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Mifepristone
Cayman Chemical Item Number 10006317
Description
Progesterone is responsible for preparing the uterine lining for implantation of a fertilized ovum and to maintain pregnancy, eliciting its action through the nuclear progesterone receptor (PR). Mifepristone is a potent PR and glucocorticoid receptor (GR) antagonist with Ki values of approximately 1 nM.1↗ It is used in combination with misoprostol for the oral induction of first trimester abortions.1↗ Mifepristone promotes efficient binding of PR to hormone response elements (HRE) on DNA, but prevents transcriptional activation of the receptor.2↗,3↗,4↗ The IC50 of mifepristone for PR dimerization and activation is 0.6 nM; the IC50 for mifepristone-induced competitive binding of wild-type PR with a constitutively active PR for HRE is 0.01 nM.2↗ In anti-estrogen-resistant breast cancer cells, mifepristone induces growth arrest, caspase activation, and cell death, indicating the effectiveness of PR antagonism as a novel approach to treatment of select cancers.5↗
Synonyms RU-486
Formal Name 11β-[4-(dimethylamino)phenyl]-17β-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one
CAS Number 84371-65-3
Molecular Formula C29H35NO2
Formula Weight 429.6
Formulation A crystalline solid
Purity>98%
λmax 261, 303 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CN(C)C1=CC=C(C=C1)[C@H]2C[C@@]3(C)[C@](CC[C@]3(C#CC)O)([H])[C@]4([H])CCC5=CC(CCC5=C42)=O
InCHI Code 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 |