Omapatrilat

Omapatrilat
Clinical data
Other names	BMS-186716
ATC code	None;
Legal status
Legal status	Development terminated;
Identifiers
	IUPAC name (4S,7S,10aS)-Octahydro-4--5-oxo-7H-pyridothiazepine-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(=O)N2CCS3CCC(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.

References

^ "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.

Liao WC, Vesterqvist O, Delaney C, Jemal M, Ferreira I, Ford N, et al. (October 2003). "Pharmacokinetics and pharmacodynamics of the vasopeptidase inhibitor, omapatrilat in healthy subjects". British Journal of Clinical Pharmacology. 56 (4): 395–406. doi:10.1046/j.1365-2125.2003.01888.x. PMC 1884361. PMID 12968984.

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[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.

[1]

[2]

[3]

v t e Antihypertensive drugs acting on the renin–angiotensin system (C09)
ACE inhibitors ("-pril")	Sulfhydryl-containing: Captopril Rentiapril Zofenopril Dicarboxylate-containing: Enalapril^# Benazepril Cilazapril Delapril Imidapril Lisinopril (+amlodipine, +HCT) Moexipril Perindopril (+indapamide) Quinapril (+HCT) Ramipril Spirapril Temocapril Trandolapril Phosphonate-containing: Ceronapril Fosinopril (+HCT) Other/ungrouped: Alacepril
AIIRAs ("-sartan")	Azilsartan Candesartan Eprosartan Fimasartan Irbesartan (+HCT) Losartan (+HCT) Olmesartan (+amlodipine, +amlodipine and HCT, +HCT) Tasosartan^§ Telmisartan (+amlodipine, +HCT) Valsartan (+amlodipine, +amlodipine and HCT, +HCT, +nebivolol)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine, +HCT, +amlodipine and HCT) Remikiren^§
Dual ACE/NEP inhibitors	Gemopatrilat Ilepatril Omapatrilat Sampatrilat
Neprilysin inhibitors	Sacubitril (+valsartan)
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

See also

References

Further reading