Characterization and quantification of fluoxymesterone metabolite in horse urine by gas chromatography/mass spectrometry.
Fluoxymesterone, an anabolic steroid with the 17alpha-methyl,17beta-hydroxy group, has been developed as an oral formulation for therapeutic purposes. However, it is also used illegally in racehorses to enhance racing performance. In this study, we detected 9alpha-fluoro-17,17-dimethyl-18-norandrostane-4,13-dien-11beta-ol-3-one by gas chromatography/mass spectrometry (GC/MS), which has not been reported as a fluoxymesterone metabolite so far in horse. It was synthesized for use as a reference standard, and characterized on the basis of (1)H NMR and (13)C NMR spectra, as well as GC/MS EI mass spectra of TMS derivatives. It was excreted as the main metabolite in horse urine, and its reference standard could be synthesized easily. Therefore, this metabolite could be a useful target for a doping test of fluoxymesterone in racehorses.
Yamada
Masayuki
M
Laboratory of Racing Chemistry, Utsunomiya, Japan. m-yamada@lrc.or.jp
Aramaki
Sugako
S
Hosoe
Tomoo
T
Kurosawa
Masahiko
M
Kijima-Suda
Isao
I
Saito
Koichi
K
Nakazawa
Hiroyuki
H
D045930:Anabolic Agents / Q000652:urine*; D000818:Animals; D004300:Doping in Sports; D005474:Fluoxymesterone / Q000652:urine*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006736:Horses; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D015813:Substance Abuse Detection / Q000379:methods*
D045930:Anabolic Agents; D005474:Fluoxymesterone