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Segesterone

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Chemical compound This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see segesterone acetate. Pharmaceutical compound
Segesterone
Clinical data
Other names17α-Hydroxy-16-methylene-19-norprogesterone; 16-Methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione; 17α-Deacetylnestorone
Identifiers
IUPAC name
  • (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-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O3
Molar mass328.452 g·mol
3D model (JSmol)
SMILES
  • CC(=O)C1(C(=C)CC2C1(CCC3C2CCC4=CC(=O)CCC34)C)O
InChI
  • 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), 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. An acetate ester, segesterone acetate, better known as nestorone or elcometrine, is marketed for clinical use. Segesterone acetate produces segesterone as a metabolite.

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.
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens


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