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Details

Stereochemistry ACHIRAL
Molecular Formula C11H15Cl2N5
Molecular Weight 288.176
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROGUANIL

SMILES

CC(C)NC(=N)NC(=N)NC1=CC=C(Cl)C(Cl)=C1

InChI

InChIKey=ISZNZKHCRKXXAU-UHFFFAOYSA-N
InChI=1S/C11H15Cl2N5/c1-6(2)16-10(14)18-11(15)17-7-3-4-8(12)9(13)5-7/h3-6H,1-2H3,(H5,14,15,16,17,18)

HIDE SMILES / InChI
Molecular Formula C11H15Cl2N5
Molecular Weight 288.176
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Chlorproguanil is a biguanide. Chlorproguanil is active against P. falciparum and P. malariae. Chlorproguanil acts by inhibition of dihydrofolate reductase after cytochrome P450-catalysed cyclization. Chlorproguanil combined with dapsone was developing for the treatment of falciparum malaria. The anti-malarial combination chloroproguanil and dapsone has been withdrawn following demonstration of post-treatment haemolytic anaemia in glucose-6-phosphate dehydrogenase (G6PD) deficient patients in a phase III clinical trial.

Originator

Approval Year

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Mutations in dhfr in Plasmodium falciparum infections selected by chlorproguanil-dapsone treatment.
2002-12-15
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001-10-13
Molecular evidence of greater selective pressure for drug resistance exerted by the long-acting antifolate Pyrimethamine/Sulfadoxine compared with the shorter-acting chlorproguanil/dapsone on Kenyan Plasmodium falciparum.
2000-06
Identification of highly potent and selective inhibitors of Toxoplasma gondii dihydrofolate reductase.
1993-09
Pneumocystis carinii dihydrofolate reductase used to screen potential antipneumocystis drugs.
1991-07
Pharmacokinetics of Aryldihydro-s-triazines with antifolate activity II: Blood levels and their relevance to antineoplastic activity in rats.
1978-03
Patents

Patents

5565451
5
JP2002520419A
58
JP2006503898A
44
JP2011524365A
34
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:20:22 GMT 2025
Edited
by admin
on Mon Mar 31 18:20:22 GMT 2025
Record UNII
8O3249M729
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORPROGUANIL [MI]
Preferred Name English
CHLORPROGUANIL
INN   MI   WHO-DD  
INN  
Official Name English
1-(3,4-DICHLOROPHENYL)-5-ISOPROPYLBIGUANIDE
Systematic Name English
Chlorproguanil [WHO-DD]
Common Name English
PROGUANIL RELATED COMPOUND F (FREE BASE)
Common Name English
chlorproguanil [INN]
Common Name English
PROGUANIL HYDROCHLORIDE RELATED COMPOUND F [USP IMPURITY]
Common Name English
N1-3,4-DICHLOROPHENYL-N5-ISOPROPYLBIGUANIDE
Systematic Name English
PROGUANIL RELATED COMPOUND F FREE BASE
Common Name English
PROGUANIL HYDROCHLORIDE IMPURITY F [EP IMPURITY]
Common Name English
BIGUANIDE, 1-(3,4-DICHLOROPHENYL)-5-ISOPROPYL-
Systematic Name English
N1-3,4-DICHLOROPHENYL-N5-ISOPROPYLDIGUANIDE
Systematic Name English
Code System Code Type Description
ChEMBL
CHEMBL1213553
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
INN
795
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
NCI_THESAURUS
C79941
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-660-3
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
SMS_ID
100000081874
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
EVMPD
SUB06207MIG
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
MERCK INDEX
m3460
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY Merck Index
CAS
537-21-3
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
DRUG CENTRAL
620
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
DRUG BANK
DB12314
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
WIKIPEDIA
CHLORPROGUANIL
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
PUBCHEM
22323
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
MESH
C007030
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID5022807
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
FDA UNII
8O3249M729
Created by admin on Mon Mar 31 18:20:22 GMT 2025 , Edited by admin on Mon Mar 31 18:20:22 GMT 2025
PRIMARY
Related Record Type Details
Structure of CHLORPROGUANIL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Chlorcycloguanil
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of PROGUANIL HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of Chlorcycloguanil
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