Chemical substance record

Pyrimethamine

58-14-0C₁₂H₁₃ClN₄248.717 g/mol

Organic/Inorganic Small MoleculeChEBI source record

An aminopyrimidine that is pyrimidine-2,4-diamine which is substituted at position 5 by a p-chlorophenyl group and at position 6 by an ethyl group. It is a folic acid antagonist used as an antimalarial or with a sulfonamide to treat toxoplasmosis. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	58-14-0	ChEBI ↗
Molecular formula	C₁₂H₁₃ClN₄	ChEBI ↗
Molar mass	248.717 g/mol	ChEBI ↗
Monoisotopic mass	248.08287 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:8673	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	248.71 g/mol	PubChem ↗
Exact mass	248.0828741 Da	PubChem ↗
Computed XLogP	2.7	PubChem ↗
Topological polar surface area (Å²)	77.8	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

pyrimethamine

IUPAC name

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

InChIKey

WKSAUQYGYAYLPV-UHFFFAOYSA-N

SMILES

CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1

InChI

InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)

Names & synonyms

5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diaminepirimetaminapyrimethaminum

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

Classification & relationships

ChEBI ontology

aminopyrimidineChEBI parent class · 38338 ↗monochlorobenzenesChEBI parent class · 83403 ↗

organochlorine compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antiparasitic agentantidepressantantipsychotic agentantineoplastic agentantifungal agentantiprotozoal drugantimalarialEC 1.5.1.3 (dihydrofolate reductase) inhibitoranti-HIV agentanti-anaemic 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

0.00402063 mol

Uses 248.717 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 · 12 atoms

57.95%

N

Nitrogen · 4 atoms

22.53%

Cl

Chlorine · 1 atom

14.25%

H

Hydrogen · 13 atoms

5.27%

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

In vitro generation of novel pyrimethamine resistance mutations in the Toxoplasma gondii dihydrofolate reductase. ↗Antimicrobial agents and chemotherapy · 2001 Apr · PMID 11257045

Genome comparison of progressively drug resistant Plasmodium falciparum lines derived from drug sensitive clone. ↗Memorias do Instituto Oswaldo Cruz · 2001 Apr · PMID 11313656

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:8673

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

Additional molecular descriptorsNCBI PubChem · CID 4993 · 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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