CHEBI:8455 - proguanil

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ChEBI Name proguanil
ChEBI ID CHEBI:8455
Definition A biguanide compound which has isopropyl and p-chlorophenyl substituents on the terminal N atoms. A prophylactic antimalarial drug, it works by inhibiting the enzyme dihydrofolate reductase, which is involved in the reproduction of the malaria parasites Plasmodium falciparum and P. vivax within the red blood cells.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H16ClN5
Net Charge 0
Average Mass 253.73100
Monoisotopic Mass 253.109
InChI InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
InChIKey SSOLNOMRVKKSON-UHFFFAOYSA-N
SMILES CC(C)NC(=N)NC(=N)Nc1ccc(Cl)cc1
Roles Classification
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.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
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).
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.
hypoglycemic agent
A drug which lowers the blood glucose level.
(via biguanides )
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ChEBI Ontology
Outgoing proguanil (CHEBI:8455) has role antimalarial (CHEBI:38068)
proguanil (CHEBI:8455) has role antiprotozoal drug (CHEBI:35820)
proguanil (CHEBI:8455) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
proguanil (CHEBI:8455) is a biguanides (CHEBI:53662)
proguanil (CHEBI:8455) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
N-(4-chlorophenyl)-N'-(propan-2-yl)imidodicarbonimidic diamide
INNs Sources
proguanil ChemIDplus
proguanilum ChemIDplus
Synonyms Sources
1-(p-chlorophenyl)-5-isopropylbiguanide ChEBI
Chlorguanide ChemIDplus
Chloroguanide KEGG COMPOUND
N-(4-Chlorophenyl)-N'-(isopropyl)-imidodicarbonimidic diamide KEGG COMPOUND
N-(4-Chlorophenyl)-N'-(isopropyl)-imidodicarbonimidic diamide KEGG COMPOUND
Database Links Databases
2282 DrugCentral
C07631 KEGG COMPOUND
D08428 KEGG DRUG
DB01131 DrugBank
HMDB15263 HMDB
LSM-2618 LINCS
Proguanil Wikipedia
View more database links
Registry Numbers Types Sources
2811599 Reaxys Registry Number Reaxys
2811599 Beilstein Registry Number Beilstein
500-92-5 CAS Registry Number KEGG COMPOUND
500-92-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10348748 PubMed citation Europe PMC
10848923 PubMed citation Europe PMC
15504827 PubMed citation Europe PMC
8866915 PubMed citation Europe PMC
Last Modified
22 February 2017