Title: Eplerenone
CAS Registry Number: 107724-20-9
CAS Name: (7a,11a,17a)-9,11-Epoxy-17-hydroxy-3-oxopregn-4-ene-7,21-dicarboxylic acid g-lactone methyl ester
Synonyms: 9a,11-epoxy-7a-(methoxycarbonyl)-3-oxo-17a-pregn-4-ene-21,17-carbolactone; 9a,11a-epoxy-7a-methoxycarbonyl-20-spirox-4-ene-3,21-dione; epoxymexrenone
Manufacturers' Codes: CGP-30083; SC-66110
Trademarks: Inspra (Pfizer)
Molecular Formula: C24H30O6
Molecular Weight: 414.49
Percent Composition: C 69.54%, H 7.30%, O 23.16%
Literature 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).
Properties: Crystals from methylene chloride + isopropanol, mp 240-242°. [a]D +5° (c = 0.437 in chloroform). uv max: 240 nm (e 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.
Melting point: mp 240-242°
Optical Rotation: [a]D +5° (c = 0.437 in chloroform)
Log P: Partition coefficient (octanol/water): 7.1 (pH 7.0)
Absorption maximum: uv max: 240 nm (e 16800)
Therap-Cat: Antihypertensive. In treatment of congestive heart failure.
Keywords: Aldosterone Antagonist; Antihypertensive.
