3717. Ethacrynic Acid
Nomenclature
CAS number: 58-54-8
2-[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid; [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid; [4-(methylenebutyryl)-2,3-dichlorophenoxy]acetic acid; MK-595; Edecril (Merck & Co.); Edecrin (Merck & Co.); Hydromedin (Merck & Co.). C13H12Cl2O4; mol wt 303.14.
C 51.51%, H 3.99%, Cl 23.39%, O 21.11%.
Description and references
Unsaturated ketone derivative of an aryloxyacetic acid. Prepn: Schultz et al., J. Med. Pharm. Chem. 5, 660 (1962); E. M. Schultz, J. M. Sprague, BE 612755 C.A. 59, 12712b (1963); eidem, US 3255241 (1962, 1966 both to Merck & Co.). HPLC determn in plasma: F. P. LaCreta et al., J. Chromatogr. 571, 271 (1991); in urine: P. Campíns-Falcó et al.,, Anal. Chim. Acta 284, 67 (1993). Pharmacology: Beyer et al., J. Pharmacol. Exp. Ther. 147, 1 (1965). Crystal structure: J. Lamotte et al., Acta Crystallogr. B34, 2636 (1978). Toxicity study: Peck et al., Fed. Proc. 23, 438 (1964). Reviews: Kim et al., Am. J. Cardiol. 27, 407-415 (1971); H. E. Williamson, J. Clin. Pharmacol. 17, 663-672 (1977).
Properties
White, or practically white, crystalline powder, mp 121-122° (corr). pKa′ 3.50. Very slightly sol in water; sol in most organic solvents such as alcohols, chloroform, benzene. LD50 in mice (mg/kg): 176 i.v.; 627 orally (Peck).Derivative
Sodium salt.Nomenclature
CAS number: 6500-81-8
Ethacrynate sodium. C13H11Cl2NaO4; mol wt 325.12.
C 48.03%, H 3.41%, Cl 21.81%, Na 7.07%, O 19.68%.
Properties
uv max (water): 225 nm (ε 15287). Soly in water at 25°: up to 7%. Solns at pH 7 at 25° stable for short periods of time. Stability decreased with an increase in pH, temperature and time.Therapeutic Category
Diuretic.
Therapeutic Category (Veterinary)
Diuretic.Keywords
Diuretic