title: Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine.
abstract: Anabolic-androgenic steroids are some of the most frequently detected drugs in amateur and professional sports. Doping control laboratories have developed numerous assays enabling the determination of administered drugs and/or their metabolic products that allow retrospectives with respect to pharmacokinetics and excretion profiles of steroids and their metabolites. A new metabolite generated from metandienone has been identified as 18-nor-17beta-hydroxymethyl,17alpha-methyl-androst-1,4,13-trien-3-one in excretion study urine samples providing a valuable tool for the long-term detection of metandienone abuse by athletes in sports drug testing. The metabolite was characterized using gas chromatography/(tandem) mass spectrometry, liquid chromatography/tandem mass spectrometry and liquid chromatography/high-resolution/high-accuracy (tandem) mass spectrometry by characteristic fragmentation patterns representing the intact 3-keto-1,4-diene structure in combination with typical product ions substantiating the proposed C/D-ring structure of the steroid metabolite. In addition, structure confirmation was obtained by the analysis of excretion study urine specimens obtained after administration of 17-CD(3)-labeled metandienone providing the deuterated analogue to the newly identified metabolite. 18-Nor-17beta-hydroxymethyl,17alpha-methyl-androst-1,4,13-trien-3-one was determined in metandienone administration study urine specimens up to 19 days after application of a single dose of 5 mg, hence providing an extended detection period compared with commonly employed strategies.
authors.affiliation: Center for Preventive Doping Research-Institute of Biochemistry, German Sport University Cologne, Carl-Diem Weg 6, 50933 Cologne, Germany.
authors.forename: Wilhelm
authors.initials: W
authors.lastname: Schänzer
authors.forename: Hans
authors.initials: H
authors.lastname: Geyer
authors.forename: Gregor
authors.initials: G
authors.lastname: Fusshöller
authors.forename: Natalia
authors.initials: N
authors.lastname: Halatcheva
authors.forename: Maxie
authors.initials: M
authors.lastname: Kohler
authors.forename: Maria-Kristina
authors.initials: MK
authors.lastname: Parr
authors.forename: Sven
authors.initials: S
authors.lastname: Guddat
authors.forename: Andreas
authors.initials: A
authors.lastname: Thomas
authors.forename: Mario
authors.initials: M
authors.lastname: Thevis
mesh_terms: D000328:Adult; D002849:Chromatography, Gas / Q000379:methods*; D002853:Chromatography, Liquid / Q000379:methods*; D006801:Humans; D008297:Male; D013058:Mass Spectrometry / Q000379:methods*; D008657:Metabolic Clearance Rate; D008696:Methandrostenolone / Q000737:chemistry* / Q000652:urine*; D008875:Middle Aged; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013048:Specimen Handling / Q000379:methods; D015813:Substance Abuse Detection / Q000379:methods*; D016482:Urinalysis / Q000379:methods*
chemical_list: D008696:Methandrostenolone