page_title: Diethylstilbestrol
section_title: Chemistry
hierarchical_section_title: Diethylstilbestrol / Chemistry
caption_attribution_description: English: I made this, anyone can use it. Made with Marvin JS. Chemical structures of the natural steroidal estrogen estradiol and the synthetic nonsteroidal estrogen diethylstilbestrol.
context_page_description: Diethylstilbestrol, also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is 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. Today, it is only used in the treatment of prostate cancer and less commonly breast cancer. While most commonly taken by mouth, DES was available for use by other routes as well, for instance, vaginal, topical, and by injection.
  DES 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, DES 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.
context_section_description: DES belongs to the stilbestrol (4,4'-dihydroxystilbene) group of compounds. It is a nonsteroidal open-ring analogue of the steroidal estrogen estradiol. DES can be prepared from anethole, which also happens to be weakly estrogenic. Anethole was demethylated to form anol and anol then spontaneously dimerized into dianol and hexestrol, with DES subsequently being synthesized via structural modification of hexestrol. As shown by X-ray crystallography, the molecular dimensions of DES are almost identical to those of estradiol, particularly in regards to the distance between the terminal hydroxyl groups.
caption: Chemical structures of estradiol and DES.[82] Note the preservation of the two hydroxyl groups in DES and the similar distance between them relative to estradiol, which is notable when it is considered that DES was discovered serendipitously.[82][83][84]
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