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Chemical Properties

White crystalline powder with no aroma. 

Indications and Uses

Testim 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 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

Testim 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. 

Description

Testim (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.

Uses

Testim 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.

Definition

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

General Description

Testim is a naturally occurring androgen in men. In women, it mainly serves as a biosynthetic precursor to estradiolbut also has other hormonal effects.

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.

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, 17β-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 17β-hydroxy compound. In the given example, reduction by sodium borohydride or hydrogen over Raney nickel leads to the formation of 3β-acetoxy-5-androsten-17β-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–C6 to C4–C5 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.]