Omapatrilat - CAS 167305-00-2
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Angiotensin-converting Enzyme (ACE)
Omapatrilat, an octahydropyridothiazepine derivative, has been found to be an ACE inhibitor as well as an endopeptidase inhibitor and was once studied in heart failure and hypertension.
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Omapatrilat; BMS-186716; Vanlev; Bms 186716; UNII-36NLI90E7T; CHEMBL289556; (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
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
For research use only
Quality Standard:
In-house standard
Boiling Point:
724.2ºC at 760mmHg
1.37 g/cm3
Canonical SMILES:
1.Comparison of the Effects of Omapatrilat and Lisinopril on Circulating Neurohormones and Cytokines in Patients With Chronic Heart Failure
Tej Sheth, Tom Parker, Alan Block. The American Journal of Cardiology Vol. 90 September 1, 2002
A number of endogenous systems exist to counter the effects of vasoconstricting neurohormones that are increased in congestive heart failure (CHF). These include natriuretic peptides, nitric oxide, and prostaglandins. A major pathway for the clearance of these endogenous vasodilator substances is through the enzyme neutral endopeptidase. The development of vasopeptidase inhibitors (VPIs), which inhibit both neutral endopeptidase and angiotensin-converting enzyme (ACE), may allow for enhanced natriuretic peptide and bradykinin effects. However, bradykinin in supraphysiologic doses is a potent stimulant for inflammation. Alternatively, by stimulating nitric oxide in more physiologic doses, bradykinin may prove to be anti-inflammatory. In addition, neutral endopeptidase is involved in the degradation of endothelin-1, a vasoconstrictor neurohormone that is elevated in patients with heart failure and has been associated with a poor outcome. Overall, if an improvement in the balance between endogenous vasoconstrictor and vasodilator substances can be achieved, VPIs may prove to be superior to ACE inhibitors alone in treating patients with CHF. We randomized patients with stable chronic CHF, a left ventricular ejection fraction<40%, and who were currently receiving an ACE inhibitor to either the VPI, omapatrilat, or the ACE inhibitor, lisinopril. Baseline, 12-, and 24-week circulating neurohormone and cytokine levels were measured and the effects of the 2 treatments on neurohormones and cytokines were compared.
2. Comparison of vasopeptidase inhibitor, omapatrilat, and lisinopril on exercise tolerance and morbidity in patients with heart failure: IMPRESS randomised trial
Jean L Rouleau, Marc A Pfeffer, Duncan J Stewart. THE LANCET Vol 356 August 19, 2000
Omapatrilat (BMS-186716) is the first of a new class of cardiovascular agents termed vasopeptidase inhibitors. Omapatrilat is an orally active, long acting, selective, competitive inhibitor of neutral endopeptidase (NEP; enkephalinase, neprilysin, EC and angiotensin converting enzyme (ACE; EC with similar K1 values for both NEP and ACE. As a result, omapatrilat potentiates multiple endogenous vasodilatory peptides including natriuretic peptides (atrial, brain, and calcium activated neutral protease), bradykinin, and adrenomedullin, while also inhibiting the generation of the vasoconstrictive peptide, angiotensin II. Omapatrilat has an oral bioavailability of about 30%, it may be given with or without food, its protein binding is 80%, and it has a very large volume of distribution (1800 L) suggesting tissue penetration. Time to maximum concentration of an oral dose is about 2 h. Its effective half-life is 14-19 h. This drug is metabolised in the liver. Omapatrilat forms disulphide bonds with endogenous thiols, and is extensively metabolised via S-methylation, amide hydrolysis, S-oxidation, and glucuronidation. There are no substantial concentrations of active metabolites of omapatrilat in plasma. About 80% of an intravenous radioactive dose and 64% of an oral radioactive dose were recovered in urine, with less than 1% excreted as unchanged drug (data available). Based on bio-transformation data in vitro and in vivo, cytochrome P450 enzymes do not seem to be involved in the metabolism of omapatrilat. In-vitro studies show that omapatrilat does not inhibit P450 isoenzmes CYP-1A2, CYP-3A4, CYP-2C9, CYP-2C19, and CYP-2D6. Omapatrilat has no known interaction with other medications.
TOM BACKLUND, EEVA PALOJOKI, TINA GRONHOLMP, MIKA LAINE*. harmacological Research, Vol. 44, No. 5, 2001
One of these dual ACE/NEP inhibitors is a single molecule, omapatrilat. So far only limited experimental data is available on the actual effect of vasopeptidase inhibitors on the ACE and NEP in vivo. The haemodynamic and neurohormonal effects are dependent on the ratio of NEP vs ACE inhibition of the particular molecule. On the other hand, penetration of the drug to tissues, such as myocardium, determines the effectiveness of the drug in the end-organ protection.The purpose of this study was to find out the pharmacological profile of omapatrilat treatment in vivo. Renal as well as local cardiac ACE/NEP enzyme inhibition was examined as compared with the specific ACE inhibitor captopril. As hormonal parameters of in vivo NEP and ACE inhibition we measured plasma ANP, BNP and N-terminal proANP (N-ANP).
4. Enzymatic synthesis of chiral intermediates for Omapatrilat, an antihypertensive drug
Ramesh N. Patel*. Biomolecular Engineering 17 (2001) 167–182
Tailor-made enzymes with modified activity and the preparation of thermostable and pH stable enzymes produced by random and site-directed mutagenesis have lead to the production of novel stereoselective biocatalysts. The use of enzymes in organic solvents has led to hundreds of publications on enzyme-catalyzed asymmetric synthesis and resolution processes. Molecular recognition and selective catalysis are key chemical processes in life which are embodied in enzymes. A number of review articles have been published on the use of biocatalysis in organic synthesis. This chapter provides different approaches towards the use of microbial enzymes for the synthesis of chiral intermediates for Omapatrilat 1 by three different routes. Omapatrilat 1 is an antihypertensive drug which acts by inhibiting angiotensin-converting enzyme (ACE) and neutral endopeptidase.
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CAS 167305-00-2 Omapatrilat

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