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omapatrilat
Sign in to saveAlso known as Omapatrilate
Omapatrilat (INN, proposed trade name Vanlev) is an experimental antihypertensive agent that was never marketed. It inhibits both neprilysin (neutral endopeptidase, NEP) and angiotensin-converting enzyme (ACE). NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling.
Chemical data
- Formula
- C19H24N2O4S2
- Molecular weight
- 408.5 g/mol
- IUPAC name
- (4S,7S,10aS)-5-oxo-4-[[(2S)-3-phenyl-2-sulfanylpropanoyl]amino]-2,3,4,7,8,9,10,10a-octahydropyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
- SMILES
- C1C[C@H](N2[C@H](C1)SCC[C@@H](C2=O)NC(=O)[C@H](CC3=CC=CC=C3)S)C(=O)O
- InChIKey
- LVRLSYPNFFBYCZ-VGWMRTNUSA-N
- XLogP
- 2.8
- Polar surface area
- 113 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
281 papers- Omapatrilat. Bristol-Myers Squibb.Current opinion in investigational drugs (London, England : 2000) · 2001
- Omapatrilat: a unique new agent for the treatment of cardiovascular disease.Heart disease (Hagerstown, Md.) · 2000
- Omapatrilat--the story of Overture and Octave.International journal of cardiology · 2002
- Recent clinical trials with omapatrilat: new developments.Current hypertension reports · 2003
- Omapatrilat.Circulation · 2002
via PubMed
Wikidata facts
- Subclass of
- carboxylic acid
- Mass
- 408.117749
Show 3 more facts
- chemical formula
- C₁₉H₂₄N₂O₄S₂
- canonical SMILES
- C1CC(N2C(C1)SCCC(C2=O)NC(=O)C(CC3=CC=CC=C3)S)C(=O)O
- isomeric SMILES
- C1C[C@H](N2[C@H](C1)SCC[C@@H](C2=O)NC(=O)[C@H](CC3=CC=CC=C3)S)C(=O)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- Further reading
Omapatrilat (INN, proposed trade name Vanlev) is an experimental antihypertensive agent that was never marketed. It inhibits both neprilysin (neutral endopeptidase, NEP) and angiotensin-converting enzyme (ACE). NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling.
It was discovered and developed by Bristol-Myers Squibb but failed in clinical trials as a potential treatment for congestive heart failure due to safety concerns about its causing angioedema.
Excerpted from Wikipedia’s “omapatrilat” article, available under the CC BY-SA 4.0 licence.