Hormones testosterone

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. 

The male sex hormone testosterone contains C, H, and O and has a mass of 288.2089 amu as determined by high-resolution mass spectrometry. What is the likely molecular formula of testosterone ... 

Sex Hormones Testosterone and androsterone are the two most important male sex hormones, or androgens. Androgens are responsible for the development of male secondary sex characteristics during puberty and for promoting tissue and muscle growth. Both are synthesized in the testes from cholesterol. Androstenedione is another minor hormone that has received particular attention because of its use by prominent athletes. 

The chemical formula of a compound represents its composition in terms of chemical symbols. Subscripts show the numbers of atoms of each element present in the smallest unit that is representative of the compound. For molecular compounds, it is common to give the molecular formula, a chemical formula that shows how many atoms of each type of element are present in a single molecule of the compound. For instance, the molecular formula for water is H20 each molecule contains one O atom and two H atoms. The molecular formula for estrone, a female sex hormone, is Clgl-I2202, showing that a single molecule of estrone consists of 18 C atoms, 22 FI atoms, and 2 O atoms. A molecule of a male sex hormone, testosterone, differs by only a few atoms its molecular formula is (lyH2802. Think of the consequences of that tiny difference ... 

Another intriguing observation is that the female sex-hormone 17/i-estradiol (28) could dramatically potentiate capsaicin responses, whereas the male hormone testosterone had marginal inhibitory activity. Sex differences in pain responses have long been known, with women being more sensitive to capsaicin-induced pain than men [94]. The differential modulation of capsaicin responses by female and male hormones might provide a rationale to explain this observation. 

DHEA is an adrenal hormone that is a precursor to the sex hormones testosterone and estrogen, as well as other hormones. DHEA is reported to increase testosterone and decrease total body fat, and also to have anabolic and anti-aging effects. The... 

A second example can be found in the metabolism of the male sex steroid hormone testosterone. In addition to 7a -hydroxy- and 6a-hydroxytestosterone, CYP2A1 was also found to form A6-testosterone (136) (Fig. 4.69). Using selectively deuterated analogs (136), A6-testosterone was established as being formed in competition with 6o -hydroxytestosterone after initial hydrogen atom abstraction from C6 to form the common radical intermediate. Little, if any, A6-testosterone was found to be formed in competition with la-hydroxytestosterone after initial hydrogen abstraction from Cl. 

Lozenges and troehes are solid preparations designed to dissolve or disintegrate slowly in the mouth their base is usually flavored and sweetened. Examples of eom-pounded troehes include anesthetic (lidocaine), hormonal (testosterone), analgesie (ketamine), and antifungal (nystatin) preparations (Table 2). 

Androgens are male sex hormones testosterone and dihydrotestosterone are good examples ... 

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. 

Testosterone (5.45) is the prototypic androgen sex hormone. Testosterone is synthesized by the testes, and must be reduced to dihydrotestosterone (5.46, DHT) before it will bind to the receptor. Among highly active synthetic testosterone analogs, 7a-methyl-19-nortestosterone (5.47) and oxandrolone (5.48) have about 100 times greater activity than testosterone as androgens. 17a-Methyltestosterone (5.49) is orally active. 

Anabolic-androgenic steroids (AAS), which are analogs of the male hormone testosterone, are used among athletes and bodybuilders. AAS alter the hormonal systems of males and females, and induce many adverse effects. In addition to the sex-related changes, violent behavior and psychological dependence can also occur. The use of AAS in professional sports as well as in high school sports has aroused considerable attention. 

Steroids like cholesterol 335, cholic acid 336, or the sex hormone testosterone 337 play an important role in almost all living organisms. Therefore they are the... 

Sex hormones control tissue growth and reproduction. Male sex hormones are testosterone and Sa-dibydrotestosterone, also known as androgens, which are secreted by the testes. The primary male hormone, testosterone, is responsible for the development of secondary sex characteristics during puberty. They also promote muscle growth. The two most important female sex hormones are oestradiol and oestrone, also known as oestrogem estrogens). They are responsible for the development of female secondary sex characteristics. 

Two female sex hormones, estradiol-17 and progesterone, and one male sex hormone, testosterone, are used as growth promoters on beef cattle (Fig. 7.1). By nature, they are all endogenous products playing an important role in controlling reproductive functions in humans and animals. When applied exogenously they will enter the same metabolic pathways as the endogenously produced molecules. 

Estimate the Kiow values at 25°C of (a) ethylacetate, (b) 2,3,7,8-tetrachloro-dibenzodioxin, (c) the herbicide 2-s-butyl-4,6-dinitrophenol (Dinoseb), (d) the insecticide parathion, and (e) the hormone testosterone using solely the fragment coefficients and correction factors given in Tables 7.4 and 7.5 (Eq. 7-15). 

The step-by-step synthesis of the steroid hormones pregnenolone and progesterone from cholesterol (C27) was presented in chapter 20 (see fig 20.22). Note that pregneno-lone (C2i) and progesterone (table 20.4) (C2 ) are intermediates in the biosynthesis of all of the major adrenal steroids, including cortisol (C2i), corticosterone (C21), and aldosterone (C21). The same two compounds are intermediates in the synthesis of the gonadal steroid hormones, testosterone (C,9) and 17/3-estradiol (CI8). Because the synthesis of all these hormones follows a common pathway, a defect in the activity or amount of an enzyme along that pathway can lead to both a deficiency in the hormones beyond the affected step and an excess of the hormones, or metabolites, prior to that step. 

Mendelson JH, Sholar MB, Mutschler NH, Jaszyna-Gasior M, Goletiani NV, Siegel AJ, Mello NK. Effects of intravenous cocaine and cigarette smoking on luteinizing hormone, testosterone, and prolactin in men. J Pharmacol Exp Ther 2003 307 339 18. 

FIGURE 29-1 Pathways of adrenal steroid biosynthesis. Cholesterol is the precursor for the three steroid hormone pathways. Note the similarity between the structures of the primary mineralocorticoid (aldosterone), the primary glucocorticoid (cortisol), and the sex hormones (testosterone, estradiol). See text for further discussion. 

Target Organ Hormone (Testosterone, Estrogens, Inhibin)... 

Other steroids include the sex hormones testosterone, progesterone, and the estrogen family (estrone, estradiol, estratriol, etc. Figure 12.30). 

A young adult male produces about 2.4 x 10-5 mol per day of the steroid sex hormone testosterone. The molecular mass of testosterone is 288. How many grams of testosterone per day does a young adult male produce ... 

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