Lilopristone

Lilopristone

Clinical data
Other names	ZK-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	97747-88-1
PubChem CID	13490845
ChemSpider	11644476
UNII	3GL26H7N6T
ChEMBL	ChEMBL1908329
CompTox Dashboard (EPA)	DTXSID801034575
Chemical and physical data
Formula	C29H37NO3
Molar mass	447.619 g·mol−1
3D model (JSmol)	Interactive image
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

Lilopristone (INN; development codes ZK-98734 and 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]

See also

• Aglepristone
• Onapristone
• Telapristone
• Toripristone

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

• Puri CP, Katkam RR, D'Souza A, Elger WA, Patil RK (September 1990). "Effects of progesterone antagonist, lilopristone (ZK 98.734), on induction of menstruation, inhibition of nidation, and termination of pregnancy in bonnet monkeys". Biology of Reproduction. 43 (3): 437–43. doi: 10.1095/biolreprod43.3.437 . PMID   2271724.
• Puri CP, Patil RK, Kholkute SD, Elger WA, Swamy XR (July 1989). "Progesterone antagonist lilopristone: a potent abortifacient in the common marmoset". American Journal of Obstetrics and Gynecology. 161 (1): 248–53. doi:10.1016/0002-9378(89)90274-3. PMID   2502015.