Chemicals and Drugs

Cytarabine

A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)

Chemical Identity

Chemical Information

Molecular Formula
C9H13N3O5
Molecular Weight
243.22 g/mol
CAS Registry No.
147-94-4
IUPAC Name
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
InChIKey
UHDGCWIWMRVCDJ-CCXZUQQUSA-N
SMILES
C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
MeSH Unique ID
D003561
Source
PubChem CID 6253

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

See Also

MeSH Record

Synonyms

15 entry terms
  • Arabinofuranosylcytosine
  • Arabinosylcytosine
  • Aracytidine
  • Cytosine Arabinoside
  • Arabinoside, Cytosine
  • Ara-C
  • Aracytine
  • Cytarabine Hydrochloride
  • Cytonal
  • Cytosar
  • Cytosar-U
  • beta-Ara C
  • Ara C
  • Cytosar U
  • beta Ara C

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

1966

MeSH Hierarchy

Tree Numbers

  1. D03w.383.742.680.245w.453w
  2. D13.570w.065.300w
  3. D13.570w.685.245w.453w

MeSH Record

NLM Classification

QV 269

AMA Style

References

  1. National Library of Medicine. Cytarabine. Medical Subject Headings (MeSH). 2026. Unique ID D003561. http://id.nlm.nih.gov/mesh/2026/D003561
  2. Cytarabine. In: Wikipedia. https://en.wikipedia.org/wiki/Cytarabine
  3. Cytarabine. In: Wikidata. https://www.wikidata.org/wiki/Q180983
  4. Cytarabine. In: PubChem Compound. CID 6253. https://pubchem.ncbi.nlm.nih.gov/compound/6253