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

Item No. 44830

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1E)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol
CAS Number
174592-47-3
Synonyms
  • (E)-Afimoxifene
  • (E)-4-OHT
  • cis-4-hydroxy Tamoxifen
Molecular Formula
C26H29NO2
Formula Weight
387.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
CC/C(C1=CC=CC=C1)=C(C2=CC=C(C=C2)O)\C3=CC=C(OCCN(C)C)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-OCEACIFDSA-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

    (E)-4-hydroxy Tamoxifen is an active metabolite of tamoxifen (Item Nos. 13258 | 11629) and (Z)-4-hydroxy tamoxifen (Item No. 14854).1 It is formed from tamoxifen via transisomerization of the (Z)-4-hydroxy tamoxifen intermediate by the cytochrome P450 isoforms CYP1A1, CYP1B1, CYP2B6, CYP2D6, CYP3A4, and CYP3A5. (E)-4-hydroxy Tamoxifen inhibits estradiol benzoate-induced increases in oviduct weight in quails (ED50 = 2.2 mg/kg).2

    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. Fanidi, A., Courion-Guichardaz, C., Fayard, J.M., et al. Effects of tamoxifen, tamoxifen metabolites, and nafoxidine on adenosine 3',5'-monophosphate phosphodiesterase: Correlations with growth inhibitory activities but not estrogen receptor affinities. Endocrinology 125(3), 1187-1193 (1989).