A metabolite of tamoxifen
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Tamoxifen N-oxide

Item No. 18642

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-oxide-2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl, ethanamine
CAS Number
75504-34-6
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
237, 276 nm
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=CC=C2)/C3=CC=C(OCC[N+](C)(C)[O-])C=C3
InChi Code
InChI=1S/C26H29NO2/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)29-20-19-27(2,3)28/h5-18H,4,19-20H2,1-3H3/b26-25-
InChi Key
YAASNACECBQAFW-QPLCGJKRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tamoxifen N-oxide is a metabolite of tamoxifen that is produced by the action of flavin-containing monooxygenases.1,2 It can be converted back to tamoxifen by cytochrome P450 isoforms and hemoglobin.3,2 Like the parent compound, tamoxifen N-oxide can form DNA adducts.4,5,1 Tamoxifen N-oxide is a weak inhibitor of human hydroxysteroid sulfotransferase 2A1 (Kis = 9.1 and 16.9 µM for the sulfonation of dehydroepiandrosterone and pregnenolone, respectively).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, L., Krishnan, S., Zhang, Y., et al. Differences in metabolitw-mediated toxicity of Tamoxifen in rodents vs. humans elucidated with DNA/microsomes electro-optical arrays and nanoreactors. Chem. Res. Toxicol. 22(2), 341-347 (2009).

    2. Parte, P., and Kupfer, D. Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab. Dispos. 33(10), 1446-1452 (2005).

    3. Gjerde, J., Gandini, S., Guerrieri-Gonzaga, A., et al. Tissue distribution of 4-hydroxy-N-desmethyltamoxifen and tamoxifen-N-oxide. Breast Cancer Res. Treat. 134(2), 693-700 (2012).

    4. Phillips, D.H., Hewer, A., Horton, M.N., et al. N-demethylation accompanies α-hydroxylation in the metabolic activation of tamoxifen in rat liver cells. Carcinogenesis 20(10), 2003-2009 (1999).

    5. Shibutani, S., Suzuki, N., Laxmi, S.Y.R., et al. Identification of tamoxifen-DNA adducts in monkeys treated with tamoxifen. Cancer Res. 63(15), 4402-4406 (2003).

    6. Squirewell, E.J., Qin, X., and Duffel, M.W. Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab. Dispos. 42(11), 1843-1850 (2014).