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Ethisterone

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Title: Ethisterone  
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Subject: Progestin, Progestin-induced virilisation, Danazol, Quingestanol acetate, Delmadinone acetate
Collection: Abandoned Drugs, Androgens, Progestogens, Steroids
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Ethisterone

Ethisterone
Systematic (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-cyclopenta[a]phenanthren-3-one
Identifiers
CAS Registry Number  N
ATC code G03
PubChem CID:
ChemSpider  Y
UNII  N
ChEBI  N
ChEMBL  Y
Chemical data
Formula C21H28O2
Molecular mass 312.446 g/mol
 N   

Ethisterone (INN, USAN, also known as pregneninolone, 17α-ethynyltestosterone, and 19-norandrostane, is a steroidal progestin. It is the 17α-ethynyl analog of testosterone, and 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. It was the first orally-active progestin.

Ethisterone was also marketed in the U.S. from the 1950s into the 1960s under a variety of trade names by other Roussel).

Ethisterone has weak androgenic effects similarly to the closely related progestin norethisterone.[1]

See also

References

  1. ^ Richard M. Eglen; Mont R. Juchau; Gillian Edwards; Arthur H. Weston, Helen Wise, M. D. Murray, D. Craig Brater, Olivier Valdenaire, Philippe Vernier, Annemarie Polak (6 December 2012). Progress in Drug Research: Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 72–.  
  • Inhoffen HH, Logemann W, Hohlweg W, Serini A (May 4, 1938). "Untersuchungen in der Sexualhormon-Reihe (Investigations in the sex hormone series)" (abstract page).  
  • Petrow V (1970). "The contraceptive progestagens". Chem Rev 70 (6): 713–26.  
  • Kugener, André (2004). Tabletten der Fa. Schering (Tablets of Schering AG) Proluton C tablets c. 1939
  • Quinkert G (2004). "Hans Herloff Inhoffen in His Times (1906-1992)" (abstract page). Eur J Org Chem 2004 (17): 3727–48.  
  • Sneader, Walter (2005). "Hormone analogues". Drug discovery : a history. Hoboken NJ: John Wiley & Sons. pp. 188–225.  
  • Djerassi C (2006). "Chemical birth of the pill". Am J Obstet Gynecol 194 (1): 290–8.  


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