lonaprisan

{{Short description|Chemical compound}}

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| 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

| image = Lonaprisan skeletal.svg

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| routes_of_administration = Oral

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| CAS_number = 211254-73-8

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| PubChem = 6918548

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| ChemSpiderID = 5293745

| UNII = F5Z5EL4D26

| KEGG = D10016

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| ChEMBL = 146032

| C=28 | H=29 | F=5 | O=3

| 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

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = VHZPUDNSVGRVMB-RXDLHWJPSA-N

| synonyms = 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

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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.{{cite web|url=https://adisinsight.springer.com/drugs/800017206|title=Lonaprisan - AdisInsight|website=adisinsight.springer.com}}{{cite journal | vauthors = Whitaker LH, Williams AR, Critchley HO | title = Selective progesterone receptor modulators | journal = Curr. Opin. Obstet. Gynecol. | volume = 26 | issue = 4 | pages = 237–42 | year = 2014 | pmid = 24950125 | doi = 10.1097/GCO.0000000000000082 | s2cid = 37474964 }}{{cite journal | vauthors = Pluchino N, Freschi L, Wenger JM, Streuli I | title = Innovations in classical hormonal targets for endometriosis | journal = Expert Rev Clin Pharmacol | volume = 9 | issue = 2 | pages = 317–27 | year = 2016 | pmid = 26645363 | doi = 10.1586/17512433.2016.1129895 | s2cid = 8624056 }} It is a potent and highly selective silent antagonist of the progesterone receptor (PR).{{cite journal | vauthors = Busia L, Faus H, Hoffmann J, Haendler B | title = The antiprogestin Lonaprisan inhibits breast cancer cell proliferation by inducing p21 expression | journal = Mol. Cell. Endocrinol. | volume = 333 | issue = 1 | pages = 37–46 | year = 2011 | pmid = 21138753 | doi = 10.1016/j.mce.2010.11.034 | s2cid = 12818061 }} The drug reached phase II clinical trials prior to its discontinuation.