This Article Full Text (PDF) Submit a related Letter to the Editor Alert me when this article is cited Alert me when eLetters are posted Alert me if a correction is posted Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Reprints, Permissions and Rights Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by SEGALOFF, A. Articles by GABBARD, R. B. Search for Related Content PubMed PubMed Citation Articles by SEGALOFF, A. Articles by GABBARD, R. B.

Steroid Structure and Androgenicity

Division of Endocrine Research, Alton Ochsner Medical Foundation New Orleans, Louisiana

This study was aided in part by a grant from the American Cancer Society and in part by a grant (CY-3603) from the National Institutes of Health, USPHS.

Abstract

Fifteen derivatives of androstane were compared with testosterone for their androgenic effects on the cockerel comb or the levator ani, seminal vesicle and ventral prostate of immature castrated male rats. The ventral prostate response was a more sensitive end-point for testosterone than the seminal vesicle, while the levator ani response was the least senstive. The cockerel comb response was generally found to parallel that of the rat ventral prostate. In rat bio-assays, testosterone was about 100 times more effective administered parenterally than orally.

The presence of a 17β-hydroxyl group was shown to be necessary for maximal androgenic activity regardless of the type of end-point observed. The 17-ketone group was found to be somewhat less active than 17β-hydroxyl in cockerel comb or ventral prostate bio-assays, while the seminal vesicle and levator ani responses were greatly decreased. 5β-Androstanes were invariably much less androgenic than the A4 or 5 a compounds, regardless of the nature of substitution on positions 3 or 17, the route of administration or the bio-assay end-points employed. Removal of the 3-oxy function, as in the 3-desoxy-5a or ⁴-17β-ol derivatives, results in compounds which either equal or exceed testosterone in androgenicity after oral administration but are less active than testosterone when both are given parenterally. A low level of androgenicity was demonstrated for the hydrocarbons 5 a- and 5β-androstane and ⁴-androstene in the cockerel comb and the rat bio-assays. Because these hydrocarbons are more effective if given orally than parenterally to rats, they are probably proandrogens.

Received June 6, 1962.

This article has been cited by other articles:

				J. S. Strauss and P. E. Pochi Recent Advances in Androgen Metabolism and Their Relation to the Skin Arch Dermatol, November 1, 1969; 100(5): 621 - 636. [Abstract] [PDF]