Chemical substance record

Lamivudine

134678-17-4C₈H₁₁N₃O₃S229.261 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase, it is used as an antiviral in the treatment of AIDS and hepatitis B. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	134678-17-4	ChEBI ↗
Molecular formula	C₈H₁₁N₃O₃S	ChEBI ↗
Molar mass	229.261 g/mol	ChEBI ↗
Monoisotopic mass	229.05211 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:63577	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	229.26 g/mol	PubChem ↗
Exact mass	229.05211239 Da	PubChem ↗
Computed XLogP	-0.9	PubChem ↗
Topological polar surface area (Å²)	113	PubChem ↗
H-bond donors	2	PubChem ↗
H-bond acceptors	4	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

lamivudine

IUPAC name

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one

InChIKey

JTEGQNOMFQHVDC-NKWVEPMBSA-N

SMILES

Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1

InChI

InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

Names & synonyms

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-oneEpivir

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

primary alcoholChEBI parent class · 15734 ↗oxacycleChEBI parent class · 38104 ↗monothioacetalChEBI parent class · 59793 ↗nucleoside analogueChEBI parent class · 60783 ↗

alcohol organosulfur compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antiviral agentantitubercular agentantiinfective agentantineoplastic agentantiviral drugprodrugallergenHIV-1 reverse transcriptase inhibitorEC 2.7.7.49 (RNA-directed DNA polymerase) inhibitorhepatoprotective agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00436184 mol

Uses 229.261 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 8 atoms

41.91%

O

Oxygen · 3 atoms

20.94%

N

Nitrogen · 3 atoms

18.33%

S

Sulfur · 1 atom

13.99%

H

Hydrogen · 11 atoms

4.84%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Nucleoside analogues for chronic hepatitis B: antiviral efficacy and viral resistance. ↗The American journal of gastroenterology · 2002 Jul · PMID 12135009

On-line coupling of anion exchange and ion-pair chromatography for measurement of intracellular triphosphate metabolites of reverse transcriptase inhibitors. ↗Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2009 Nov 1 · PMID 19783232

WO9117159 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:63577

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 60825 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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