A mixture of (E)-endoxifen and (Z)-endoxifen
Related Products
Parent Compound(s)
13258Tamoxifen 11629Tamoxifen (citrate)
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(E/Z)-Endoxifen

Item No. 21502

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
CAS Number
110025-28-0
Synonyms
  • (E/Z)-N-desmethyl-4-hydroxy Tamoxifen
Molecular Formula
C25H27NO2
Formula Weight
373.5
Purity
≥98% (mixture of isomers)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 2 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.3 mg/ml
λmax
244, 286 nm
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=C(C=C2)OCCNC)\C3=CC=C(C=C3)O
InChi Code
InChI=1S/C25H27NO2/c1-3-24(19-7-5-4-6-8-19)25(20-9-13-22(27)14-10-20)21-11-15-23(16-12-21)28-18-17-26-2/h4-16,26-27H,3,17-18H2,1-2H3/b25-24-
InChi Key
MHJBZVSGOZTKRH-IZHYLOQSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    5 mg

    $49

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    10 mg

    $74

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    25 mg

    $147

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    100 mg

    $343

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    Product Description

    (E/Z)-Endoxifen is a mixture of (E)-endoxifen and (Z)-endoxifen.1 (Z)-Endoxifen is an active metabolite of the estrogen receptor antagonist tamoxifen (Item Nos. 13258 | 11629) and is formed from tamoxifen primarily by the cytochrome P450 (CYP) isoform CYP2D6 via an N-desmethyltamoxifen (Item No. 40673) intermediate.2 (Z)-Endoxifen (100 nM) inhibits 17β-estradiol-induced increases in mRNA encoding the progesterone receptor in MCF-7 breast cancer cells.3 (E)-Endoxifen is a potential impurity in commercial preparations of (Z)-endoxifen.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brauch, H., Mürdter, T.E., Eichelbaum, M., et al. Pharmacogenomics of tamoxifen therapy. Clin. Chem. 55(10), 1770-1782 (2009).

    2. Desta, Z., Ward, B.A., Soukhova, N.V., et al. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J. Pharmacol. Exp. Ther. 310(3), 1062-1075 (2004).

    3. Y.C., L., Desta, Z., Flockhart, D.A., et al. Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen. Cancer Chemother. Pharmacol. 55(5), 471-478 (2005).

    4. Elkins, P., Coleman, D., Burgess, J., et al. Characterization of the isomeric configuration and impurities of (Z)-endoxifen by 2D NMR, high resolution LC‒MS, and quantitative HPLC analysis. J. Pharm. Biomed. Anal. 88, 174-179 (2014).