Abstract
In the urine of subjects given an oral dose of spironolactone [3-(3-oxo-7 α-acetylthio-17 β-hydroxy-4-androsten-17 α-y1)propionic acid γ-lactone], six metabolites have been detected. One of the major metabolites was found to be the previously characterized de-thioacetylated compound, 3-(3-oxo-17 β-hydroxy-4,6-androstadien-17 α-y1)propionic acid γ-lactone (canrenone). Besides this a new major sulfur-containing metabolite has been isolated and identified as 3-(3-oxo-7 α-methylsulfinyl-6 β,17 β-dihydroxy-4-androsten-17 α-y1)propionic acid γ-lactone. This structural assignment was based on detailed analysis of its IR, NMR and UV spectra as well as comparison of its physical constants and chromatographic (TLC and GLC) characteristics with a synthetic sample. The three minor metabolites were found to be very labile and were readily converted to canrenone.
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