Metabolism of stanozolol: Chemical synthesis and identification of a major canine urinary metabolite by liquid chromatography–electrospray ionisation ion trap mass spectrometry

Stewart, Rhiannon; McKinney, Andrew R.; Kerwick, Carmel M; Young, Eun; Vadasz, Andrew; Cade, Ian A.; Willis, Anthony C.; McLeod, Malcolm D.

doi:10.1016/j.jsbmb.2009.09.002

Cited by 11 publications

(16 citation statements)

References 23 publications

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“…This shows one distinct peak for stanozolol glucuronide, two peaks for mono‐hydroxylated stanozolol glucuronide, and four peaks for di‐hydroxylated metabolites. Without suitable reference standards it is not possible to positively identify the stereochemistry of the detected metabolites, but the presence of multiple mono‐ and di‐hydroxylated metabolites is entirely consistent with previous work on the excretion of stanozolol in canine and equine urine …”

Section: Resultssupporting

confidence: 84%

“…The selection of appropriate analytes for inclusion in the method was based upon a number of factors, primarily the experience available within the laboratory, gained from many years of analyzing race‐day canine urine samples [unpublished], along with reference to published work on the metabolism of anabolic steroids in the canine . As per the work presented by Mckinney et al three compounds were included for the detection of boldenone.…”

Section: Resultsmentioning

confidence: 99%

“…For the detection of nandrolone, two glucuronide conjugated metabolites were selected for inclusion in the method, being 19‐norepiandrosterone glucuronide and 19‐noreticholanolone glucuronide . Detection of stanozolol was achieved via the monitoring of three analytes, glucuronidated stanozolol itself and mono‐ and di‐hydroxylated stanozolol conjugates …”

Section: Resultsmentioning

confidence: 99%

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Investigations into the analysis of intact drug conjugates in animal sport doping control – Development and assessment of a rapid and economical approach for screening greyhound urine

Gray

Tuckley²,

Cutler³

et al. 2020

Drug Testing and Analysis

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Animal sport doping control laboratories are constantly reviewing ways in which they can improve their service offering whilst ensuring that they remain economically viable. This paper describes the development and assessment of a rapid and economical method for the detection of intact glucuronide conjugates of three anabolic steroids and their metabolites along with three corticosteroids in canine urine. The analysis of intact drug conjugates for animal sport doping control is generally not performed routinely as it presents a number of analytical challenges, not least of which is the lack of availability of appropriate reference standards. Here, we report the development of a UHPLC–MS/MS method using APCI in the negative ion mode for the detection of intact phase II conjugates, including the importance of in vitro incubations in order to provide appropriate reference materials. Cross‐validation of the developed method demonstrated that the detection capability of the intact phase II conjugates of stanozolol, boldenone, nandrolone, and their metabolites along with the corticosteroids dexamethasone and methylprednisolone was equivalent to that achieved in routine race‐day screens. The new process has been in operation for approximately 2 years and has been used to analyze in excess of 13500 canine urine samples, resulting in a number of positive screening findings. To the best of our knowledge, this is the first reported use of a routine screen for intact drug conjugates within animal sport doping control.

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Section: Resultssupporting

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Investigations into the analysis of intact drug conjugates in animal sport doping control – Development and assessment of a rapid and economical approach for screening greyhound urine

Gray

Tuckley²,

Cutler³

et al. 2020

Drug Testing and Analysis

View full text Add to dashboard Cite

show abstract

“…During each investigation, useful forensic markers were unambiguously identified and, where otherwise unavailable, synthesized and characterized. Stanozolol is the subject of a separate publication [10]. The remaining data is presented herein.…”

Section: Introductionmentioning

confidence: 99%

The Metabolism of Anabolic-Androgenic Steroids in The Greyhound

et al. 2013

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“…AAS is a class of synthetic substances normally derived from testosterone, which is an endogenous androgen and protein anabolic hormone . Because of this, AAS is an important class of performance‐enhancing drugs with the potential for misuse in sports . Stanozolol is an exogenous anabolic steroid designed from testosterone, and like sibutramine, it is prohibited by WADA .…”

Section: Introductionmentioning

confidence: 99%

Is zebrafish (Danio rerio) a tool for human‐like metabolism study?

Anselmo

Sardela

Matias

et al. 2017

Drug Testing and Analysis

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One of the greatest challenges in anti-doping science is the large number of substances available and the difficulty in finding the best analytical targets to detect their misuse. Therefore, metabolism studies involving prohibited substances are fundamental. However, metabolism studies in humans could face an important ethical bottleneck, especially for non-approved substances. An emerging model for metabolism assessment is the zebrafish, due to its genetic similarities with humans. In the present study, the ability of adult zebrafish to produce metabolites of sibutramine and stanozolol, substances with a well-known metabolism that are widely used as doping agents in sports, was evaluated. They represent 2 of the most abused classes of doping agents, namely, stimulants and anabolic steroids. These are classes that have been receiving attention because of the upsurge of synthetic analogues, for which the side effects in humans have not been assessed. The samples collected from the zebrafish tank water were hydrolysed, extracted by solid-phase extraction, and analysed by liquid chromatography with high resolution mass spectrometry (LC-HRMS). Adult zebrafish could produce several sibutramine and stanozolol metabolites, including demethylated, hydroxylated, dehydroxylated, and reduced derivatives, all of which have already been detected in human urine. This study demonstrates that adult zebrafish can absorb, oxidise, and excrete several metabolites in a manner similar to humans. Therefore, adult zebrafish seem to be a very promising tool to study human-like metabolism when aiming to find analytical targets for doping control.

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Metabolism of stanozolol: Chemical synthesis and identification of a major canine urinary metabolite by liquid chromatography–electrospray ionisation ion trap mass spectrometry

Cited by 11 publications

References 23 publications

Investigations into the analysis of intact drug conjugates in animal sport doping control – Development and assessment of a rapid and economical approach for screening greyhound urine

Investigations into the analysis of intact drug conjugates in animal sport doping control – Development and assessment of a rapid and economical approach for screening greyhound urine

The Metabolism of Anabolic-Androgenic Steroids in The Greyhound

Is zebrafish (Danio rerio) a tool for human‐like metabolism study?

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