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Eprosartan

Names

[ CAS No. ]:
133040-01-4

[ Name ]:
Eprosartan

[Synonym ]:
2-Thiophenepropanoic acid, α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-
MFCD08141807
4-({2-Butyl-5-[2-carboxy-3-(2-thienyl)-1-propen-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid
Eprosartan
4-[[2-butyl-5-[(E)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid

Biological Activity

[Description]:

Eprosartan (SKF-108566J free base) is a selective, competitive, nonpeptid and orally active angiotensin II receptor antagonist, used as an antihypertensive. Eprosartan binds angiotensin II receptor with IC50s of 9.2 nM and 3.9 nM in rat and human adrenal cortical membranes, respectively [1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease
Signaling Pathways >> GPCR/G Protein >> Angiotensin Receptor

[In Vitro]

Eprosartan (SKF-108566J) inhibits [125I]AII binding to human liver membranes (IC50 of 1.7 nM) and to rat mesenteric artery membranes (IC50 of 1.5 nM). In rabbit aortic smooth muscle cells, Eprosartan caused a concentration-dependent inhibition of AII-induced increases in intracellular Ca2+ levels[1].

[In Vivo]

In conscious normotensive rats, i.v. administration of Eprosartan (0.01-0.3 mg/kg) produced dose-dependent parallel shifts in the AII pressor dose-response curve. Administration of Eprosartan (3-10 mg/kg) intraduodenally or intragastrically to conscious normotensive rats resulted in a dose-dependent inhibition of the pressor response to AII (250 ng/kg, i.v.). At 10 mg/kg, i.d., significant inhibition of the pressor response to AII was observed for 3 hr[1].

[References]

[1]. R M Edwards, et al. Pharmacological characterization of the nonpeptide angiotensin II receptor antagonist, SK&F 108566. J Pharmacol Exp Ther. 1992 Jan;260(1):175-81.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
660.6±55.0 °C at 760 mmHg

[ Melting Point ]:
250-253ºC

[ Molecular Formula ]:
C23H24N2O4S

[ Molecular Weight ]:
424.513

[ Flash Point ]:
353.3±31.5 °C

[ Exact Mass ]:
424.145691

[ PSA ]:
120.66000

[ LogP ]:
4.96

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.628

[ Storage condition ]:
-20°C Freezer

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds