Gas chromatographic/mass spectrometric analysis of 19-nortestosterone urinary metabolites in man

Massé, Robert; Laliberté, Claude; Tremblay, Lyne; Dugal, Robert

doi:10.1002/bms.1200120305

Cited by 47 publications

(19 citation statements)

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“…The major metabolites of nandrolone are 3a-hydroxy5a-estran-17-one (19-norandrosterone), 3a-hydroxy5b-estran-17-one (19-noretiocholanolone) and 3b-hydroxy-5a-estran-17-one (19-norepiandrosterone), but with no 3b-hydroxy-5b-estran-17-one (19-norepietiocholanolone) being observed. 92 For con¢rma-tory analysis of positive samples, following hydrolysis of steroid glucuronides, the abundance of 19-norandrosterone was usually found to be greater than that of 19-noretiocholanolone. Relative to these two metabolites, 19-norepiandrosterone glucuronide is present in smaller amounts, although there is some evidence to suggest that larger quantities may be present as the sulphate conjugate.…”

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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Section: Metabolism Of Nandrolonementioning

confidence: 99%

Anabolic steroids in sport: biochemical, clinical and analytical perspectives

2003

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“…La nandrolone (19- 19-norandrostérone (3 a-hydroxy-5a-estran-17-one, NA) et la 19-norétiocholanolone (3a -hydroxy-56-estran-17-one, NE) ont été mises en évidence dans les urines ( Figure 1) (4), excrétés sous forme de glucuronides (5,6). D'autres metabolites sont également produits, tels que la 19-norépiandrostérone.…”

Section: Resumeunclassified

Détermination des concentrations physiologiques de la norandrostérone et de la norétiocholanolone, métabolites urinaires de la nandrolone par CPG/SM. Résultats d'une étude multicentrique

et al. 2000

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“…Because of its anabolic properties, nandrolone is used among athletes as a doping agent to accelerate muscle growth; to increase lean body mass, strength and aggressiveness [3]. Detection of nandrolone according to the protocols set down by the World Anti-Doping Agency (WADA) are based on the identification of 19-norandrosterone (19-NA; 3␣-hydroxy-5␣-androstan-17-one) and 19-noretiocholanolone (19-NE; 3␣-hydroxy-5␤-androstan-17-one) which are usually the two principal urinary metabolites [4,5]. An adverse analytical finding is reported when the total of free 19-NA and its glucuronide expressed as mass concentration of 19-NA in urine is greater than the threshold of 2 ng/mL established by WADA [6].…”

Section: Introductionmentioning

confidence: 99%