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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 The anti-malarial combination chloroproguanil and dapsone has been withdrawn following demonstration of post-treatment haemolytic anaemia in glucose-6-phosphate dehydrogenase (G6PD) deficient patients in a phase III clinical trial.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
139594
PubMed

PubMed

TitleDatePubMed
Pneumocystis carinii dihydrofolate reductase used to screen potential antipneumocystis drugs.
1991 Jul
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 16:09:13 UTC 2023
Edited
by admin
on Fri Dec 15 16:09:13 UTC 2023
Record UNII
8O3249M729
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CHLORPROGUANIL [MI]
Common 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 Fri Dec 15 16:09:13 UTC 2023 , Edited by admin on Fri Dec 15 16:09:13 UTC 2023
PRIMARY
INN
795
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
NCI_THESAURUS
C79941
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-660-3
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
SMS_ID
100000081874
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
EVMPD
SUB06207MIG
Created by admin on Fri Dec 15 16:09:13 UTC 2023 , Edited by admin on Fri Dec 15 16:09:13 UTC 2023
PRIMARY
MERCK INDEX
m3460
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY Merck Index
CAS
537-21-3
Created by admin on Fri Dec 15 16:09:13 UTC 2023 , Edited by admin on Fri Dec 15 16:09:13 UTC 2023
PRIMARY
DRUG CENTRAL
620
Created by admin on Fri Dec 15 16:09:13 UTC 2023 , Edited by admin on Fri Dec 15 16:09:13 UTC 2023
PRIMARY
DRUG BANK
DB12314
Created by admin on Fri Dec 15 16:09:13 UTC 2023 , Edited by admin on Fri Dec 15 16:09:13 UTC 2023
PRIMARY
WIKIPEDIA
CHLORPROGUANIL
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
PUBCHEM
22323
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
MESH
C007030
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID5022807
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
PRIMARY
FDA UNII
8O3249M729
Created by admin on Fri Dec 15 16:09:14 UTC 2023 , Edited by admin on Fri Dec 15 16:09:14 UTC 2023
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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