ChemFOnt: Showing chemical card for Pyrimethamine (CFc000008745)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:39 UTC

Chemfont ID

CFc000008745

Molecule Identification

Common Name

Pyrimethamine

Definition

Pyrimethamine is only found in individuals that have used or taken this drug. It is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]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.

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 Weight

248.711

Monoisotopic Molecular Weight

248.082874143

IUPAC Name

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

Traditional Name

pyrimethamine

CAS Registry Number

58-14-0

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014350)

Process

Not Available

Role

Not Available

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon