Description
Mifepristone is a progesterone receptor antagonist with partial agonist activity. It is an abortifacient.
Synonyms
(11β,17β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-17-(1-propyn-1-yl)estra-4,9-dien-3-one; RU-486; RU-38486; Mifegyne; Mifeprex; Mifestone; VGX 410
IUPAC Name
(8S,11R,13S,14S,17S)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
Molecular Formula
C29H35NO2
Canonical SMILES
CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O
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
InChIKey
VKHAHZOOUSRJNA-GCNJZUOMSA-N
Boiling Point
628.6±55.0 °C | Condition: Press: 760 Torr
Density
1.18±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
Solubility
DMSO: ≥ 59 mg/mL
Appearance
Yellow crystalline powder
Application
Mifepristone is used as an abortifacient in the first months of pregnancy, and in smaller doses as an emergency contraceptive. It has occasionally been used in refractory Cushing's Syndrome. It is used in combination with misoprostol for the oral induction of first trimester abortions. It induces growth arrest, caspase activation, and cell death in anti-estrogen-resistant breast cancer cells, which indicats the effectiveness of PR antagonism as a novel approach to treatment of select cancers.
Shelf Life
2 month in rt, long time