Testosterone structure

Chemical Name 17/3-(3-Cyclopentyl-1-oxopropoxy)androst-4-en-3-one Common Name Depo-testosterone Structural Formula ... 

The next logical approach was to investigate the 19-nor-testosterone structure (devoid of the CH3 at C-10). Norethynodrel—A5( 10)-17-ethynylnortesterone—was introduced by Pincus in 1958 as an orally active antifertility agent and became the starting point for the oral contraceptives to follow (vide infra). The 13-ethyl substituent (norgestrel) enhanced this activity. 

Slight structural changes of the model compound testosterone may therefore further reduce the inherently low reactivity and favor the competition of... 

Polycyclic compounds are common in nature, and many valuable substances have fused-ring structures. For example, steroids, such as the male hormone testosterone, have 3 six-membered rings and 1 five-membered ring fused together. Although steroids look complicated compared with cyclohexane or decalin, the same principles that apply to the conformational analysis of simple cyclohexane lings apply equally well (and often better) to steroids. 

Testosterone, conformation of, 129 molecular model of, 129 structure and function of, 1082 Tetracaine, structure of, 967 Tetrahedral geometry, conventions for drawing. 8... 

The structures of the drugs used as a small test set for the model are listed in Table 17.1. Loperamide and asimadoline are P-gp substrates terfenadine and ebastine are compounds that are rapidly metabolized alprazolam, dobazam, di-and mono-hydroxy-L66858 [11] are benzodiazepines testosterone and corticosterone are hormones and cefadroxyl, cefaclor, cephalotin and cefmetazole are cephalosporins [12]. Finally, peptides 1 to 10 are peptidomimetic drugs [13]. 

FIGURE 4.20 Structures of the CYP3A4 substrates, erythromycin, nifedipine, testosterone, and midazolam, and their metabolites. 

There are comparatively few studies addressing the structure-metabolism relationships of phosphoric acid monoester hydrolysis. For example, kinetics of decomposition in rat whole blood were examined for the phosphoric acid monoesters of estrone, 17a- and 17/J-testosterone, 3-(hydroxyme-thyl)phenytoin (see Fig. 9.7,a), and 1-phenylvinyl alcohol (9.28, the enolic form of acetophenone) [87]. As a general trend, the rate of hydrolysis increased with the acidity of the leaving hydroxylated compound. In other words, hydrolysis was the fastest for the phosphoric acid aryl monoester (estrone 3-phosphate), and slowest for the two testosterone phosphoric acid... 

General structure of a fatty acid ester (R) of testosterone Girard hydrazone... 

Phthalates do not seem to act via direct hormonal mimicking. However, in rodents, some phthalates (BBP, DiBP, DBP, DEP, DEHP, and DiNP) can modulate the endogenous production of fetal testicular testosterone [85-87], resulting in functional and structural impairment of male reproduction and development [85, 88-90], but these effects have not been proved when tested in non-human primates. 

This annulation process was of considerable value in early approaches to steroid synthesis. The structural relationship of the bicyclic product obtained here to the male sex hormone testosterone is immediately apparent. Further, the non-conjugated carbonyl is now activating the adjacent carbon that subsequently features in building up the third ring system. 

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