Metabolic studies of oxyguno in horses

April S Y Wong, Emmie N M Ho, Terence S M Wan, Kenneth K H Lam, Brian D Stewart
Analytica Chimica Acta 2015 September 3, 891: 190-202
Oxyguno (4-chloro-17α-methyl-17β-hydroxy-androst-4-ene-3,11-dione) is a synthetic oral anabolic androgenic steroid commercially available without a prescription. Manufacturers of oxyguno claim that its anabolic effect in metabolic enhancement exceeds that of the classic anabolic steroid testosterone by seven times, but its androgenic side-effects are only twelve percent of testosterone. Like other anabolic androgenic steroids, oxyguno is prohibited in equine sports. The metabolism of oxyguno in either human or horse has not been reported and therefore little is known about its metabolic fate. This paper describes the in vitro and in vivo metabolic studies of oxyguno in racehorses with an objective to identify the most appropriate target metabolites for detecting oxyguno administration. In vitro studies of oxyguno were performed using horse liver microsomes. Metabolites in the incubation mixtures were isolated by liquid-liquid extraction and analysed by gas chromatography-mass spectrometry in the EI mode after trimethylsilylation. In vitro metabolites identified include the stereoisomers of 4-chloro-17α-methyl-androst-4-ene-3-keto-11,17β-diol (M1a & M1b); 20-hydroxy-oxyguno (M2); and 4-chloro-17α-methyl-androst-4-ene-3-keto-11,17β,20-triol (M3). These novel metabolites were resulted from hydroxylation at C20, and/or reduction of the keto group at C11. For the in vivo studies, two geldings were each administered orally with a total dose of 210 mg oxyguno (52.5 mg twice daily for 2 days). Pre- and post-administration urine and blood samples were collected for analysis. The parent drug oxyguno was detected in both urine and blood, while numerous novel metabolites were detected in urine. The stereoisomers (M1a & M1b) observed in the in vitro studies were also detected in post-administration urine samples. Three other metabolites (M4 - M6) were detected. M4, 4-chloro-17α-methyl-androstane-11-keto-3,17β-diol, was resulted from reductions of the olefin group at C4 and the keto group at C3. M5 was resulted from hydroxylation at C20 and two reductions at either the olefin group at C4, the keto group at C3, or the keto group at C11. M6 was assigned as the 17-epimer of oxyguno. The major biotransformation pathways of oxyguno identified were reduction, hydroxylation and epimerisation. The structures of all metabolites were tentatively assigned by mass spectral interpretation. The longest detection time observed in urine was up to 10 h for the in vivo metabolite M4. Urinary and plasma oxyguno decreased rapidly and was no longer detectable at respectively 7 and 12 h post-administration. The above studies have provided useful information for the monitoring of oxyguno administration in racehorses.

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