Omapatrilat
new
featured

We are open as normal during COVID-19 pandemic. Order online, same day shipping out from North Carolina, USA

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525780

CAS#: 167305-00-2

Description: Omapatrilat is a novel antihypertensive agent that inhibits both neutral endopeptidase (NEP) and angiotensin converting enzyme. NEP inhibition results in elevated natriuretic peptide levels, promoting natriuresis, diuresis, vasodilation, and reductions in preload and ventricular remodeling. The drug was promoted for possible uses in congestive heart failure.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 1750 2 Weeks
200mg USD 2350 2 Weeks
500mg USD 3250 2 Weeks
1g USD 4250 2 Weeks
2g USD 6750 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-23. Prices are subject to change without notice.

Omapatrilat, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 525780
Name: Omapatrilat
CAS#: 167305-00-2
Chemical Formula: C19H24N2O4S2
Exact Mass: 408.1177
Molecular Weight: 408.5349
Elemental Analysis: C, 55.86; H, 5.92; N, 6.86; O, 15.67; S, 15.70


Synonym: BMS 186716; BMS-186716; BMS186716; Vanlev; Omapatrilat

IUPAC/Chemical Name: (4S,7S,10aS)-4-((S)-2-mercapto-3-phenylpropanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid

InChi Key: LVRLSYPNFFBYCZ-VGWMRTNUSA-N

InChi Code: 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

SMILES Code: O=C([C@@H]1CCC[C@](N21)([H])SCC[C@H](NC([C@@H](S)CC3=CC=CC=C3)=O)C2=O)O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Schmedt Auf der Günne W, Zhao Y, Hedderich J, Gohlke P, Culman J. Omapatrilat: penetration across the blood-brain barrier and effects on ischaemic stroke in rats. Naunyn Schmiedebergs Arch Pharmacol. 2015 Sep;388(9):939-51. doi: 10.1007/s00210-015-1126-1. Epub 2015 May 8. PubMed PMID: 25953200.
2: Dalzell JR, Seed A, Berry C, Whelan CJ, Petrie MC, Padmanabhan N, Clarke A, Biggerstaff F, Hillier C, McMurray JJ. Effects of neutral endopeptidase (neprilysin) inhibition on the response to other vasoactive peptides in small human resistance arteries: studies with thiorphan and omapatrilat. Cardiovasc Ther. 2014 Feb;32(1):13-8. doi: 10.1111/1755-5922.12053. PubMed PMID: 24138103.
3: Ichiki T, Izumi R, Cataliotti A, Larsen AM, Sandberg SM, Burnett JC Jr. Endothelial permeability in vitro and in vivo: protective actions of ANP and omapatrilat in experimental atherosclerosis. Peptides. 2013 Oct;48:21-6. doi: 10.1016/j.peptides.2013.07.020. Epub 2013 Aug 6. PubMed PMID: 23927843; PubMed Central PMCID: PMC3787947.
4: Palaniyappan A, Uwiera RR, Idikio H, Menon V, Jugdutt C, Jugdutt BI. Attenuation of increased secretory leukocyte protease inhibitor, matricellular proteins and angiotensin II and left ventricular remodeling by candesartan and omapatrilat during healing after reperfused myocardial infarction. Mol Cell Biochem. 2013 Apr;376(1-2):175-88. doi: 10.1007/s11010-013-1565-2. Epub 2013 Jan 30. PubMed PMID: 23361363.
5: Hegde LG, Yu C, Renner T, Thibodeaux H, Armstrong SR, Park T, Cheruvu M, Olsufka R, Sandvik ER, Lane CE, Budman J, Hill CM, Klein U, Hegde SS. Concomitant angiotensin AT1 receptor antagonism and neprilysin inhibition produces omapatrilat-like antihypertensive effects without promoting tracheal plasma extravasation in the rat. J Cardiovasc Pharmacol. 2011 Apr;57(4):495-504. doi: 10.1097/FJC.0b013e318210fc7e. PubMed PMID: 21297495.
6: Yamazaki T. [Omapatrilat for treatment of heart failure]. Nihon Rinsho. 2007 May 28;65 Suppl 5:173-5. Review. Japanese. PubMed PMID: 17571381.
7: Lobo M, Patel J, Kamins G, Francis R, Breza B, Jerzewski R. Interaction of omapatrilat with FD&C Blue No. 2 lake during dissolution of modified release tablets. Int J Pharm. 2007 Jul 18;339(1-2):168-74. Epub 2007 Mar 4. PubMed PMID: 17398043.
8: Wong V, Szeto L, Uffelman K, Fantus IG, Lewis GF. Enhancement of muscle glucose uptake by the vasopeptidase inhibitor, omapatrilat, is independent of insulin signaling and the AMP kinase pathway. J Endocrinol. 2006 Aug;190(2):441-50. PubMed PMID: 16899577.
9: Loch D, Hoey A, Brown L. Attenuation of cardiovascular remodeling in DOCA-salt rats by the vasopeptidase inhibitor, omapatrilat. Clin Exp Hypertens. 2006 Jul;28(5):475-88. PubMed PMID: 16820344.
10: Basso N, Paglia N, Cini R, Inserra F, Terragno NA. Effect of omapatrilat on the aging process of the normal rat. Cell Mol Biol (Noisy-le-grand). 2005 Nov 8;51(6):557-64. Review. PubMed PMID: 16309580.
11: Ishimura K, Nishikimi T, Akimoto K, Ono H, Kangawa K, Matsuoka H. Renoprotective effect of long-term combined treatment with adrenomedullin and omapatrilat in hypertensive rats. J Hypertens. 2005 Dec;23(12):2287-96. PubMed PMID: 16269971.
12: Sulpizio AC, Pullen MA, Edwards RM, Louttit JB, West R, Brooks DP. Mechanism of vasopeptidase inhibitor-induced plasma extravasation: comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406. J Pharmacol Exp Ther. 2005 Dec;315(3):1306-13. Epub 2005 Sep 6. PubMed PMID: 16144980.
13: Lapointe N, Parker TG, Tsoporis JN, Nguyen QT, Marcotte F, Adam A, Lou I, Rouleau JL. Effects of the vasopeptidase inhibitor omapatrilat on peri- and postmyocardial infarction in Zucker lean rats. Can J Cardiol. 2005 Mar;21(3):291-7. PubMed PMID: 15776120.
14: Perlini S. The potential advantage of omapatrilat: dual anti-fibrotic and anti-inflammatory effects in one single molecule. J Hypertens. 2005 Feb;23(2):273-5. PubMed PMID: 15662213.
15: Abassi ZA, Yahia A, Zeid S, Karram T, Golomb E, Winaver J, Hoffman A. Cardiac and renal effects of omapatrilat, a vasopeptidase inhibitor, in rats with experimental congestive heart failure. Am J Physiol Heart Circ Physiol. 2005 Feb;288(2):H722-8. Epub 2004 Oct 21. PubMed PMID: 15498826.
16: Kothny W, Kaaden R, Ludwig P, Chase D, Krekler M. 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. Arzneimittelforschung. 2004;54(8):474-9. PubMed PMID: 15460215.
17: Graham D, Hamilton C, Beattie E, Spiers A, Dominiczak AF. Comparison of the effects of omapatrilat and irbesartan/hydrochlorothiazide on endothelial function and cardiac hypertrophy in the stroke-prone spontaneously hypertensive rat: sex differences. J Hypertens. 2004 Feb;22(2):329-37. PubMed PMID: 15076191.
18: Persson J, Morsing P, Grände PO. Vasopeptidase inhibition with omapatrilat increases fluid and protein microvascular permeability in cat skeletal muscle. J Hypertens. 2004 Mar;22(3):637-44. PubMed PMID: 15076171.
19: Cheng TO. Is omapatrilat a novel therapy of the past rather than the future? Drugs. 2004;64(6):630-1; author reply 631. PubMed PMID: 15018594.
20: Mifsud SA, Burrell LM, Kubota E, Jaworski K, Cooper ME, Wilkinson-Berka JL. Cardiorenal protective effects of vasopeptidase inhibition with omapatrilat in hypertensive transgenic (mREN-2)27 rats. Clin Exp Hypertens. 2004 Jan;26(1):69-80. PubMed PMID: 15000298.