EPIMESTROL

Originator

Stimovul,Organon,W. Germany,1976

The Uses of EPIMESTROL

Anterior pituitary activator.

Definition

ChEBI: Epimestrol is a steroid. It derives from a hydride of an estrane.

Manufacturing Process

Reduction of 16-keto-17(α)-hydroxyestratrienol-3-methyl to 16,17- dihydroxyestratrienol-3-methyl ether: A solution of 800 mg of the alpha ketol methyl ether in 100 cc of ethanol and 10 cc of acetic acid was carefully maintained at 40°C (water bath), and 200 g of freshly prepared sodium amalgam (2%) were added in small pieces with efficient swirling. Before all ofthe amalgam had been added, a precipitation of sodium acetate occurred, and at this point an additional 100 cc of 50% acetic acid were added. After all the reducing agent had been added, the mixture was transferred to a separatory funnel with ether and water. The mercury plus aqueous phase was separated, after partitioning, from the ether; the latter may be further washed with water, with 0.5N sodium hydroxide, and again with water to purify the alpha glycol. Evaporation of the ethereal phase yielded a crystalline residue of the isomeric transoid (16(β),17(α)-dihydroxy-steroid-3-methyl ether and cisoid 16(α),17(α)dihydroxy-steroid-3-methyl ether.

Therapeutic Function

Anterior pituitary activator