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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

Description

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.

Originator

Approval Year

Targets

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

PubMed

Sample Use Guides

In Vivo Use Guide
120 mg 3 times a day
Route of Administration: Oral