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Steroids Related to Testosterone

Oil-soluble derivatives of testosterone itself predate those of its 19-nor congener these agents too are used to administer depot injections so as to provide in effect long-term blood levels of drug. Thus, acylation of testosterone with propionyl chloride in the presence of pyridine yields testosterone propionate (76a)acylation by means of decanoic anhydride yields testosterone decanoate (76b).Finally, reaction of 75 with 3-cyclopentylpropionyl chloride affords testosterone cypionate (76c)This last undergoes hydrolysis unusually slowly because of the presence of two substituents at the 5 position (see Newman s Rule of 6).  [Pg.172]

Hydroxylation of the double bond of methyltestosterone by means of osmium tetroxide and hydrogen peroxide affords the 4,5 diol. This undergoes beta elimination on treatment with base to yield oxymestrone (83).  [Pg.173]

Conjugate addition of methyl magnesium iodide in the presence of cuprous chloride to the enone (91) leads to the la-methyl product mesterolone (92) Although this is the thermodynamically unfavored axially disposed product, no possibility for isomerization exists in this case, since the ketone is once removed from this center. In an interesting synthesis of an oxa steroid, the enone (91) is first oxidized with lead tetraacetate the carbon at the 2 position is lost, affording the acid aldehyde. Reduction of this intermediate, also shown in the lactol form, with sodium borohydride affords the steroid lactone oxandrolone [Pg.174]

Another example of resort to heteroatoms to obtain both oral potency and a split between androgenic and anabolic activities Ls tiomestrone (99). Trienone, 98, prepared in much the same way as 23, undergoes sequential 1,6 and 1,4 conjugate addition of thioacetic acid under either irradiation or free radical catalysis to afford the compound containing two sulfur atoms. [Pg.175]

The inclusion of a 6a-methyl group is known to potentiate the effect of progestins. Dlmethistarone represents an appllca- [Pg.176]


Testolactone is a synthetic drug related to testosterone. It is used for palliative treatment of advanced breast cancer in postmenopausal women and in women who have had their ovaries removed. The principal action of testolactone is reported to be inhibition of steroid aromatase activity and the reduction in estrone synthesis. The most common adverse effects are nausea, vomiting, and anorexia. An advantage is that it does not cause women to develop male characteristics such as a deep voice or facial hair. [Pg.459]

A) The term "anabolic steroid" means any drug or hormonal substance, chemically and pharmacologically related to testosterone (other than estrogens, progestins, and corticosteroids) that promotes muscle growth, and includes --... [Pg.10]

Recently, Voogt et al. [91] have reported on the d5-pathway in steroid metabolism of Asterias rubens. These workers established the existence of the d5-pathway (Scheme 20), analogous to the pathway found in mammals this conclusion was based on the observation that radiolabeled cholesterol (1) was converted to pregnenolone (112), 17a-hydroxypregnenolone (141), and androstenediol (142). Labeled pregnenolone was converted additionally to progesterone (129). Androstenediol (142) was the main metabolite of de-hydroepiandrosterone (143), a reaction catalyzed by 17/i-hydroxysteroid dehydrogenase (17/1-HSD). The metabolic conversion of androstenedione (131) to testosterone (132) is also mediated by 17/J-HSD and is related to... [Pg.32]

Androsterone and 5)3-androsterone, which are the major metabolites, were thought to be uniquely derived from the plasma androstenedione pool. Korenman et al. [170,388] demonstrated by the double isotope tracer method using carbon-14-labeled testosterone and tritium-labeled androstenedione that neither androsterone nor 5 -androsterone is a unique metabolite of a plasma androstenedione pool. A unique steroid metabolite has been defined by Dorfman [326] as a steroid persisting or formed during metabolism which can be related to one and only one tissue steroid. Korenman et al. obtained different tritium/carbon-14 ratios for androsterone and 5/3-androsterone, suggesting that other pathways of testosterone and androstenedione metabolism also exist. These other pathways, possibly metabolism of testosterone and androstenedione by peripheral tissue, may be responsible for the relative enrichment of either the 5a- or the 5/8-isomer of the urinary metabolites [305]. [Pg.18]

Anabolic steroids, which are related in structure and activity to testosterone, are used to improve muscle... [Pg.1532]

A related compound, androstenedionc is a precursor to testosterone and was marketed over the counter as an alternative to the illegal steroids to enhance strength and performance. Mark McGwire made Andro famous when he admitted to using it during his record-breaking home run streak in 1998. Because androstenedione was associated with many of the side effects of anabolic steroids, the FDA made it an illegal substance in 2004. [Pg.361]


See other pages where Steroids Related to Testosterone is mentioned: [Pg.172]    [Pg.173]    [Pg.175]    [Pg.177]    [Pg.13]    [Pg.191]    [Pg.192]    [Pg.194]    [Pg.196]    [Pg.93]    [Pg.253]    [Pg.971]    [Pg.172]    [Pg.173]    [Pg.175]    [Pg.177]    [Pg.13]    [Pg.191]    [Pg.192]    [Pg.194]    [Pg.196]    [Pg.93]    [Pg.253]    [Pg.971]    [Pg.631]    [Pg.460]    [Pg.254]    [Pg.1032]    [Pg.66]    [Pg.538]    [Pg.455]    [Pg.217]    [Pg.155]    [Pg.54]    [Pg.139]    [Pg.88]    [Pg.104]    [Pg.342]    [Pg.650]    [Pg.51]    [Pg.366]    [Pg.270]    [Pg.78]    [Pg.284]    [Pg.657]    [Pg.303]    [Pg.1193]    [Pg.226]    [Pg.538]    [Pg.168]    [Pg.66]    [Pg.127]    [Pg.241]    [Pg.613]    [Pg.21]    [Pg.212]   


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