3635. Eprosartan

Nomenclature

CAS number: 133040-01-4
(αE)-α-[[2-Butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazol-5-yl]methylene]-2-thiophenepropanoic acid; (E)-3-[2-butyl-1-[(4-carboxyphenyl)methyl]-imidazol-5-yl]-2-(2-thienylmethyl)-2-propenoic acid; SKF-108566.
C23H24N2O4S; mol wt 424.51.
C 65.07%, H 5.70%, N 6.60%, O 15.08%, S 7.55%.

Description and references

Prototype of the imidazoleacrylic acid angiotensin II receptor antagonists. Prepn: J. A. Finkelstein et al., EP 403159 (1990 to SmithKline Beckman); eidem, US 5185351 (1993 to SmithKline Beecham); J. Weinstock et al., J. Med. Chem. 34, 1514 (1991); R. M. Keenan et al., ibid. 36, 1880 (1993). Pharmacology: R. M. Edwards et al., J. Pharmacol. Exp. Ther. 260, 175 (1992). Receptor binding study: H. T. Schambye et al., Mol. Pharmacol. 47, 425 (1995). Clinical pharmacokinetics: D. Tenero et al., Biopharm. Drug Dispos. 19, 351 (1998). Clinical trial in hypertension: W. J. Elliott et al., J. Hum. Hypertens. 13, 413 (1999). Review of clinical experience: L. Ruilope, B. J"ager, Expert Opin. Pharmacother. 4, 107-114 (2003).

Chemical structure

Properties

Crystals from methanol, mp 260-261°.

Derivative

Monomethanesulfonate.

Nomenclature

CAS number: 144143-96-4
Eprosartan mesylate; SKF-108566J; Teveten (Solvay).
C23H24N2O4S.CH3SO3H; mol wt 520.62.
C 55.37%, H 5.42%, N 5.38%, O 21.51%, S 12.32%.

Properties

White to off-white crystalline powder, mp 248-250°. Insol in water. Freely sol in ethanol.

Therapeutic Category

Antihypertensive.

Keywords

Angiotensin II Receptor Antagonist; Antihypertensive; Imidazoleacrylic Acid Derivatives