ISolation and identification of a sulfur-containing metabolite of spironolactone from human urine

In the urine of normal subjects Who were given an oral dose of 500 mg spironolactone (3-(3-oxo-7α-acetylthio-17β-hydroxy-4-androsten-17α-yl)-propionic acid γ-lactone; Aldactone^R) together with 100, uCi H-20, 21 spironolactone, a so far unknown major metabolite has been detected by thin layer chromatography. The metabolite then could be isolated by means of counter-current-distribution. According to masspectral and magnetic resonance data, the metabolite has been assigned the structure of 3-(3-oxo-7α-niethyl sulfonyl-6β, 17β-dihydroxy-4-androsten-17α-yl)-propionic acid γ-lactone. By oxidation of the corresponding methylsulfinyl compound — another already known metabolite of spironolactone-with m-chloroperbenzoic acid, a compound has been isolated which proved to be identical with the new metabolite according to TIC, MS and NMR.