An ER antagonist and active metabolite of tamoxifen
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4’-hydroxy Tamoxifen

Item No. 19519

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1Z)-1-[[4-[2-(dimethylamino)ethoxy]phenyl]phenylmethylene]propyl]-phenol
CAS Number
82413-23-8
Molecular Formula
C26H29NO2
Formula Weight
387.5
Purity
≥98% (may contain up to 10% of the (E) isomer)
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
241, 288 nm
SMILES
CC/C(C1=CC=C(O)C=C1)=C(C2=CC=CC=C2)/C3=CC=C(OCCN(C)C)C=C3
InChi Code
InChI=1S/C26H29NO2/c1-4-25(20-10-14-23(28)15-11-20)26(21-8-6-5-7-9-21)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
DODQJNMQWMSYGS-QPLCGJKRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    4'-hydroxy Tamoxifen is an estrogen receptor (ER) antagonist (IC50 = 2.4 nM for the rabbit receptor) and active metabolite of tamoxifen (Item Nos. 13258 | 11629).1,2 It is formed from tamoxifen by the cytochrome P450 (CYP) isoforms CYP2D6, CYP3A4, CYP2B6, and CYP2C19.2 4'-hydroxy Tamoxifen inhibits the proliferation of MCF-7 and MDA-MB-231 breast cancer cells (IC50s = 27 and 16 µM, respectively).3 It reduces the survival percentage of HEC-1A and HEC-1B endometrial cancer cells when used at concentrations of 10 and 100 nM.4 Administration of liposomes encapsulating 4'-hydroxy tamoxifen (4 mg/kg twice per week) reduces tumor growth in an RPMI-8226 multiple myeloma mouse xenograft model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Löser, R., Seibel, K., Roos, W., et al. In vivo and in vitro antiestrogenic action of 3-hydroxytamoxifen, tamoxifen and 4-hydroxytamoxifen. Eur. J. Cancer Clin. Oncol. 21(8), 985-990 (1985).

    2. 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).

    3. Seeger, H., Huober, J., Wallwiener, D., et al. Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm. Metab. Res. 36(5), 277-280 (2004).

    4. Cuevas, M.E., and Lindeman, T.E. In vitro cytotoxicity of 4'-OH-tamoxifen and estradiol in human endometrial adenocarcinoma cells HEC-1A and HEC-1B. Oncol. Rep. 33(1), 464-470 (2016).

    5. 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).