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
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 |
|---|---|---|
| Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans. | 2006-06 |
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| Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921. | 2003-08-21 |
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| Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes. | 2003-01 |
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| Vasopeptidase inhibitors. | 2002-06 |
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| In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat. | 2001-05 |
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| 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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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)