Omapatrilat
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Omapatrilat
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CAS No:
167305-00-2
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Formula:
C19H24N2O4S2
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Chemical Name:
Omapatrilat
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Synonyms:
7H-Pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid,octahydro-4-[[(2S)-2-mercapto-1-oxo-3-phenylpropyl]amino]-5-oxo-,(4S,7S,10aS)-;7H-Pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid,octahydro-4-[(2-mercapto-1-oxo-3-phenylpropyl)amino]-5-oxo-,[4S-[4α(R*),7α,10aβ]]-;(4S,7S,10aS)-Octahydro-4-[[(2S)-2-mercapto-1-oxo-3-phenylpropyl]amino]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid;BMS 186716;Omapatrilat;BMS 186716-01;159317-63-2
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CAS No:
Description
Omapatrilat is a dipeptide.|Omapatrilat is an investigational drug that inhibits both neutral endopeptidase (NEP) and angiotensin converting enzyme (ACE). The inhibition of NEP elevates natriuretic peptide levels, increasing excretion of sodium in urine, dilating blood vessels, and reducing preload and ventricular remodeling. This drug from BMS was not approved by the FDA due to angioedema safety concerns.|Omapatrilat is a vasopeptidase inhibitor with antihypertensive activity. Omapatrilat exerts its effect by inhibiting angiotensin converting enzyme (ACE) and neutral endopeptidase (NEP). ACE inhibition results in inhibition of the renin-angiotensin-aldosterone system thereby leading to the reduction of vasoconstriction. Inhibition of NEP leads to the inhibition of hydrolyzation of a number of endogenous vasoactive peptides, such as bradykinin and substance P and as NEP is the principal enzyme degrading natriuretic peptides, NEP inhibition also results in an increase in natriuretic peptidase circulation. Ultimately both effects result in blood vessel relaxation.
Toxicity
Side effects include hyperkalemia, cough, hypotension, increased SrCr, and dizziness. Dizziness, diarrhea, vision disturbance, hypotension and angioedema
Drug Information
For the treatment of hypertension.
Omapatrilat is used to treat hypertension. Vasopeptidase inhibitor that simultaneously inhibits angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP). Omapatrilat lowers blood pressure by inhibiting the action of the angiotensin converting enzyme (ACE), which causes blood vessels to constrict. But unlike other drugs, omapatrilat also inhibits another enzyme known as neutral endopeptidase (NEP), which helps blood vessels relax. Omapatrilat demonstrated greater reduction in blood pressure than the ACE inhibitor lisinopril in individuals with salt-sensitive hypertension who typically do not respond well to ACE inhibitors.
A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)|A class of cardiovascular drugs indicated for hypertension and congestive heart failure that simultaneously inhibit both NEUTRAL ENDOPEPTIDASE and ANGIOTENSIN CONVERTING ENZYME. They increase the availability of NATRIURETIC PEPTIDES and BRADYKININ and inhibit production of ANGIOTENSIN II. (See all compounds classified as Vasopeptidase Inhibitors.)
The absolute oral bioavailability of omapatrilat is 20% to 30% and the absorption is not affected by food intake.
Hepatic
Omapatrilat binds to both angiotensin converting enzyme and neutral endopeptidase. This results in a decrease renin-angiotensin-aldosterone production and increase natriuretic peptidase circulation.
BMS 186716
Computed Properties
Molecular Weight:408.5
XLogP3:2.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:408.11774960
Monoisotopic Mass:408.11774960
Topological Polar Surface Area:113
Heavy Atom Count:27
Complexity:568
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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