Metabolism of Steroids and Sport Drug Testing

Stojanović, Biljana; Göschl, Lorenz; Forsdahl, Guro; Gmeiner, Günter

doi:10.4155/bio-2020-0077

Cited by 9 publications

(10 citation statements)

References 11 publications

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“…Usually, AASs undergo two phases of enzyme-controlled metabolism to inactivate the drug and facilitate its elimination from the body via the bioconversion of AAS into more hydrophilic compounds. 1 Phase I reactions mainly include oxidation and reduction, making the compounds more suitable for subsequent phase II reactions. The most common phase II reactions are conjugations with sulfonic acid and glucuronic acid.…”

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confidence: 99%

“…1,5,6 Routine analyses of AAS metabolites often use indirect methods such as hydrolysis of phase II metabolites, followed by liquid−liquid extraction and derivatization reactions for increased volatility and thermal stability for gas chromatography−mass spectrometry (GC−MS)/MS detection. 1,7 Sensitivity challenges in atmospheric pressure ionization (API) methods have been extensively described for the aglycone counterparts of AASs. 8,9 Thus, the sensitivity required in drug testing is difficult to achieve.…”

mentioning

confidence: 99%

“…Exogenous anabolic-androgenic steroids (AASs) are performance enhancement drugs obtained by structural modifications of testosterone. AASs are the most reported prohibited substances in competitive sports. − Urine sampling is the matrix of choice for testing the presence of AAS because many steroid metabolites are eliminated through urine. AAS metabolites may exhibit a slow elimination rate in the urinary system, allowing drug testing laboratories to detect them over an extended period following exposure.…”

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confidence: 99%

“…Furthermore, urine is a noninvasive sample collection strategy. Usually, AASs undergo two phases of enzyme-controlled metabolism to inactivate the drug and facilitate its elimination from the body via the bioconversion of AAS into more hydrophilic compounds . Phase I reactions mainly include oxidation and reduction, making the compounds more suitable for subsequent phase II reactions.…”

mentioning

confidence: 99%

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Multidimensional Separations of Intact Phase II Steroid Metabolites Utilizing LC–Ion Mobility–HRMS

et al. 2021

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The detection and unambiguous identification of anabolic-androgenic steroid metabolites are essential in clinical, forensic, and antidoping analyses. Recently, sulfate phase II steroid metabolites have received increased attention in steroid metabolism and drug testing. In large part, this is because phase II steroid metabolites are excreted for an extended time, making them a potential long-term chemical marker of choice for tracking steroid misuse in sports. Comprehensive analytical methods, such as liquid chromatography–tandem mass spectrometry (LC–MS/MS), have been used to detect and identify glucuronide and sulfate steroids in human urine with high sensitivity and reliability. However, LC–MS/MS identification strategies can be hindered by the fact that phase II steroid metabolites generate nonselective ion fragments across the different metabolite markers, limiting the confidence in metabolite identifications that rely on exact mass measurement and MS/MS information. Additionally, liquid chromatography–high-resolution mass spectrometry (LC–HRMS) is sometimes insufficient at fully resolving the analyte peaks from the sample matrix (commonly urine) chemical noise, further complicating accurate identification efforts. Therefore, we developed a liquid chromatography–ion mobility–high resolution mass spectrometry (LC–IM–HRMS) method to increase the peak capacity and utilize the IM-derived collision cross section (CCS) values as an additional molecular descriptor for increased selectivity and to improve identifications of intact steroid analyses at low concentrations.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Multidimensional Separations of Intact Phase II Steroid Metabolites Utilizing LC–Ion Mobility–HRMS

et al. 2021

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“…And yet, AAS appear to remain popular amongst recreational athletes 44–46 and elite athletes as supported by WADA's annually published anti‐doping testing figures 47 . Consequently, much effort was invested also during the past 12 months into improving test methods concerning AAS (and anabolic agents in general), aiming at enhanced initial testing procedures (ITPs) as well as further insights into the drugs' metabolism that, consequently, allow for optimized selection of target analytes in routine sports drug testing programs 48 …”

Section: Anabolic Agentsmentioning

confidence: 99%

Annual banned‐substance review: Analytical approaches in human sports drug testing 2019/2020

Thevis

Kuuranne

Geyer

2020

Drug Testing and Analysis

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Analytical chemistry-based research in sports drug testing has been a dynamic endeavor for several decades, with technology-driven innovations continuously contributing to significant improvements in various regards including analytical sensitivity, comprehensiveness of target analytes, differentiation of natural/ endogenous substances from structurally identical but synthetically derived compounds, assessment of alternative matrices for doping control purposes, and so forth. The resulting breadth of tools being investigated and developed by anti-doping researchers has allowed to substantially improve anti-doping programs and data interpretation in general. Additionally, these outcomes have been an extremely valuable pledge for routine doping controls during the unprecedented global health crisis that severely affected established sports drug testing strategies. In this edition of the annual banned-substance review, literature on recent developments in antidoping published between October 2019 and September 2020 is summarized and discussed, particularly focusing on human doping controls and potential applications of new testing strategies to substances and methods of doping specified the World Anti-Doping Agency's 2020 Prohibited List.

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New long‐standing metabolites of 17α‐methyltestosterone are detected in HepG2 cell in vitro metabolic model and in human urine

Angelis,

Sakellariou,

Fragkaki

et al. 2023

Drug Testing and Analysis

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Novel metabolites of the anabolic androgenic steroid 17α‐methyltestosterone have been detected in HepG2 cell in vitro metabolic model and in human urine. Their detection was accomplished through targeted gas chromatography–(tandem) mass spectrometry analysis that has been based on microscale synthesized standards. The related synthesis and the gas chromatography–(tandem) mass spectrometry characterization of the analytical standards are described. All newly presented metabolites have a fully reduced steroid A‐ring with either an 17,17‐dimethyl‐18‐nor‐Δ13 structure or they have been further oxidized at position 16 of the steroid backbone. Metabolites with 17,17‐dimethyl‐18‐nor‐Δ13 structure may be considered as side products of phase II metabolic sulfation of the 17β‐hydroxy group of methyltestosterone or its reduced tetrahydro‐methyltestosterone metabolites 17α‐methyl‐5β‐androstane‐3α,17β‐diol and 17α‐methyl‐5α‐androstane‐3α,17β‐diol that produce the known epimeric 17β‐methyl‐5β‐androstane‐3α,17α‐diol and 17β‐methyl‐5α‐androstane‐3α,17α‐diol metabolites. The prospective of these new metabolites to increase detection time windows and improve identification was investigated by applying the World Anti‐doping Agency TD2021IDCR criteria. The new metabolites, presented herein, complement the current knowledge on the 17α‐methyltestosterone metabolism and in some cases can be used as additional long‐term markers in the frame of sport doping drug testing.

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Metabolism of Steroids and Sport Drug Testing

Cited by 9 publications

References 11 publications

Multidimensional Separations of Intact Phase II Steroid Metabolites Utilizing LC–Ion Mobility–HRMS

Multidimensional Separations of Intact Phase II Steroid Metabolites Utilizing LC–Ion Mobility–HRMS

Annual banned‐substance review: Analytical approaches in human sports drug testing 2019/2020

New long‐standing metabolites of 17α‐methyltestosterone are detected in HepG2 cell in vitro metabolic model and in human urine

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