Eprosartan mesylate

Names

[ Name ]:
Eprosartan mesylate

[Synonym ]:
4-[[2-butyl-5-[(E)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid,methanesulfonic acid
4-({2-Butyl-5-[(1E)-2-carboxy-3-thiophen-2-ylprop-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzolcarbonsäure-methansulfonsäure(1:1)
acide 4-({2-butyl-5-[(1E)-2-carboxy-3-thiophén-2-ylprop-1-én-1-yl]-1H-imidazol-1-yl}méthyl)benzoïque - acide méthanesulfonique (1:1)
MFCD08141807
2-Thiophenepropanoic acid, α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-, (αE)-, methanesulfonate (1:1)
Eprosartan mesylate
4-({2-butyl-5-[(1E)-2-carboxy-3-thiophen-2-ylprop-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid methanesulfonate
2-Thiophenepropanoic acid, α-[[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-, (αZ)-, methanesulfonate (1:1)
Eprosartan Monomethanesulfonate SKF-108566J Teveten
4-({2-Butyl-5-[(1Z)-2-carboxy-3-(2-thienyl)-1-propen-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid methanesulfonate (1:1)
4-({2-Butyl-5-[(1E)-2-carboxy-3-(2-thienyl)-1-propen-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid methanesulfonate (1:1)
4-({2-butyl-5-[(1E)-2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid methanesulfonate (1:1)
Eprosartan (mesylate)

Biological Activity

[Description]:

Eprosartan is a nonpeptide angiotensin II receptor antagonist with IC50 of 9.2 and 3.9 nM in rat and human adrenal cortical membranes, respectively. IC50 Value: 9.2 nM(in rat adrenal cortical membranes); 3.9 nM(in human adrenal cortical membranes)Target: Angiotensin Receptor Type-1(AT1)in vitro: Eprosartan mesylate, is one of the highly selective, orally active, non-peptide angiotensin-II-receptor antagonists [1]. In rat and human adrenal cortical membranes, Eprosartan displaced specifically bound [125I]AII with IC50 of 9.2 and 3.9 nM, respectively. Eprosartan also inhibited [125I]AII binding to human liver membranes (IC50 = 1.7 nM) and to rat mesenteric artery membranes (IC50 = 1.5 nM). In rabbit aortic smooth muscle cells, Eprosartan caused a concentration-dependent inhibition of AII-induced increases in intracellular Ca++ levels. In rabbit aortic rings [2].in vivo: 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. In this same rat model, Eprosartan had no effect on base-line pressure or on the pressor response to norepinephrine or vasopressin [2]. Eprosartan is highly effective and safe in lowering blood pressure, notably SBP, in older subjects with mild to moderate hypertension [3]. Treatment with eprosartan in once-daily doses up to 1200 mg alone or in combination with HCTZ was well tolerated, with dizziness and asthenia being the most common side effects [4]. Therapy with eprosartan mesilat was associated with significant hypotensive effect (more evident in patients with high systolic blood pressure), improvement in 24-hour blood pressure profile and quality of life, and lower probability of secondary stroke. Side effects were not observed [5].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Angiotensin Receptor

Research Areas >> Cardiovascular Disease

[References]

[1]. Qian, J.J., et al., Eprosartan mesylate, an angiotensin II receptor antagonist. Acta Crystallogr Sect E Struct Rep Online, 2011. 67(Pt 4): p. o770-1.

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

[3]. Conter, H.S., D.W. McKay, and R.J. Reiz, Eprosartan mesylate effectively reduces systolic and diastolic blood pressure in a Canadian primary care setting. Can J Cardiol, 2004. 20 Suppl C: p. 6C-10C.

[4]. Punzi, H.A. and C.F. Punzi, Once-daily eprosartan mesylate in the treatment of elderly patients with isolated systolic hypertension: data from a 13-week double-blind, placebo-controlled, parallel, multicenter study. J Hum Hypertens, 2004. 18(9): p. 655-61

[5]. Martynov, M., et al., [Eprosartan mesylate in controlling of blood pressure in patients with ischemic stroke]. Zh Nevrol Psikhiatr Im S S Korsakova, 2002. 102(4): p. 26-30.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.26 g/cm3

[ Boiling Point ]:
660.6ºC

[ Melting Point ]:
248 °C

[ Molecular Formula ]:
C₂₄H₂₈N₂O₇S₂

[ Molecular Weight ]:
520.618

[ Flash Point ]:
353.3ºC

[ Exact Mass ]:
520.133789

[ PSA ]:
183.41000

[ LogP ]:
5.32920

[ Vapour Pressure ]:
2.37E-18mmHg at 25°C

[ Storage condition ]:
room temp

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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