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
Clinical data
Identifiers
CAS Registry Number	434-03-7 N
ATC code	G03DC04
PubChem	CID 5284557
ChemSpider	4447612 Y
UNII	Verifiedfields = changed P201BVY1MJ Verifiedfields = changed N
ChEBI	CHEBI:34749 N
ChEMBL	CHEMBL241694 Y
Chemical data
Formula	C21H28O2
Molecular 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  Y Key:CHNXZKVNWQUJIB-CEGNMAFCSA-N  Y
N (what is this?)  (verify)

Ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane) is a 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).

Synthesis

Ethisterone is made by the ethynylation of androstenolone with acetylene and successive oxidation of the hydroxyl group at C₃ of the steroid system.

U.S. Patent 2,272,131 U.S. Patent 4,041,055

References

• 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.