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Chemical Compound Review

AC1MHUWT     2-[4-[(E)-1,2-diphenylbut-1- enyl]phenoxy]...

Synonyms: LS-68203, ICI 55,548, AC1Q56SZ, 31750-48-8, Desmethyltamoxifen, ...
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Disease relevance of NSC372964


High impact information on NSC372964

  • However, analysis of the (32)P-postlabelled products from the reaction between alpha-acetoxytamoxifen and calf thymus DNA showed two main peaks, the smaller one of which ( approximately 15% of the total) also co-eluted with that attributed to N-desmethyltamoxifen [4].
  • An SDS concentration of 7 mM lowered the ESMS signal response for N-desmethyltamoxifen by a factor of approximately 3 [5].
  • In all but one of the treated women, tamoxifen and its N-desmethyltamoxifen metabolite could be detected in liver extracts by high performance liquid chromatography; none was detected in control samples [6].
  • Tamoxifen and its main metabolite N-desmethyltamoxifen (NDMTmx) have been shown to increase intracellular daunorubicin (DNR) levels in human leukemia cell lines that display the multidrug resistant (MDR) phenotype [7].
  • Tamoxifen (Tmx) is one of a number of agents that can reverse the multidrug resistant (MDR) phenotype in vitro; it is unique, however, in that both the parent compound and the main metabolite, N-desmethyltamoxifen (NDMTmx), have long plasma half-lives, 7 and 14 days, respectively [8].

Chemical compound and disease context of NSC372964


Biological context of NSC372964


Anatomical context of NSC372964


Associations of NSC372964 with other chemical compounds


Gene context of NSC372964


Analytical, diagnostic and therapeutic context of NSC372964


  1. High-dose oral tamoxifen, a potential multidrug-resistance-reversal agent: phase I trial in combination with vinblastine. Trump, D.L., Smith, D.C., Ellis, P.G., Rogers, M.P., Schold, S.C., Winer, E.P., Panella, T.J., Jordan, V.C., Fine, R.L. J. Natl. Cancer Inst. (1992) [Pubmed]
  2. Concentrations of tamoxifen and its major metabolites in hormone responsive and resistant breast tumours. MacCallum, J., Cummings, J., Dixon, J.M., Miller, W.R. Br. J. Cancer (2000) [Pubmed]
  3. A comparison of the relative chemosensitivity of human gliomas to tamoxifen and n-desmethyltamoxifen in vitro. Vertosick, F.T., Selker, R.G., Randall, M.S., Kristofik, M.P., Rehn, T. J. Neurooncol. (1994) [Pubmed]
  4. Further characterization of the DNA adducts formed in rat liver after the administration of tamoxifen, N-desmethyltamoxifen or N, N-didesmethyltamoxifen. Brown, K., Heydon, R.T., Jukes, R., White, I.N., Martin, E.A. Carcinogenesis (1999) [Pubmed]
  5. Analysis of tamoxifen and its metabolites by on-line capillary electrophoresis-electrospray ionization mass spectrometry employing nonaqueous media containing surfactants. Lu, W., Poon, G.K., Carmichael, P.L., Cole, R.B. Anal. Chem. (1996) [Pubmed]
  6. 32P-postlabelled DNA adducts in liver obtained from women treated with tamoxifen. Martin, E.A., Rich, K.J., White, I.N., Woods, K.L., Powles, T.J., Smith, L.L. Carcinogenesis (1995) [Pubmed]
  7. Phase I trial of high-dose tamoxifen as a modulator of drug resistance in combination with daunorubicin in patients with relapsed or refractory acute leukemia. Berman, E., McBride, M., Lin, S., Menedez-Botet, C., Tong, W. Leukemia (1995) [Pubmed]
  8. Comparative activity of tamoxifen and N-desmethyltamoxifen in human multidrug resistant leukemia cell lines. Berman, E., McBride, M., Tong, W. Leukemia (1994) [Pubmed]
  9. Inhibition of estrone sulfatase and 17 beta-hydroxysteroid dehydrogenase by antiestrogens. Santner, S.J., Santen, R.J. J. Steroid Biochem. Mol. Biol. (1993) [Pubmed]
  10. Characterization of the major DNA adduct formed by alpha-hydroxy-N-desmethyltamoxifen in vitro and in vivo. Gamboa da Costa, G., Hamilton, L.P., Beland, F.A., Marques, M.M. Chem. Res. Toxicol. (2000) [Pubmed]
  11. High-dose (480 mg/day) tamoxifen with etoposide: a study of a potential multi-drug resistance modulator. Millward, M.J., Lien, E.A., Robinson, A., Cantwell, B.M. Oncology (1994) [Pubmed]
  12. DNA cleavage and 8-hydroxydeoxyguanosine formation caused by tamoxifen derivatives in vitro. Okubo, T., Nagai, F., Ushiyama, K., Yokoyama, Y., Ozawa, S., Kano, K., Tomita, S., Kubo, H., Kano, I. Cancer Lett. (1998) [Pubmed]
  13. The steady-state pharmacokinetics of tamoxifen and its metabolites in breast cancer patients. Soininen, K., Kleimola, T., Elomaa, I., Salmo, M., Rissanen, P. J. Int. Med. Res. (1986) [Pubmed]
  14. Determination of tamoxifen and metabolites in serum by capillary electrophoresis using a nonaqueous buffer system. Sanders, J.M., Burka, L.T., Shelby, M.D., Newbold, R.R., Cunningham, M.L. J. Chromatogr. B Biomed. Sci. Appl. (1997) [Pubmed]
  15. Analysis of tamoxifen, N-desmethyltamoxifen and 4-hydroxytamoxifen levels in cytosol and KCl-nuclear extracts of breast tumours from tamoxifen treated patients by gas chromatography-mass spectrometry (GC-MS) using selected ion monitoring (SIM). Murphy, C., Fotsis, T., Pantzar, P., Adlercreutz, H., Martin, F. J. Steroid Biochem. (1987) [Pubmed]
  16. Interactions of tamoxifen, N-desmethyltamoxifen and 4-hydroxytamoxifen with P-glycoprotein and CYP3A. Bekaii-Saab, T.S., Perloff, M.D., Weemhoff, J.L., Greenblatt, D.J., von Moltke, L.L. Biopharmaceutics & drug disposition. (2004) [Pubmed]
  17. Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Rao, U.S., Fine, R.L., Scarborough, G.A. Biochem. Pharmacol. (1994) [Pubmed]
  18. Influence of polyethylene glycol and acetone on the in vitro biotransformation of tamoxifen and alprazolam by human liver microsomes. Cotreau-Bibbo, M.M., von Moltke, L.L., Greenblatt, D.J. Journal of pharmaceutical sciences. (1996) [Pubmed]
  19. Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Zhao, X.J., Jones, D.R., Wang, Y.H., Grimm, S.W., Hall, S.D. Xenobiotica (2002) [Pubmed]
  20. Oestrogenic activity of tamoxifen and its metabolites on gene regulation and cell proliferation in MCF-7 breast cancer cells. Johnson, M.D., Westley, B.R., May, F.E. Br. J. Cancer (1989) [Pubmed]
  21. Peroxidase activation of tamoxifen and toremifene resulting in DNA damage and covalently bound protein adducts. Davies, A.M., Martin, E.A., Jones, R.M., Lim, C.K., Smith, L.L., White, I.N. Carcinogenesis (1995) [Pubmed]
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