<unk>  <unk> , also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for women with a history of recurrent miscarriage, hormone therapy for menopausal symptoms and estrogen deficiency in women, treatment of prostate cancer in men and breast cancer in women, and other uses. By 2007, it was only used in the treatment of prostate cancer and breast cancer. In 2011, Hoover and colleagues reported on adverse health outcomes linked to<unk>  including infertility, miscarriage, ectopic pregnancy, preeclampsia, preterm birth, stillbirth, infant death, menopause prior to age 45, breast cancer, cervical cancer, and vaginal cancer. While most commonly taken by mouth,<unk>  was available for use by other routes as well, for instance, vaginal, topical, and by injection.<unk>  is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. It is a synthetic and nonsteroidal estrogen of the stilbestrol group, and differs from the natural estrogen estradiol in various ways. Compared to estradiol,<unk>  has greatly improved bioavailability when taken by mouth, is more resistant to metabolism, and shows relatively increased effects in certain parts of the body like the liver and uterus. These differences result in<unk>  having an increased risk of blood clots, cardiovascular issues, and certain other adverse effects.<unk>  was discovered in 1938 and introduced for medical use in 1939. From about 1940 to 1971, the medication was given to pregnant women in the incorrect belief that it would reduce the risk of pregnancy complications and losses. In 1971,<unk>  was shown to cause clear-cell carcinoma, a rare vaginal tumor, in girls and women who had been exposed to this medication in utero. The United States Food and Drug Administration subsequently withdrew approval of<unk>  as a treatment for pregnant women. Follow-up studies have indicated that<unk>  also has the potential to cause a variety of significant adverse medical complications during the lifetimes of those exposed. The United States National Cancer Institute recommends women born to mothers who took<unk>  to undergo special medical exams on a regular basis to screen for complications as a result of the medication. Individuals who were exposed to<unk>  during their mothers' pregnancies are commonly referred to as "DES daughters" and "DES sons". Since the discovery of the toxic effects of<unk> , it has largely been discontinued and is now mostly no longer marketed.
Diethylstilbestrol
Stilbestrol
Polydiethylstilbestrol phosphate
Ethinylestradiol sulfonate
Ethinylestradiol sulfate
Ethinylestradiol
Chloromethylandrostenediol
Estradiol dienantate