A reactive metabolite of tamoxifen
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α-hydroxy Tamoxifen

Item No. 17204

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(βE)-[[4-[2-(dimethylamino)ethoxy]phenyl]phenylmethylene]-α-methyl-benzeneethanol
CAS Number
97151-02-5
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 nm
SMILES
CC(O)/C(C1=CC=CC=C1)=C(C2=CC=CC=C2)/C3=CC=C(OCCN(C)C)C=C3
InChi Code
InChI=1S/C26H29NO2/c1-20(28)25(21-10-6-4-7-11-21)26(22-12-8-5-9-13-22)23-14-16-24(17-15-23)29-19-18-27(2)3/h4-17,20,28H,18-19H2,1-3H3/b26-25-
InChi Key
BPHFBQJMFWCHGH-QPLCGJKRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    α-hydroxy Tamoxifen is a reactive metabolite of the estrogen receptor (ER) modulator tamoxifen (Item No. 13258) that is formed by the action of cytochrome P450 3A4 in human liver.1,2 It can be further converted into genotoxic DNA adducts though a mechanism involving reversible O-sulfonation of the hydroxyl moiety, which in rats has been linked with hepatocarcinoma.1,3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boocock, D.J., Maggs, J.L., White, I.N.H., et al. α-Hydroxytamoxifen, a genotoxic metabolite of tamoxifen in the rat: Identification and quantification in vivo and in vitro. Carcinogenesis 20(1), 153-160 (1999).

    2. Mugundu, G.M., Sallans, L., Guo, Y., et al. Assessment of the impact of CYP3A polymorphisms on the formation of α-hydroxytamoxifen and N-desmethyltamoxifen in human liver microsomes. Drug Metab. Dispos. 40(2), 389-396 (2012).

    3. White, I.N.H., Carthew, P., Davies, R., et al. Short-term dosing of α-hydroxytamoxifen results in DNA damage but does not lead to liver tumours in female Wistar/Han rats. Carcinogenesis 22(4), 553-557 (2001).

    4. Yadollahi-Farsani, M., Davies, D.S., and Boobis, A.R. The mutational signature of α-hydroxytamoxifen at Hprt locus in Chinese hamster cells. Carcinogenesis 23(11), 1947-1952 (2002).

    5. Shibutani, S., Dasaradhi, L., Terashima, I., et al. α-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer Res. 58(4), 647-653 (1998).

    6. Kim, S.Y., Laxmi, Y.R.S., Suzuki, N., et al. Formation of tamoxifen-DNA adducts via O-sulfonation, not O-acetylation, of α-hydroxytamoxifen in rat and human livers. Drug Metab. Dispos. 33(11), 1673-1678 (2005).