Ethisterone

Ethisterone

Clinical data
ATC code	G03DC04 (WHO)
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-cyclopenta[a]phenanthren-3-one
CAS Number	434-03-7 N
PubChem CID	5284557
ChemSpider	4447612 Y
UNII	Verifiedfields = changed P201BVY1MJ Verifiedfields = changed
ChEBI	CHEBI:34749 N
ChEMBL	ChEMBL241694 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C21H28O2
Molar mass	312.446 g/mol
3D model (JSmol)	Interactive image
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
NY (what is this?)  (verify)

WikiDoc Resources for Ethisterone
Articles
Most recent articles on Ethisterone Most cited articles on Ethisterone Review articles on Ethisterone Articles on Ethisterone in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Ethisterone Images of Ethisterone Photos of Ethisterone Podcasts & MP3s on Ethisterone Videos on Ethisterone
Evidence Based Medicine
Cochrane Collaboration on Ethisterone Bandolier on Ethisterone TRIP on Ethisterone
Clinical Trials
Ongoing Trials on Ethisterone at Clinical Trials.gov Trial results on Ethisterone Clinical Trials on Ethisterone at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Ethisterone NICE Guidance on Ethisterone NHS PRODIGY Guidance FDA on Ethisterone CDC on Ethisterone
Books
Books on Ethisterone
News
Ethisterone in the news Be alerted to news on Ethisterone News trends on Ethisterone
Commentary
Blogs on Ethisterone
Definitions
Definitions of Ethisterone
Patient Resources / Community
Patient resources on Ethisterone Discussion groups on Ethisterone Patient Handouts on Ethisterone Directions to Hospitals Treating Ethisterone Risk calculators and risk factors for Ethisterone
Healthcare Provider Resources
Symptoms of Ethisterone Causes & Risk Factors for Ethisterone Diagnostic studies for Ethisterone Treatment of Ethisterone
Continuing Medical Education (CME)
CME Programs on Ethisterone
International
Ethisterone en Espanol Ethisterone en Francais
Business
Ethisterone in the Marketplace Patents on Ethisterone
Experimental / Informatics
List of terms related to Ethisterone

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.