WordNet

any of a group of steroid hormones that have the effect of progesterone (同)progestogen

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/03/21 14:27:01」(JST)

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A progestin is a synthetic^[1] progestogen that has progestational effects similar to progesterone.^[2] The two most common 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 secondary amenorrhea, dysfunctional uterine bleeding and endometriosis, and as palliative treatment of endometrial cancer, renal cell carcinoma, breast cancer, and prostate cancer. High-dose megestrol acetate is used to treat anorexia, cachexia, and AIDS-related wasting.

Progesterone (or sometimes the progestin dydrogesterone or 17α-hydroxyprogesterone caproate) is used for luteal support in IVF protocols, questionably for treatment of recurrent pregnancy loss, and for prevention of preterm birth in pregnant women with a history of at least one spontaneous preterm birth.^[3] They are also used in judicial chemical castration of sex offenders as well as a treatment options for those suffering from paraphilia.

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.^[4]^[5]^[6]^[7]^[8]

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.^[5]^[5]^[6]^[7]^[8]^[9]

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.^[5]^[6]^[7]^[8]^[10]

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, Mirena), medroxyprogesterone (Provera, Depo-Provera), desogestrel, etonogestrel (Nexplanon), and drospirenone (Yasmin, Yasminelle, YAZ).

Sometimes progestins are classified by generation:

First (estrane): norethindrone, norethynodrel,^[11] norethindrone acetate, ethynodiol diacetate

Second (gonane): levonorgestrel, norethisterone,^[12] norgestrel

Third (gonane): desogestrel, gestodene, norgestimate, drospirenone^[12]

Fourth: dienogest, drospirenone, nestorone, nomegestrol acetate and trimegestone^[13]

Tanaproget is a non-steroidal progestin which is currently undergoing clinical trials.

Methods of progestin-based contraception

It has been found that the most effective method of hormonal contraception is with a combination of estrogen and progestin. This can be done in a monophasic, biphasic, or 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 that includes 6 or 7 inert tablets is used. 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 usually observed during the first 18 months of such therapy.

Alternatively, it can be delivered by intra-muscular injection every several months, implant or used as intrauterine system.

References

^ Merriam-Webster's medical Dictionary > progestin Retrieved on Feb 13, 2010
^ MedicineNet > progestin definition Last Editorial Review: 8/9/2003
^ Loose, Davis S.; Stancel, George M. (2006). "Estrogens and Progestins". In Brunton, Laurence L.; Lazo, John S.; Parker, Keith L. (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill. pp. 1541–71. ISBN 0-07-142280-3.
^ Inhoffen HH, Logemann W, Hohlweg W, Serini A (May 4, 1938). "Untersuchungen in der Sexualhormon-Reihe (Investigations in the sex hormone series)". Ber Dtsch Chem Ges 71 (5): 1024–32. doi:10.1002/cber.19380710520. http://www3.interscience.wiley.com/cgi-bin/abstract/112367144/ABSTRACT.
^ ^a ^b ^c ^d Maisel, Albert Q. (1965). The Hormone Quest. New York: Random House. OCLC 543168.
^ ^a ^b ^c Petrow V (1970). "The contraceptive progestagens". Chem Rev 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492.
^ ^a ^b ^c Sneader, Walter (2005). "Hormone analogues". Drug discovery : a history. Hoboken, NJ: John Wiley & Sons. pp. 188–225. ISBN 0-471-89980-1.
^ ^a ^b ^c Djerassi C (2006). "Chemical birth of the pill". Am J Obstet Gynecol 194 (1): 290–8. doi:10.1016/j.ajog.2005.06.010. PMID 16389046.
^ Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F (1954). "Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone" (PDF). J Am Chem Soc 76 (16): 4089–91. doi:10.1021/ja01645a009. http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1954/76/i16/f-pdf/f_ja01645a010.pdf.
^ Colton FB (1992). "Steroids and "the pill": early steroid research at Searle". Steroids 57 (12): 624–30. doi:10.1016/0039-128X(92)90015-2. PMID 1481226.
^ "Medscape.com". http://www.medscape.com/viewarticle/502371_5.
^ ^a ^b "Birth control options for women - Oral Contraception and Combination Hormonal Methods". http://www.umm.edu/patiented/articles/what_oral_contraceptives_000091_2.htm. Retrieved 2010-04-01.
^ Sitruk-Ware R (2004). "New progestogens: a review of their effects in perimenopausal and postmenopausal women". Drugs Aging 21 (13): 865–83. PMID 15493951.

UpToDate Contents

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1. エストロゲン・プロゲスチン避妊剤の使用に関する概要 overview of the use of estrogen progestin contraceptives
2. 閉経期のホルモン療法で用いる製剤 preparations for menopausal hormone therapy
3. 避妊の概要 overview of contraception
4. 自然早産のリスクを低下させるためのプロゲステロン補充 progesterone supplementation to reduce the risk of spontaneous preterm birth
5. 子宮内避妊（IUD）：概要 intrauterine contraception iud overview

English Journal

Low-dose gold nanoparticles exert subtle endocrine-modulating effects on the ovarian steroidogenic pathway ex vivo independent of oxidative stress.

Larson JK1, Carvan MJ 3rd, Teeguarden JG, Watanabe G, Taya K, Krystofiak E, Hutz RJ.
Nanotoxicology.Nanotoxicology.2014 Dec;8(8):856-66. doi: 10.3109/17435390.2013.837208.
Gold nanoparticles (GNPs) have gained considerable attention for application in science and industry. However, the untoward effects of such particles on female fertility remain unclear. The objectives of this study were to (1) examine the effects of 10-nm GNPs on progesterone and estradiol-17β accu
PMID 23992423

Risks of Endometrial Cancer Associated With Different Hormone Replacement Therapies in the E3N Cohort, 1992-2008.

Fournier A, Dossus L, Mesrine S, Vilier A, Boutron-Ruault MC, Clavel-Chapelon F, Chabbert-Buffet N.
American journal of epidemiology.Am J Epidemiol.2014 Sep 1;180(5):508-17. doi: 10.1093/aje/kwu146. Epub 2014 Jul 9.
We assessed whether different oral progestogens in hormone replacement therapy may differentially affect the risk of endometrial cancer, using data from the Etude Epidémiologique auprès de femmes de l'Education Nationale (E3N), a French cohort study (1992-2008). Hazard ratios and their confidence
PMID 25008104

The progestin levonorgestrel disrupts gonadotropin expression and sex steroid levels in pubertal roach (Rutilus rutilus).

Kroupova HK1, Trubiroha A2, Lorenz C2, Contardo-Jara V3, Lutz I2, Grabic R4, Kocour M4, Kloas W5.
Aquatic toxicology (Amsterdam, Netherlands).Aquat Toxicol.2014 Sep;154:154-62. doi: 10.1016/j.aquatox.2014.05.008. Epub 2014 May 17.
The aim of the present study was to investigate the effects of the synthetic progestin levonorgestrel (LNG) on the reproductive endocrine system of a teleost fish, the roach (Rutilus rutilus). Pubertal roach were exposed for 28 days in a flow-through system to four concentrations of LNG (3, 31, 312,
PMID 24893273

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★リンクテーブル★

リンク元	「プロゲスチン」「progestational agent」
拡張検索	「progestin therapy」「synthetic progestin」「estrogen-progestin challenge test」

「プロゲスチン」

　　[★]

英: progestin
同: ゲスターゲン gestagen、プロゲスターゲン progestogen、黄体ホルモン作用物質 progestational agent、プロゲステロン作用薬

[show details]

プロゲスチン : 約 21,300 件
プロゲストーゲン : 約 10,300 件
プロゲスターゲン : 約 904 件
ゲスターゲン : 約 4,090 件

卵巣の黄体から分泌される黄体ホルモンと同様の黄体ホルモン活性を有する物質の総称。黄体ホルモン活性を持つ天然のものがプロゲステロン
妊娠の維持、月経異常などに用いられる。また経口避妊薬としても用いられる。

「progestational agent」

　　[★]

プロゲステロン作用薬

関: gestagen、progestagen、progestin、progestogen

「progestin therapy」

　　[★]

プロゲステロン療法、黄体ホルモン療法

「synthetic progestin」

　　[★]

合成プロゲスチン

関: progesterone congener

「estrogen-progestin challenge test」

　　[★] エストロゲン・プロゲスチン負荷テスト

[merriam-webster-1] Merriam-Webster's medical Dictionary > progestin Retrieved on Feb 13, 2010

[2] MedicineNet > progestin definition Last Editorial Review: 8/9/2003

[Loose_2006-3] Loose, Davis S.; Stancel, George M. (2006). "Estrogens and Progestins". In Brunton, Laurence L.; Lazo, John S.; Parker, Keith L. (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill. pp. 1541–71. ISBN 0-07-142280-3.

[Inhoffen_1938-4] Inhoffen HH, Logemann W, Hohlweg W, Serini A (May 4, 1938). "Untersuchungen in der Sexualhormon-Reihe (Investigations in the sex hormone series)". Ber Dtsch Chem Ges 71 (5): 1024–32. doi:10.1002/cber.19380710520. http://www3.interscience.wiley.com/cgi-bin/abstract/112367144/ABSTRACT.

[Maisel_1965-5] Maisel, Albert Q. (1965). The Hormone Quest. New York: Random House. OCLC 543168.

[Petrow_1970-6] Petrow V (1970). "The contraceptive progestagens". Chem Rev 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492.

[Sneader_2005-7] Sneader, Walter (2005). "Hormone analogues". Drug discovery : a history. Hoboken, NJ: John Wiley & Sons. pp. 188–225. ISBN 0-471-89980-1.

[Djerassi_2006-8] Djerassi C (2006). "Chemical birth of the pill". Am J Obstet Gynecol 194 (1): 290–8. doi:10.1016/j.ajog.2005.06.010. PMID 16389046.

[Djerassi_1954-9] Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F (1954). "Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone" (PDF). J Am Chem Soc 76 (16): 4089–91. doi:10.1021/ja01645a009. http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1954/76/i16/f-pdf/f_ja01645a010.pdf.

[Colton_1992-10] Colton FB (1992). "Steroids and "the pill": early steroid research at Searle". Steroids 57 (12): 624–30. doi:10.1016/0039-128X(92)90015-2. PMID 1481226.

[urlMedscape.com-11] "Medscape.com". http://www.medscape.com/viewarticle/502371_5.

[urlBirth_control_options_for_women_-_Oral_Contraception_and_Combination_Hormonal_Methods-12] "Birth control options for women - Oral Contraception and Combination Hormonal Methods". http://www.umm.edu/patiented/articles/what_oral_contraceptives_000091_2.htm. Retrieved 2010-04-01.

[pmid15493951-13] Sitruk-Ware R (2004). "New progestogens: a review of their effects in perimenopausal and postmenopausal women". Drugs Aging 21 (13): 865–83. PMID 15493951.

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progestin