Omapatrilat information

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 ;
PubChem CID	656629;
ChemSpider	570983 ;
UNII	36NLI90E7T;
KEGG	D01970 ;
ChEMBL	ChEMBL289556 ;
CompTox Dashboard (EPA)	DTXSID80168273 ;
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 ; Key:LVRLSYPNFFBYCZ-VGWMRTNUSA-N ;
	(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.

^ "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.
^ "Omapatrilat". Adis Insight. Springer Nature Switzerland AG.
^ 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.

[INN-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.

Omapatrilat information

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Omapatrilat

Sacubitril

Pulse pressure

Blood pressure

Lisinopril

Losartan

ACE inhibitor

Enalapril

Irbesartan

Neprilysin

Atrial natriuretic peptide

Renin

Candesartan

Discovery and development of angiotensin receptor blockers

Ramipril

Captopril

Discovery and development of ACE inhibitors

Olmesartan

Valsartan

Telmisartan

Perindopril

Benazepril

Angiotensin

Azilsartan