Universität zu Köln

Schaenzer, Wilhelm, Guddat, Sven, Thomas, Andreas ORCID: 0000-0003-1199-0743, Opfermann, Georg, Geyer, Hans and Thevis, Mario (2013). Expanding analytical possibilities concerning the detection of stanozolol misuse by means of high resolution/high accuracy mass spectrometric detection of stanozolol glucuronides in human sports drug testing. Drug Test. Anal., 5 (11-12). S. 810 - 819. HOBOKEN: WILEY-BLACKWELL. ISSN 1942-7611

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Abstract

Anabolic-androgenic steroids (AAS) represent one of the most frequently detected classes of prohibited substances in doping controls. Due to their long-lasting beneficial effects on athletic performance, utmost retrospectivity via urine analysis is desirable and accomplished by targeting long-term metabolites of the respective drugs. In case of stanozolol, a substantial variety of metabolites has enabled the identification of numerous adverse analytical findings in the past, and recent studies concerning complementary phase-I and phase-II metabolites has further expanded the windows of opportunity for detecting the abuse of stanozolol. In this study, the utility of liquid chromatography-high resolution/high accuracy (tandem) mass spectrometry (LC-MS/MS) for the detection of 3'-OH-stanozolol glucuronide in sports drug testing is presented and the identification of two additional and so far unreported metabolites is shown. The structures of the complementary glucuronic acid conjugates were attributed to stanozolol-N-glucuronide and 17-epistanozolol-N-glucuronide. By means of chemical synthesis, stanozolol-N-glucuronide was prepared and used to corroborate the suggested structures. The 3'-OH-stanozolol glucuronide and the newly identified target compounds were implemented into routine sports drug test assays consisting of direct injection LC-MS/MS or solid-phase extraction (SPE) followed by LC-MS/MS. A considerably expanded detection window for stanozolol abuse was demonstrated compared to the use of conventional phase-I metabolites and methodologies based on, for example, low resolution LC-MS/MS or gas chromatography-tandem mass spectrometry (GC-MS/MS). The commercial availability of 3'-OH-stanozolol glucuronide has been of great value for confirmatory purposes, and 17-epistanozolol-N-glucuronide was found to be a favourable long-term metabolite for doping controls as it was observed up to 28days post-administration of the drug. Applying the established methodology over a period of six months to 659 routine sports drug testing samples, a total of 85 adverse analytical findings was uncovered, 72 of which would have remained undetected using earlier employed GC-MS/MS approaches. Copyright (c) 2013 John Wiley & Sons, Ltd.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Schaenzer, Wilhelm UNSPECIFIED UNSPECIFIED UNSPECIFIED Guddat, Sven UNSPECIFIED UNSPECIFIED UNSPECIFIED Thomas, Andreas UNSPECIFIED orcid.org/0000-0003-1199-0743 UNSPECIFIED Opfermann, Georg UNSPECIFIED UNSPECIFIED UNSPECIFIED Geyer, Hans UNSPECIFIED UNSPECIFIED UNSPECIFIED Thevis, Mario UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-472304
DOI:	10.1002/dta.1516
Journal or Publication Title:	Drug Test. Anal.
Volume:	5
Number:	11-12
Page Range:	S. 810 - 819
Date:	2013
Publisher:	WILEY-BLACKWELL
Place of Publication:	HOBOKEN
ISSN:	1942-7611
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ELECTRON-IMPACT FRAGMENTATION; ANABOLIC-STEROID METABOLITES; HUMAN URINE; DOPING CONTROL; SCREENING METHOD; ION-TRAP; LIQUID; IDENTIFICATION; IONIZATION; METANDIENONE Multiple languages Biochemical Research Methods; Chemistry, Analytical; Pharmacology & Pharmacy Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/47230