Chemicals and Drugs

Lamivudine

A reverse transcriptase inhibitor and ZALCITABINE analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat HIV disease.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A reverse transcriptase inhibitor and ZALCITABINE analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat HIV disease.

Chemical Identity

Chemical Information

Molecular Formula
C8H11N3O3S
Molecular Weight
229.26 g/mol
CAS Registry No.
134678-17-4
IUPAC Name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
InChIKey
JTEGQNOMFQHVDC-NKWVEPMBSA-N
SMILES
C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
MeSH Unique ID
D019259
Source
PubChem CID 60825

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

15 entry terms
  • 2',3'-Dideoxy-3'-thiacytidine
  • 2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-
  • 3TC Lamivudine
  • 2',3' Dideoxy 3' thiacytidine
  • Lamivudine, 3TC
  • BCH-189
  • Epivir
  • GR-109714X
  • GR109714X
  • Lamivudine, (+)-cis-
  • Lamivudine, (+-)-trans-
  • Lamivudine, (2S-cis)-Isomer
  • BCH 189
  • BCH189
  • GR 109714X

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

97; was LAMIVUDINE (NM) 1991-96

MeSH Record

Previous Indexing

  • Cytosine/analogs & derivatives (1991-1992)
  • Zalcitabine/analogs & derivatives (1993-1996)

MeSH Hierarchy

Tree Numbers

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

AMA Style

References

  1. National Library of Medicine. Lamivudine. Medical Subject Headings (MeSH). 2026. Unique ID D019259. http://id.nlm.nih.gov/mesh/2026/D019259
  2. Lamivudine. In: Wikipedia. https://en.wikipedia.org/wiki/Lamivudine
  3. Lamivudine. In: Wikidata. https://www.wikidata.org/wiki/Q422631
  4. Lamivudine. In: PubChem Compound. CID 60825. https://pubchem.ncbi.nlm.nih.gov/compound/60825