U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N3O3S
Molecular Weight 283.347
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARIPORIDE

SMILES

CC(C)C1=C(C=C(C=C1)C(=O)NC(N)=N)S(C)(=O)=O

InChI

InChIKey=IWXNYAIICFKCTM-UHFFFAOYSA-N
InChI=1S/C12H17N3O3S/c1-7(2)9-5-4-8(11(16)15-12(13)14)6-10(9)19(3,17)18/h4-7H,1-3H3,(H4,13,14,15,16)

HIDE SMILES / InChI
Cariporide is a selective sodium-hydrogen antiporter inhibitor patented by a pharmaceutical company Hoechst A.-G. for treatment myocardial ischemia-reperfusion injury. The sodium-hydrogen exchanger is an important player in the pathophysiology of myocardial ischemia-reperfusion injury. The accumulation of hydrogen ions in the myocyte cytosol; during ischemia creates a proton gradient that promotes the efflux of hydrogen ions in exchange for the influx of sodium ions. This sodium buildup can secondary activates the sodium-calcium exchanger to operate in the reverse mode, resulting in a net calcium accumulation in myocyte cytosol, which leads to dysfunction and cell death. By inhibiting sodium-hydrogen exchange, Cariporide can prevent the accumulation of calcium in the cytosol, therefore reduce the infarct size. In clinical trials, Cariporide shows a statistically significant decline in myocardial infarction but increases mortality. Due to the increase in mortality, cariporide did not pass clinical trials.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
65.0 nM [IC50]
62000.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Antiarrhythmic effects of HOE642, a novel Na(+)-H+ exchange inhibitor, on ventricular arrhythmias in animal hearts.
1996 Dec 19
Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1.
2002 Sep 6
Endothelin causes contraction of human esophageal muscularis mucosae through interaction with both ETA and ETB receptors.
2004 Mar 15
Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules.
2014 Jan
Cariporide Enhances the DNA Damage and Apoptosis in Acid-tolerable Malignant Mesothelioma H-2452 Cells.
2017 Aug
Patents

Sample Use Guides

120 mg 3 times a day
Route of Administration: Oral
Name Type Language
CARIPORIDE
INN   MI   WHO-DD  
INN  
Official Name English
cariporide [INN]
Common Name English
N-(4-ISOPROPYL-3-METHANESULFONYL-BENZOYL)-GUANIDINE
Systematic Name English
CARIPORIDE [MI]
Common Name English
N-(DIAMINOMETHYLENE)-4-ISOPROPYL-3-(METHYLSULFONYL)BENZAMIDE
Systematic Name English
BENZAMIDE, N-(DIAMINOMETHYLENE)-4-(1-METHYLETHYL)-3-(METHYLSULFONYL)-
Systematic Name English
Cariporide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
Code System Code Type Description
MERCK INDEX
m3110
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY Merck Index
SMS_ID
100000084614
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
INN
7395
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
EVMPD
SUB06630MIG
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
NCI_THESAURUS
C76028
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
DRUG BANK
DB06468
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
FDA UNII
7E3392891K
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
MESH
C093373
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
PUBCHEM
151172
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
WIKIPEDIA
Cariporide
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL436559
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID8047345
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
CAS
159138-80-4
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY