Metabolism of anabolic steroids in humans: synthesis of 6 beta-hydroxy metabolites of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone.
Hydroxylation at position 6 beta testosterone I (17 beta-hydroxyandrost-4-en-3-one) and the anabolic steroids 17 alpha-methyltestosterone II (17 beta-hydroxy-17 alpha-methylandrost-4-en-3-one), metandienone III (17 beta-hydroxy-17 alpha-methylandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17 alpha-methyltestosterone IV (4-chloro-17 beta-hydroxy-17 alpha-methylandrosta-1,4-dien-3-one), and fluoxymesterone V (9-fluoro-11 beta, 17 beta-dihydroxy-17 alpha-methylandrost-4-en-3-one) was achieved via light-induced autooxidation of the corresponding trimethysilyl 3,5-dienol ethers dissolved in isopropanol or ethanol. The reaction further yielded the 6 alpha-hydroxy isomer in low amounts. The 6 beta-hydroxy isomer of I-V and the 6 alpha-hydroxy isomers of I, III, and IV were isolated and characterized by 1H and 13C NMR, high-performance liquid chromatography, gas chromatography, and mass spectrometry. Human excretion studies with single administered doses of boldenone (17 beta-hydroxyandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, metandienone, 17 alpha-methyltestosterone, and [16,16,17-2H3] testosterone showed that 6 beta-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17 alpha-methyltestosterone, and testosterone, 6 beta-hydroxylation is negligible.
Institut für Biochemie, Deutschen Sporthochschule Köln, Germany.
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Schänzer
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Horning
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Donike
D000328:Adult; D045930:Anabolic Agents / Q000138:chemical synthesis / Q000378:metabolism*; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D005474:Fluoxymesterone / Q000138:chemical synthesis / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D006900:Hydroxylation; D006915:Hydroxytestosterones / Q000138:chemical synthesis / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008696:Methandrostenolone / Q000138:chemical synthesis / Q000378:metabolism*; D008777:Methyltestosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D010084:Oxidation-Reduction; D010782:Photolysis; D012997:Solvents; D013739:Testosterone / Q000378:metabolism
D045930:Anabolic Agents; D006915:Hydroxytestosterones; D012997:Solvents; D013739:Testosterone; D005474:Fluoxymesterone; D008696:Methandrostenolone; D008777:Methyltestosterone