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Lonaprisan

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Lonaprisan
Clinical data

Other names	ZK-230211; BAY 86-5044; ZK-PRA; 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one
Routes of administration	Oral
Identifiers
IUPAC name (8S,11R,13S,14S,17S)-11-(4-acetylphenyl)-17-hydroxy-13-methyl-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CAS Number	211254-73-8
PubChem CID	6918548
ChemSpider	5293745
UNII	F5Z5EL4D26
KEGG	D10016
ChEMBL	ChEMBL146032
CompTox Dashboard (EPA)	DTXSID60893551
ECHA InfoCard	100.190.674
Chemical and physical data
Formula	C₂₈H₂₉F₅O₃
Molar mass	508.529 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)C1=CC=C(C=C1)[C@H]2C[C@]3([C@@H](CC[C@]3(C(C(F)(F)F)(F)F)O)[C@H]4C2=C5CCC(=O)C=C5CC4)C
InChI InChI=1S/C28H29F5O3/c1-15(34)16-3-5-17(6-4-16)22-14-25(2)23(11-12-26(25,36)27(29,30)28(31,32)33)21-9-7-18-13-19(35)8-10-20(18)24(21)22/h3-6,13,21-23,36H,7-12,14H2,1-2H3/t21-,22+,23-,25-,26-/m0/s1 Key:VHZPUDNSVGRVMB-RXDLHWJPSA-N

Lonaprisan (INN, USAN) (developmental code names ZK-230211, BAY 86-5044, ZK-PRA) is a synthetic, steroidal antiprogestogen which was under development by Bayer HealthCare Pharmaceuticals for the treatment of endometriosis, dysmenorrhea, and breast cancer but was discontinued.^[1]^[2]^[3] It is a potent and highly selective silent antagonist of the progesterone receptor (PR).^[2]^[3]^[4] The drug reached phase II clinical trials prior to its discontinuation.^[1]

References[edit]

^ ^a ^b "Lonaprisan - AdisInsight". adisinsight.springer.com.

^ ^a ^b Whitaker LH, Williams AR, Critchley HO (2014). "Selective progesterone receptor modulators". Curr. Opin. Obstet. Gynecol. 26 (4): 237–42. doi:10.1097/GCO.0000000000000082. PMID 24950125. S2CID 37474964.

^ ^a ^b Pluchino N, Freschi L, Wenger JM, Streuli I (2016). "Innovations in classical hormonal targets for endometriosis". Expert Rev Clin Pharmacol. 9 (2): 317–27. doi:10.1586/17512433.2016.1129895. PMID 26645363. S2CID 8624056.

^ Busia L, Faus H, Hoffmann J, Haendler B (2011). "The antiprogestin Lonaprisan inhibits breast cancer cell proliferation by inducing p21 expression". Mol. Cell. Endocrinol. 333 (1): 37–46. doi:10.1016/j.mce.2010.11.034. PMID 21138753. S2CID 12818061.