Testosterone
Title: Testosterone
CAS Registry Number: 58-22-0
CAS Name: (17b)-17-Hydroxyandrost-4-en-3-one
Additional Names: D4-androsten-17b-ol-3-one; trans-testosterone
Trademarks: Andro (Forest); Androderm (GSK); Andropatch (GSK); Mertestate (Sterling Winthrop); Oreton (Schering-Plough); Testoderm (Alza); Testogel (Schering AG); Testolin (Pasadena); Testro AQ (Truxton); Virosterone (Endo)
Molecular Formula: C19H28O2
Molecular Weight: 288.42
Percent Composition: C 79.12%, H 9.79%, O 11.09%
Literature References: Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5a-reductase in androgen-dependent target tissues to 5a-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).
Properties: Needles from dil acetone, mp 155°. [a]D24 +109° (c = 4 in alc). uv max: 238 nm. Insol in water. Sol in alcohol, ether, and other organic solvents.
Melting point: mp 155°
Optical Rotation: [a]D24 +109° (c = 4 in alc)
Absorption maximum: uv max: 238 nm
 
Derivative Type: Acetate
CAS Registry Number: 1045-69-8
Molecular Formula: C21H30O3
Molecular Weight: 330.46
Percent Composition: C 76.33%, H 9.15%, O 14.52%
Properties: mp 140-141°.
Melting point: mp 140-141°
 
Derivative Type: 17b-Cyclopentanepropionate
CAS Registry Number: 58-20-8
Additional Names: Testosterone cypionate
Trademarks: depAndro (Forest); Depotest (Hyrex); Depo-Testosterone (Pfizer); Depovirin (HMR); Pertestis (Orma); Virilon (Star)
Molecular Formula: C27H40O3
Molecular Weight: 412.60
Percent Composition: C 78.60%, H 9.77%, O 11.63%
Literature References: Pharmacology: A. C. Ott et al., J. Clin. Endocrinol. Metab. 12, 15 (1952).
Properties: Crystals, mp 101-102°. [a]D25 +87° (CHCl3). Sol in oils.
Melting point: mp 101-102°
Optical Rotation: [a]D25 +87° (CHCl3)
 
Derivative Type: Enanthate
CAS Registry Number: 315-37-7
Trademarks: Andro LA (Forest); Androtardyl (Schering AG); Delatestryl (BMS); Everone (Hyrex); Primoteston (Schering AG); Testinon (Mochida); Testo-Enant (Geymonat)
Molecular Formula: C26H40O3
Molecular Weight: 400.59
Percent Composition: C 77.95%, H 10.06%, O 11.98%
Literature 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°.
Melting point: mp 36-37.5°
 
Derivative Type: Propionate
CAS Registry Number: 57-85-2
Trademarks: Anertan (Boehringer, Mann.); Enarmon (Teikoku Zoki); Neo-Hombreol (amp.) (Organon); Orchisterone (Negroni); Synandrol (Pfizer); Testex (Pasadena); Testoviron (Schering AG); Virormone (Ferring)
Molecular Formula: C22H32O3
Molecular Weight: 344.49
Percent Composition: C 76.70%, H 9.36%, O 13.93%
Literature References: Prepn: K. Miescher et al., US 2109400 (1938 to Soc. Chem. Ind. Basel).
Properties: Stout prisms from alcohol + water, mp 118-122°. [a]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.
Melting point: mp 118-122°
Optical Rotation: [a]D25 +83 to +90° (100 mg in 10 ml dioxane)
 
Derivative Type: Undecanoate
CAS Registry Number: 5949-44-0
Additional Names: Testosterone 17b-undecylate
Trademarks: Andriol (Organon); Pantestone (Organon); Restandol (Organon)
Molecular Formula: C30H48O3
Molecular Weight: 456.70
Percent Composition: 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.
Therap-Cat: Androgen.
Therap-Cat-Vet: Androgen.
Keywords: Androgen.

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