9180. Testosterone

Nomenclature

CAS number: 58-22-0
(17β)-17-Hydroxyandrost-4-en-3-one; Δ4-androsten-17β-ol-3-one; trans-testosterone; Andro (Forest); Androderm (GSK); Andropatch (GSK); Mertestate (Sterling Winthrop); Oreton (Schering-Plough); Testoderm (Alza); Testogel (Schering AG); Testolin (Pasadena); Testro AQ (Truxton); Virosterone (Endo).
C19H28O2; mol wt 288.42.
C 79.12%, H 9.79%, O 11.09%.

Description and references

Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dihydrotestosterone which is required for normal male sexual differentiation. Also converted by aromatization to estradiol, q.v. Isoln from bull testes: David et al., Z. Physiol. Chem. 233, 281 (1935). Prepn from cholesterol and confirmation of structure: A. Butenandt, G. Hanisch, Ber. 68, 1859 (1935); eidem, Z. Physiol. Chem. 237, 89 (1935); from dehydroandrosterone: L. Ruzicka, A. Wettstein, Helv. Chim. Acta 18, 1264 (1935); from mixed esters: L. Ruzicka et al., ibid. 1478. Crystal structure: P. J. Roberts et al., J. Chem. Soc. Perkin Trans. 2 1973, 1978. Historical review: J. M. Hoberman, C. E. Yesalis, Sci. Am. 272, 76-81 (Feb. 1995). Review of role in aging males: F. E. Kaiser, J. E. Morley, Neurobiol. Aging 15, 559-563 (1994); of clinical relevance in females: R. S. Rittmaster, Am. J. Med. 98, Suppl. 1A, 17S-21S (1995).

Chemical structure

Properties

Needles from dil acetone, mp 155°. [α]D24 +109° (c = 4 in alc). uv max: 238 nm. Insol in water. Sol in alcohol, ether, and other organic solvents.

Derivative

Acetate.

Nomenclature

CAS number: 1045-69-8
C21H30O3; mol wt 330.46.
C 76.33%, H 9.15%, O 14.52%.

Properties

mp 140-141°.

Derivative

17β-Cyclopentanepropionate.

Nomenclature

CAS number: 58-20-8
Testosterone cypionate; depAndro (Forest); Depotest (Hyrex); Depo-Testosterone (Pfizer); Depovirin (HMR); Pertestis (Orma); Virilon (Star).
C27H40O3; mol wt 412.60.
C 78.60%, H 9.77%, O 11.63%.

Description and references

Pharmacology: A. C. Ott et al., J. Clin. Endocrinol. Metab. 12, 15 (1952).

Properties

Crystals, mp 101-102°. [α]D25 +87° (CHCl3). Sol in oils.

Derivative

Enanthate.

Nomenclature

CAS number: 315-37-7
Andro LA (Forest); Androtardyl (Schering AG); Delatestryl (BMS); Everone (Hyrex); Primoteston (Schering AG); Testinon (Mochida); Testo-Enant (Geymonat).
C26H40O3; mol wt 400.59.
C 77.95%, H 10.06%, O 11.98%.

Description and references

Prepn: Junkmann et al., US 2840508 (1958 to Schering AG). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 4, 452-465 (1975).

Properties

Crystals, mp 36-37.5°.

Derivative

Propionate.

Nomenclature

CAS number: 57-85-2
Anertan (Boehringer, Mann.); Enarmon (Teikoku Zoki); Neo-Hombreol (amp.) (Organon); Orchisterone (Negroni); Synandrol (Pfizer); Testex (Pasadena); Testoviron (Schering AG); Virormone (Ferring).
C22H32O3; mol wt 344.49.
C 76.70%, H 9.36%, O 13.93%.

Description and references

Prepn: K. Miescher et al., US 2109400 (1938 to Soc. Chem. Ind. Basel).

Properties

Stout prisms from alcohol + water, mp 118-122°. [α]D25 +83 to +90° (100 mg in 10 ml dioxane). Insol in water. Freely sol in alcohol, ether, pyridine, in other organic solvents. Sol in vegetable oils.

Derivative

Undecanoate.

Nomenclature

CAS number: 5949-44-0
Testosterone 17β-undecylate; Andriol (Organon); Pantestone (Organon); Restandol (Organon).
C30H48O3; mol wt 456.70.
C 78.90%, H 10.59%, O 10.51%.

Note

This is a controlled substance (anabolic steroid): 21 CFR, 1308.13, as defined in 1300.01.

Therapeutic Category

Androgen.

Therapeutic Category (Veterinary)

Androgen.

Keywords

Androgen