Segesterone

Segesterone (INN, USAN),[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]

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see segesterone acetate.

Segesterone

Clinical data
Other names	17α-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-cyclopenta[a]phenanthren-3-one
CAS Number	7690-08-6
PubChem CID	11823650
ChemSpider	9998301
UNII	09Q5UV3747
KEGG	D10987
ChEMBL	ChEMBL2107778
CompTox Dashboard (EPA)	DTXSID00998190
Chemical and physical data
Formula	C21H28O3
Molar mass	328.452 g·mol^−1
3D model (JSmol)	Interactive image
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

References

1. http://www.who.int/medicines/publications/druginformation/innlists/PL89.pdf
2. http://chem.sis.nlm.nih.gov/chemidplus/rn/7690-08-6
3. https://pubchem.ncbi.nlm.nih.gov/compound/11823650
4. Thomas L. Lemke; David A. Williams (24 January 2012). 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 (2010). "Single-dose pharmacokinetics of Nestorone, a potential female-contraceptive". Steroids. 75 (3): 252–64. doi:10.1016/j.steroids.2009.12.011. PMID 20064539.