6,6-Difluoronorethisterone

6,6-Difluoronorethisterone, also known as 6,6-difluoro-17α-ethynyl-19-nortestosterone or as 6,6-difluoro-17α-ethynylestr-4-en-17β-ol-3-one, is a steroidal progestin of the 19-nortestosterone group that was described in 1971 but was never marketed.[1][2][3] It is a fluorinated derivative of norethisterone. The C17β acetate ester, 6,6-difluoronorethisterone acetate, has also been synthesized and described.[1]

6,6-Difluoronorethisterone
Clinical data
Other names6,6-Difluoro-17α-ethynyl-19-nortestosterone; 6,6-Difluoro-17α-ethynylestr-4-en-17β-ol-3-one
Identifiers
IUPAC name
  • (1S,2R,10R,11S,14S,15S)-14-Ethynyl-8,8-difluoro-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
CAS Number
Chemical and physical data
FormulaC20H24F2O2
Molar mass334.407 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@@H](CC(F)(F)C4=CC(=O)CC[C@H]34)[C@@H]1CC[C@]2(O)C#C
InChI
  • InChI=1S/C20H24F2O2/c1-3-19(24)9-7-16-15-11-20(21,22)17-10-12(23)4-5-14(17)13(15)6-8-18(16,19)2/h1,10,13-16,24H,4-9,11H2,2H3/t13-,14-,15-,16+,18?,19-/m1/s1
  • Key:ZNTYQLFNPTXSPS-ZBWOJIPPSA-N

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 522–. ISBN 978-1-4757-2085-3.
  2. Overton KH (January 1973). Terpenoids and Steroids. Royal Society of Chemistry. pp. 432–. ISBN 978-0-85186-276-7.
  3. Morrow DF, Gallo D (January 1972). "Steroids and Biologically Related Compounds.". In Pachter I (ed.). Annual Reports in Medicinal Chemistry. Vol. 7. Academic Press. pp. 182-193 (187). ISBN 978-0-08-058351-8.


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