Chemicals and Drugs

Zidovudine

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. 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, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.

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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. 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, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.

Chemical Identity

Chemical Information

Molecular Formula
C10H13N5O4
Molecular Weight
267.24 g/mol
CAS Registry No.
30516-87-1
IUPAC Name
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
InChIKey
HBOMLICNUCNMMY-XLPZGREQSA-N
SMILES
CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
MeSH Unique ID
D015215
Source
PubChem CID 35370

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

14 entry terms
  • 3'-Azido-2',3'-Dideoxythymidine
  • 3'-Azido-3'-deoxythymidine
  • AZT (Antiviral)
  • AZT Antiviral
  • AZT, Antiviral
  • Azidothymidine
  • 3' Azido 2',3' Dideoxythymidine
  • 3' Azido 3' deoxythymidine
  • Antiviral AZT
  • BW A509U
  • BWA-509U
  • Retrovir
  • BWA 509U
  • BWA509U

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

89

MeSH Record

Previous Indexing

  • Thymidine/analogs & derivatives (1975-1988)

MeSH Hierarchy

Tree Numbers

  1. D03w.383.742.680.705w.950w
  2. D13.570w.230w.500.950w
  3. D13.570w.230w.855w.950w
  4. D13.570w.685.705w.950w

AMA Style

References

  1. National Library of Medicine. Zidovudine. Medical Subject Headings (MeSH). 2026. Unique ID D015215. http://id.nlm.nih.gov/mesh/2026/D015215
  2. Zidovudine. In: Wikipedia. https://en.wikipedia.org/wiki/Zidovudine
  3. Zidovudine. In: Wikidata. https://www.wikidata.org/wiki/Q198504
  4. Zidovudine. In: PubChem Compound. CID 35370. https://pubchem.ncbi.nlm.nih.gov/compound/35370