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A Review of the Chemistry, Biological Action, and Clinical Applications of Anabolic-Androgenic Steroids

Preface 1. The medical and cultural history of testosterone and the testes Eberhard Nieschlag and Susan Nieschlag 2. Testosterone: biosynthesis, transport, metabolism and (non-genomic) actions C. Marc Luetjens and Gerhard F. Weinbauer 3. Pathophysiology of the androgen receptor Olaf Hiort, R. Werner and Michael Zitzmann 4. Methodology for measuring testosterone, DHT and SHBG in a clinical setting Manuela Simoni, Flaminia Fanelli, Laura Roli and Uberto Pagotto 5. The behavioral correlates of testosterone John Bancroft 6. The role of testosterone in spermatogenesis Liza O'Donnell and Robert I. McLachlan 7. Androgens and hair: a biological paradox with clinical consequences Valerie Anne Randall 8. Testosterone and bone Dirk Vanderschueren, Mieke Sinnesael, E. Gielen, F. Claessens and S. Boonen 9. Androgens effects on the skeletal muscle Shalender Bhasin, Ravi Jasuja, Carlo Serra, Rajan Singh, Thomas W. Storer, Wen Guo, Thomas G. Travison and Shezad Basaria 10. Testosterone and cardiovascular disease Kevin S. Channer and T. Hugh Jones 11. Testosterone, obesity, diabetes and the metabolic syndrome T. Hugh Jones and Kevin S. Channer 12. Testosterone and erection Mario Maggi and Hermann M. Behre 13. Testosterone and the prostate John T. Isaacs and Samuel R. Denmeade 14. Clinical use of testosterone in hypogonadism and other conditions Eberhard Nieschlag and Hermann M. Behre 15. Testosterone preparations for clinical use in males Hermann M. Behre and Eberhard Nieschlag 16. Androgens in male senescence Jean-Marc Kaufman, Guy T'Sojen and Alex Verleulen 17. Androgen therapy in non-gonadal disease David J. Handelsman 18. Review of guidelines on diagnosis and treatment of testosterone deficiency Ronald S. Swerdloff and Christina C. L. Wang 19. Pathophysiology of estrogen action in men Vincenzo Rochira, Daniele Santi and Cesare Carani 20. Dehydroepiandrosterone (DHEA) and androstenedione Bruno Allolio, Wiebke Arlt and Stefanie Hahner 21. The state-of-the-art in the development of selective androgen receptor modulators (SARMs) Ravi Jasuja, M. Zacharov and Shalender Bhasin 22. The essential role of testosterone in hormonal male contraception Eberhard Nieschlag and Hermann M. Behre 23. Testosterone use in women Susan R. Davis 24. Detection of illegal use of androgens and SARMs Wilhelm Schanzer and Mario Thevis 25. Clinical effects of doping with anabolic steroids Elena Vorona and Eberhard Nieschlag Index.

Testosterone : action, deficiency, substitution

Anabolic androgenic steroids (AAS) are misused to a high extent in sports by athletes to improve their physical performance. Sports federations consider the use of these drugs in sports as doping. The misuse of AAS is controlled by detection of the parent AAS (when excreted into urine) and (or) their metabolites in urine of athletes. I present a review of the metabolism of AAS. Testosterone is the principal androgenic steroid and its metabolism is compared with that of AAS. The review is divided into two parts: the general metabolism of AAS, which is separated into phase I and phase II metabolism and includes a systematic discussion of metabolic changes in the steroid molecule according to the regions (A-D rings), and the specific metabolism of AAS, which presents the metabolism of 26 AAS in humans.

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Metabolism of anabolic androgenic steroids.

Interest in the development and therapeutic potential of nonsteroidal tissue-selective androgen receptor modulators (SARMs) has increased dramatically within the past decade. Rapidly expanding knowledge of nuclear hormone receptor structure and function and successful proof-of-principle clinical trials with SARMs have revived an almost dormant search for improved androgens. This Award Address attempts to chronicle the landmark discoveries (with emphasis on our work), organize the SARM landscape into clinically relevant bins, and provide insight into the clinical prospects for SARMs. 1.1. Origins of Androgen Use. An early (1889) and unusual experiment in androgen therapy was performed by Charles Edouard Brown-Sequard, age 72. He administered a testicular extract to himself and reported that he felt “increased vigor and capacity for work”. Despite retrospective suggestions that any effect was purely placebo, this report resulted in widespread use of testicular extracts throughout Europe and North America for several decades. Attempts to isolate the active components of testicular extract failed until 1935 when testosterone (17 hydroxy-4-andosten-3-one) was isolated from bull testes. Shortly thereafter, its synthesis was reported. In the same year, extracts of urine from males were shown to cause nitrogen retention, an indicator of anabolic metabolism. Testosterone was the first anabolic androgen to be used clinically, but its use is limited by its androgenicity and pharmacokinetic (PK) issues. 1 In the latter half of the 20th century, the chemical scaffold of testosterone was modified extensively, producing many

Nonsteroidal selective androgen receptor modulators (SARMs): dissociating the anabolic and androgenic activities of the androgen receptor for therapeutic benefit.

Owing to the sensitive, selective, and unambiguous nature of mass spectrometric analyses, chromatographic techniques interfaced to various kinds of mass spectrometers have become the most frequently employed strategy in the fight against doping. To obtain utmost confidence in analytical assays, mass spectrometric characterization of target analytes and typical dissociation pathways have been utilized as basis for the development of reliable and robust screening as well as confirmation procedures. Methods for qualitative and/or quantitative determinations of prohibited low and high molecular weight drugs have been established in doping control laboratories preferably employing gas or liquid chromatography combined with electron, chemical, or atmospheric pressure ionization followed by analyses using quadrupole, ion trap, linear ion trap, or hyphenated techniques. The versatility of modern mass spectrometers enable specific as well as comprehensive measurements allowing sports drug testing laboratories to determine the misuse of therapeutics such as anabolic-androgenic steroids, stimulants, masking agents or so-called designer drugs in athletes' blood or urine specimens, and a selection of recent developments is summarized in this review.

Mass spectrometry in sports drug testing: Structure characterization and analytical assays

Über Testosteron. Umwandlung des Dehydro-androsterons in Androstendiol und Testosteron; ein Weg zur Darstellung des Testosterons aus Cholesterin.

Über die Umwandlung des Dehydro‐androsterons in Δ4‐Androsten‐ol‐(17)‐0n‐(3) (Testosteron); ein Weg zur Darstellung des Testosterons aus Cholesterin (Vorläuf. Mitteil.)

Günter Hanisch

Papers

Über Testosteron. Umwandlung des Dehydro-androsterons in Androstendiol und Testosteron; ein Weg zur Darstellung des Testosterons aus Cholesterin.

Über die Umwandlung des Dehydro‐androsterons in Δ4‐Androsten‐ol‐(17)‐0n‐(3) (Testosteron); ein Weg zur Darstellung des Testosterons aus Cholesterin (Vorläuf. Mitteil.)

Über einige neue Vertreter der Androsteron-Gruppe

Über Dehydro-androsteron.