Omapatrilat

Omapatrilat (INN,[1] proposed trade name Vanlev) is an experimental antihypertensive agent that was never marketed.[2] 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.

Omapatrilat
Clinical data
Other namesBMS-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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H24N2O4S2
Molar mass408.53 g·mol−1
3D model (JSmol)
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)

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.[3]

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

References
  1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 40" (PDF). World Health Organization. p. 190. Retrieved 2 March 2017.
  2. "Omapatrilat". Adis Insight. Springer Nature Switzerland AG.
  3. Venugopal J (2 March 2005). "Pharmacological Modulation of the Natriuretic Peptide System". Expert Opinion on Therapeutic Patents. 13 (9): 1389–1409. doi:10.1517/13543776.13.9.1389. S2CID 85007768.

Further reading
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