Lilopristone

Lilopristone (INN) (developmental code names ZK-98734, ZK-734) is a synthetic, steroidal antiprogestogen with additional antiglucocorticoid activity which was developed by Schering and was patented in 1985.[1][2][3][4] It is described as an abortifacient and endometrial contraceptive.[1][4][5] The drug differs from mifepristone only in the structure of its C17α side chain, and is said to have much reduced antiglucocorticoid activity in comparison.[6]

Lilopristone
Clinical data
Other namesZK-98734; ZK-734; 11β-(4-(Dimethylamino)phenyl)-17β-hydroxy-17α-((Z)-3-hydroxypropenyl)estra-4,9-dien-3-one
Identifiers
IUPAC name
  • (8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-[(Z)-3-hydroxyprop-1-enyl]-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC29H37NO3
Molar mass447.619 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12C[C@@H](C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(/C=C\CO)O)C5=CC=C(C=C5)N(C)C
InChI
  • InChI=1S/C29H37NO3/c1-28-18-25(19-5-8-21(9-6-19)30(2)3)27-23-12-10-22(32)17-20(23)7-11-24(27)26(28)13-15-29(28,33)14-4-16-31/h4-6,8-9,14,17,24-26,31,33H,7,10-13,15-16,18H2,1-3H3/b14-4-/t24-,25+,26-,28-,29-/m0/s1
  • Key:RCOWGILQXUPXEW-FUSOFXSQSA-N

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 733–. ISBN 978-1-4757-2085-3.
  2. Rao KA (November 2009). Textbook of Gynaecology. Elsevier India. pp. 187–. ISBN 978-81-312-1526-5.
  3. Baird DT, Schütz G, Krattenmacher R (9 March 2013). Organ-Selective Actions of Steroid Hormones. Springer Science & Business Media. pp. 108–. ISBN 978-3-662-09153-1.
  4. Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 23–. ISBN 978-1-351-78989-9.
  5. Deshpande H (12 February 2016). Practical Management of Ovulation Induction. JP Medical Ltd. pp. 29–. ISBN 978-93-5250-028-4.
  6. Van Look PF, Pérez-Palacios G, World Health Organization (1994). Contraceptive research and development, 1984 to 1994: the road from Mexico City to Cairo and beyond. Oxford University Press. p. 169. ISBN 978-0-19-563630-7. [...] lilopristone, which differs from mifepristone only in the structure of the 17a side chain, is said to have a much reduced antiglucocorticoid activity (Neef et al., 1984).

Further reading
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