Detection and Characterization of a New Metabolite of 17α-Methyltestosterone
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Otros documentos de la autoría: Pozo, Óscar J.; Van Eenoo, Peter; Deventer, Koen; Lootens, Leens; Van Thuyne, Wim; Parr, Maria K.; Schänzer, Wilhelm; Sancho, Juan V; Hernandez, Felix; Meuleman, Philip; Leroux-Roels, Geert; Delbeke, Frans T.
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Metadatos
Título
Detection and Characterization of a New Metabolite of 17α-MethyltestosteroneAutoría
Fecha de publicación
2009-11Editor
The American Society for Pharmacology and Experimental TherapeuticsISSN
0090-9556Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
http://dmd.aspetjournals.org/content/37/11/2153.shortVersión
info:eu-repo/semantics/publishedVersionPalabras clave / Materias
Resumen
The misuse of the anabolic steroid methyltestosterone is currently routinely monitored in doping control laboratories by gas chromatography-mass spectrometry (GC-MS) of two of its metabolites: 17α-methyl-5β-androsta ... [+]
The misuse of the anabolic steroid methyltestosterone is currently routinely monitored in doping control laboratories by gas chromatography-mass spectrometry (GC-MS) of two of its metabolites: 17α-methyl-5β-androstane-3α,17β-diol and 17α-methyl-5α-androstane-3α,17β-diol. Because of the absence of any easy ionizable moiety, these metabolites are poorly detectable using liquid chromatography-tandem mass spectrometry (LC-MS/MS) with electrospray ionization (ESI). In this study, the metabolism of methyltestosterone has been reinvestigated by the use of a precursor ion scan method in LC-ESI-MS/MS. Two metabolites have been detected using this method. Both compounds have been confirmed in postadministration urine samples of an urokinase plasminogen activator-severe combined immunodeficiency (uPA-SCID) mouse with humanized liver and were characterized by LC-MS/MS and GC-MS using both quadrupole and time of flight analyzers. From the detailed study of the fragmentation, these metabolites were proposed to be epimethyltestosterone and a dehydrogenated compound. Epimethyltestosterone has previously been described as a minor metabolite, whereas the occurrence of the oxidized metabolite has not been reported. Comparison with the synthesized reference revealed that the structure of the dehydrogenated metabolite is 6-ene-epimethyltestosterone. A selected reaction monitoring method including three transitions for each metabolite has been developed and applied to samples from an excretion study and to samples declared positive after GC-MS analysis. 6-Ene-epimethyltestosterone was found in all samples, showing its applicability in the detection of methyltestosterone misuse. [-]
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DRUG METABOLISM AND DISPOSITION, 37, 11, p. 2153-2162Derechos de acceso
Copyright © 2009 by The American Society for Pharmacology and Experimental Therapeutics
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