Omapatrilat

Omapatrilat

Systematic (IUPAC) name
(4S,7S,10aS)-5-oxo-4-{[(2S)-3-phenyl-2- sulfanylpropanoyl]amino}-2,3,4,7,8,9,10,10a-octahydropyrido[6,1-b] [1,3]thiazepine-7-carboxylic acid
Identifiers
CAS Number	167305-00-2
ATC code	none
PubChem	CID 656629
ChemSpider	570983
UNII	36NLI90E7T
ChEMBL	CHEMBL289556
Chemical data
Formula	C19H24N2O4S2
Molar mass	408.534 g/mol
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 Key:LVRLSYPNFFBYCZ-VGWMRTNUSA-N
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Omapatrilat (INN) is a novel antihypertensive agent that inhibits both neutral endopeptidase (NEP) and angiotensin converting enzyme. NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling.

This drug from Bristol-Myers Squibb was not approved by the U.S. Food and Drug Administration due to angioedema safety concerns.^[1]

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

Clinical uses

The drug was promoted for possible uses in congestive heart failure.

See also

• Sacubitril

References

1. Joshi Venugopal. (2003) Pharmacological modulation of the natriuretic peptide system. Expert Opinion on Therapeutic Patents 13:9, 1389