lamivudine

CHEBI:63577 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:15734
Label unavailable CHEBI:38104
Label unavailable CHEBI:59793
Label unavailable CHEBI:60783

Chemical structure

Computed structure properties
Molecular formula	C8H11N3O3S
Charge	0
Average mass	229.261 Da
Monoisotopic mass	229.05211 Da
Source	ChEBI
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

Also called

Epivir (BRAND_NAME)— chebi
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (EXACT_SYNONYM)— chebi
(-)-2'-Deoxy-3'-thiacytidine (EXACT_SYNONYM)— chebi
2',3'-Dideoxy-3'-thiacytidine (EXACT_SYNONYM)— chebi
3'-Thia-2',3'-dideoxycytidine (EXACT_SYNONYM)— chebi
3TC (EXACT_SYNONYM)— chebi
Lamivudine (EXACT_SYNONYM)— chebi
beta-L-2',3'-Dideoxy-3'-thiacytidine (EXACT_SYNONYM)— chebi
beta-L-3'-Thia-2',3'-dideoxycytidine (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral drug CHEBI:36044
HIV-1 reverse transcriptase inhibitor CHEBI:53756
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor CHEBI:59897
anti-HBV agent CHEBI:64951

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:63577`	lamivudine	`antibioticmech:chebi-73c1d41050`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor), CHEBI:59897 (EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-28 · seed_from_sources
Re-seeded; changed: genotype_resistance_score_rules (HIVDB_HIVFACTS be1c11a5145fea9073fdb71801919d4a34265336). Upstream retrieval date 2026-08-30, unchanged.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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