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Chemical Compound Review

Benzfetamine     N-benzyl-N-methyl-1-phenyl- propan-2-amine

Synonyms: Benzfetamina, Benzfetaminum, Benzofetamina, benzphetamine, Benzphetaminum, ...
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Disease relevance of Didrex

  • CYP3A9 cDNA was expressed in E. coli and the expressed P450 3A9 is active in the demethylation of erythromycin as well as benzphetamine [1].
  • In the reconstituted system, hepatoma P-450MCI catalyzed 3-hydroxylation of benzo[a]pyrene and O-deethylation of 7-ethoxycoumarin, but showed low activities for N-demethylation of benzphetamine and aminopyrine, O-demethylation of p-nitroanisole, and p-hydroxylation of aniline [2].
  • When 1,1-di(p-chlorophenyl)-2,2-dichloroethylene (DDE) (100 mg/kg body weight) was injected into rats, the benzphetamine N-demethylation and 7-ethoxycoumarin O-deethylation activities of liver microsomes increased by 7-fold and 3-fold, respectively, at 7 days after the injection, whereas the benzo(a)pyrene 3-hydroxylation activity did not increase [3].
  • Additional evidence for thiram-induced liver toxicity is provided by the observation that there was approximately 50% inhibition of the activity of hepatic microsomal benzphetamine N-demethylase with a concomitant decrease in the concentration of cytochrome P-450, an important component of the mixed-function oxidase system [4].

High impact information on Didrex

  • Monooxygenase activities (pmol product/min/protein) in the bladder microsomal fraction were observed for benzphetamine N-demethylation (290), 7-ethoxyresorufin O-deethylation (29), 7-ethoxycoumarin O-deethylation (28), benzo(a)pyrene hydroxylation (10), and 2-aminofluorene hydroxylation (1400) [5].
  • In vitro addition of (+)-catechin gave rise to a dose-dependent inhibition of the cytochrome P-450-dependent benzphetamine N-demethylase and ethoxyresorufin O-deethylase activities [6].
  • The protein expressed in COS-7 cells using the cDNA in an expression vector, pKCRH2, shows benzphetamine N-demethylase activity and gives a band identical with that of P-450ib in its mobility on sodium dodecyl sulfate-polyacrylamide gel electrophoresis [7].
  • Cytochrome P-450 LM2 reduction was measured at a series of NADPH concentrations in the absence of substrate and in the presence of 1 mM benzphetamine [8].
  • When examined either in the absence or presence of benzphetamine, the rate constant and fraction of LM2 reduced in the fast phase were decreased as the NADPH concentration was decreased [8].

Biological context of Didrex


Anatomical context of Didrex


Associations of Didrex with other chemical compounds


Gene context of Didrex


Analytical, diagnostic and therapeutic context of Didrex


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  2. Microsomal monooxygenase system in Morris hepatoma: purification and characterization of cytochromes P-450 from Morris hepatoma 5123D of 3-methylcholanthrene-treated rats. Ohmachi, T., Sagami, I., Fujii, H., Watanabe, M. Arch. Biochem. Biophys. (1985) [Pubmed]
  3. Induction of a phenobarbital-inducible form of cytochrome P-450 in rat liver microsomes by 1,1-di(p-chlorophenyl)-2,2-dichloroethylene. Yoshioka, H., Miyata, T., Omura, T. J. Biochem. (1984) [Pubmed]
  4. Thiram-induced toxic liver injury in male Sprague-Dawley rats. Dalvi, R.R., Robbins, T.J., Williams, M.K., Deoras, D.P., Donastorg, F., Banks, C. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. (1984) [Pubmed]
  5. The cytochrome P-450 monooxygenase system of rabbit bladder mucosa: enzyme components and isozyme 5-dependent metabolism of 2-aminofluorene. Vanderslice, R.R., Boyd, J.A., Eling, T.E., Philpot, R.M. Cancer Res. (1985) [Pubmed]
  6. Inhibition of the mutagenicity of aromatic amines by the plant flavonoid (+)-catechin. Steele, C.M., Lalies, M., Ioannides, C. Cancer Res. (1985) [Pubmed]
  7. A novel species of cytochrome P-450 (P-450ib) specific for the small intestine of rabbits. cDNA cloning and its expression in COS cells. Kikuta, Y., Sogawa, K., Haniu, M., Kinosaki, M., Kusunose, E., Nojima, Y., Yamamoto, S., Ichihara, K., Kusunose, M., Fujii-Kuriyama, Y. J. Biol. Chem. (1991) [Pubmed]
  8. The effect of NADPH concentration on the reduction of cytochrome P-450 LM2. Backes, W.L., Reker-Backes, C.E. J. Biol. Chem. (1988) [Pubmed]
  9. Direct evidence for electron transfer from ferrous cytochrome b5 to the oxyferrous intermediate of liver microsomal cytochrome P-450 LM2. Bonfils, C., Balny, C., Maurel, P. J. Biol. Chem. (1981) [Pubmed]
  10. Hepatic mitochondrial cytochrome P-450 system. Distinctive features of cytochrome P-450 involved in the activation of aflatoxin B1 and benzo(a)pyrene. Niranjan, B.G., Wilson, N.M., Jefcoate, C.R., Avadhani, N.G. J. Biol. Chem. (1984) [Pubmed]
  11. Sex differences in cytochrome P-450 isozyme composition and activity in kidney microsomes of mature rainbow trout. Williams, D.E., Masters, B.S., Lech, J.J., Buhler, D.R. Biochem. Pharmacol. (1986) [Pubmed]
  12. Mechanistic studies with N-benzyl-1-aminobenzotriazole-inactivated CYP2B1: differential effects on the metabolism of 7-ethoxy-4-(trifluoromethyl)coumarin, testosterone, and benzphetamine. Kent, U.M., Pascual, L., Roof, R.A., Ballou, D.P., Hollenberg, P.F. Arch. Biochem. Biophys. (2004) [Pubmed]
  13. A kinetic study comparing the light-reversal properties of carbon monoxide inhibition of ethylmorphine, benzphetamine, and 7-ethoxycoumarin dealkylation with those of hydroxylation of 17-hydroxyprogesterone and testosterone. Hamill, S.J., Cooper, D.Y., Schleyer, H., Rosenthal, O. Arch. Biochem. Biophys. (1983) [Pubmed]
  14. Inhibition of rat liver cytochrome P-450 by benzyl hydrodisulfide. Sawahata, T., Neal, R.A. Mol. Pharmacol. (1982) [Pubmed]
  15. Immunological comparison of rat, rabbit, and human liver NADPH-cytochrome P-450 reductases. Guengerich, F.P., Wang, P., Mason, P.S. Biochemistry (1981) [Pubmed]
  16. Differential effects of adrenocorticotropin in vivo on cytochromes P4502D16 and P450c17 in the guinea pig adrenal cortex. Jiang, Q., Huang, Y., Voigt, J.M., DeBolt, K.M., Kominami, S., Takemori, S., Funae, Y., Colby, H.D. Endocrinology (1996) [Pubmed]
  17. Inactivation of chick embryo hepatic cytochrome P450 1A, 2H and 3A following in ovo administration of 3,5-diethoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-ethylpyridine and 3-[2-(2,4,6-trimethylphenyl)thioethyl]-4-methylsydnone. McNamee, J.P., Kimmett, S.M., Marks, G.S. Biochem. Pharmacol. (1995) [Pubmed]
  18. Polychlorinated biphenyls and dibenzofurans in patients with yusho and their toxicological significance: a review. Masuda, Y., Yoshimura, H. Am. J. Ind. Med. (1984) [Pubmed]
  19. The obligatory intermediacy of 16,17 alpha- and 16,17 beta-epoxides in the biotransformation of androsta-5,16-dien-3 beta-ol to androst-5-ene-3 beta, 16 alpha, 17 beta- and -3 beta, 16 beta, 17 alpha-triols by male rat liver microsomes. Watabe, T., Komatsu, T., Kobayashi, K., Isobe, M., Ozawa, N., Saitoh, Y. J. Biol. Chem. (1985) [Pubmed]
  20. Multiple forms of rat liver cytochrome P-450. Immunochemical evidence with antibody against cytochrome P-448. Thomas, P.E., Lu, A.Y., Ryan, D., West, S.B., Kawalek, J., Levin, W. J. Biol. Chem. (1976) [Pubmed]
  21. Purified liver microsomal cytochrome P-450. Electron-accepting properties and oxidation-reduction potential. Guengerich, F.P., Ballou, D.P., Coon, M.J. J. Biol. Chem. (1975) [Pubmed]
  22. Sex-related differences in the expression of cytochrome P450 in hamsters: cDNA cloning and examination of the expression of three distinct CYP2C cDNAs. Sakuma, T., Masaki, K., Itoh, S., Yokoi, T., Kamataki, T. Mol. Pharmacol. (1994) [Pubmed]
  23. Site-directed mutageneses of rat liver cytochrome P-450d: catalytic activities toward benzphetamine and 7-ethoxycoumarin. Furuya, H., Shimizu, T., Hirano, K., Hatano, M., Fujii-Kuriyama, Y., Raag, R., Poulos, T.L. Biochemistry (1989) [Pubmed]
  24. Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice. Ueng, Y.F., Ko, H.C., Chen, C.F., Wang, J.J., Chen, K.T. Life Sci. (2002) [Pubmed]
  25. Initial characterization of the major mouse cytochrome P450 enzymes involved in the reductive metabolism of the hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1,4-di-N-oxide (tirapazamine, SR 4233, WIN 59075). Riley, R.J., Hemingway, S.A., Graham, M.A., Workman, P. Biochem. Pharmacol. (1993) [Pubmed]
  26. The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. Mäenpää, J., Pelkonen, O., Cresteil, T., Rane, A. J. Steroid Biochem. Mol. Biol. (1993) [Pubmed]
  27. Characterization of the cytochrome P-450 monooxygenase system of hamster liver microsomes. Effects of prior treatment with ethanol and other xenobiotics. Ardies, C.M., Lasker, J.M., Lieber, C.S. Biochem. Pharmacol. (1987) [Pubmed]
  28. p,p'-Dichlorodiphenyl sulfone metabolism and disposition in rats. Mathews, J.M., Black, S.L., Matthews, H.B. Drug Metab. Dispos. (1996) [Pubmed]
  29. Effects of three recombinant human leukocyte interferons on drug metabolism in mice. Parkinson, A., Lasker, J., Kramer, M.J., Huang, M.T., Thomas, P.E., Ryan, D.E., Reik, L.M., Norman, R.L., Levin, W., Conney, A.H. Drug Metab. Dispos. (1982) [Pubmed]
  30. Development of a method for the quantitation of benzphetamine metabolites in human urine by high-performance liquid chromatography. Fujinami, A., Miyazawa, T., Kobayashi, Y. Ann. Clin. Biochem. (1998) [Pubmed]
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