Methenmadinone

Methenmadinone, also known as deacetylsuperlutin or as 16-methylene-6-dehydro-17α-hydroxyprogesterone, is a pregnane steroid which was never marketed.[1][2][3] It is a parent compound of methenmadinone acetate (the C17α acetate ester), melengestrol (the C6 methyl derivative), and chlormethenmadinone (the C6 chloro derivative).[1][2]

Methenmadinone
Clinical data
Other namesDeacetylsuperlutin; 16-Methylene-6-dehydro-17α-hydroxyprogesterone; 16-Methylenepregna-4,6-diene-3,20-dione; 16-Methyl-4,6,16-pregnatriene-3,20-dione
Drug classProgestogen; Progestin
Identifiers
IUPAC name
  • (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-16-methylidene-2,8,9,11,12,14,15,17-octahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
Chemical and physical data
FormulaC22H28O2
Molar mass324.464 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)[C@H]1C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@]34C)C
InChI
  • InChI=1S/C22H28O2/c1-13-11-19-17-6-5-15-12-16(24)7-9-21(15,3)18(17)8-10-22(19,4)20(13)14(2)23/h5-6,12,17-20H,1,7-11H2,2-4H3/t17-,18+,19+,20-,21+,22+/m1/s1
  • Key:SLRUDSFURBMIQT-HQZKGGBDSA-N

References
  1. G.W.A Milne (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–. ISBN 978-1-351-74347-1.
  2. George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1572–. ISBN 978-1-351-78989-9.
  3. Shapiro EL, Weber L, Harris H, Miskowicz C, Neri R, Herzog HL (July 1972). "Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17 -hydroxyprogesterones". J. Med. Chem. 15 (7): 716–20. doi:10.1021/jm00277a006. PMID 5043870.



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