GEMOPATRILAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H26N2O4S
Molecular Weight	378.486
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CCC[C@H](NC(=O)[C@@H](S)CC2=CC=CC=C2)C(=O)N1CC(O)=O

InChI

InChIKey=YRSVDSQRGBYVIY-GJZGRUSLSA-N

InChI=1S/C19H26N2O4S/c1-19(2)10-6-9-14(18(25)21(19)12-16(22)23)20-17(24)15(26)11-13-7-4-3-5-8-13/h3-5,7-8,14-15,26H,6,9-12H2,1-2H3,(H,20,24)(H,22,23)/t14-,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H26N2O4S
Molecular Weight	378.486
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/11393678 | https://www.ncbi.nlm.nih.gov/pubmed/16540589 | https://www.ncbi.nlm.nih.gov/pubmed/12228848

Gemopatrilat is a vasopeptidase inhibitor, that was found to inhibit plasma and renal angiotensin converting enzyme (ACE), as well as renal neutral endopeptidase (NEP). Gemopatrilat is rapidly absorbed, and causes inhibition of circulating and renal ACE and renal NEP after a single oral dose for up to 48 hours in rats. Potentially, this is because the free sulfhydryl group of gemopatrilat forms reversible disulfide linkages with plasma and tissue proteins and is thus eliminated from the body at a very slow rate. Similar metabolism of the compound was found in rat, dog, and human. Gemopatrilat was evaluated for its potential in treatment of antihypertensive activity in hypertension (independent of age, renin and salt status or ethnic origin), as well as its potential as a new therapeutic modality for the treatment of congestive heart failure. The drug was never marketed. A phase II study for treatment of hypertension and heart failure has been discontinued.

Approval Year

PubMed

Title	Date	PubMed
In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat.	2001 May	11393678
Vasopeptidase inhibitors.	2002 Jun	12228848
Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.	2003 Aug 21	12917005
Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes.	2003 Jan	12472769
Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans.	2006 Jun	16540589

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:35:29 UTC 2023` Edited by `admin` on `Fri Dec 15 15:35:29 UTC 2023`
Record UNII	MU9089C77W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GEMOPATRILAT

Official Name

English

Gemopatrilat [WHO-DD]

Common Name

English

GEMOPATRILAT [USAN]

Common Name

English

1H-AZEPINE-1-ACETIC ACID, HEXAHYDRO-6-(((2S)-2-MERCAPTO-1-OXO-3-PHENYLPROPYL)AMINO)-2,2-DIMETHYL-7-OXO-, (6S)-

Common Name

English

(6S)-Hexahydro-6-[(αS)-α-mercaptohydrocinnamamido]-2,2-dimethyl-7-oxo-1H-azepine-1-acetic acid

Common Name

English

gemopatrilat [INN]

Common Name

English

BMS-189921

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C247