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Ethisterone: Difference between revisions

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'''Ethisterone''' is a ] hormone. '''Ethisterone''' is a ] hormone.


The first orally active ], ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-] analog of ], was ] in ] by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at ] in ] and marketed in ] in 1939 as ''Proluton C'' and by ] in the ] in 1945 as ''Pranone''. The first orally active ], ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-] analog of ], was ] in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at ] in ] and marketed in ] in 1939 as ''Proluton C'' and by ] in the ] in 1945 as ''Pranone''.


Ethisterone was also marketed in the U.S. from the 1950s into the 1960s under a variety of trade names by other ] that had been members of the pre-] European hormone ] (], ], ]). Ethisterone was also marketed in the U.S. from the 1950s into the 1960s under a variety of trade names by other ] that had been members of the pre-] European hormone ] (], ], ]).
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* {{cite journal |doi=10.1002/cber.19380710520 |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=] |volume=71 |issue=5 |pages=1024–32 |url=http://www3.interscience.wiley.com/cgi-bin/abstract/112367144/ABSTRACT |format=abstract page}} * {{cite journal |doi=10.1002/cber.19380710520 |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=] |volume=71 |issue=5 |pages=1024–32 |url=http://www3.interscience.wiley.com/cgi-bin/abstract/112367144/ABSTRACT |format=abstract page}}
* {{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}} * {{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}}
* Kugener, André (2004). () ''Proluton C'' tablets circa 1939 * Kugener, André (2004). () ''Proluton C'' tablets c. 1939
* {{cite journal |author=Quinkert G |year=2004 |title=Hans Herloff Inhoffen in His Times (1906-1992) |journal=Eur J Org Chem |volume=2004 |issue=17 |pages=3727–48 |url=http://www3.interscience.wiley.com/cgi-bin/abstract/109594495/ABSTRACT |doi=10.1002/ejoc.200300813 |format=abstract page}} * {{cite journal |author=Quinkert G |year=2004 |title=Hans Herloff Inhoffen in His Times (1906-1992) |journal=Eur J Org Chem |volume=2004 |issue=17 |pages=3727–48 |url=http://www3.interscience.wiley.com/cgi-bin/abstract/109594495/ABSTRACT |doi=10.1002/ejoc.200300813 |format=abstract page}}
* {{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=188–225}} * {{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=188–225}}
* {{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}} * {{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}}




{{Sex hormones}} {{Sex hormones}}

Revision as of 07:23, 3 February 2012

Pharmaceutical compound
Ethisterone
Clinical data
ATC code
Identifiers
IUPAC name
  • (8R,9S,10R,13R,14S,17R)-17-Ethynyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.452 Edit this at Wikidata
Chemical and physical data
FormulaC21H28O2
Molar mass312.446 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C4\C=C3/(2CC1((CC1(C#C)O)2CC3)C)(C)CC4
InChI
  • InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
  • Key:CHNXZKVNWQUJIB-CEGNMAFCSA-N
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Ethisterone is a progestogen hormone.

The first orally active progestin, ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-ethynyl analog of testosterone, was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering AG in Berlin and marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone.

Ethisterone was also marketed in the U.S. from the 1950s into the 1960s under a variety of trade names by other pharmaceutical companies that had been members of the pre-World War II European hormone cartel (Ciba, Organon, Roussel).

References

Template:Sex hormones


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