Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 37, 2007 - Issue 1
59
Views
2
CrossRef citations to date
0
Altmetric
Research Article

Metabolism of [14C]-5-chloro-1,3-benzodioxol-4-amine in male Wistar-derived rats following intraperitoneal administration

, , , , &
Pages 44-58 | Received 01 May 2006, Accepted 05 Jul 2006, Published online: 22 Sep 2008

References

  • Adams NH, Levi PA, Hodgson E. Regulation of cytochrome P-450 isozymes by methylenedioxyphenyl compounds. Chemico-Biological Interactions 1993; 86: 255–274
  • Anders MW, Sunram JM, Wilkinson CF. Mechanism of the metabolism of 1,3-benzodioxoles to carbon monoxide. Biochemical Pharmacology 1984; 33: 577–580
  • Bronson ME, Jiang W, DeRuiter J, Clark CR. Structure–activity relationships of BDB and its monomethyl and dimethyl derivatives. Pharmacology Biochemistry and Behavior 1995; 51: 477–479
  • Cook JC, Hodgson E. Induction of cytochrome P-450 by methylenedioxyphenyl compounds: Importance of the methylene carbon. Toxicology and Applied Pharmacology 1983; 68: 131–139
  • Duckett CJ, Lindon JC, Walker H, Abou-Shakra F, Wilson ID, Nicholson JK. Metabolism of 3-chloro-4-fluoroaniline in rat using [14C]-radiolabelling, 19F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR. Xenobiotica 2006; 36: 59–77
  • Jaffe H, Fujii K, Sengupta M, Guerin H, Epstein SS. In vivo inhibition of mouse liver microsomal hydroxylating systems by methylenedioxyphenyl insecticidal synergists and related compounds. Life Sciences 1968; 7: 1051–1062
  • Kumagai Y, Wickham KA, Schmitz DA, Cho AK. Metabolism of methylenedioxyphenyl compounds by rabbit liver preparations. Biochemical Pharmacology 1991; 42: 1061–1067
  • Murray M. Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependant drug oxidation. Current Drug Metabolism 2000; 1: 67–84
  • Nichols DE, Brewster WK, Johnson MP, Oberlander R, Riggs RM. Nonneurotoxic tetralin and indan analogues of 3,4-{methylenedioxy}amphetamine (MDA). Journal of Medicinal Chemistry 1990; 44: 703–710
  • Scarfe GB, Clayton E, Wilson ID, Nicholson JK. Identification and quantification of metabolites of 2,3,5,6-tetrafluoro-4-trifluoromethylaniline in rat using 19F nuclear magnetic resonance spectroscopy, high-performance liquid chromatography-nuclear magnetic resonance spectroscopy and high-performance liquid chromatography-mass spectrometry. Journal of Chromatography B 2000; 748: 311–319
  • Scarfe GB, Lindon JC, Nicholson JK, Wright B, Clayton E, Taylor S, Wilson ID. Investigation of the quantitative metabolic fate and excretion of 3-methyl-4-trifluoromethylaniline and 3-methyl-4-trifluoromethylacetanilide in the rat. Drug Metabolism and Disposition 1999c; 27: 1171–1178
  • Scarfe GB, Nicholson JK, Lindon JC, Wilson ID, Taylor S, Clayton E, Wright B. Identification of the urinary metabolites of 4-bromoaniline and 4-bromo-[carbonyl-13C]-acetanilide in rat. Xenobiotica 2002a; 32: 325–337
  • Scarfe GB, Tugnait M, Wilson ID, Nicholson JK. Studies on the metabolism of 4-fluoroaniline and 4-fluoroaceanilide in rat: Formation of 4-acetamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation. Xenobiotica 1999a; 29: 205–216
  • Scarfe GB, Wilson ID, Warne MA, Holmes E, Nicholson JK, Lindon JC. Structure–metabolism relationships of substituted anilines: Prediction of N-acetylation and N-oxanilic acid formation using computational chemistry. Xenobiotica 2002b; 32: 267–277
  • Scarfe GB, Wright B, Clayton E, Taylor S, Wilson ID, Lindon JC, Nicholson JK. Quantitative studies on the urinary metabolic fate of 2-chloro-4-trifluoromethylaniline in the rat using 19F-NMR spectroscopy and directly coupled HPLC-NMR-MS. Xenobiotica 1999b; 29: 77–91
  • Selim K, Kaplowitz N. Hepatotoxicity of psycotropic drugs. Hepatology 1999; 29: 1347–1351
  • Stephenson CP, Hunt GE, Topple AN, McGregor IS. The distribution of 3,4-methylenedioxymethamphetamine ‘Ecstasy-induced c-fos expression in rat brain. Neuroscience 1999; 92: 1011–1023
  • Tugnait M, Lenz EM, Phillips P, Hofmann M, Spraul M, Lindon JC, Nicholson JK, Wilson ID. The metabolism of 4-trifluoromethoxyaniline and [13C]-4-trifluoromethoxyaniline in the rat: Detection and identification of metabolites excreted in the urine by NMR and HPLC NMR. Journal of Pharmaceutical and Biomedical Analysis 2002; 8: 875–885
  • Yu L, Wilkinson CF, Anders MW. Generation of carbon monoxide during the microsomal metabolism of methylenedioxyphenyl compounds. Biochemical Pharmacology 1980; 29: 1113–1122
  • Zhu BT. Catechol-O-methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: Importance in pathophysiology and pathogenesis. Current Drug Metabolism 2002; 3: 321–349

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.