.

Chemical Identity

Chemical Information

Molecular Formula
C51H79NO13
Molecular Weight
914.2 g/mol
CAS Registry No.
53123-88-9
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
InChIKey
QFJCIRLUMZQUOT-HPLJOQBZSA-N
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
MeSH Unique ID
D020123
Source
PubChem CID 5284616

MeSH Record

Classification

Broader headings

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

8 entry terms
  • Rapamycin
  • AY 22-989
  • I-2190A
  • Rapamune
  • AY 22 989
  • AY 22989
  • I 2190A
  • I2190A

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

1999; use SIROLIMUS (NM) 1980-1997

MeSH Record

Previous Indexing

  • Polyenes (1976-1998)

MeSH Hierarchy

Tree Number

  1. D02w.540w.505w.760w

AMA Style

References

  1. National Library of Medicine. Sirolimus. Medical Subject Headings (MeSH). 2026. Unique ID D020123. http://id.nlm.nih.gov/mesh/2026/D020123
  2. Sirolimus. In: Wikipedia. https://en.wikipedia.org/wiki/Sirolimus
  3. Sirolimus. In: Wikidata. https://www.wikidata.org/wiki/Q32089
  4. Sirolimus. In: PubChem Compound. CID 5284616. https://pubchem.ncbi.nlm.nih.gov/compound/5284616