METHYLANDROSTENEDIOL

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Abstract
METHYLANDROSTENEDIOL is a steroid that was first synthesized in Ruzicka's laboratory (1) in 1935. Since it exhibits some unusual properties, renewed interest has been aroused in recent months, and in view of this we have undertaken to compile the present survey of the data available to us. Although its behavior is rather different, methylandrostenediol is most closely related to methyltestosterone, the structural difference being an alcohol rather than a ketone at carbon 3, associated with the characteristic shift of the double-bond from 4:5 to 5:6. The respective structural formulae may be compared: One readily supposes that the compound, in metabolism, might be modified to become methyltestosterone and in this way some, but not all, of its behavior can be explained. Quite different modifications have also to be considered. The intensity of its several actions is found to vary considerably in animals, depending upon whether it is administered orally or parenterally; and the variation does not have the simple quantitative character, seen with many steroids, that oral administration is merely less efficacious. Contrariwise, methylandrostenediol on oral administration exhibits a moderate androgenic activity and a capacity to inhibit certain experimental tumors, which properties disappear or are impaired on subcutaneous injection. When given parenterally to the experimental animal there is a well marked protein-anabolic action which is only poorly manifest when the substance is given by mouth. Some other properties might also suggest that two or more different steroids are involved, depending upon the metabolic history of the single substance administered. Whereas the literature has dwelt at length upon conjectured interconversions among steroids, and indeed these have afforded a rather facile interpretation of experimental findings, it does appear that in the case of methylandrostenediol an explanation in these terms is well founded.