Megestrol acetate is metabolized by homogenates of rat adrenal glands to three more polar metabolites Y2, Y3 and Y4. Their structures were investigated by microchemical reactions, paper chromatography, and ultraviolet and infrared spectroscopy. Metabolite Y3 was identified as 17α-acetoxy-11β-hydroxy-6-methyl-pregna-4,6-diene-3,20-dione, its oxidation product being identical with authentic 17α-acetoxy-6-methylpregna-4,6-diene-3,11,20-trione. It is suggested that metabolite Y2 is 17,18-dihydroxy-6-methylpregna-4,6-diene-3,20-dione and that it also exists in the form of an α-ketol formed between the 18-hydroxyl and 20-oxo groups. Metabolite Y4 is probably a tautomeric form of metabolite Y2 as they were partially interconverted on chromatography and also have similar properties.

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