ContaminantDB: Pyrimethamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:14 UTC

Update Date

2026-03-26 19:53:48 UTC

Accession Number

CHEM003736

Identification

Common Name

Pyrimethamine

Class

Small Molecule

Description

One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antimalarial
Antiprotozoal Agent
Drug
Folic Acid Antagonist
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine	ChEBI
2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine	ChEBI
2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine	ChEBI
5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine	ChEBI
5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine	ChEBI
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine	ChEBI
CD	ChEBI
Chloridine	ChEBI
Chloridyn	ChEBI
Diaminopyritamin	ChEBI
Ethylpyrimidine	ChEBI
Pirimetamina	ChEBI
Primethamine	ChEBI
Pyrimethaminum	ChEBI
Daraprim	Kegg
Chloridin	HMDB
Pirimetamin	HMDB
Pyremethamine	HMDB
Pyrimethamin	HMDB
Glaxo wellcome brand OF pyrimethamine	HMDB
GlaxoSmithKline brand OF pyrimethamine	HMDB
Tindurine	HMDB
Aventis brand OF pyrimethamine	HMDB
Wellcome brand OF pyrimethamine	HMDB
Malocide	HMDB

Chemical Formula

C₁₂H₁₃ClN₄

Average Molecular Mass

248.711 g/mol

Monoisotopic Mass

248.083 g/mol

CAS Registry Number

58-14-0

IUPAC Name

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

Traditional Name

pyrimethamine

SMILES

CCC1=C(C(N)=NC(N)=N1)C1=CC=C(Cl)C=C1

InChI Identifier

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)

InChI Key

WKSAUQYGYAYLPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminopyrimidines and derivatives. These are organic compounds containing an amino group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Aminopyrimidines and derivatives

Alternative Parents

Substituents

Aminopyrimidine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Hydropyrimidine
Benzenoid
Heteroaromatic compound
Azacycle
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Primary amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyrimidine (CHEBI:8673 )
monochlorobenzenes (CHEBI:8673 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	233.5°C
Boiling Point	Not Available
Solubility	121 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.75	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.22	ChemAxon
pKa (Strongest Basic)	7.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.54 m³·mol⁻¹	ChemAxon
Polarizability	25.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0090000000-4e966bed391e234a23e3	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0090000000-4e966bed391e234a23e3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pk-0290000000-f67f41257c448ad0d840	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0090000000-a146b85d59fc9835ed4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0090000000-84e4cea277c64351f21b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0190000000-d931593de00f33f04587	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0059-0980000000-a232e355dd50976aea07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-005a-0920000000-7d48f7cfecbd7823803a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0290000000-b6d3f56ade24c0e6984c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0290000000-415b60a9caab352df184	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0032-2960000000-583d00b81182f34e5a94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-84e4cea277c64351f21b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-a146b85d59fc9835ed4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0059-0980000000-a232e355dd50976aea07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0190000000-d931593de00f33f04587	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0090000000-a5bd8cb5be16b08fe352	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-0090000000-ec976a2cca417c4abd83	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-0090000000-142231cbd9fb9d4cd7ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-005a-0920000000-7d48f7cfecbd7823803a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-005a-0910000000-74228f82abe0906b09dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0190000000-2277a786baa63a6f391c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-005a-0920000000-aacf5c362f2e7330e364	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-cc03baac614916e188ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0190000000-8c90fdad9d6f513cfdcf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ec-2940000000-ad7ab31613780bee7745	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-7cec7981debaccce56c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1190000000-3e6ac4ed3d9334756216	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9740000000-b92682f3660029c1045d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2590000000-6434b6f0181741b3ca41	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed with peak levels occurring between 2 to 6 hours following administration

Mechanism of Toxicity

Pyrimethamine inhibits the dihydrofolate reductase of plasmodia and thereby blocks the biosynthesis of purines and pyrimidines, which are essential for DNA synthesis and cell multiplication. This leads to failure of nuclear division at the time of schizont formation in erythrocytes and liver.

Metabolism

Hepatic Half Life: 96 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine

Minimum Risk Level

Not Available