Title: Spironolactone
CAS Registry Number: 52-01-7
CAS Name: (7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone
Additional Names: 17-hydroxy-7a-mercapto-3-oxo-17a-pregn-4-ene-21-carboxylic acid g-lactone, acetate; 3-(3-oxo-7a-acetylthio-17b-hydroxy-4-androsten-17a-yl)propionic acid g-lactone
Manufacturers' Codes: SC-9420
Trademarks: Aldactone (Pharmacia & Upjohn); Aquareduct (Azupharma); Practon (Pfizer); Osyrol (Aventis); Sincomen (Schering AG); Spirobeta (Betapharm); Spiroctan (Ferlux); Spirolone (APS); Spironone (Dexo); Verospiron (Richter Gedeon); Xenalon (Mepha)
Molecular Formula: C24H32O4S
Molecular Weight: 416.57
Percent Composition: C 69.20%, H 7.74%, O 15.36%, S 7.70%
Literature References: Aldosterone antagonist. Prepn: Cella, Tweit, J. Org. Chem. 24, 1109 (1959); US 3013012 (1961 to Searle); Tweit et al., J. Org. Chem. 27, 3325 (1962). Activity and metabolic studies: Gerhards, Engelhardt, Arzneim.-Forsch. 13, 972 (1963). Crystal and molecular structure: Dideberg, Dupont, Acta Crystallogr. B28, 3014 (1972). Comprehensive description: J. L. Sutter, E. P. K. Lau, Anal. Profiles Drug Subs. 4, 431-451 (1975). Review of carcinogenetic risk: IARC Monographs 24, 259-273 (1980). Review of antiandrogen effects and clinical use in hirsutism: R. R. Tremblay, Clin. Endocrinol. Metab. 15, 363-371 (1986); of clinical efficacy in hypertension: A. N. Brest, Clin. Ther. 8, 568-585 (1986). Review of pharmacology: H. A. Skluth, J. G. Gums, DICP Ann. Pharmacother. 24, 52-59 (1990). Clinical trial in congestive heart failure: B. Pitt et al., N. Engl. J. Med. 341, 709 (1999).
Properties: Crystals from methanol, mp 134-135° (resolidifies and dec 201-202°). [a]D20 -33.5° (chloroform). uv max: 238 nm (e 20200). Practically insol in water. Sol in alcohol; freely sol in benzene, chloroform. LD50 in rats, mice, rabbits (mg/kg): 790, 360, 870 i.p. (IARC, 1980).
Melting point: mp 134-135° (resolidifies and dec 201-202°)
Optical Rotation: [a]D20 -33.5° (chloroform)
Absorption maximum: uv max: 238 nm (e 20200)
Toxicity data: LD50 in rats, mice, rabbits (mg/kg): 790, 360, 870 i.p. (IARC, 1980)
Therap-Cat: Diuretic.
Therap-Cat-Vet: Diuretic.
Keywords: Aldosterone Antagonist; Diuretic; Steroids.

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