An active metabolite of tamoxifen
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(Z)-4-hydroxy Tamoxifen

Item No. 14854

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
CAS Number
68047-06-3
Synonyms
  • ICI 79280
  • trans-4-hydroxy Tamoxifen
Molecular Formula
C26H29NO2
Formula Weight
387.5
Purity
≥98%
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
246, 287 nm
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(C)C)C=C2)\C3=CC=C(O)C=C3
InChi Code
InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
InChi Key
TXUZVZSFRXZGTL-QPLCGJKRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (Z)-4-hydroxy Tamoxifen is an active metabolite of the estrogen receptor (ER) modulator tamoxifen (Item No. 13258).1 It is primarily formed from tamoxifen by the cytochrome P450 (CYP) isoforms CYP2D6 and CYP2B6.2 (Z)-4-hydroxy Tamoxifen (10 nM) decreases progesterone receptor (PR) mRNA expression induced by the estrogen steroid 17β-estradiol (Item No. 10006315) in MCF-7 breast cancer cells.3 Liposomal administration of (Z)-4-hydroxy tamoxifen (4 mg/kg twice per week) reduces tumor growth in an RPMI-8226 multiple myeloma mouse xenograft model.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crewe, H.K., Notley, L.M., Wunsch, R.M., et al. Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: Formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab. Dispos. 30(8), 869-874 (2002).

    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. Urbinati, G., Audisio, D., Marsaud, V., et al. Therapeutic potential of new 4-hydroxy-tamoxifen-loaded pH-gradient liposomes in a multiple myeloma experimental model. Pharm. Res. 27(2), 327-339 (2010).

    Product Citations

    Nagakannan, P., Islam, M.I., Conrad, M., et al. Cathepsin B is an excutioner of ferroptosis. Biochim. Biophys. Acta Mol. Cell Res. 1868(3), 118928 (2021).