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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 of GEMOPATRILAT

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
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

PubMed

TitleDatePubMed
Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans.
2006 Jun
Name Type Language
GEMOPATRILAT
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
NCI_THESAURUS C783
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C99557
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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SMS_ID
300000034217
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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ChEMBL
CHEMBL107747
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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FDA UNII
MU9089C77W
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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PUBCHEM
9886079
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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USAN
LL-99
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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CAS
160135-92-2
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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WIKIPEDIA
GEMOPATRILAT
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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INN
8055
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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EPA CompTox
DTXSID901029484
Created by admin on Fri Dec 15 15:35:29 GMT 2023 , Edited by admin on Fri Dec 15 15:35:29 GMT 2023
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