title: Use of an electrochemically synthesised metabolite of a selective androgen receptor modulator for mass spectrometry-based sports drug testing.
abstract: The elucidation of the metabolism of new therapeutics is a major task for pharmaceutical companies and of great interest for drug testing laboratories. The latter in particular need to determine the presence or absence of drugs or their metabolic products in urine to test for a misuse of these compounds. Commonly, in vitro or animal models are used to mimic the human metabolism and produce potential targets in amounts allowing for method development. An alternative route based on electrochemical reactions of drugs was reported to allow for the generation of selected metabolites. The utility of this approach for doping control purposes was demonstrated with a novel class of anabolic agents termed selective androgen receptor modulators (SARMs). An arylpropionamide- derived drug candidate was subjected to electrochemical "metabolism" and a major phase-I- metabolite, resulting from the elimination of a substituted phenol residue as identified in in vitro experiments, was generated and characterised using liquid chromatography/nuclear magnetic resonance spectroscopy and high resolution/high accuracy mass spectrometry. The metabolite was included in routine doping control procedures based on liquid chromatography/tandem mass spectrometry and has served as a reference compound for 5000 doping control specimens.
authors: Center for Preventive Doping Research-Institute of Biochemistry, German Sport University Cologne, Am Sportpark Müngersdorf 6, 50933 Cologne, Germany. thevis@dshs-koeln.de
authors: Mario
authors: M
authors: Thevis
authors: Wiebke
authors: W
authors: Lohmann
authors: Yvonne
authors: Y
authors: Schrader
authors: Maxie
authors: M
authors: Kohler
authors: Wolfgang
authors: W
authors: Bornatsch
authors: Uwe
authors: U
authors: Karst
authors: Wilhelm
authors: W
authors: Schänzer
mesh_terms: D045930:Anabolic Agents / Q000138:chemical synthesis / Q000378:metabolism*; D000726:Androgen Antagonists / Q000138:chemical synthesis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004300:Doping in Sports; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011944:Receptors, Androgen / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: D045930:Anabolic Agents; D000726:Androgen Antagonists; D011944:Receptors, Androgen