U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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
In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat.
2001 May
Vasopeptidase inhibitors.
2002 Jun
Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.
2003 Aug 21
Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes.
2003 Jan
Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans.
2006 Jun
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:35:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:29 GMT 2023
Record UNII
MU9089C77W
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
EXCRETED UNCHANGED
No gemopatrilat was detected in urine and feces.
FECAL; URINE
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MAJOR
Term
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
Metabolites M9 and M10, which were not well resolved, accounted for 8% of the radioactivity
PLASMA
METABOLITE -> PARENT
The prominent metabolites in the 1-h human plasma before DTT reduction were M2, M13, and M14, which together accounted for 31% of the radioactivity.
MAJOR
PLASMA
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
MAJOR
FECAL
METABOLITE -> PARENT
FECAL; URINE
METABOLITE -> PARENT
Metabolites M9 and M10, which were not well resolved, accounted for 8% of the radioactivity
PLASMA
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
FECAL
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

Biological Half-life PHARMACOKINETIC P.O. ADMINISTRATION

Tmax PHARMACOKINETIC P.O. DMINISTRATION

ORAL BIOAVAILABILITY PHARMACOKINETIC
Tmax PHARMACOKINETIC INTRAVENOUS ADMINISTRATION