AntibioticMech

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

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:15734 CHEBI:15734
• CHEBI:38104 CHEBI:38104
• CHEBI:59793 CHEBI:59793
• CHEBI:60783 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

Equivalent identifiers for this same structure in other resources.

• cas:134678-17-4
• drugbank:DB00709
• drugcentral:1539
• kegg.compound:C07065
• kegg.drug:D00353
• lincs.smallmolecule:LSM-5215
• patent:WO9117159
• pdb-ccd:3TC
• reaxys:5480511
• wikipedia.en:Lamivudine

Activity roles

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

• CHEBI:36044 CHEBI:36044
• CHEBI:53756 CHEBI:53756
• CHEBI:59897 CHEBI:59897
• CHEBI:64951 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

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

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