Segesterone

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see segesterone acetate.
Segesterone
Clinical data
Other names17α-Hydroxy-16-methylene-19-norprogesterone; 16-Methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione; 17α-Deacetylnestorone
Identifiers
  • (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-16-methylidene-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O3
Molar mass328.452 g·mol−1
3D model (JSmol)
  • CC(=O)C1(C(=C)CC2C1(CCC3C2CCC4=CC(=O)CCC34)C)O
  • InChI=InChI=1S/C21H28O3/c1-12-10-19-18-6-4-14-11-15(23)5-7-16(14)17(18)8-9-20(19,3)21(12,24)13(2)22/h11,16-19,24H,1,4-10H2,2-3H3/t16-,17+,18+,19-,20-,21-/m0/s1
  • Key:SFLXYFZGKSGFKA-XUDSTZEESA-N

Segesterone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name),[1][2] also known as 17α-hydroxy-16-methylene-19-norprogesterone or as 17α-deacetylnestorone, is a steroidal progestin of the 19-norprogesterone group that was never marketed.[3] An acetate ester, segesterone acetate, better known as nestorone or elcometrine, is marketed for clinical use.[4] Segesterone acetate produces segesterone as a metabolite.[5]

References

  1. ^ International Nonproprietary Names for Pharmaceutical Substances (INN) (PDF). Vol. 17. World Health Organization. 2003. p. 210. Archived from the original (PDF) on 2022-01-20.
  2. ^ "7690-08-6 - SFLXYFZGKSGFKA-XUDSTZEESA-N - Segesterone [USAN:INN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". ChemIDplus. U.S. National Library of Medicine. Archived from the original on 2016-08-11. Retrieved 2016-06-17.
  3. ^ "Segesterone". PubChem. U.S. National Library of Medicine.
  4. ^ Zavod RM (24 January 2012). "Chapter 41: Women's Health". In Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1403–. ISBN 978-1-60913-345-0.
  5. ^ Prasad PV, Bashir M, Sitruk-Ware R, Kumar N (March 2010). "Single-dose pharmacokinetics of Nestorone, a potential female-contraceptive". Steroids. 75 (3): 252–264. doi:10.1016/j.steroids.2009.12.011. PMID 20064539. S2CID 205253216.


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