3625. Eplerenone

Nomenclature

CAS number: 107724-20-9
(7α,11α,17α)-9,11-Epoxy-17-hydroxy-3-oxopregn-4-ene-7,21-dicarboxylic acid γ-lactone methyl ester; 9α,11-epoxy-7α-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone; 9α,11α-epoxy-7α-methoxycarbonyl-20-spirox-4-ene-3,21-dione; epoxymexrenone; CGP-30083; SC-66110; Inspra (Pfizer).
C24H30O6; mol wt 414.49.
C 69.54%, H 7.30%, O 23.16%.

Description and references

Selective aldosterone receptor antagonist (SARA); structurally similar to spironolactone, q.v. Prepn: J. Grob, J. Kalvoda, EP 122232; eidem, US 4559332 (1984, 1985 both to Ciba-Geigy); J. Grob et al., Helv. Chim. Acta 80, 566 (1997). Pharmacology and receptor binding studies: M. de Gasparo et al., J. Pharmacol. Exp. Ther. 240, 650 (1987). Clinical pharmacokinetics: W. R. Ravis et al., J. Clin. Pharmacol. 45, 810 (2005). Clinical trial in congestive heart failure after myocardial infarction: B. Pitt et al., N. Engl. J. Med. 348, 1309 (2003); in hypertension vs losartan: M. H. Weinberger et al., Am. Heart J. 150, 426 (2005). Review of pharmacology and clinical experience: J. A. Delyani et al., Cardiovasc. Drug Rev. 19, 185-200 (2001); E. Burgess, Expert Opin. Pharmacother. 5, 2573-2581 (2004).

Chemical structure

Properties

Crystals from methylene chloride + isopropanol, mp 240-242°. [α]D +5° (c = 0.437 in chloroform). uv max: 240 nm (ε 16800). Partition coefficient (octanol/water): 7.1 (pH 7.0). Sol in dichloromethane, acetonitrile; slightly sol in ethanol; sparingly sol in methyl ethyl ketone, methanol; very slightly sol in water.

Therapeutic Category

Antihypertensive. In treatment of congestive heart failure.

Keywords

Aldosterone Antagonist; Antihypertensive