Gas chromatographic and capillary column gas chromatographic—mass spectrometric determination of synthetic anabolic steroids

Dürbeck, H. W.; Büker, I.; Scheulen, B.; Telin, B.

doi:10.1016/s0021-9673(00)91150-6

Cited by 47 publications

(9 citation statements)

References 14 publications

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“…C-6␤ hydroxylation is more pronounced for 17␣-methyl,17␤-hydroxyl steroids such as methandienone and oral turinabol, where the A-ring reduction is hampered by the presence of a C-1,2 double bond [30,33,34]. • M6 concerns hydroxylation at C-16 position (␣-or/and ␤-isomers).…”

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

confidence: 99%

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: 99%

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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“…Other major unconjugated metabolites subsequently identi¢ed were the 17a-hydroxy epimer of methandienone (17-epimethandienone) and the 6b-hydroxylated metabolite of epimethandienone. 84,86 In the conjugate fraction of urine, three major bishydroxylated metabolites (5b-H orientation) have been identi¢ed; 88 these steroids have a 3a-hydroxyl group which facilitates conjugation to glucuronic acid in the human. A fourth metabolite has a 1-ene-3-oxo con¢guration but has also been found in the conjugate fraction, 88 presumably because of formation of a 3-hydroxyl group by keto-enol tautomerism, which can then be conjugated with uridine diphosphoglucuronic acid.…”

Section: Metabolism Of Nandrolonementioning

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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“…[8] Based on the common ionization and collision-induced dissociation (CID) behaviour of steroid glucuronides, [16] a series of open detection methods based on neutral loss (NL) and precursor ion (PI) scan have been proposed to detect them by LC-MS/MS. [2,3,5,6,12,[18][19][20][21][22][23][24] The most important metabolites are glucuronoconjugates that have been studied using β-glucuronidase hydrolysis. [11,12,17] Metandienone (MTD) is one of the most frequently detected AAS, and its metabolism has been widely studied.…”

Section: Introductionmentioning

confidence: 99%

LC‐MS/MS detection of unaltered glucuronoconjugated metabolites of metandienone

Esquivel

Pozo

Garrostas

et al. 2016

Drug Testing and Analysis

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The aim of this study was to evaluate the direct detection of glucuronoconjugated metabolites of metandienone (MTD) and their detection times. Metabolites resistant to enzymatic hydrolysis were also evaluated. Based on the common mass spectrometric behaviour of steroid glucuronides, three liquid chromatography-tandem mass spectrometry (LC-MS/MS) strategies were applied for the detection of unpredicted and predicted metabolites: precursor ion scan (PI), neutral loss scan (NL), and theoretical selected reaction monitoring (SRM) methods. Samples from four excretion studies of MTD were analyzed for both the detection of metabolites and the establishment of their detection times. Using PI and NL methods, seven metabolites were observed in post-administration samples. SRM methods allowed for the detection of 13 glucuronide metabolites. The detection times, measured by analysis with an SRM method, were between 1 and 22 days. The metabolite detected for the longest time was 18-nor-17β-hydroxymethyl-17α-methyl-5β-androsta-1,4,13-triene-3-one-17-glucuronide. One metabolite was resistant to hydrolysis with β-glucuronidase; however it was only detected in urine up to four days after administration. The three glucuronide metabolites with the highest retrospectivity were identified by chemical synthesis or mass spectrometric data, and although they were previously reported, this is the first time that analytical data of the intact phase II metabolites are presented for some of them. The LC-MS/MS strategies applied have demonstrated to be useful for detecting glucuronoconjugated metabolites of MTD, including glucuronides resistant to enzymatic hydrolysis which cannot be detected by conventional approaches. Copyright © 2016 John Wiley & Sons, Ltd.

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Gas chromatographic and capillary column gas chromatographic—mass spectrometric determination of synthetic anabolic steroids

Cited by 47 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

LC‐MS/MS detection of unaltered glucuronoconjugated metabolites of metandienone

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