AntibioticMech

emtricitabine

CHEBI:31536 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:37143 CHEBI:37143
• CHEBI:38337 CHEBI:38337
• CHEBI:59793 CHEBI:59793
• CHEBI:60783 CHEBI:60783

Chemical structure

Computed structure properties

Molecular formula	C8H10FN3O3S
Charge	0
Average mass	247.251 Da
Monoisotopic mass	247.04269 Da
Source	ChEBI
InChIKey	XQSPYNMVSIKCOC-NTSWFWBYSA-N

SMILES

Nc1nc(=O)n([C@@H]2CS[C@H](CO)O2)cc1F

InChI

InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1

Also called

• 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
• (2R-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone (EXACT_SYNONYM)— chebi
• (−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine (EXACT_SYNONYM)— chebi
• (−)-2'-deoxy-5-fluoro-3'-thiacytidine (EXACT_SYNONYM)— chebi
• (−)-FTC (EXACT_SYNONYM)— chebi
• (−)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one (EXACT_SYNONYM)— chebi
• (−)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidine (EXACT_SYNONYM)— chebi
• 4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one (EXACT_SYNONYM)— chebi
• 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one (EXACT_SYNONYM)— chebi
• 5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (EXACT_SYNONYM)— chebi
• EMTRICITABINE (EXACT_SYNONYM)— chebi
• Emtricitabine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• beilstein:5908714
• cas:143491-57-0
• drugbank:DB00879
• drugcentral:1003
• kegg.compound:C12599
• kegg.drug:D01199
• patent:US5538975
• patent:WO9214743
• pdb-ccd:ETV
• wikipedia.en:Emtricitabine

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

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:31536	emtricitabine	antibioticmech:chebi-141b825977	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 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.