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 Number	434-03-7
ATC code	G03DC04 (WHO)
PubChem	CID 5284557
ChemSpider	4447612
UNII	Verifiedfields = changed P201BVY1MJ Verifiedfields = changed
ChEBI	CHEBI:34749
ChEMBL	CHEMBL241694
Synonyms	Ethindrone
Chemical data
Formula	C21H28O2
Molar mass	312.446 g/mol
SMILES O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]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 (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 pharmaceutical companies that had been members of the pre-World War II European hormone cartel (Ciba, Organon, Roussel).

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

See also

• Dimethisterone
• Noretynodrel

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–. ISBN 978-3-0348-8863-9. Cite uses deprecated parameter |coauthors= (help)

• Inhoffen HH, Logemann W, Hohlweg W, Serini A (May 4, 1938). "Untersuchungen in der Sexualhormon-Reihe (Investigations in the sex hormone series)" (abstract page). Ber Dtsch Chem Ges 71 (5): 1024–32. doi:10.1002/cber.19380710520.
• Petrow V (1970). "The contraceptive progestagens". Chem Rev 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492.
• 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. doi:10.1002/ejoc.200300813.
• Sneader, Walter (2005). "Hormone analogues". Drug discovery : a history. Hoboken NJ: John Wiley & Sons. pp. 188–225. ISBN 0-471-89980-1.
• 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.