mifepristone   

GtoPdb Ligand ID: 2805

Synonyms: Mifeprex® | RU-486 | RU486
mifepristone is an approved drug (FDA (2000))
Compound class: Synthetic organic
Comment: An antagonist of both the glucocorticoid receptor and the progesterone receptor.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 40.54
Molecular weight 429.27
XLogP 4.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC#CC1(O)CCC2C1(C)CC(c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CCC21
Isomeric SMILES CC#C[C@]1(O)CC[C@@H]2[C@]1(C)C[C@H](c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@H]21
InChI InChI=1S/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24-,25+,26-,28-,29-/m0/s1
InChI Key VKHAHZOOUSRJNA-GCNJZUOMSA-N
References
1. Heikinheimo O, Kontula K, Croxatto H, Spitz I, Luukkainen T, Lähteenmäki P. (1987)
Plasma concentrations and receptor binding of RU 486 and its metabolites in humans.
J. Steroid Biochem., 26 (2): 279-84. [PMID:3560943]
2. Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA. (1998)
The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions.
J. Clin. Invest., 102 (5): 1016-23. [PMID:9727070]
3. Rupprecht R, Reul JM, van Steensel B, Spengler D, Söder M, Berning B, Holsboer F, Damm K. (1993)
Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands.
Eur. J. Pharmacol., 247 (2): 145-54. [PMID:8282004]
4. von Geldern TW, Tu N, Kym PR, Link JT, Jae HS, Lai C, Apelqvist T, Rhonnstad P, Hagberg L, Koehler K et al.. (2004)
Liver-selective glucocorticoid antagonists: a novel treatment for type 2 diabetes.
J. Med. Chem., 47 (17): 4213-30. [PMID:15293993]
5. Zhi L, Tegley CM, Pio B, Edwards JP, Jones TK, Marschke KB, Mais DE, Risek B, Schrader WT. (2003)
Synthesis and biological activity of 5-methylidene 1,2-dihydrochromeno[3,4-f]quinoline derivatives as progesterone receptor modulators.
Bioorg. Med. Chem. Lett., 13 (12): 2071-4. [PMID:12781197]