A glucocorticoid, progesterone, and androgen receptor antagonist
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Active Metabolite(s)
36380Metapristone
Labeled Version(s)
10010660Mifepristone-d3
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Mifepristone

Item No. 10006317

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11β-[4-(dimethylamino)phenyl]-17β-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one
CAS Number
84371-65-3
Synonyms
  • RU-486
Molecular Formula
C29H35NO2
Formula Weight
429.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2)(1:4): .2 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlMethanol: 1 mg/ml
λmax
261, 303 nm
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
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Cayman Chemical
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    Product Description

    Mifepristone is an antagonist of glucocorticoid, progesterone, and androgen receptors (Kis = 0.1, 0.64, and 0.65 nM, respectively).1,2,3 It is selective for these receptors over the mineralocorticoid receptor (MR), estrogen receptor α (ERα), and ERβ (Kis = 640, >200, and >750 nM, respectively).1 In cell-based assays, mifepristone inhibits alkaline phosphatase activity stimulated by the progesterone receptor agonist R5020 as well as reporter transcription stimulated by either dexamethasone (Item No. 11015) or R5020 (IC50s = 7, 5.9, and 1.3 nM, respectively).3 It also inhibits synthetic androgen R1881-stimulated reporter transcription in a concentration-dependent manner.2 Mifepristone (10 µM) inhibits growth of 4-OHT-resistant MCF-7 breast cancer cells in vitro.4 It also inhibits tumor growth in an SKOV3 ovarian cancer nude mouse xenograft model when administered at doses of 0.5 or 1 mg per day.5 Formulations containing mifepristone have been used for the induction of medical abortions.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. von Gerldern, T.W., Tu, N., Kym, P.R., et al. Liver-selective glucocorticoid antagonists: A novel treatment for type 2 diabetes. J. Med. Chem. 47(17), 4213-4230 (2004).

    2. Song, L.-N., Coghlan, M.J., and Gelmann, E.P. Antiandrogen effects of mifepristone on coactivator and corepressor interactions with the androgen receptor. Mol. Endocrinol. 18(1), 70-85 (2004).

    3. Attardi, B.J., Burgenson, J., Hild, S.A., et al. In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J. Steroid Biochem. Mol. Biol. 88(3), 277-288 (2004).

    4. Gaddy, V.T., Barrett, J.T., Delk, J.N., et al. Mifepristone induces growth arrest, caspase activation, and apoptosis of estrogen receptor-expressing, antiestrogen-resistant breast cancer cells. Clin. Cancer Res. 10, 5215-5225 (2004).

    5. Goyeneche, A.A., Carón, R.W., and Telleria, C.M. Mifepristone inhibits ovarian cancer cell growth in vitro and in vivo. Clin. Cancer Res. 13(11), 3370-3379 (2007).

    Product Citations

    Lee, J.-H., Dean, M., Austin, J.R., et al. Irilone from red clover (Trifolium pratense) potentiates progesterone signaling. J. Nat. Prod. 81(9), 1962-1967 (2018).

    d'Alencon, C.A., Peña, O.A., Wittmann, C., et al. A high-throughput chemically induced inflammation assay in zebrafish. BMC Biol. 8, 151 (2010).