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55 Steroids of the estratriene and androstane type with substituents in pos. 16 alpha, 17 alpha or 17 beta were tested for inhibition of the 3beta-hydroxysteroid oxidoreductase of Pseudomonas testosteroni. Estratrien-3-ols were strong and competitive inhibitors (Ki less than 1 micron). Substituents in pos. 16 alpha of estradiol influenced the inhibitory activity distinctly. Substituents in 17 alpha- or 17 beta-position were of slight influence. 3-Methoxy estratrienes gave no inhibition of the enzymic 3 beta-OH-dehydrogenation. The 4-unsaturated 3-oxo-steroids tested were moderate inhibitors (Ki 2.4-70 micron). The activity was slightly influenced by 17 alpha-substituents. It was increased by 10 beta-substituents in the order H less than CH3 less than N3. The inhibition test can be used to select and eliminate very strong synthetic inhibitors, which are known to disturb the metabolism of steroid hormones.
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