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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H15NO3S
Molecular Weight 217.285
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICAPTOPRIL

SMILES

C[C@@H](CS)C(=O)N1CCC[C@H]1C(O)=O

InChI

InChIKey=FAKRSMQSSFJEIM-BQBZGAKWSA-N
InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H15NO3S
Molecular Weight 217.285
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Epicaptopril is an impurity of Captopril, which is an orally active angiotensin-converting enzyme (ACE) inhibitor used in the treatment of hypertension and congestive heart failure. Epicaptopril does not show any inhibition of angiotensin-converting enzyme (ACE), and can be used as negative control in ACE inhibition experiments

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Rats: 5 mg/kg twice daily for 10 days, per os.
Route of Administration: Oral
In Vitro Use Guide
The protective effects of SH-ACEIs from free radical-induced cell damage have been also assessed in cultured endothelial cells exposed to a superoxide anion and hydroxyl radicals generating system. Preincubation of the cells with captopril, epicaptopril, or zofenopril produced a concentration-dependent (10–200 mkM) inhibition of malonyldialdehyde formation. Both loss of cell viability and membrane blebbing were reduced by SH-ACEIs at concentrations as low as 10 mkM. In contrast, lisinopril and enalaprilat at concentrations up to 200 mkM were ineffective
Substance Class Chemical
Record UNII
PPW0ENH1HA
Record Status Validated (UNII)
Record Version