An active metabolite of mifepristone
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Parent Compound(s)
10006317Mifepristone
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Metapristone

Item No. 36380

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(11β,17β)-17-hydroxy-11-[4-(methylamino)phenyl]-17-(1-propyn-1-yl)-estra-4,9-dien-3-one
CAS Number
104004-96-8
Synonyms
  • N-desmethyl Mifepristone
  • RU-42633
  • N-desmethyl RU-486
Molecular Formula
C28H33NO2
Formula Weight
415.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Sparingly soluble: 1-10 mg/mlMethanol: Sparingly soluble: 1-10 mg/ml
λmax
255, 303 nm
SMILES
C[C@@]12[C@](CC[C@@]2(O)C#CC)([H])[C@@]3([H])C([C@](C4=CC=C(C=C4)NC)([H])C1)=C5C(CC3)=CC(CC5)=O
InChi Code
InChI=1S/C28H33NO2/c1-4-14-28(31)15-13-25-23-11-7-19-16-21(30)10-12-22(19)26(23)24(17-27(25,28)2)18-5-8-20(29-3)9-6-18/h5-6,8-9,16,23-25,29,31H,7,10-13,15,17H2,1-3H3/t23-,24+,25-,27-,28-/m0/s1
InChi Key
IBLXOBHABOVXDY-WKWWZUSTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

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    5 mg

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    10 mg

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    Product Description

    Metapristone is an active metabolite of the glucocorticoid, progesterone, and androgen receptor antagonist mifepristone (Item No. 10006317).1 It is formed from mifepristone by the cytochrome P450 (CYP) isoform CYP3A4. Metapristone is an antagonist of human glucocorticoid and progesterone receptors with relative affinities of 61 and 21%, respectively, compared to mifepristone.2 It decreases the proliferation of A375 human and B16/F10 murine melanoma cells (IC50s = 57.4 and 75.8 µM, respectively).3 It induces cell cycle arrest at the G1 phase in B16/F10 cells when used at a concentration of 80 µM. Metapristone (2.5, 10, and 50 mg/kg per day) decreases the number of lung metastases in a B16/F10 murine model of lung metastasis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Khan, K.K., He, Y.Q., Correia, M.A., et al. Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: Selective inactivation of P450 3A4. Drug Metab. Dispos. 30(9), 985-990 (2002).

    2. Heikinheimo, O., Kontula, K., Croxatto, H., et al. Plasma concentrations and receptor binding of RU 486 and its metabolites in humans. J. Steroid Biochem. 26(2), 279-284 (1987).

    3. Zheng, N., Chen, J., Liu, W., et al. Metapristone (RU486 derivative) inhibits cell proliferation and migration as melanoma metastatic chemopreventive agent. Biomed. Pharmacother. 90, 339-349 (2017).

    4. Wang, J., Chen, J., Zhu, Y., et al. In vitro and in vivo efficacy and safety evaluation of metapristone and mifepristone as cancer metastatic chemopreventive agents. Biomed. Pharmacother. 78, 291-300 (2016).