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PubMed1954

Chemical structure of steroids in relation to promotion of growth of the vagina and uterus of the hypophysectomized rat.

In the hypophysectomized albino rat which is protected from contact with steroids in the ration and environment the uterus and vagina are highly atrophic but are sensitive indicators of activity of substances which promote their growth. Both the pituitary growth hormone and certain steroids have the common property of inducing growth of these tissues. The vaginal epithelium consists of 2 layers of cells which differ profoundly in their growth in response to steroids, depending on the molecular structure of these compounds. The differential response to modifications of chemical structures of steroids permits evaluation of the importance of the intramolecular components for the process of growth. The number and site of functional groups, the geometry of the molecule and the state of oxidation are of high importance in determining physiologic activity of steroids in the androstane series; these features are less specific in the estrane series. Side groups at positions C(3) and C(17) are of importance in the promotion of growth by steroids in the androstane series, but these active centers are not equivalent in their physiological influence. As a generalization, hydrogenation of the oxygen function at C(17) (but not at C(3)) and dehydrogenation at critical areas of the ring structure increase the quantitative efficacy of steroids in promoting growth. The position of double bonds and the state of oxidation at both C(3) and C(17) determine the qualitative type of growth-cellular pattern, which a compound in the androstane series induces in the vaginal epithelium.

Animals↗
PubMed1954

Significance of the hydroxyl groups of steroids in promoting growth.

The presence of a 17beta-hydroxyl group endows the simple androstane molecule with the ability to produce growth of the uterus, vagina, and prostate of the female hypophysectomized albino rat. It appears that hydrogen atoms at position 17 are of critical importance since related compounds with a ketone group at this site are inactive. Monofunctional steroids with a hydroxyl or a ketone group at position 3 likewise are devoid of activity. If a phenolic A-ring is present in monofunctional steroids the 17beta-hydroxyl group is not obligatory for growth. Proliferation of the uterus and vagina were found to follow the administration of 17-desoxyestradiol.

Androstanes↗
PubMed1955

The depression of growth of the uterus, adrenals, and ovaries by fluorinated steroids in the pregnane series.

Progesterone, 5-pregnene-3,20-dione, and desoxycorticosterone were found to be partial but significant inhibitors of estrone-induced growth of the uterus of hypophysectomized rats but they did not depress the amount of growth elicited by testosterone. The presence of both the 2-carbon side chain at position 17 and an oxygenated function at position 3 is necessary for the inhibitory activity of progesterone. The introduction of a hydroxyl group in the progesterone molecule at positions 6 (beta), 11 (alpha), 16 (alpha) or 17 (alpha) destroyed its growth-inhibitory activity. 11beta-Hydroxyprogesterone is weaker than progesterone in the inhibition of estrone-induced uterine growth; unlike progesterone it has the capacity to depress growth elicited by testosterone. The introduction of a flourine atom in the 9 (alpha) position resulted in a striking increase of the growth-inhibitory activity of 11beta-hydroxyprogesterone and hydrocortisone. 9alpha-Flouro-11beta-hydroxyprogesterone is a partial but significant inhibitor of growth of the uterus in hypophysectomized rats injected simultaneously with large doses of estrone or testosterone. It is more powerful than progesterone in transforming the vaginal epithelium to mucus cells in the presence of estrone. Administered alone, the only detectable growth was a slight increase in size of the preputial glands. 9alpha-Flouro-11beta-hydroxyprogesterone suppresses in part the growth of the adrenals, ovaries, and uterus in intact rats at a dose level which does not cause loss of body weight or inhibit body growth. Many rats treated with this compound in small amount had extensive mucification of the vagina resembling that of late pregnancy.

Adrenal Cortex↗