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

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
Antiarrhythmic effects of HOE642, a novel Na(+)-H+ exchange inhibitor, on ventricular arrhythmias in animal hearts.
1996 Dec 19
An overview of inhibitors of Na(+)/H(+) exchanger.
2003 Jun
Direct inhibition of the sodium/hydrogen exchanger after prolonged regional ischemia improves contractility on reperfusion independent of myocardial viability.
2003 Nov
Na+-H+ exchange activity in taste receptor cells.
2004 Mar
Endothelin causes contraction of human esophageal muscularis mucosae through interaction with both ETA and ETB receptors.
2004 Mar 15
Endothelin isoforms and the response to myocardial stretch.
2005 Jun
Coordinated role of voltage-gated sodium channels and the Na+/H+ exchanger in sustaining microglial activation during inflammation.
2013 Dec 1
Oxidative stress parameters induced by exposure to either cadmium or 17β-estradiol on Mytilus galloprovincialis hemocytes. The role of signaling molecules.
2014 Jan
Patents

Sample Use Guides

120 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:21:17 UTC 2023
Edited
by admin
on Fri Dec 15 16:21:17 UTC 2023
Record UNII
7E3392891K
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
Code System Code Type Description
MERCK INDEX
m3110
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY Merck Index
SMS_ID
100000084614
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
INN
7395
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
EVMPD
SUB06630MIG
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
NCI_THESAURUS
C76028
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
DRUG BANK
DB06468
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
FDA UNII
7E3392891K
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
MESH
C093373
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
PUBCHEM
151172
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
WIKIPEDIA
Cariporide
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL436559
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID8047345
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
CAS
159138-80-4
Created by admin on Fri Dec 15 16:21:17 UTC 2023 , Edited by admin on Fri Dec 15 16:21:17 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY