Studies on anabolic steroids. VII Analysis of urinary metabolites of formebolone in man by gas chromatography—mass spectrometry

Massé, Robert; Bi, Honggang; Du, Ping

doi:10.1016/s0003-2670(00)83815-5

Cited by 25 publications

(20 citation statements)

References 14 publications

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“…Oxidation of the 2-formyl group to ␤-keto acid, reduction of the C-1,2 double bond and then decarboxylation leads to its metabolite; 11␣-hydroxymethyltestosterone. No metabolites from 3-keto group, epimerization at C-17 position or hydroxylation at other positions of the steroid were detected [35].…”

Section: Proposed Metabolism Scheme For Steroids With Androst-14-diementioning

confidence: 90%

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Fragkaki

Angelis

Tsantili‐Kakoulidou

et al. 2009

The Journal of Steroid Biochemistry and Molecular Biology

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Section: Proposed Metabolism Scheme For Steroids With Androst-14-diementioning

confidence: 90%

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Fragkaki

Angelis

Tsantili‐Kakoulidou

et al. 2009

The Journal of Steroid Biochemistry and Molecular Biology

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“…Hence, extraction e¤ciency is governed by the choice of pH of the aqueous phase 83 and chromatographic performance by the number of unwanted polar sites exposed on a GC column employing a non-polar liquid phase (e.g. methylsilicone).…”

Section: Metabolism Of Stanozololmentioning

confidence: 99%

“…9 As opposed to most anabolic steroids which have neutral properties (note: the phase II metabolites of AASs are analysed as aglycones), the pyrazole moiety confers the parent steroid and metabolites with polar properties. Hence, extraction e¤ciency is governed by the choice of pH of the aqueous phase 83 and chromatographic performance by the number of unwanted polar sites exposed on a GC column employing a non-polar liquid phase (e.g. methylsilicone).…”

Section: Metabolism Of Stanozololmentioning

confidence: 99%

Anabolic steroids in sport: biochemical, clinical and analytical perspectives

2003

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International Olympic Committee accredited laboratories play a key role in upholding the principle of fair play and innate ability, as desired by the majority of sports competitors and spectators. Not only does doping damage the image of sport, but it can also be harmful to the individual. The great majority of samples test negative but, when an adverse nding is declared, the analytical data must be of a suf ciently high standard to withstand legal challenges by third parties. The most widely misused performance-enhancing drugs are the anabolic-androgenic steroids, commonly referred to as 'anabolic steroids'. This review attempts to address the complex issues concerning anabolic steroids in sport by considering the clinical, biochemical and analytical perspectives. Fifty years of anabolic steroids and sport: an overviewThe discovery of a process for synthesizing the steroid testosterone (T) from cholesterol in 1935 1 greatly accelerated scienti¢c investigations into the e¡ects of this endogenous androgen. T rapidly became noted for its anabolic properties in increasing muscle size and strength and in its androgenic properties of increasing virilization and aggression. In a comprehensive review of the history of the use of anabolic steroids in sport, Todd 2 noted that, as early as 1945, the science writer Paul de Kreuf had speculated that`it would be interesting to watch the productive power of [a] . . . professional group [of athletes] that would try a systematic supercharge with testosterone . . .'.In the early 1950s, the ¢rst suspicion that T was actually being administered to improve sporting performance came with the allegation that Soviet weightlifters were administering T to gain strength. 2 Also, around that time, pharmaceutical companies were developing synthetic analogues of T with the aim of treating patients in a`catabolic state', the objective being to enhance the anabolic e¡ects of T and to dissociate the unwanted androgenic e¡ects (particularly to minimize the viriliz ing e¡ects). Nandrolone (19-nortestosterone) was the ¢rst synthetic analogue of T to show enough anabolic-androgenic dissociation in animal experiments 3 to justify its introduction as a therapeutic agent. 4 Subsequently, numerous analogues of T [and also its 5a-reduced metabolite, 5a-dihydrotestosterone (DHT)] were developed (see Fig. 1), such as methandienone (methandrostenolone), oxymesterone and stanozolol (for dates of patent awards see Ref. 5). With the growing availability of these licensed compounds, competitors began to experiment with them in an attempt to gain improvements in sporting performance without imparting the full androgenic e¡ects associated with T. During the 1960s, a number of deaths occurred in sports competitors from the use of stimulants and, as a result, in 1967 the International Olympic Committee (IOC) reestablished a medical commission (an IOC Medical Commission was rst established in Athens in 1961; see Ref. 6) which banned the practice of doping in sport, the banned classes including stimula...

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“…In addition to the enormous health risks, the use of the analyzed products can lead to positive doping results in sports, especially for metabolites of metandienone and stanozolol (Masse et al, 1989;Schänzer et al, 1990Schänzer et al, , 1991.…”

Section: Discussionmentioning

confidence: 99%

High amounts of 17‐methylated anabolic‐androgenic steroids in effervescent tablets on the dietary supplement market

Parr

Geyer

B³

et al. 2006

Biomedical Chromatography

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In numerous studies it has been demonstrated that several nutritional supplements contain prohormones not declared on the label. In the current study two products (effervescent tablets) containing high amounts of the 17-methylated anabolic androgenic steroids metandienone (product 1: 16.8 mg/tablet) and stanozolol (product 2: 14.5 mg/tablet) were identified. Additionally in both products norandrostenedione was detected, in product 2 with minor amounts of several other steroids. The substances identified can cause enormous health risks. In addition, the use of the analyzed tablets can lead to positive doping results for metabolites of the respective steroids in sports. This study again shows the insufficient surveillance of the production and trade of dietary supplements. Consumers should be aware of the enormous health and doping risks connected with the use of such products. For GC-MS identification of the analytes the trimethylsilyl derivatives of the steroids and the mixed N-t-butyldimethylsilyl,O-trimethylsilyl derivatives were used. The quantitation of metandienone, norandrostenedione, and stanozolol was performed using HPLC-DAD.

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Studies on anabolic steroids. VII Analysis of urinary metabolites of formebolone in man by gas chromatography—mass spectrometry

Cited by 25 publications

References 14 publications

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Anabolic steroids in sport: biochemical, clinical and analytical perspectives

High amounts of 17‐methylated anabolic‐androgenic steroids in effervescent tablets on the dietary supplement market

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