Ethisterone - Misplaced Pages

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Revision as of 16:51, 29 October 2011 by CheMoBot (talk | contribs) (Updating {{drugbox}} (changes to verified fields - updated 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs))(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound

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-cyclopentaphenanthren-3-one
CAS Number	434-03-7
PubChem CID	5284557
ChemSpider	4447612
UNII	Verifiedfields = changed P201BVY1MJ Verifiedfields = changed
ChEMBL	ChEMBL241694
CompTox Dashboard (EPA)	DTXSID2023016
ECHA InfoCard	100.006.452
Chemical and physical data
Formula	C₂₁H₂₈O₂
Molar mass	312.446 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C4\C=C3/(2CC1((CC1(C#C)O)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 is a progestogen hormone.

The first orally active progestin, ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-ethynyl analog of testosterone, 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.

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).

References

Inhoffen HH, Logemann W, Hohlweg W, Serini A (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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 circa 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.

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