Ethisterone

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Ethisterone
Ethisterone.png
Etisterona3D.png
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
Legal status
?
Identifiers
CAS number 434-03-7 N
ATC code G03DC04
PubChem CID 5284557
ChemSpider 4447612 YesY
UNII Verifiedfields = changed P201BVY1MJ Verifiedfields = changed N
ChEBI CHEBI:34749 N
ChEMBL CHEMBL241694 YesY
Chemical data
Formula C21H28O2 
Mol. mass 312.446 g/mol
 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[edit]

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[edit]