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History The recognition of progesterone's ability to suppress ovulation during pregnancy spawned a search for a similar hormone that could bypass the problems associated with administering progesterone (low bioavailability when administered orally and local irritation and pain when continually administered parenterally) and, at the same time, serve the purpose of controlling ovulation. The many synthetic hormones that resulted are known as progestins.

The first orally active progestin, ethisterone (pregneninolone, 17α-ethynyltestosterone), the 17α-ethynyl analog of testosterone, synthesized in 1938 from dehydroandrosterone by adding acetylene either before or after oxidation of the 3-OH group to the ketone, with rearrangement of the 5,6 double bond to the 4,5 position, by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg and Arthur Serini at Schering AG in Berlin, was marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone.<ref name="Inhoffen 1938">{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref><ref name="Maisel 1965">{{#invoke:citation/CS1|citation |CitationClass=book }}</ref><ref name="Petrow 1970">{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref><ref name="Sneader 2005">{{#invoke:citation/CS1|citation |CitationClass=book }}</ref><ref name="Djerassi 2006">{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>

A more potent orally active progestin, norethisterone (norethindrone, 19-nor-17α-ethynyltestosterone), the 19-nor analog of ethisterone, synthesized in 1951 by Carl Djerassi, Luis Miramontes, and George Rosenkranz at Syntex in Mexico City, was marketed by Parke-Davis in the U.S. in 1957 as Norlutin, and was used as the progestin in some of the first oral contraceptives (Ortho-Novum, Norinyl, etc.) in the early 1960s.<ref name="Maisel 1965">{{#invoke:citation/CS1|citation |CitationClass=book }}</ref><ref name="Maisel 1965"/><ref name="Petrow 1970"/><ref name="Sneader 2005"/><ref name="Djerassi 2006"/><ref name="Djerassi 1954">{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>

Norethynodrel, an isomer of norethisterone, was synthesized in 1952 by Frank B. Colton at Searle in Skokie, Illinois and used as the progestin in Enovid, marketed in the U.S. in 1957 and approved as the first oral contraceptive in 1960.<ref name="Maisel 1965"/><ref name="Petrow 1970"/><ref name="Sneader 2005"/><ref name="Djerassi 2006"/><ref name="Colton 1992">{{#invoke:Citation/CS1|citation |CitationClass=journal }}</ref>

Progestin sections
Intro  History  Examples  Classification by structure  Methods of progestin-based contraception  See also  References  

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