Testosterone derivatives

Fig. 1 Fluorescence scan of a blank track (A) and of the testosterone derivative (B, 2 jig). Start (1), testosterone-INH derivative hRf 39) (2), unknown substances (3, 4).

A highly modified methyl testosterone derivative also exhibits antiandrogenic activity. One synthesis of this compound Involves initial alkylation of methyl testosterone (3 ) by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative Formylation with alkoxide and... 

Anabolics are testosterone derivatives (e.g., clostebol, metenolone, nan-drolone, stanozolol) that are used in debilitated patients, and misused by athletes, because of their protein anabolic effect. They act via stimulation of androgen receptors and, thus, also display androgenic actions (e.g., virilization in females, suppression of spermatogenesis). 

Mesterolone is a non-17-alkylated derivative which is also has weak activity orally. Testosterone itself has little activity when taken orally and is used sublingually or as an implant. By esterification of testosterone formulations of long-acting testosterone derivatives in oily solutions for intramuscular injection were developed. 

Mechanism of Action A testosterone derivative that suppresses the pituitary-ovarian axis by inhibiting the output of pituitary gonadotropins. Causes atrophy of both normal and ectopic endometrial tissue in endometriosis. Follicle-stimulating hormone (FSH) and luteinizing hormone (LH) are depressed in fibrocystic breast disease. Inhibits steroid synthesis and binding of steroids to their receptors in breast tissues. Increases serum levels of esterase inhibitor. Therapeutic Effect Produces anovulation and amenorrhea, reduces the production of est rogen, corrects biochemical deficiency as seen in hereditary angioedema. 

Brand Name(s) Android, Android-10, Android-25, Oreton Methyl, Testred, Virilon Chemical Class Androgen testosterone derivative... 

Mechanism of Action A synthetic testosterone derivative with androgen activity that promotes growth and development of male sex organs and maintains secondary sex characteristics in androgen-deficient males, TIicrapcuticE/fcct Treats hypogonadism in males. 

Chemical Class Anabolic steroid testosterone derivative... 

Chemical Class Anabolic steroid testosterone derivative DEA Class-. Schedule III... 

Mechanism of Action A synthetic testosterone derivative that promotes growth and development of male sex organs, maintains secondary sex characteristics in androgen-deficient males. Therapeutic Effect Androgenic and anabolic actions. Pharmacokinetics Well absorbed from fhe gastrointestinal (GI) tract. Protein binding 94%-97%. Metabolized in liver. Primarily excreted in urine. Unknown if removed by hemodialysis. Half-life 5-13 hr. 

Mechanism of Action A synthetic testosterone derivative that increases circulating levels of Cl INH and C4 through an increase in general protein anabolism, and more specifically, through an increase in the synthesis of messenger RNA, Therapeutic Effect Decreases swelling of the face, extremities, genitalia, bowel wall, and upper respiratory tract... 

Testosterone, when administered by mouth, is rapidly absorbed. However, it is largely converted to inactive metabolites, and only about one sixth of the dose administered is available in active form. Testosterone can be administered parenterally, but it has a more prolonged absorption time and greater activity in the propionate, enanthate, undecanoate, or cypionate ester forms. These derivatives are hydrolyzed to release free testosterone at the site of injection. Testosterone derivatives alkylated at the 17 position, eg, methyltestosterone and fluoxymesterone, are active when given by mouth. 

The structure of the cyclic enone affects the stereoselectivity in the formation of the four-membered ring, as could be seen in the photoaddition of testosterone derivatives 159 and 162 to cyclopentene. Rubin and colloborators88 reported favored cis -fused product... 

The effects of time, temperature, reactant concentrations, and the presence of oestratriene and testosterone derivatives on the formation of oestrogen from C19... 

Figure 6. Linear relationship between Rm values of testosterone derivatives and acetone concentration in the mobile phase...

Isotestosterone and 8a, 1 Oa-testosterone can be considered as substituted testosterone derivatives where the 8-H is substituted by an alkyl group. In the case of 8a,10a-testosterone other structural features are prohibitive for biological activity. However, 8-isotestosterone displays decreased, but definite androgenic and anabolic properties. Nagata [160] prepared some 8/3-substituted testosterone homologs —8-methyl-testosterone (E-30) and others. In all cases decreased androgenic and anabolic potencies were observed. These facts point to the importance of /3-face attachment to the receptor at carbon-8. 

Bulky substituents in 10-positions decrease the androgenic and anabolic activities to a large extent. This definitely points to the /8-face attachment at C-10. Results obtained with 9a,10a-testosterone derivatives confirm the importance of /3-face attachment. However the steric requirement of the methyl group, as measured by the 2.0 A van der Waals radius [222], is no bar to /3-face attachment to the receptor at C-10. The steric requirements at C-10 can accommodate 10-methyl substitution (the presence of the 19-methyl group). 

I7)3-Hydroxy-5a-androstane derivatives containing a ring A unsaturation, excluding testosterone derivatives. 

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