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.

Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites

The selective functionalization of remote C–H bonds via intramolecular hydrogen atom transfer (HAT) is transformative for organic synthesis This radical-mediated strategy provides access to novel reactivity that is complementary to closed-shell pathways As modern methods for mild generation of radicals are continually developed, inherent selectivity paradigms of HAT mechanisms offer unparalleled opportunities for developing new strategies for C–H functionalization This review outlines the history, recent advances, and mechanistic underpinnings of intramolecular HAT as a guide to addressing ongoing challenges in this arena 1 	Introduction 2 	Nitrogen-Centered Radicals 21 	sp 3 N-Radical Initiation 22 	sp 2 N-Radical Initiation 3 	Oxygen-Centered Radicals 31 	Carbonyl Diradical Initiation 32 	Alkoxy Radical Initiation 33 	Non-alkoxy Radical Initiation 4 	Carbon-Centered Radicals 41 	sp 2 C-Radical Initiation 42 	sp 3 C-Radical Initiation 5 	Conclusion

Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Considerable problems attend the synthesis of biologically important natural products whose carbohydrate components display a greater or lesser degree of complexity. The present progress report surveys recent developments in the formation of O-glycosidic bonds starting from 1-halo sugars and from sugar 1,2-orthoesters. Particular emphasis is placed on attempts to reach a better understanding of the steric course of glycosylation reactions on the basis of mechanistic considerations. Studies on the silver-salt dependence of the Koenigs-Knorr synthesis led to improvements in preparative applications and to new concepts concerning the reaction course. The introduction of sugar 1,2-orthoesters as glycosylation components has greatly enriched our preparative armoury for the synthesis of trans glycosides. Remarkable progress has also been made in the synthesis of cis glycosides, in part by exploiting novel neighbouring group effects.

Results and Problems of O-Glycoside Synthesis

1
The purification of a tyrosinase from cell-free extracts of Streptomyces glaucescens is described. The enzyme obtained is homogeneous according to the criteria of ultracentrifuge analysis and polyacrylamide gel electrophoresis.

2
An average molecular weight of 29100 was determined by dodecylsulfate-gel electrophoresis and by sedimentation equilibrium analysis in the ultracentrifuge. The amino acid composition of the pure enzyme is also reported.

3
The enzyme contains one atom of copper in the cuprous form per molecule and is strongly inhibited by KCN and 4-nitro-catechol.

4
The enzyme shows optimal activity at pH 6.8; it has an isoelectric point at pH 6.95 and is most stable at pH 8.0.

5
Variations of Km values between pH 5.0 and 8.9 when l-tyrosine methylester and 3,4-di-hydroxy-l-phenylalanine were used as substrate was interpreted by assuming that different ionizable groups are involved in the oxidation of these two substrates.

6
The Michaelis-Menten constants and KCat are strongly dependent on the oxygen concentration for 3,4-dihydroxy-l-phenylalanine and almost independent for l-tyrosine methyl ester. Kinetic parameters obtained for a series of mono- and o-diphenol substrates are also reported.

https://febs.onlinelibrary.wiley.com/doi/pdf/10.1111/j.1432-1033.1972.tb02549.x

Purification and Characterization of a Tyrosinase from Streptomyces glaucescens

It has been shown that the compounds, the formation of which by incubation of cortisone and 17α-hydroxy-cortexone with molds of the genus Fusarium was mentioned in an earlier paper, are the corresponding 1-dehydro compounds.

Mikrobiologische Herstellung von 1‐Dehydro‐Steroiden. Mikrobiologische Reaktionen, 6. Mitteilung

The partial synthesis of aldosterone from readily available steroidal starting materials is described.

Partialsynthese von Aldosteron. Über Steroide, 177. Mitteilung

Some fungi, especially strains of the genus Trichothecium were found to be able of introducing a hydroxy group into the 17 α-position of the steroid molecule. By means of this microbiological process, cortexone was converted into 17 α-hydroxy-cortexone (Reichstein's substance S), 11-dehydro-corticosterone into cortisone, and finally corticosterone into 17 α-hydroxy-corticosterone (hydrocortisone) and cortisone.

Mikrobiologische Hydroxylierung von Steroiden in der 17α‐ und 21‐Stellung. Mikrobiologische Reaktionen, 4. Mitteilung

Reaktionen von Steroid-Hypojoditen VIII 1,4-Verschiebung der Nitrilgruppe (18-Cyano-pregnane) Über Steroide, 206. Mitteilung†‡§

Under the conditions of the ‘hypoiodite reaction’, i.e. with iodine and lead tetraacetate, mercuric acetate, silver acetate or N-iodosuccinimide, 6β-hydroxy steroids are transformed into 6β, 19-ethers in high yield.

Ch. Meystre

Papers

Mikrobiologische Herstellung von 1‐Dehydro‐Steroiden. Mikrobiologische Reaktionen, 6. Mitteilung

Partialsynthese von Aldosteron. Über Steroide, 177. Mitteilung

Mikrobiologische Hydroxylierung von Steroiden in der 17α‐ und 21‐Stellung. Mikrobiologische Reaktionen, 4. Mitteilung

Reaktionen von Steroid-Hypojoditen VIII 1,4-Verschiebung der Nitrilgruppe (18-Cyano-pregnane) Über Steroide, 206. Mitteilung†‡§

Reaktionen von Steroid‐Hypojoditen III. Sterische Effekte bei 6β‐Hydroxysteroiden Über Steroide, 191. Mitt.