Chemicals and Drugs

Zalcitabine

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.

Chemical Identity

Chemical Information

Molecular Formula
C9H13N3O3
Molecular Weight
211.22 g/mol
CAS Registry No.
7481-89-2
IUPAC Name
4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
InChIKey
WREGKURFCTUGRC-POYBYMJQSA-N
SMILES
C1C[C@@H](O[C@@H]1CO)N2C=CC(=NC2=O)N
MeSH Unique ID
D016047
Source
PubChem CID 24066

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

9 entry terms
  • 2',3'-Dideoxycytidine
  • Dideoxycytidine
  • ddC (Antiviral)
  • 2',3' Dideoxycytidine
  • HIVID Roche
  • Hivid
  • NSC-606170
  • NSC 606170
  • NSC606170

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

94; was DIDEOXYCYTIDINE 1990-93

MeSH Record

Previous Indexing

  • Deoxycytidine/analogs & derivatives (1986-1989)
  • Dideoxynucleosides (1989)

MeSH Hierarchy

Tree Numbers

  1. D03w.383.742.680.245w.500w.950w
  2. D13.570w.230w.329w.950w
  3. D13.570w.230w.500.925w
  4. D13.570w.685.245w.500w.950w

AMA Style

References

  1. National Library of Medicine. Zalcitabine. Medical Subject Headings (MeSH). 2026. Unique ID D016047. http://id.nlm.nih.gov/mesh/2026/D016047
  2. Zalcitabine. In: Wikipedia. https://en.wikipedia.org/wiki/Zalcitabine
  3. Zalcitabine. In: Wikidata. https://www.wikidata.org/wiki/Q2344582
  4. Zalcitabine. In: PubChem Compound. CID 24066. https://pubchem.ncbi.nlm.nih.gov/compound/24066