Testosterone

Chemical Properties

White crystalline powder with no aroma. Its melting point is 155℃, specific rotary power is [α]24D+109° (4%, ethanol), and its ethanol solution has the greatest absorbance at a wavelength of 240nm. It is easily soluble in ethanol (1:5), soluble in ether (1:100), and insoluble in water. LD50 (Large mice, venal transfusion) 326mg/kg. Studies show that it has latent carcinogenic effects on test animals.

Indications and Uses

Testosterone is the main natural male sex hormone in mammals and is a steroid hormone with 19 carbon atoms. It is the main male sex hormone secreted by the testes, and it is also the most active male sex hormone. It promotes humans’ and animals’ sex organ and secondary sex characteristic development, sperm maturation, and protein metabolism for muscle strengthening. Testosterone controls the growth and development of male sex organs and male secondary sex characteristics. It is mainly used in replacement therapy for eunuchism, treatment for male menopause syndrome, and treatment for impotence, and it is also used in biochemical research.

Pharmacokinetics

Testosterone can bind non-specifically with plasma albumins in blood, and it can also bind with plasma sex hormone binding globulins. It can be converted into estradiol and estrone in peripheral tissue. Testosterone is mostly degraded in the liver, where its A-ring is restored, and it is converted into 17- ketosteroid under the effects of 17β-Hydroxysteroid dehydrogenase. Along with androsterone, epiandrosterone, and etiocholanlone, it is combined with glucuronic acid or sulfate and excreted in urine. Most metabolites in urine that are excreted by binding to glucuronic acid belong to 17-ketosteroids.

Application in Particular Diseases

In Osteoporosis:

• Testosterone replacement is not FDA approved for the prevention or treatment of osteoporosis. It should not be used solely for these indications but might be beneficial to reduce bone loss in patients needing therapy for hypogonadal symptoms. In a few studies, women receiving oral methyltestosterone 1.25 or 2.5 mg daily or testosterone implants 50 mg every 3 months had increased BMD. Various salt forms of testosterone were associated with increased BMD in some studies of hypogonadal men or senior men with normal hormone levels or mild hormonal deficiency. Transdermal gel, oral, intramuscular, and pellet testosterone products are available.
• Patients using them should be evaluated within 1 to 2 months of initiation and then every 3 to 6 months thereafter.

Description

Testosterone (Item No.15645) is an analytical reference material categorized as an anabolic androgenic steroid. Testosterone is an endogenous metabolite of androstenedione (Item Nos. ISO60161 | 15874) and estradiol (Item Nos. ISO60155 | 10006315). Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes. Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Description

Testosterone (CRM) (Item No. ISO60154) is a certified reference material categorized as an anabolic androgenic steroid. Testosterone is an endogenous metabolite of androstenedione (Item Nos. ISO60161 | 15874) and estradiol (Item Nos. ISO60155 | 10006315). Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes. Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Chemical Properties

white crystalline odourless solid

Uses

Secreted by the testis and is converted to dihydrotestosterone in the target tissue where is appears to mediate many of the biological actions of testosterone. CONTROLLED SUBSTANC

Uses

androgen, antineoplastic

Uses

Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.

Uses

Testosterone, Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dehydrotestosterone which is required for normal male sexual differentiation. Also converted by aromatization to Estradiol. Testerone is a controlled substance (anabolic steroid). Androgen.

Uses

Rivastigmine metabolite

Definition

ChEBI: An androstanoid having 17beta-hydroxy and 3-oxo groups, together with unsaturation at C-41C-5..

General Description

Testosterone, 17β-hydroxyandrost-4-en-3-one, is a naturally occurring androgen in men. Inwomen, it mainly serves as a biosynthetic precursor to estradiolbut also has other hormonal effects. It is rapidly metabolizedto relatively inactive 17-ones, however,preventing significant oral activity. Testosterone is availablein a transdermal delivery system (patch), a gel formulation, abuccal system, and as implantable pellets.

Hazard

A confirmed carcinogen.

Health Hazard

Controls secondary male sex characteristics Maintains functional competence of male reproductive ducts and glands
Increases protein anabolism; maintains spermatogenesis; inhibits follotropin
Increases male sex behavior; increases closure of epiphyseal plates

Biological Activity

Endogenous androgen receptor agonist.

Biochem/physiol Actions

Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.

Safety Profile

Confirmed carcinogen with experimental neoplastigenic and teratogenic data. Poison by intraperitoneal route. Human teratogenic effects by unspecified route: developmental abnormalities of the urogenital system. Experimental reproductive effects. Human mutation data reported. Workers engaged in manufacture and packagmg have shown effects from this hormone, e.g., enlargement of the breasts in male workers. A promoter. When heated to decomposition it emits acrid smoke and irritating fumes. Used as a drug for the treatment of hypogonadism and metastatic breast cancer.

Synthesis

Testosterone, 17|?-hydroxyandrost-4-ene-3-one (29.1.5), is made in a number of ways from different substances, including cholesterol, although it is most often made from androstenolone acetate. In order to do this, the keto-group at C17 of the steroid system of androstenolone acetate is reduced to a hydroxyl group by either sodium borohydride, lithium aluminum hydride, or hydrogen over Raney nickel, all of which result in a 17|?-hydroxy compound. In the given example, reduction by sodium borohydride or hydrogen over Raney nickel leads to the formation of 3|?-acetoxy-5-androsten-17|?-ol (29.1.1). The hydroxyl group resulting from reduction then undergoes acylation by benzoyl chloride in pyridine, which forms a diester (29.1.2). After that, taking into consideration the differences in the acidic region of the two ester groups present in the molecule as well as the long-known fact that 17-hydroxy-group ester derivatives are harder to hydrolyze than 3-hydroxy-group ester derivatives, the acetyl protection of the hydroxyl group at C3 is removed by selective hydrolysis using potassium hydroxide in ethanol, and the resulting alcohol (29.1.3) is oxidized to a ketone (29.1.4) by aluminum isopropylate in the presence of cyclohexanone as a hydrogen acceptor, during which isomerization of the double bond from position C5¨CC6 to C4¨CC5 simultaneously takes place. Subsequent hydrolysis of the remaining ester region of the molecule using an alkali gives the desired testosterone (29.1.5) . When necessary to convert this into the corresponding ester (propionate, enantate, cypionate, and a few other testosterone esters), the necessary acylation can be accomplished.

Purification Methods

Crystallise testosterone from aqueous acetone, hexane or isoPrOH. The long needles that separated from EtOH/AcOH were used for X-ray crystallography [Roberts et al. J Chem Soc Perkin Trans II 1978 1973.] The acetate [1045-69-8] crystallises from MeOH or aqueous Me2CO, with m 140-141o and [] D 20 +87.8o (c 1, EtOH). [Ruzicka et al. Helv Chim Acta 18 1478 1935 and 19 99, 842 1936, Beilstein 8 IV 974.]