Structured Summary
Abstract
A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.
Chemical Identity
Chemical Information
- Molecular Formula
- C8H12N4O5
- Molecular Weight
- 244.20 g/mol
- CAS Registry No.
- 320-67-2
- IUPAC Name
- 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
- InChIKey
- NMUSYJAQQFHJEW-KVTDHHQDSA-N
- SMILES
- C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
- MeSH Unique ID
- D001374
- Source
- PubChem CID 9444
MeSH Record
Classification
Broader headings
Narrower headings
Related Concepts
Knowledge Graph
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Drug Class
Pharmacological Action
MeSH Record
Synonyms
7 entry terms
- 5-Azacytidine
- Azacytidine
- 5 Azacytidine
- NSC-102816
- Vidaza
- NSC 102816
- NSC102816
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
96; was AZACYTIDINE 1972-95 (Prov 1972-73)
MeSH Record
Previous Indexing
- Nucleosides (1966-1971)
- Triazines (1966-1971)
MeSH Hierarchy
Tree Numbers
AMA Style
References
- National Library of Medicine. Azacitidine. Medical Subject Headings (MeSH). 2026. Unique ID D001374. http://id.nlm.nih.gov/mesh/2026/D001374
- Azacitidine. In: Wikipedia. https://en.wikipedia.org/wiki/Azacitidine
- Azacitidine. In: Wikidata. https://www.wikidata.org/wiki/Q416451
- Azacitidine. In: PubChem Compound. CID 9444. https://pubchem.ncbi.nlm.nih.gov/compound/9444