Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human.
Two major unconjugated acidic metabolites of oxymetholone (17 beta-hydroxy-2-hydroxymethylene-17 alpha-methyl-5 alpha-androstan-3-one, 1), namely, 17 beta-hydroxy-17 alpha-methyl-2,3-seco-5 alpha-androstane-2,3-dioic acid (2) and 3 alpha,17 beta-dihydroxy-17 alpha-methyl-5 alpha-androstane-2 beta-carboxylic acid (6a), were detected by gas chromatography/mass spectrometry in urine samples collected after oral administration of 1 to a human volunteer. Reference steroid 2 was synthesized and identified. The identification of urinary metabolite 6a was based on the synthesis of its stereoisomers and the isomerization of the methyl ester 6b to its 2-epimer, 3 alpha,17 beta-dihydroxy-17 alpha-methyl-5 alpha-androstane-2 alpha-carboxylic acid methyl ester (9b). The mechanisms accounting for the formation of these acidic metabolites are discussed.
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Institut National de la Recherche Scientifique, INRS Santé, Université du Québec, Pointe-Claire, Canada.
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D000143:Acids / Q000652:urine*; D000328:Adult; D015113:Androstane-3,17-diol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000732:Androstanols / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D010110:Oxymetholone / Q000138:chemical synthesis* / Q000652:urine; D012015:Reference Standards; D013237:Stereoisomerism
C078539:17-hydroxy-17-methyl-2,3-secoandrostane-2,3-dioic acid; C078540:3,17-dihydroxy-17-methylandrostane-2-carboxylic acid; D000143:Acids; D000732:Androstanols; D015113:Androstane-3,17-diol; D010110:Oxymetholone