Conjugated estriol

Progynon was an orally active formulation of estrogen that was developed by Adolf Butenandt at Schering and introduced in Germany in 1928. It was reportedly the first sex hormone product and hence also the first estrogen product to be introduced for medical use. but Schering soon switched for economic reasons to using the urine of women who were in late pregnancy. Ayerst followed suit, with the introduction of Premarin (conjugated equine estrogens) in 1941. Both Progynon and Emmenin contained a mixture of water-soluble estrogens, which was determined later to be mostly estriol glucuronide. Conjugates of estriol like estriol glucuronide and estriol sulfate constitute more than 90% of the estrogens in the urine of pregnant women. Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate estriol sulfate glucuronide (probably estriol 3-sulfate 16α-glucuronide) also occurs. Progynon was also the name that Butenandt originally gave estrone (which he had isolated in 1929) in his first publication on the substance (and later referred to as folliculine, with the name estrone not finally being adopted until 1935). Aside from Progynon and Progynon 2, the Progynon name has also been used in a variety of other estrogenic products marketed by Schering, including Progynon-B (estradiol benzoate), Progynon-DH (estradiol; "dihydroxyestrin"), Progynon-DP (estradiol dipropionate), Progynon-C (ethinylestradiol), Progynova (estradiol valerate), and Progynon Depot (estradiol valerate, estradiol undecylate). ==Emmenin==

Emmenin was an orally active formulation of estrogen that was developed by James Collip at Ayerst and introduced in Canada in 1930 and the United States in 1934. At some point, it seems to have been changed to an extract of the urine of women who were in late pregnancy, which was equivalent in composition but was less expensive to source, and was essentially the same product as Progynon, a related estrogen developed by Adolf Butenandt at Schering and introduced in Germany. To reduce the costs of manufacturing Emmenin and Progynon, Ayerst and Schering eventually switched to using the urine of pregnant mares (which contains conjugated equine estrogens, primarily estrone sulfate) and called their new products Premarin and Progynon 2, respectively. Premarin was introduced by Ayerst in 1941 and has become not only a very widely used estrogen, but one of the most widely prescribed drugs in North America. Both Emmenin and Progynon contained a mixture of water-soluble conjugated estrogens, later determined to be mostly estriol glucuronide. Conjugates of estriol like estriol glucuronide and estriol sulfate constitute more than 90% of the estrogens in the urine of pregnant women. Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate estriol sulfate glucuronide (probably estriol 3-sulfate 16α-glucuronide) also occurs. Unlike unconjugated estrogens like estradiol and estrone, these estrogens were orally active. == See also ==