Metrotropic Activity of Some 21-Haloprogesterone Derivatives.

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Abstract
A series of C-21 haloprogestins was assayed in the Clauberg, uterine carbonic an-hydrase, and intrauterine (McGinty) assays. C-21-Fluorination of both 17[alpha]-acetoxyprogesterone and 6[alpha]-methyl- 17[alpha]-acetoxyprogesterone resulted in a marked increase in the oral potency of both substances. Replacement of F with the heavier halogens in these agents tended to decrease the potency of the parent compound regardless of the assay used. The most potent metrotropic agent tested was 6[alpha]-methyl-17[alpha]-acetoxy-21-fluoroprogesterone. Orally, it was twice as potent as its non-fluorinated analogue and 10 times more potent than subcutaneously administered progesterone. It was 50 times more potent than progesterone when both were given subcutaneously and about 50 times more potent than progesterone when instilled in the uterus.