Progestin 239990 225140403 2008-07-12T02:32:56Z Fennec 39197 Removed commentary on article correctness (moving to talk page) [[Image:miramontes notebook.jpg|thumb|right|250px|Co-inventor [[Luis E. Miramontes]] signed laboratory notebook. October 15, 1951]] A '''progestin''' is a [[Chemical synthesis|synthetic]] [[progestogen]] that has some biological activity similar to [[progesterone]]. The two most frequent uses of progestins are for [[hormonal contraception]] (either alone or with an [[estrogen]]), and to prevent [[endometrial hyperplasia]] from unopposed estrogen in [[hormone replacement therapy]]. Progestins are also used to treat [[amenorrhoea#Secondary amenorrhoea|secondary amenorrhea]], [[dysfunctional uterine bleeding]] and [[endometriosis]], and as [[palliative care|palliative]] treatment of [[endometrial cancer]], [[renal cell carcinoma]], [[breast cancer]], and [[prostate cancer]]. High dose [[megestrol acetate]] is used to treat [[anorexia (symptom)|anorexia]], [[cachexia]] and [[AIDS]]-related [[wasting]]. Progesterone (or sometimes the progestin [[dydrogesterone]] or [[17-Hydroxyprogesterone caproate|17α-hydroxyprogesterone caproate]]) is used for [[corpus luteum|luteal]] support in [[in vitro fertilisation|IVF]] protocols, questionably for treatment of [[habitual abortion|recurrent pregnancy loss]], and for prevention of [[premature birth|preterm birth]] in pregnant women with a history of at least one spontaneous preterm birth.<!-- --><ref name="Loose 2006">{{cite book |author=Loose, Davis S.; Stancel, George M. |editor=Brunton, Laurence L.; Lazo, John S.; Parker, Keith L. (eds.) |year=2006 |chapter=Estrogens and Progestins |title=Goodman & Gilman's The Pharmacological Basis of Therapeutics |edition=11th ed. |pages=pp. 1541-71 |location=New York |publisher=McGraw-Hill |id=ISBN 0-07-142280-3}}</ref> ==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 radical|ethynyl]] analog of [[testosterone]], [[chemical synthesis|synthesized]] in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg and Arthur Serini at [[Schering|Schering AG]] in [[Berlin]], was marketed in [[Germany]] in 1939 as ''Proluton C'' and by [[Schering-Plough|Schering]] in the [[United States|U.S.]] in 1945 as ''Pranone''<!-- --><ref name="Inhoffen 1938">{{cite journal |author=Inhoffen HH, Logemann W, Hohlweg W, Serini A |month=May 4, |year=1938 |title=Untersuchungen in der Sexualhormon-Reihe (Investigations in the sex hormone series) |journal=[[Chemische Berichte|Ber Dtsch Chem Ges]] |volume=71 |issue=5 |pages=1024–32|url=http://www3.interscience.wiley.com/cgi-bin/abstract/112367144/ABSTRACT}}</ref><!-- --><ref name="Maisel 1965">{{cite book |author=Maisel, Albert Q. |year=1965 |title=The Hormone Quest |location=New York |publisher=Random House |oclc=543168 }}</ref><!-- --><ref name="Petrow 1970">{{cite journal |author=Petrow V |year=1970 |title=The contraceptive progestagens |journal=Chem Rev |volume=70 |issue=6 |pages=713–26 |pmid=4098492 |doi=10.1021/cr60268a004}}</ref><!-- --><ref name="Sneader 2005">{{cite book |author=Sneader, Walter |year=2005 |title=Drug discovery : a history |location=Hoboken, NJ |publisher=John Wiley & Sons |isbn=0-471-89980-1 |chapter=Hormone analogues |pages=pp. 188-225}}</ref><!-- --><ref name="Djerassi 2006">{{cite journal |author=Djerassi C |year=2006 |title=Chemical birth of the pill |journal=Am J Obstet Gynecol |volume=194 |issue=1 |pages=290–8 |pmid=16389046 |doi=10.1016/j.ajog.2005.06.010}}</ref> A more potent orally active progestin, [[norethisterone]] (norethindrone, 19-nor-17α-ethynyltestosterone), the 19-[[nor-|nor]] analog of ethisterone, synthesized in 1951 by [[Carl Djerassi]], [[Luis E. Miramontes|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 [[combined oral contraceptive pill|first oral contraceptives]] (''Ortho-Novum'', ''Norinyl'', etc.) in the early 1960s.<!-- --><ref name="Maisel 1965">{{cite book |author=Maisel, Albert Q. |year=1965 |title=The Hormone Quest |location=New York |publisher=Random House}}</ref><!-- --><ref name="Maisel 1965"/><!-- --><ref name="Petrow 1970"/><!-- --><ref name="Sneader 2005"/><!-- --><ref name="Djerassi 2006"/><!-- --><ref name="Djerassi 1954">{{cite journal |author=Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F |year=1954 |title=Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone |journal=[[Journal of the American Chemical Society|J Am Chem Soc]] |volume=76 |issue=16 |pages=4089–91 |url=http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1954/76/i16/f-pdf/f_ja01645a010.pdf |doi=10.1021/ja01645a009}}</ref> [[Norethynodrel]], an [[isomer]] of norethisterone, was synthesized in 1952 by [[Frank B. Colton]] at [[G. D. Searle & Company|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">{{cite journal |author=Colton FB |year=1992 |title=Steroids and "the pill": early steroid research at Searle |journal=Steroids |volume=57 |issue=12 |pages=624–30 |pmid=1481226 |doi=10.1016/0039-128X(92)90015-2}}</ref> ==Examples== Some examples of progestins that have been used in hormonal contraceptives are [[norethynodrel]] (Enovid), [[norethindrone]] (many brand names, most notably Ortho-Novum and Ovcon) [[norgestimate]] (Ortho Tricyclen, Ortho-Cyclen), [[norgestrel]], [[levonorgestrel]] (Alesse, Trivora-28, [[Plan B]]), [[medroxyprogesterone]] (Provera, Depo-Provera), [[desogestrel]], and [[drospirenone]] (Yasmin, Yasminelle, YAZ). == Methods of progestin-based contraception == It has been found that the most effective method of contraception was with a combination of [[estrogen]] and progestin. This can be done in a monophasic, biphasic, or in a triphasic manner. In the monophasic method, both an estrogen and a progestin are administered for 20 or 21 days and stopped for a 7 or 8 day period that includes the 5 day menstrual period. Sometimes, a 28 day regimen is used that includes 6 or 7 inert tablets. Newer biphasic and triphasic methods are now used to more closely simulate the normal menstrual cycle. Yet another method is to administer a small dose of progestin only (no estrogen) in order to decrease certain risks associated with administering estrogen, but a major side effect is irregular bleeding that is usually observed during the first 18 months of such therapy. ==See also== [[List of steroid abbreviations]] ==References== {{Reflist}} [[Category:Progestagens]] [[es:Levonorgestrel]] [[fr:Progestagène de synthèse]] [[lt:Progestinas]] [[nl:Progestativum]] [[no:Progestin]] [[pt:Progestina]]