A comparative study of the metabolic fate of testosterone, 17α-methyl-testosterone, 19-nor-testos-terone, 7α-methyl-19-nor-testosterone and 17α-methyl-estr-5(10)-ene-17β-ol-3-one in normal males

Dimick, Dean F.; M, Heron; Baulieu, Étienne-Émile; Jayle, M F

doi:10.1016/0009-8981(61)90037-7

Cited by 40 publications

(17 citation statements)

References 18 publications

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“…2 and 3). Indeed, the ratio for 5a/5b urinary metabolites of norsteroids is similar to that reported for androgens and very close to 1 for endogenous androgens (Mauvais-Jarvis and Bercovici 1968; Mauvais-Jarvis et al 1969a, 1969bDonike et al 1989Donike et al , 1993, but also for 19-NT (Dimick et al 1961). Intake of xenobiotic steroids by different routes of administration affects the metabolism of these substances (MauvaisJarvis et al 1969a) and changes the ratio for the recovered 5a/5b urinary metabolites since 5b reductase is an important feature of liver metabolism, whereas 5a reductase is an important feature of androgen metabolism in target organs such as the skin (Mauvais Jarvis et al 1969b).…”

Section: Research Evolution In the Detection Of Nandrolone And Norstesupporting

confidence: 71%

“…However, one has to remember that anabolic and androgenic effects cannot be separated since both are obtained through the unique nuclear androgen receptor (Bergink et al 1985;Wilson 1988). Recovery in urine of labelled norsteroid metabolites (Dimick et al 1961) such as 19-NA (5a hydroxylated) or 19-NE (5b hydroxylated) which arise indifferently from either 19-NT or 19-ND 4 (and any 19-norandrogen precursor) was also reported in humans (Figs. 2 and 3).…”

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 80%

“…Norsteroids were thus reported to be produced in small quantities by testis, prostate, adipose tissue, bone marrow, placenta and ovarian follicles in animals and humans (Dimick et al 1961;Farnsworth 1966;Frisch et al 1980;Frost et al 1980;Osawa and Yarborough 1983;Segaloff 1963, Short 1961, 1964. Segaloff (1963) even proposed a daring hypothesis on the role of 19-NT, stating that due to its very small production rate this could be the active substance in androgen target cells.…”

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 96%

“…The only difference between the two metabolic pathways (Figs. 2, 3) resides in their metabolic clearance rates (MCRs), since norsteroids are not bound to the specific testosterone and estradiol plasma binding globulin (TeBg or SBP) and are therefore excreted more rapidly (Bergink et al 1985;Dimick et al 1961;MauvaisJarvis 1984). A recent paper by Reznick et al (1999) has reported the presence of small quantities of 19-NA in the urine of ten male subjects (calculated rate of production for 19-NA: 3.17±0.35 ng h )1 ) and of 19-NE in five out of the ten male subjects studied (calculated rate of production for 19-NE: 0.8-4.7 ng h )1 ).…”

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 99%

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Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Bricout

Wright

2004

European Journal of Applied Physiology

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Norsteroids are xenobiotics with androgenic and anabolic properties known since as far back as the 1930s. In doping controls, the use of the banned xenobiotic norsteroids is detected in the competitor's urines by the measurement of norandrosterone (19-NA) and noretiocholanolone (19-NE), which are the main metabolites for nandrolone (NT) and most norsteroids with anabolic properties. In 1996, the IOC subcommission "Doping and Biochemistry of Sport" informed the Heads of the "IOC Accredited Laboratories" that the recommended cut-off limit for reporting an offence was to be 1-2 ng ml(-1) urine for either 19-NA or 19-NE. We will discuss how technical progress in gas chromatography coupled to high-resolution mass spectrometry permitted a dramatic increase in sensitivity with a detection limit of 1 pg ml(-1) urine, or less, and an assay limit of 20-50 pg ml(-1) urine, for either 19-NA or 19-NE. As a paradox, norsteroids have been known for decades as not only xenobiotics but also obligatory endogenous intermediates in the biosynthesis of estrogens from androgens in all species, man included. It is this biochemical observation which fed the active scientific and medical controversy initiated in 1998 over the possibly endogenous production of nandrolone and metabolites well over the new IOC's recommended cut-off limit of 2 ng ml(-1) urine. Notwithstanding the particular technical difficulties attached, we will provide data and discuss the minute endogenous levels detected and measured in man either at rest, after performance or training and compare them to the relatively high levels reported in male athlete's doping controls today. We will also discuss data on the pharmacological effects of some contraceptive therapies containing norsteroids in women. In view of the well-documented noxious effects repeatedly observed after anabolic steroid misuse, the confirmation and implementation of technically proven procedures for reporting norsteroid abuse in sports seems an important enough goal to protect athlete's health against such abuses and justifies up dating the review of the patent scientific and medical experience and knowledge gained over the last 50 years on nandrolone and its minor production in man and woman.

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Section: Research Evolution In the Detection Of Nandrolone And Norstesupporting

confidence: 71%

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 80%

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 96%

Section: Research Evolution In the Detection Of Nandrolone And Norstementioning

confidence: 99%

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Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Bricout

Wright

2004

European Journal of Applied Physiology

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“…Correlations of SHBG with overall adiposity (BMI), body fat distribution (waist-to-hip ratio (WHR) Unlike the effect of anabolic steroids [1,2], the effect of testosterone has not led to changes in insulin sensitivity [14], The differences in the effects of anabolic steroids and testosterone may be partially due to differences in the route of administration, since anabolic steroids arc usual ly given orally while testosterone is usually administered by intramuscular injection. Testosterone readily aroma tizes to 17(3-estradiol while oral androgens do not form potent estrogens [ 15]. In the Rancho Bernardo Study, Barrett-Connor and Laakso [ 16] have shown that estrogen use is associated with lower insulin concentrations in post menopausal women.…”

mentioning

confidence: 99%

Sex Hormone-Binding Protein, Hyperinsulinemia, Insulin Resistance and Noninsulin-Dependent Diabetes

Haffner¹

1996

Horm Res

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Possible data implicating sex hormones, especially testosterone, in the etiology of cardiovascular disease and noninsulin-dependent diabetes mellitus (NIDDM) comes from the much higher rates of cardiovascular disease in men than in women. Pharmacological administration of anabolic steroids to both men and women increases both glucose and insulin concentrations and also insulin resistance. In vivo assessment of sex hormones and binding proteins in both premenopausal and postmenopausal women has suggested that increased free testosterone and decreased sex hormone-binding globulin (SHBG) is associated with higher glucose and insulin concentrations. In a few studies, increased insulin resistance has been associated with decreased SHBG levels. Some data suggests that visceral fat mediated the associations of sex hormones with insulin in women. Little prospective data is available on the association of sex hormones to the development of NIDDM in women but in two studies, low SHBG concentrations predicted NIDDM in Gothenburg and San Antonio. Recently, attention has focused on the role of sex hormones in relation to insulin in men. Surprisingly, higher levels of testosterone have been associated with improved cardiovascular risk factors (such as high-density lipoprotein cholesterol) and lower glucose and insulin levels. Total testosterone and SHBG have been associated with defects in nonoxidative glucose disposal and upper body adiposity in normoglycemic Finnish men. The latter observation is of interest since specific defects in nonoxidative glucose disposal are observed in normoglycemic relatives of subjects with NIDDM. The temporal relationship between sex hormones and insulin has been controversial. The traditional view of sex hormones increasing insulin resistance has been challenged in women by studies showing that insulin stimulates androgen production in the ovary. Recent data [JCEM 1995;80:654-658] suggests that insulin stimulates testosterone production and suppresses SHBG production in normal and obese men. On the other hand, administration of testosterone to centrally obese hypogonadal middle-aged men has improved insulin sensitivity [Int J Obes 1992;16:991-997].

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

Massé

Laliberté

Tremblay

et al. 1985

Biol. Mass Spectrom.

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A sensitive and highly specific method based on capillary column gas chromatography/mass spectrometry has been developed for the detection of 19-nortestosterone (17 beta-hydroxy-4-estren-3-one) metabolites in urine. After intramuscular administration of 19-nortestosterone decanoate to man, urine samples were collected during several days and treated with Helix pomatia digestive juice. The free steroids were extracted and converted into O-methyl-oxime-trimethylsilyl or the trimethylsilyl ether derivatives and analysed by capillary column gas chromatography/mass spectrometry (GC/MS). Three isomeric metabolites were detected and identified as 3 alpha-hydroxy-5 alpha-extran-17-one (19-norandrosterone), 3 alpha-hydroxy-5 beta-estran-17-one (19-noretiocholanolone) and 3 beta-hydroxy-5 alpha-estran-17-one (19-norepiandrosterone). Packed column GC/MS was also employed in the selected ion monitoring mode for the specific detection of 19-norandrosterone, the most abundant urinary metabolite of 19-nortestosterone. These gas chromatographic/mass spectrometric methods are highly specific tests which can be used on a routine basis for the confirmation of 19-nortestosterone administration to athletes as well as for therapeutic monitoring following administration of the drug.

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A comparative study of the metabolic fate of testosterone, 17α-methyl-testosterone, 19-nor-testos-terone, 7α-methyl-19-nor-testosterone and 17α-methyl-estr-5(10)-ene-17β-ol-3-one in normal males

Cited by 40 publications

References 18 publications

Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Sex Hormone-Binding Protein, Hyperinsulinemia, Insulin Resistance and Noninsulin-Dependent Diabetes

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

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