Therapeutically diethylstilbestrol

The compound shown is diethylstilbestrol (DES) it has a number of therapeutic uses in estrogen replacement therapy DES is not a steroid but can adopt a shape that allows it to mimic estrogens such as estradiol (p 1100) and bind to the same receptor sites Construct molecular models of DES and estradiol that illustrate this similanty in molecular size shape and location of polar groups... 

The parenteral formulation diethylstilbestrol diphosphate is less commonly used than the oral formulation. In Japan, 24 elderly patients with advanced relapsed prostatic cancer were treated with high doses supplemented with ethi-nylestradiol (doses unclear) there was some slight therapeutic effect, but there were gastrointestinal symptoms and fluid retention (48). Also in Japan, a few patients with advanced disease were treated using intravenous diethylstilbestrol diphosphate 500 mg/day for 20 consecutive days to a total dose of 10 g the authors conclusion was more positive but adverse events were not specified (49). 

Dieckmann WJ, Davis ME, Rynkiewicz LM, Pottinger RE. Does the administration of diethylstilbestrol during pregnancy have therapeutic value Am J Obstet Gynecol 1953 66(5) 1062-81. 

Diethylstilbestrol Sustaining pregnancy (discontinued) and cancer therapeutic (discontinued) 400... 

The steroid nucleus is not required for estrogenic action. Several derivatives of stilbene (diphenylethylene) that were used therapeutically demonstrate potent estrogenic activity. Diethylstilbestrol (DES), prepared in 1939, was one of these stilbenes (Fig. 46.8). A trans stilbene, DES has 10-fold the estrogenic potency of its cis isomer, largely because the trans isomer more closely resembles estradiol (20). Unfortunately, when DES was administered to relieve pregnancy-related symptoms, it was correlated with abnormal growth in the offspring. 

V. Gimenez, C. James, A. Arminan, R. Schweins, A. Paul, M. Vicent, Demonstrating the importance of polymer-conjugate conformation in solution on its therapeutic output diethylstilbestrol (DES)-polyacetals as prostate cancer treatment, J. Control. Release 159 (2012) 290-301. 

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