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
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
Molecular Formula | C19H26N2O4S |
Molecular Weight | 378.486 |
Charge | 0 |
Count |
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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
Title | Date | PubMed |
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In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat. | 2001 May |
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Vasopeptidase inhibitors. | 2002 Jun |
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Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921. | 2003 Aug 21 |
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Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes. | 2003 Jan |
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Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans. | 2006 Jun |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:35:29 GMT 2023
by
admin
on
Fri Dec 15 15:35:29 GMT 2023
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Record UNII |
MU9089C77W
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Code | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C247
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NCI_THESAURUS |
C783
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Code System | Code | Type | Description | ||
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C99557
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300000034217
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CHEMBL107747
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MU9089C77W
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9886079
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LL-99
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160135-92-2
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GEMOPATRILAT
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8055
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DTXSID901029484
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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EXCRETED UNCHANGED |
No gemopatrilat was detected in urine and feces.
FECAL; URINE
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
Term
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
Metabolites M9 and M10, which were not well resolved, accounted for 8% of the radioactivity
PLASMA
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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
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
MAJOR
FECAL
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METABOLITE -> PARENT |
FECAL; URINE
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METABOLITE -> PARENT |
Metabolites M9 and M10, which were not well resolved, accounted for 8% of the radioactivity
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
FECAL
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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P.O. ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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P.O. DMINISTRATION |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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