Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control
Stanozolol (STAN) is one of the most frequently detected anabolic androgenic steroids in sports drug testing. STAN misuse is commonly detected by monitoring metabolites excreted conjugated with glucuronic acid after enzymatic hydrolysis or using direct detection by liquid chromatography-tandem mass...
| Autores: | , , |
|---|---|
| Formato: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2017 |
| País: | España |
| Recursos: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:10230/33551 |
| Acesso em linha: | http://hdl.handle.net/10230/33551 http://dx.doi.org/10.1002/dta.2107 |
| Access Level: | acceso abierto |
| Palavra-chave: | Dopatge en els esports Anabolitzants Hormones esteroides LC-MS/MS Stanozolol Anabolic steroids Doping analysis Sulfate metabolites |
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Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping controlBalcells Aribau, Georgina, 1987-Matabosch Geronès, XavierVentura Alemany, RosaDopatge en els esportsAnabolitzantsHormones esteroidesLC-MS/MSStanozololAnabolic steroidsDoping analysisSulfate metabolitesStanozolol (STAN) is one of the most frequently detected anabolic androgenic steroids in sports drug testing. STAN misuse is commonly detected by monitoring metabolites excreted conjugated with glucuronic acid after enzymatic hydrolysis or using direct detection by liquid chromatography-tandem mass spectrometry (LC-MS/MS). It is well known that some of the previously described metabolites are the result of the formation of sulfate conjugates in C17, which are converted to their 17-epimers in urine. Therefore, sulfation is an important phase II metabolic pathway of STAN that has not been comprehensively studied. The aim of this work was to evaluate the sulfate fraction of STAN metabolism by LC-MS/MS to establish potential long-term metabolites valuable for doping control purposes. STAN was administered to six healthy male volunteers involving oral or intramuscular administration and urine samples were collected up to 31 days after administration. Sulfation of the phase I metabolites commercially available as standards was performed in order to obtain MS data useful to develop analytical strategies (neutral loss scan, precursor ion scan and selected reaction monitoring acquisitions modes) to detect potential sulfate metabolites. Eleven sulfate metabolites (M-I to M-XI) were detected and characterized by LC-MS/MS. This paper provides valuable data on the ionization and fragmentation of O-sulfates and N-sulfates. For STAN, results showed that sulfates do not improve the retrospectivity of the detection compared to the previously described long-term metabolite (epistanozolol-N-glucuronide). However, sulfate metabolites could be additional markers for the detection of STAN misuse.The financial support received from the World Anti-Doping AgencyWADA (12A21RV), Ministerio de Economía y Competividad(Gob ierno de España) (Project number DEP2012-35612) andGeneralitat de Catalunya (Consell Català de l’Esport, DIUE 2014SGR 692) is gratefully acknowl edged.Wiley20172017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttp://hdl.handle.net/10230/33551http://dx.doi.org/10.1002/dta.2107reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésDrug Testing and Analysis. 2017 Jul;9(7):1001-10info:eu-repo/grantAgreement/ES/3PN/DEP2012-35612This is the peer reviewed version of the following article: Balcells G, Matabosch X, Ventura R. Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control. Drug Test Anal. 2017 Jul;9(7):1001-1010, which has been published in final form at http://dx.doi.org/10.1002/dta.2107. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.info:eu-repo/semantics/openAccessoai:recercat.cat:10230/335512026-05-29T05:05:01Z |
| dc.title.none.fl_str_mv |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| title |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| spellingShingle |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control Balcells Aribau, Georgina, 1987- Dopatge en els esports Anabolitzants Hormones esteroides LC-MS/MS Stanozolol Anabolic steroids Doping analysis Sulfate metabolites |
| title_short |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| title_full |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| title_fullStr |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| title_full_unstemmed |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| title_sort |
Detection of stanozolol O- and N-sulfate metabolites and their evaluation as additional markers in doping control |
| dc.creator.none.fl_str_mv |
Balcells Aribau, Georgina, 1987- Matabosch Geronès, Xavier Ventura Alemany, Rosa |
| author |
Balcells Aribau, Georgina, 1987- |
| author_facet |
Balcells Aribau, Georgina, 1987- Matabosch Geronès, Xavier Ventura Alemany, Rosa |
| author_role |
author |
| author2 |
Matabosch Geronès, Xavier Ventura Alemany, Rosa |
| author2_role |
author author |
| dc.subject.none.fl_str_mv |
Dopatge en els esports Anabolitzants Hormones esteroides LC-MS/MS Stanozolol Anabolic steroids Doping analysis Sulfate metabolites |
| topic |
Dopatge en els esports Anabolitzants Hormones esteroides LC-MS/MS Stanozolol Anabolic steroids Doping analysis Sulfate metabolites |
| description |
Stanozolol (STAN) is one of the most frequently detected anabolic androgenic steroids in sports drug testing. STAN misuse is commonly detected by monitoring metabolites excreted conjugated with glucuronic acid after enzymatic hydrolysis or using direct detection by liquid chromatography-tandem mass spectrometry (LC-MS/MS). It is well known that some of the previously described metabolites are the result of the formation of sulfate conjugates in C17, which are converted to their 17-epimers in urine. Therefore, sulfation is an important phase II metabolic pathway of STAN that has not been comprehensively studied. The aim of this work was to evaluate the sulfate fraction of STAN metabolism by LC-MS/MS to establish potential long-term metabolites valuable for doping control purposes. STAN was administered to six healthy male volunteers involving oral or intramuscular administration and urine samples were collected up to 31 days after administration. Sulfation of the phase I metabolites commercially available as standards was performed in order to obtain MS data useful to develop analytical strategies (neutral loss scan, precursor ion scan and selected reaction monitoring acquisitions modes) to detect potential sulfate metabolites. Eleven sulfate metabolites (M-I to M-XI) were detected and characterized by LC-MS/MS. This paper provides valuable data on the ionization and fragmentation of O-sulfates and N-sulfates. For STAN, results showed that sulfates do not improve the retrospectivity of the detection compared to the previously described long-term metabolite (epistanozolol-N-glucuronide). However, sulfate metabolites could be additional markers for the detection of STAN misuse. |
| publishDate |
2017 |
| dc.date.none.fl_str_mv |
2017 2017 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion |
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article |
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acceptedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10230/33551 http://dx.doi.org/10.1002/dta.2107 |
| url |
http://hdl.handle.net/10230/33551 http://dx.doi.org/10.1002/dta.2107 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
Drug Testing and Analysis. 2017 Jul;9(7):1001-10 info:eu-repo/grantAgreement/ES/3PN/DEP2012-35612 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf application/pdf |
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Wiley |
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Wiley |
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reponame:Recercat. Dipósit de la Recerca de Catalunya instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
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Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
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Recercat. Dipósit de la Recerca de Catalunya |
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Recercat. Dipósit de la Recerca de Catalunya |
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