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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=CC=C(C=C1S(C)(=O)=O)C(=O)NC(N)=N

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

Molecular Formula C12H17N3O3S
Molecular Weight 283.347
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Cariporide Enhances the DNA Damage and Apoptosis in Acid-tolerable Malignant Mesothelioma H-2452 Cells.
2017-08
Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules.
2014-01
Coordinated role of voltage-gated sodium channels and the Na+/H+ exchanger in sustaining microglial activation during inflammation.
2013-12-01
Endothelin isoforms and the response to myocardial stretch.
2005-06
Endothelin causes contraction of human esophageal muscularis mucosae through interaction with both ETA and ETB receptors.
2004-03-15
Na+-H+ exchange activity in taste receptor cells.
2004-03
Direct inhibition of the sodium/hydrogen exchanger after prolonged regional ischemia improves contractility on reperfusion independent of myocardial viability.
2003-11
An overview of inhibitors of Na(+)/H(+) exchanger.
2003-06
Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1.
2002-09-06
[Protective effect of Na(+)-H+ exchanger inhibitor cariporide on the injury of vascular endothelial function induced by hypercholesterolemia].
2002-02-28
Influence of ammonia on sodium absorption in rat proximal colon.
2000-08
Antiarrhythmic effects of HOE642, a novel Na(+)-H+ exchange inhibitor, on ventricular arrhythmias in animal hearts.
1996-12-19
Patents

Sample Use Guides

120 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:25:52 GMT 2025
Edited
by admin
on Mon Mar 31 18:25:52 GMT 2025
Record UNII
7E3392891K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARIPORIDE [MI]
Preferred Name English
CARIPORIDE
INN   MI   WHO-DD  
INN  
Official Name English
cariporide [INN]
Common Name English
N-(4-ISOPROPYL-3-METHANESULFONYL-BENZOYL)-GUANIDINE
Systematic 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 Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
Code System Code Type Description
MERCK INDEX
m3110
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY Merck Index
SMS_ID
100000084614
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
INN
7395
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
EVMPD
SUB06630MIG
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
NCI_THESAURUS
C76028
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
DRUG BANK
DB06468
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
FDA UNII
7E3392891K
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
MESH
C093373
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
PUBCHEM
151172
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
WIKIPEDIA
Cariporide
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL436559
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID8047345
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
CAS
159138-80-4
Created by admin on Mon Mar 31 18:25:52 GMT 2025 , Edited by admin on Mon Mar 31 18:25:52 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY