Omapatrilat

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
 ☒NcheckY (what is this?)  (verify)

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.

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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