pyrimethamine (CHEBI:8673)

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ChEBI Name	pyrimethamine

ChEBI ID	CHEBI:8673

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C12H13ClN4

Net Charge

Average Mass

248.71100

Monoisotopic Mass

248.08287

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)

InChIKey

WKSAUQYGYAYLPV-UHFFFAOYSA-N

SMILES

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

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. EC 1.5.1.3 (dihydrofolate reductase) inhibitor An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3). antiprotozoal drug Any antimicrobial drug which is used to treat or prevent protozoal infections.

Application(s):	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. antiprotozoal drug Any antimicrobial drug which is used to treat or prevent protozoal infections.

ChEBI Ontology
Outgoing	pyrimethamine (CHEBI:8673) has role antimalarial (CHEBI:38068) pyrimethamine (CHEBI:8673) has role antiprotozoal drug (CHEBI:35820) pyrimethamine (CHEBI:8673) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683) pyrimethamine (CHEBI:8673) is a aminopyrimidine (CHEBI:38338) pyrimethamine (CHEBI:8673) is a monochlorobenzenes (CHEBI:83403)

IUPAC Name

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

Synonyms	Sources
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine	ChemIDplus
2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine	ChemIDplus
2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine	ChemIDplus
5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine	ChemIDplus
5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine	ChemIDplus
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine	ChemIDplus
CD	DrugBank
Chloridine	DrugBank
Chloridyn	DrugBank
Diaminopyritamin	ChemIDplus
Ethylpyrimidine	ChemIDplus
Primethamine	DrugBank

Last Modified

19 June 2017