Chemical substance record

Emtricitabine

143491-57-0C₈H₁₀FN₃O₃S247.251 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	143491-57-0	ChEBI ↗
Molecular formula	C₈H₁₀FN₃O₃S	ChEBI ↗
Molar mass	247.251 g/mol	ChEBI ↗
Monoisotopic mass	247.04269 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:31536	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	247.25 g/mol	PubChem ↗
Exact mass	247.04269053 Da	PubChem ↗
Computed XLogP	-0.6	PubChem ↗
Topological polar surface area (Å²)	113	PubChem ↗
H-bond donors	2	PubChem ↗
H-bond acceptors	5	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

emtricitabine

IUPAC name

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

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

Names & synonyms

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

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

Classification & relationships

ChEBI ontology

organofluorine compoundChEBI parent class · 37143 ↗pyrimidoneChEBI parent class · 38337 ↗monothioacetalChEBI parent class · 59793 ↗nucleoside analogueChEBI parent class · 60783 ↗

organofluorine compound organosulfur compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antiviral agentantitubercular agentantiinfective agentimmunosuppressive agentantiviral druginsulin-sensitizing drugHIV-1 reverse transcriptase inhibitoranti-HIV agentanti-HBV 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

0.00404447 mol

Uses 247.251 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

38.86%

O

Oxygen · 3 atoms

19.41%

N

Nitrogen · 3 atoms

17.00%

S

Sulfur · 1 atom

12.97%

F

Fluorine · 1 atom

7.68%

H

Hydrogen · 10 atoms

4.08%

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

Antiretroviral activity of emtricitabine, a potent nucleoside reverse transcriptase inhibitor. ↗Antiviral therapy · 2001 Jun · PMID 11491420

Emtricitabine: an antiretroviral agent for HIV infection. ↗Drugs · 2003 · PMID 14609348

US5538975 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

WO9214743 · 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:31536

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

Additional molecular descriptorsNCBI PubChem · CID 60877 · 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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