Influence of the 17 beta-hydroxyl group of androstane compounds in promotion of growth in the hypophysectomized female rat.

Abstract

Studies by Huggins and Jensen (1954) on the participation of functional groups of the steroid molecule in growth-promoting processes have shown that androstan-17β-ol, but not androstan-17-one or any of the 3-monosubstituted derivatives, shared the ability of testosterone and certain 3,17-dioxygenated androstane compounds to promote growth of the vaginal epithelium and uterus in the hypophysectomized rat. Although these investigators suggested that the 17β-hydroxyl group of the androstane molecule plays a key role in the promotion of growth, there remains some uncertainty whether the monofunctional steroid (androstan-17β-ol) is biologically active per se, or whether an oxygenated function at position 3 is introduced in vivo, so that it is actually a difunctional steroid which is the growth-promoting agent. Since the fluorine atom at C3 is rather tightly bound and oxj’genation at this site seems unlikely, two 3β-fluorosteroids, 3β-fluorandrostan-17β-ol and 3β-fluorandrostan-17-one, were compared with andros...