Publisher Summary This chapter discusses receptor-proteins for androgens and the mode of action of androgens on gene transcription in ventral prostate. The primary molecular processes by which hormones elicit their remarkable effects are still unclear. Historically, the study of the mechanism of action of hormones has followed very closely the advance in knowledge of the basic molecular processes operating in living organisms. It is quite natural that one of the most widely used approaches has been to study the effect of hormones on isolated enzymes. With few exceptions, the results have been rather disappointing. Generally, the effects were observable only under conditions unlikely to be physiological, or they could not be correlated with in vivo situations. In the search for the trigger mechanisms of hormones, one generally relies on the trial addition of hormones to an in vitro system believed to be the earliest event in a sequence of hormone effects in vivo. However, the in vivo time sequences for visible hormone effects may depend more on the relative time required to magnify each of the sequential events than on the true order in the initial chain of processes.

Receptor-proteims for androgens and the mode of action of androgens on gene transcription in ventral prostate.

Norbolethone (13-ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-3-one) is a 19-nor anabolic steroid first synthesized in 1966. During the 1960s it was administered to humans in efficacy studies concerned with short stature and underweight conditions. It has never been reported by doping control laboratories. Norbolethone was identified in two urine samples from one athlete by matching the mass spectra and chromatographic retention times with those of a reference standard. The samples also contained at least one likely metabolite. The samples were also unusual because the concentrations of endogenous steroids were exceptionally low. Since norbolethone is not known to be marketed by any pharmaceutical company, a clandestine source of norbolethone may exist. Copyright © 2002 John Wiley & Sons, Ltd.

Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine

Metabolism and excretion of anabolic steroids in doping control—New steroids and new insights

Colloquially referred to by various misleading monikers ('pro-hormones', 'natural steroids', 'testosterone boosters', etc.) designer anabolic steroids have been popular now for over a decade as a way to achieve classic anabolic steroid-like results from products sold in the legal marketplace. Recent evidence suggests that anabolic steroid use may be the most common cause of hypogonadism in men of reproductive age. Despite recent regulatory efforts that have banned specific compounds, many anabolic-androgenic steroids (AAS) remain available in over-the-counter dietary supplements that are legally sold in the United States. Severe side effects including hepatotoxicity, cholestasis, renal failure, hypogonadism, gynecomastia, and infertility have been reported secondary to the use of these products. While some of these side effects may be reversible, more aggressive use may result in more permanent end-organ damage as has been previously described for the case of aggressive AAS users (Rahnema et al., Fertil Steril, 2014). Designer AAS remain easily available for purchase in over-the-counter bodybuilding supplements and these products appear to be increasingly popular, despite the known health risks associated with their use. We conducted a systematic search to identify the designer steroids that are most commonly sold in dietary supplements as of April 2014 and review what is known regarding their potency and toxicity. We propose that the impact of AAS use on the reproductive and hormonal health of men is underestimated in the literature owing to previous studies' failure to account for designer steroid use. Lastly, we make clinical recommendations to help physicians steer patients away from potentially harmful supplements, and summarize key regulatory obstacles that have allowed potent androgens to remain unregulated in the legal marketplace.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/andr.307

Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem.

Transition metal-catalyzed intramolecular [4 + 2] cycloadditions: Mechanistic and synthetic investigations

Es wird uber die Totalsynthese von verschiedenen Derivaten des (±)-6-Oxa- und Aza-Ostrons und die Umwandlung von (±)-17β-Oxy-3-methoxy-6-oxa-ostratrien-1, 3, 510 zu Verbindungen der (±)-19-Nor-6-oxa-testosteron-Klasse berichtet. Die biologische Wirksamkeit der Glieder in der 6-Oxa-Reihe wird beschrieben.

Total synthesis of derivatives of (±)-6-oxa and aza-estrone

Totally synthetic steroid hormones. VII. Some (+ or-)-8-alpha-estrane and (+ or -)-13-beta-alkyl-8-alpha-gonane derivatives.

The interesting steroid hormonal activity reported for a number of 7-alpha-methyltestosterone and 7-alpha-methyl-19-nortestosterone derivatives induced investigators to extend their studies on the structure-biological activity relationships of 13-beta-ethyl- and higher alkylonane derivatives to various (plus or minus)-13-beta-ethyl-7-alpha-methylgon-4-en-3-ones. The synthesis of the ketones 2 are reported and their anabolic androgenic and progestational activities are compared with the same activities of the corresponding 7-demethyl homologs.

Totally synthetic steroid hormones. X. Some (plus or minus)-13beta-ethyl-7alpha-methylgonane derivatives.

Totally synthetic steroid hormones—VI : (±)-6α- and β-methylestra-1,3,5(10)-trienes, (±)-13β-ethyl-6β-methylgona-1,3,5(10)-trienes, and related compounds

C. R. Walk

Papers

Total synthesis of derivatives of (±)-6-oxa and aza-estrone

Totally synthetic steroid hormones. VII. Some (+ or-)-8-alpha-estrane and (+ or -)-13-beta-alkyl-8-alpha-gonane derivatives.

Totally synthetic steroid hormones. X. Some (plus or minus)-13beta-ethyl-7alpha-methylgonane derivatives.

Totally synthetic steroid hormones—VI : (±)-6α- and β-methylestra-1,3,5(10)-trienes, (±)-13β-ethyl-6β-methylgona-1,3,5(10)-trienes, and related compounds

Totally synthetic steroid hormones. V. (+ -)-2,3-Dimethoxyestra-1,3,5(10)-trien-17-beta-ol and some congeners.