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Chemical Compound Review

SureCN936134     (Z)-4-[4-(2- dimethylaminoethoxy)phenyl]- 3...

Synonyms: CCRIS 8953, CHEMBL1908109, LS-30269, AC1MI1FE, C16544, ...
 
 
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Disease relevance of alpha-Hydroxytamoxifen

 

High impact information on alpha-Hydroxytamoxifen

 

Biological context of alpha-Hydroxytamoxifen

 

Anatomical context of alpha-Hydroxytamoxifen

 

Associations of alpha-Hydroxytamoxifen with other chemical compounds

 

Gene context of alpha-Hydroxytamoxifen

 

Analytical, diagnostic and therapeutic context of alpha-Hydroxytamoxifen

  • The resolving power of this HPLC system has further extended this result to show that six of the peaks, including the two major peaks, are formed by the reaction of an activated alpha-hydroxytamoxifen with DNA [18].

References

  1. Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture. Glatt, H., Davis, W., Meinl, W., Hermersdörfer, H., Venitt, S., Phillips, D.H. Carcinogenesis (1998) [Pubmed]
  2. Interactions of the stereoisomers of alpha-hydroxytamoxifen with human hydroxysteroid sulfotransferase SULT2A1 and rat hydroxysteroid sulfotransferase STa. Apak, T.I., Duffel, M.W. Drug Metab. Dispos. (2004) [Pubmed]
  3. Mechanism of lower genotoxicity of toremifene compared with tamoxifen. Shibutani, S., Ravindernath, A., Terashima, I., Suzuki, N., Laxmi, Y.R., Kanno, Y., Suzuki, M., Apak, T.I., Sheng, J.J., Duffel, M.W. Cancer Res. (2001) [Pubmed]
  4. Sex differences in the activation of tamoxifen to DNA binding species in rat liver in vivo and in rat hepatocytes in vitro: role of sulfotransferase induction. Davis, W., Hewer, A., Rajkowski, K.M., Meinl, W., Glatt, H., Phillips, D.H. Cancer Res. (2000) [Pubmed]
  5. Lack of genotoxicity of tamoxifen in human endometrium. Carmichael, P.L., Ugwumadu, A.H., Neven, P., Hewer, A.J., Poon, G.K., Phillips, D.H. Cancer Res. (1996) [Pubmed]
  6. The mutational signature of alpha-hydroxytamoxifen at Hprt locus in Chinese hamster cells. Yadollahi-Farsani, M., Davies, D.S., Boobis, A.R. Carcinogenesis (2002) [Pubmed]
  7. Identification of human CYP forms involved in the activation of tamoxifen and irreversible binding to DNA. Boocock, D.J., Brown, K., Gibbs, A.H., Sanchez, E., Turteltaub, K.W., White, I.N. Carcinogenesis (2002) [Pubmed]
  8. Short-term dosing of alpha-hydroxytamoxifen results in DNA damage but does not lead to liver tumours in female Wistar/Han rats. White, I.N., Carthew, P., Davies, R., Styles, J., Brown, K., Brown, J.E., Smith, L.L., Martin, E.A. Carcinogenesis (2001) [Pubmed]
  9. Alpha-hydroxytamoxifen, a genotoxic metabolite of tamoxifen in the rat: identification and quantification in vivo and in vitro. Boocock, D.J., Maggs, J.L., White, I.N., Park, B.K. Carcinogenesis (1999) [Pubmed]
  10. The metabolic activation of tamoxifen and alpha-hydroxytamoxifen to DNA-binding species in rat hepatocytes proceeds via sulphation. Davis, W., Venitt, S., Phillips, D.H. Carcinogenesis (1998) [Pubmed]
  11. The deuterium isotope effect for the alpha-hydroxylation of tamoxifen by rat liver microsomes accounts for the reduced genotoxicity of [D5-ethyl]tamoxifen. Jarman, M., Poon, G.K., Rowlands, M.G., Grimshaw, R.M., Horton, M.N., Potter, G.A., McCague, R. Carcinogenesis (1995) [Pubmed]
  12. Determination of DNA damage in F344 rats induced by geometric isomers of tamoxifen and analogues. Brown, K., Brown, J.E., Martin, E.A., Smith, L.L., White, I.N. Chem. Res. Toxicol. (1998) [Pubmed]
  13. Aspects of metabolism of tamoxifen by rat liver microsomes. Identification of a new metabolite: E-1-[4-(2-dimethylaminoethoxy)-phenyl]-1, 2-diphenyl-1-buten-3-ol N-oxide. McCague, R., Seago, A. Biochem. Pharmacol. (1986) [Pubmed]
  14. N-demethylation accompanies alpha-hydroxylation in the metabolic activation of tamoxifen in rat liver cells. Phillips, D.H., Hewer, A., Horton, M.N., Cole, K.J., Carmichael, P.L., Davis, W., Osborne, M.R. Carcinogenesis (1999) [Pubmed]
  15. Tamoxifen: is it safe? Comparison of activation and detoxication mechanisms in rodents and in humans. White, I.N. Curr. Drug Metab. (2003) [Pubmed]
  16. Sulfation of alpha-hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen-DNA adducts. Shibutani, S., Shaw, P.M., Suzuki, N., Dasaradhi, L., Duffel, M.W., Terashima, I. Carcinogenesis (1998) [Pubmed]
  17. Organ specificity of DNA adduct formation by tamoxifen and alpha-hydroxytamoxifen in the rat: implications for understanding the mechanism(s) of tamoxifen carcinogenicity and for human risk assessment. Phillips, D.H., Hewer, A., Osborne, M.R., Cole, K.J., Churchill, C., Arlt, V.M. Mutagenesis (2005) [Pubmed]
  18. Evaluation of tamoxifen and alpha-hydroxytamoxifen 32P-post-labelled DNA adducts by the development of a novel automated on-line solid-phase extraction HPLC method. Martin, E.A., Heydon, R.T., Brown, K., Brown, J.E., Lim, C.K., White, I.N., Smith, L.L. Carcinogenesis (1998) [Pubmed]
 
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