EPICAPTOPRIL

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11026653
Curator's Comment: The description was created based on several sources, including http://www.nevapress.com/cdr/full/17/2/115.pdf | https://www.ncbi.nlm.nih.gov/pubmed/8138187

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

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Reactions of captopril and epicaptopril with transition metal ions and hydroxyl radicals: an EPR spectroscopy study.	1993 Dec	8138187

Patents

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 Created by `admin` on `Sat Dec 16 01:39:08 GMT 2023` Edited by `admin` on `Sat Dec 16 01:39:08 GMT 2023`
Record UNII	PPW0ENH1HA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPICAPTOPRIL

Common Name

English

SQ-14534

Code

English

CAPTOPRIL IMPURITY F [EP IMPURITY]

Common Name

English

(2S)-1-((2R)-2-METHYL-3-SULFANYLPROPANOYL)PYRROLIDINE-2-CARBOXYLIC ACID

Systematic Name

English

2-D-METHYL-3-MERCAPTOPROPANOYL-L-PROLINE

Common Name

English

SQ 14534

Code

English

L-PROLINE, 1-((2R)-3-MERCAPTO-2-METHYL-1-OXOPROPYL)-

Systematic Name

English

Code System Code Type Description

CAS

63250-36-2