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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.
Supplier Information
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Formula Source
C12H13ClN4 ChEBI
Net Charge 0
Average Mass 248.71100
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): 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).
Biological Role(s): 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).
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.
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.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing pyrimethamine (CHEBI:8673) has role antimalarial (CHEBI:38068)
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 organochlorine compound (CHEBI:36683)
IUPAC Name
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
INNs Sources
pirimetamina ChemIDplus
pyriméthamine WHO MedNet
pyrimethamine ChemIDplus
pyrimethaminum ChemIDplus
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
Database Links Databases
C07391 KEGG COMPOUND
D00488 KEGG DRUG
DB00205 DrugBank
HMDB14350 HMDB
Pyrimethamine Wikipedia
View more database links
Registry Numbers Types Sources
219864 Reaxys Registry Number Reaxys
219864 Beilstein Registry Number Beilstein
58-14-0 CAS Registry Number ChemIDplus
58-14-0 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11257045 PubMed citation CiteXplore
11313656 PubMed citation CiteXplore
12543697 PubMed citation CiteXplore
16157660 PubMed citation CiteXplore
19435820 PubMed citation CiteXplore
3377143 PubMed citation CiteXplore
Last Modified
17 February 2014

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