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Details

Stereochemistry ACHIRAL
Molecular Formula C11H15Cl2N5.ClH
Molecular Weight 324.637
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROGUANIL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=SVJMILFDDBKCGG-UHFFFAOYSA-N
InChI=1S/C11H15Cl2N5.ClH/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);1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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 The anti-malarial combination chloroproguanil and dapsone has been withdrawn following demonstration of post-treatment haemolytic anaemia in glucose-6-phosphate dehydrogenase (G6PD) deficient patients in a phase III clinical trial.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
139594
PubMed

PubMed

TitleDatePubMed
Pneumocystis carinii dihydrofolate reductase used to screen potential antipneumocystis drugs.
1991 Jul
Identification of highly potent and selective inhibitors of Toxoplasma gondii dihydrofolate reductase.
1993 Sep
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 Jun
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
Mutations in dhfr in Plasmodium falciparum infections selected by chlorproguanil-dapsone treatment.
2002 Dec 15
Patents

Patents

5565451
5
JP2002520419A
58
JP2006503898A
44
JP2011524365A
34
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:32:53 GMT 2023
Edited
by admin
on Fri Dec 15 16:32:53 GMT 2023
Record UNII
6T04V14CU9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORPROGUANIL HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
PROGUANIL RELATED COMPOUND F [USP-RS]
Common Name English
PROGUANIL RELATED COMPOUND F
USP   USP-RS  
Common Name English
CHLORPROGUANIL HCL
Common Name English
1-(3,4-DICHLOROPHENYL)-5-ISOPROPYLBIGUANIDE HYDROCHLORIDE
Systematic Name English
IMIDODICARBONIMIDIC DIAMIDE, N-(3,4-DICHLOROPHENYL)-N'-(1-METHYLETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
PROGUANIL RELATED COMPOUND F [USP IMPURITY]
Common Name English
CHLORPROGUANIL HYDROCHLORIDE [MI]
Common Name English
CHLORPROGUANIL HYDROCHLORIDE [MART.]
Common Name English
LAPUDRINE
Brand Name English
Chlorproguanil hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
Code System Code Type Description
CAS
6001-93-0
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
RS_ITEM_NUM
1568084
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
MERCK INDEX
m3460
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY Merck Index
EVMPD
SUB01253MIG
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-846-5
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID00892386
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
WIKIPEDIA
Chlorproguanil hydrochloride
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
SMS_ID
100000092716
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
NCI_THESAURUS
C78096
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
DRUG BANK
DBSALT002176
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
FDA UNII
6T04V14CU9
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
CAS
15537-76-5
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
SUPERSEDED
ChEMBL
CHEMBL1213553
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
PUBCHEM
22322
Created by admin on Fri Dec 15 16:32:53 GMT 2023 , Edited by admin on Fri Dec 15 16:32:53 GMT 2023
PRIMARY
Related Record Type Details
Structure of CHLORPROGUANIL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CHLORPROGUANIL
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