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OMAPATRILAT

CAS No.:
167305-00-2
Catalog Number:
AG00AOX7
Molecular Formula:
C19H24N2O4S2
Molecular Weight:
408.5349
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
97%
1 week
United States
$182
- +
10mg
97%
1 week
United States
$273
- +
25mg
97%
1 week
United States
$523
- +
50mg
97%
1 week
United States
$923
- +
100mg
97%
1 week
United States
$1623
- +
Product Description
Catalog Number:
AG00AOX7
Chemical Name:
OMAPATRILAT
CAS Number:
167305-00-2
Molecular Formula:
C19H24N2O4S2
Molecular Weight:
408.5349
MDL Number:
MFCD00673764
IUPAC Name:
(4S,7S,10aS)-5-oxo-4-[[(2S)-3-phenyl-2-sulfanylpropanoyl]amino]-2,3,4,7,8,9,10,10a-octahydropyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
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
InChI Key:
LVRLSYPNFFBYCZ-VGWMRTNUSA-N
SMILES:
S[C@H](C(=O)N[C@H]1CCS[C@@H]2N(C1=O)[C@@H](CCC2)C(=O)O)Cc1ccccc1
UNII:
36NLI90E7T
Properties
Complexity:
568  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
408.118g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
408.531g/mol
Monoisotopic Mass:
408.118g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
113A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.8  
Literature
Title Journal
Antihypertrophic effects of combined inhibition of the renin-angiotensin system (RAS) and neutral endopeptidase (NEP) in progressive, tachycardia-induced experimental heart failure. Naunyn-Schmiedeberg's archives of pharmacology 20121101
Concomitant angiotensin AT1 receptor antagonism and neprilysin inhibition produces omapatrilat-like antihypertensive effects without promoting tracheal plasma extravasation in the rat. Journal of cardiovascular pharmacology 20110401
Combined neutral endopeptidase inhibitors. Expert opinion on investigational drugs 20110401
Phosphinic tripeptides as dual angiotensin-converting enzyme C-domain and endothelin-converting enzyme-1 inhibitors. Journal of medicinal chemistry 20100114
Portal pressure responses and angiotensin peptide production in rat liver are determined by relative activity of ACE and ACE2. American journal of physiology. Gastrointestinal and liver physiology 20090701
Endothelium-dependent relaxation factor released by perivascular adipose tissue. Journal of hypertension 20090401
Comparison of vasopeptidase inhibitor omapatrilat and angiotensin receptor blocker candesartan on extracellular matrix, myeloperoxidase, cytokines, and ventricular remodeling during healing after reperfused myocardial infarction. Molecular and cellular biochemistry 20090101
The natriuretic peptide neurohormonal system modulation by vasopeptidase inhibitors--the novel therapeutical approach of hypertension treatment. Folia medica Cracoviensia 20090101
Synthesis and antihypertensive effects of new methylthiomorpholinphenol derivatives. European journal of medicinal chemistry 20080301
Effect of bradykinin metabolism inhibitors on evoked hypotension in rats: rank efficacy of enzymes associated with bradykinin-mediated angioedema. British journal of pharmacology 20080301
Omapatrilat enhances adrenomedullin's reduction of cardiomyocyte cell death. European journal of pharmacology 20070521
Chronic effect of combined treatment with omapatrilat and adrenomedullin on the progression of heart failure in rats. American journal of hypertension 20061001
Enhancement of muscle glucose uptake by the vasopeptidase inhibitor, omapatrilat, is independent of insulin signaling and the AMP kinase pathway. The Journal of endocrinology 20060801
Attenuation of cardiovascular remodeling in DOCA-salt rats by the vasopeptidase inhibitor, omapatrilat. Clinical and experimental hypertension (New York, N.Y. : 1993) 20060701
Bioenergetic protection of failing atrial and ventricular myocardium by vasopeptidase inhibitor omapatrilat. American journal of physiology. Heart and circulatory physiology 20060401
Study of bradykinin metabolism by rat lung tissue membranes and rat kidney brush border membranes by HPLC with inductively coupled plasma-mass spectrometry and orthogonal acceleration time-of-flight mass spectrometry. Journal of peptide science : an official publication of the European Peptide Society 20060301
Evaluation of the enhanced oral effect of omapatrilat-monolein nanoparticles prepared by the emulsification-diffusion method. Journal of nanoscience and nanotechnology 20060101
Pharmacological enhancement of the kallikrein-kinin system promotes anti-fibrotic responses in human mesangial cells. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20060101
Mechanism of vasopeptidase inhibitor-induced plasma extravasation: comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406. The Journal of pharmacology and experimental therapeutics 20051201
Renoprotective effect of long-term combined treatment with adrenomedullin and omapatrilat in hypertensive rats. Journal of hypertension 20051201
Effect of omapatrilat on the aging process of the normal rat. Cellular and molecular biology (Noisy-le-Grand, France) 20051108
Anti-atherosclerotic and renoprotective effects of combined angiotensin-converting enzyme and neutral endopeptidase inhibition in diabetic apolipoprotein E-knockout mice. Journal of hypertension 20051101
Changes in aortic stiffness and augmentation index after acute converting enzyme or vasopeptidase inhibition. Hypertension (Dallas, Tex. : 1979) 20051101
Glomerular abundance of nephrin and podocin in experimental nephrotic syndrome: different effects of antiproteinuric therapies. American journal of physiology. Renal physiology 20051001
Vasopeptidase inhibition peri- and post-MI in Zucker insulin resistant rats: effect on MI size, arrhythmias, remodeling, function and fetal gene expression. Cardiovascular drugs and therapy 20051001
Vasopeptidase inhibition has beneficial cardiac effects in spontaneously diabetic Goto-Kakizaki rats. European journal of pharmacology 20050920
Vascular and renal effects of vasopeptidase inhibition and angiotensin-converting enzyme blockade in spontaneously diabetic Goto-Kakizaki rats. Journal of hypertension 20050901
Effects of omapatrilat on cardiac nerve sprouting and structural remodeling in experimental congestive heart failure. Heart rhythm 20050901
The kallikrein-kinin system: current and future pharmacological targets. Journal of pharmacological sciences 20050901
Angiotensin I-converting enzyme-dependent and neutral endopeptidase-dependent generation and degradation of angiotensin II contrarily modulate noradrenaline release: implications for vasopeptidase-inhibitor therapy? Journal of hypertension 20050801
Effect of angiotensin-converting enzyme or vasopeptidase inhibition on ventricular size and function in patients with heart failure: the Omapatrilat Versus Enalapril Randomized Trial of Utility in Reducing Events (OVERTURE) echocardiographic study. American heart journal 20050801
Effects of vasopeptidase inhibition on renal function and tubuloglomerular feedback in spontaneously hypertensive rats. Hypertension research : official journal of the Japanese Society of Hypertension 20050701
Predicting drug metabolism--an evaluation of the expert system METEOR. Chemistry & biodiversity 20050701
Effects of the vasopeptidase inhibitor omapatrilat on peri- and postmyocardial infarction in Zucker lean rats. The Canadian journal of cardiology 20050301
The potential advantage of omapatrilat: dual anti-fibrotic and anti-inflammatory effects in one single molecule. Journal of hypertension 20050201
Dual angiotensin-converting enzyme/neutral endopeptidase inhibition on cardiac and renal fibrosis and inflammation in DOCA-salt hypertensive rats. Journal of hypertension 20050201
The cardioprotective effect of dual metallopeptidase inhibition: respective roles of endogenous kinins and natriuretic peptides. Canadian journal of physiology and pharmacology 20050201
Changes in production and metabolism of brain natriuretic peptide in rats with myocardial necrosis. European journal of pharmacology 20050110
Dual inhibition of angiotensin converting enzyme and neutral endopeptidase produces effective blood pressure control in spontaneously hypertensive rats. Bratislavske lekarske listy 20050101
Cardioprotective effects of vasopeptidase inhibition vs. angiotensin type 1-receptor blockade in spontaneously hypertensive rats on a high salt diet. Hypertension research : official journal of the Japanese Society of Hypertension 20040801
[OCTAVE and OPERA: discordance in hypertension therapy?]. Herz 20040501
Vasopeptidase inhibition reverses myocardial vasoactive intestinal peptide depletion and decreases fibrosis in salt sensitive hypertension. European journal of pharmacology 20040206
Omapatrilat and enalapril in patients with hypertension: the Omapatrilat Cardiovascular Treatment vs. Enalapril (OCTAVE) trial. American journal of hypertension 20040201
Dual inhibition of ACE and NEP provides greater cardioprotection in mice with heart failure. Journal of cardiac failure 20040201
Comparison of the effects of omapatrilat and irbesartan/hydrochlorothiazide on endothelial function and cardiac hypertrophy in the stroke-prone spontaneously hypertensive rat: sex differences. Journal of hypertension 20040201
Systemic and renal effect of chronic omapatrilat in sodium-restricted, one-kidney, one-clip hypertensive rats. Journal of hypertension 20040201
Omapatrilat decreased macrophage oxidative status and atherosclerosis progression in atherosclerotic apolipoprotein E-deficient mice. Journal of cardiovascular pharmacology 20040101
Cardiorenal protective effects of vasopeptidase inhibition with omapatrilat in hypertensive transgenic (mREN-2)27 rats. Clinical and experimental hypertension (New York, N.Y. : 1993) 20040101
Role of Angiotensin-converting enzyme and neutral endopeptidase in flow-dependent remodeling. Journal of vascular research 20040101
[The new class of drugs-- metalloprotease inhibitors -- in the treatment of heart failure]. Klinicheskaia meditsina 20040101
Trial logistics, implementation, and conduct of the OCTAVE mega study in Germany. Prospective, randomised, double-blind study to compare the efficacy and tolerability of omapatrilat and enalapril. Arzneimittel-Forschung 20040101
Direct inhibition of neutral endopeptidase in vasopeptidase inhibitor-mediated amelioration of cardiac remodeling in rats with chronic heart failure. Molecular and cellular biochemistry 20031201
Omapatrilat increases renal endothelin in deoxycorticosterone acetate-salt hypertensive rats. Vascular pharmacology 20031201
Renal effects of omapatrilat and captopril in salt-loaded, nitric oxide-deficient rats. Hypertension (Dallas, Tex. : 1979) 20031101
Effect of dual angiotensin converting enzyme/neutral endopeptidase inhibition, angiotensin converting enzyme inhibition, or AT1 antagonism on coronary microvasculature in spontaneously hypertensive rats. American journal of hypertension 20031101
Role of systolic blood pressureon the progression of kidney damage in an experimental model of type 2 diabetes mellitus, obesity, and hypertension (Zucker rats). American journal of hypertension 20031101
Pharmacokinetics and pharmacodynamics of the vasopeptidase inhibitor, omapatrilat in healthy subjects. British journal of clinical pharmacology 20031001
Beneficial and adverse renal and vascular effects of the vasopeptidase inhibitor omapatrilat in renovascular hypertensive rats. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20031001
Regression of left ventricular hypertrophy is a key goal of hypertension management. Current hypertension reports 20030801
Recent clinical trials with omapatrilat: new developments. Current hypertension reports 20030801
Omapatrilat induces profound renal vasodilation but does not affect coronary hemodynamics. Journal of cardiovascular pharmacology and therapeutics 20030601
Vasopeptidase inhibitor omapatrilat induces profound insulin sensitization and increases myocardial glucose uptake in Zucker fatty rats: Studies comparing a vasopeptidase inhibitor, angiotensin-converting enzyme inhibitor, and angiotensin II type I receptor blocker. Circulation 20030415
Comparative biotransformation of radiolabeled [(14)C]omapatrilat and stable-labeled [(13)C(2)]omapatrilat after oral administration to rats, dogs, and humans. Drug metabolism and disposition: the biological fate of chemicals 20030101
Quantitative determination of omapatrilat and its metabolites in human plasma by HPLC coupled with tandem mass spectrometry. Acta pharmacologica Sinica 20030101
Effects of omapatrilat on blood pressure and renal injury in L-NAME and L-NAME plus DOCA-treated rats. American journal of hypertension 20030101
Comparison of the cardiovascular protection by omapatrilat and lisinopril treatments in DOCA-salt hypertension. Journal of hypertension 20030101
[The best of cardiac failure in 2002]. Archives des maladies du coeur et des vaisseaux 20030101
Omapatrilat, an angiotensin-converting enzyme and neutral endopeptidase inhibitor, attenuates early atherosclerosis in diabetic and in nondiabetic low-density lipoprotein receptor-deficient mice. International journal of experimental diabesity research 20030101
Renoprotective effects of omapatrilat are mediated partially by bradykinin. American journal of nephrology 20030101
[From basic research to clinical results. The OVERTURE, ENABLE, and RENEWAL studies]. Archivos de cardiologia de Mexico 20030101
Effects of the vasopeptidase inhibitor, omapatrilat, in 723 patients with coronary heart disease. Journal of the renin-angiotensin-aldosterone system : JRAAS 20021201
Omapatrilat--the story of Overture and Octave. International journal of cardiology 20021101
Physiologic consequences of vasopeptidase inhibition in humans: effect of sodium intake. Journal of the American Society of Nephrology : JASN 20021001
Homocysteine and vascular disease. European heart journal 20021001
Hemodynamic and humoral effects of vasopeptidase inhibition in canine hypertension. Hypertension (Dallas, Tex. : 1979) 20021001
Dose-dependent effects of folic acid on plasma homocysteine in a randomized trial conducted among 723 individuals with coronary heart disease. European heart journal 20021001
Recent clinical trial updates. Circulation 20020917
Comparison of the effects of omapatrilat and lisinopril on circulating neurohormones and cytokines in patients with chronic heart failure. The American journal of cardiology 20020901
Vasopeptidase inhibitors in heart failure. Journal of the renin-angiotensin-aldosterone system : JRAAS 20020901
Comparison of omapatrilat and enalapril in patients with chronic heart failure: the Omapatrilat Versus Enalapril Randomized Trial of Utility in Reducing Events (OVERTURE). Circulation 20020820
Vasopeptidase inhibition in a canine model of exercise-induced left ventricular dysfunction. Clinical and experimental pharmacology & physiology 20020801
Results from late-breaking clinical trial sessions at the American College of Cardiology 51st Annual Scientific Session. Journal of the American College of Cardiology 20020703
Omapatrilat reduces pulse pressure and proximal aortic stiffness in patients with systolic hypertension: results of the conduit hemodynamics of omapatrilat international research study. Circulation 20020625
Effects of omapatrilat on the renin-angiotensin system in salt-sensitive hypertension. American journal of hypertension 20020601
Vasopeptidase inhibitor reduces inhospital costs for patients with congestive heart failure: results from the IMPRESS trial. Inhibition of Metallo Protease by BMS-186716 in a Randomized Exercise and Symptoms Study in Subjects With Heart Failure. American heart journal 20020601
Recent heart failure trials of neurohormonal modulation (OVERTURE and ENABLE): approaching the asymptote of efficacy? Journal of cardiac failure 20020601
Comparison of angiotensin-converting enzyme (ACE), neutral endopeptidase (NEP) and dual ACE/NEP inhibition on blood pressure and resistance arteries of deoxycorticosterone acetate-salt hypertensive rats. Journal of hypertension 20020501
Promises kept and broken: new pharmaceuticals. The Canadian journal of cardiology 20020501
Differential actions of vasopeptidase inhibition versus angiotensin-converting enzyme inhibition on diuretic therapy in experimental congestive heart failure. Circulation 20020205
Neprilysin inhibitors potentiate effects of bradykinin on b2 receptor. Hypertension (Dallas, Tex. : 1979) 20020201
[Heart failure and vasopeptidase inhibitors]. Archives des maladies du coeur et des vaisseaux 20020201
A review of vasopeptidase inhibitors: a new modality in the treatment of hypertension and chronic heart failure. Pharmacotherapy 20020101
The cardiovascular actions of omapatrilat in spontaneously hypertensive rats. Current hypertension reports 20011201
Omapatrilat versus lisinopril: efficacy and neurohormonal profile in salt-sensitive hypertensive patients. Hypertension (Dallas, Tex. : 1979) 20011201
Pharmacodynamics and pharmacokinetics of omapatrilat in heart failure. Journal of clinical pharmacology 20011201
Omapatrilat: neurohormonal and pharmacodynamic profile when administered with furosemide. Journal of clinical pharmacology 20011201
LC/MS/MS determination of omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor, and its sulfhydryl- and thioether-containing metabolites in human plasma. Analytical chemistry 20011115
Vasopeptidase inhibition affords greater renoprotection than angiotensin-converting enzyme inhibition alone. Journal of the American Society of Nephrology : JASN 20011001
Omapatrilat. Bristol-Myers Squibb. Current opinion in investigational drugs (London, England : 2000) 20011001
Effects of omapatrilat on hemodynamics and safety in patients with heart failure. The American journal of cardiology 20010915
Vasopeptidase inhibition attenuates the progression of renal injury in subtotal nephrectomized rats. Kidney international 20010801
Efficacy and safety of omapatrilat with hydrochlorothiazide for the treatment of hypertension in subjects nonresponsive to hydrochlorothiazide alone. American journal of hypertension 20010801
Endogenous natriuretic peptides participate in renal and humoral actions of acute vasopeptidase inhibition in experimental mild heart failure. Hypertension (Dallas, Tex. : 1979) 20010801
Enzymatic synthesis of chiral intermediates for Omapatrilat, an antihypertensive drug. Biomolecular engineering 20010601
Effects of the vasopeptidase inhibitor omapatrilat on cardiac endogenous kinins in rats with acute myocardial infarction. Peptides 20010601
Update in pharmacologic treatment of hypertension. Cardiology clinics 20010501
Omapatrilat, a dual angiotensin-converting enzyme and neutral endopeptidase inhibitor, prevents fatty streak deposit in apolipoprotein E-deficient mice. Atherosclerosis 20010401
Comparison of a vasopeptidase inhibitor with neutral endopeptidase and angiotensin-converting enzyme inhibitors on bradykinin metabolism in the rat coronary bed. Journal of cardiovascular pharmacology 20010401
Vasopeptidase inhibition exhibits endothelial protection in salt-induced hypertension. Hypertension (Dallas, Tex. : 1979) 20010401
Angioedema and antihypertensive therapy. Wiener klinische Wochenschrift 20010315
Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans. Drug metabolism and disposition: the biological fate of chemicals 20010101
[Comparison of vasopeptidase inhibitor, omapatrilat, and lisinopril on exercise tolerance and morbidity in patients with heart failure]. Italian heart journal. Supplement : official journal of the Italian Federation of Cardiology 20010101
Advances in antihypertensive combination therapy: benefits of low-dose thiazide diuretics in conjunction with omapatrilat, a vasopeptidase inhibitor. Journal of clinical hypertension (Greenwich, Conn.) 20010101
Omapatrilat normalizes renal function curve in spontaneously hypertensive rats. BMC pharmacology 20010101
Effects of omapatrilat on blood pressure and insulin sensitivity in an animal model of insulin resistance. Blood pressure 20010101
Properties