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Merck
CN

475838

Mifepristone

≥99% (titration), solid, progesterone and glucocorticoid receptor antagonist, Calbiochem®

Synonym(s):

Mifepristone, (11β,17β)-11-(4-(Dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)estra-4,9-dien-3-one, RU-486

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About This Item

Empirical Formula (Hill Notation):
C29H35NO2
CAS Number:
84371-65-3
Molecular Weight:
429.59
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00867226

Key Documents

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Product Name

Mifepristone, A cell-permeable synthetic steroid that acts as a potent antagonist of progesterone and glucocorticoid receptors.

SMILES string

N(C)(C)c1ccc(cc1)[C@H]2C[C@]3([C@H]([C@@H]4CCC5=CC(=O)CCC5=C42)CC[C@@]3(O)C#CC)C

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

description

Merck USA index - 14, 6186

assay

≥99% (titration)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

impurities

≤0.1% Steroid substances

color

yellow

solubility

ethanol: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Progesterone and glucocorticoid receptors
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

General description

A cell-permeable synthetic steroid that acts as a potent antagonist of progesterone and glucocorticoid receptors. Inhibits P-glycoprotein (P-gp) function and down-modulates P-gp mediated drug resistance. Displays anti-angiogenic effects and suppresses vascular endothelial growth factor (VEGF) production. Regulates the expression of Fas and FasL in mouse endometrium and TRAIL in prostate cancer cells. As an antioxidant, it offers neuroprotection against controlled cortical impact (CCI) in CA1 pyramidal cells, as well as Aβ-, H2O2-, and glutamate-induced injury to mouse hippocampal HT22 cells.
A cell-permeable, synthetic steroid that acts as a potent antagonist of progesterone and glucocorticoid receptors. Reported to inhibit P-glycoprotein (P-gp) function and down-modulate P-gp mediated drug resistance. Also displays anti-angiogenic effects and suppresses vascular endothelial growth factor (VEGF) production. Shown to regulate the expression of Fas and FasL in mouse endometrium and of TRAIL in prostate cancer cells. As an antioxidant, it is reported to offer neuroprotection against controlled cortical impact (CCI) in CA1 pyramidal cells, as well as Aβ-, H2O2-, and glutamate-induced injury to mouse hippocampal HT22 cells.

Other Notes

McCullers, D.L., et al. 2002. Neuroscience109, 219.
Sidell, N., et al. 2002. Ann. N. Y. Acad. Sci.955, 159.
Gao, F., et al. 2001. Acta Pharmacol. Sin.22, 524.
Hyder, S.M., et al. 2001. Int. J. Cancer92, 469.
Lam, F.C., et al. 2001. J. Neurochem. 76, 1121.
Sridhar, S., et al. 2001. Cancer Res.61, 7179.
Behl, C., et al. 1997. Eur. J. Neurosci.9, 912.
Greb, R.R., et al. 1997. Hum. Reprod.12, 1280.
Gruol, D.J., et al. 1994. Cancer Res.54, 3088.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sang Ngo et al.
Current biology : CB, 30(8), 1537-1546 (2020-04-04)
In healthy adult organs, robust feedback mechanisms control cell turnover to enforce homeostatic equilibrium between cell division and death [1, 2]. Nascent tumors must subvert these mechanisms to achieve cancerous overgrowth [3-7]. Elucidating the nature of this subversion can reveal
Maude Giroud et al.
Diabetologia, 64(8), 1850-1865 (2021-05-21)
Adipocytes are critical cornerstones of energy metabolism. While obesity-induced adipocyte dysfunction is associated with insulin resistance and systemic metabolic disturbances, adipogenesis, the formation of new adipocytes and healthy adipose tissue expansion are associated with metabolic benefits. Understanding the molecular mechanisms
Peng Ma et al.
iScience, 24(6), 102507-102507 (2021-07-27)
Lipid digestion and absorption are tightly regulated to cope with metabolic demands among tissues. How these processes are coordinated is not well characterized. Here, we found that mifepristone (RU486) prevents lipid digestion both in flies and mice. In flies, RU486
Jakob Hartmann et al.
Cell reports, 35(9), 109185-109185 (2021-06-03)
Responding to different dynamic levels of stress is critical for mammalian survival. Disruption of mineralocorticoid receptor (MR) and glucocorticoid receptor (GR) signaling is proposed to underlie hypothalamic-pituitary-adrenal (HPA) axis dysregulation observed in stress-related psychiatric disorders. In this study, we show

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