Chemistry:Omapatrilat

Short description: Chemical compound

Omapatrilat

Clinical data
Other names	BMS-186716
ATC code	None
Legal status
Legal status	Development terminated
Identifiers
IUPAC name (4S,7S,10aS)-Octahydro-4-[(S)-α-mercaptohydrocinnamamido]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
CAS Number	167305-00-2 Y
PubChem CID	656629
ChemSpider	570983 N
UNII	36NLI90E7T
KEGG	D01970 N
ChEMBL	ChEMBL289556 N
Chemical and physical data
Formula	C19H24N2O4S2
Molar mass	408.53 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1ccc(cc1)C[C@@H](C(=O)N[C@H]2CCS[C@H]3CCC[C@H](N3C2=O)C(=O)O)S
InChI InChI=1S/C19H24N2O4S2/c22-17(15(26)11-12-5-2-1-3-6-12)20-13-9-10-27-16-8-4-7-14(19(24)25)21(16)18(13)23/h1-3,5-6,13-16,26H,4,7-11H2,(H,20,22)(H,24,25)/t13-,14-,15-,16-/m0/s1 N Key:LVRLSYPNFFBYCZ-VGWMRTNUSA-N N
NY (what is this?)  (verify)

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.

Omapatrilat angioedema was attributed to its dual mechanism of action, inhibiting both angiotensin-converting enzyme (ACE), and neprilysin (neutral endopeptidase), both of these enzymes are responsible for the metabolism of bradykinin which causes vasodilation, angioedema, and airway obstruction.

See also

• Gemopatrilat
• Cilazapril
• Sacubitril

Further reading

• "Pharmacokinetics and pharmacodynamics of the vasopeptidase inhibitor, omapatrilat in healthy subjects". British Journal of Clinical Pharmacology 56 (4): 395–406. October 2003. doi:10.1046/j.1365-2125.2003.01888.x. PMID 12968984.