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Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 10
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Research Article

Fungal transformations of antihistamines: metabolism of brompheniramine, chlorpheniramine, and pheniramine to N-oxide and N-demethylated metabolites by the fungus Cunninghamella elegans

E. B. Hansen Department of Health and Human Services, Food and Drug Administration, Divisions of Chemistry, National Center for Toxicological Research, Jefferson, AR, 72079, USA
,
B. P. Cho Department of Health and Human Services, Food and Drug Administration, Divisions of Chemistry, National Center for Toxicological Research, Jefferson, AR, 72079, USA; Department of Medicinal Chemistry, University of Rhode Island, Kingston, RI, 02881-0809, USA
,
W. A. Korfmacher Department of Health and Human Services, Food and Drug Administration, Divisions of Chemistry, National Center for Toxicological Research, Jefferson, AR, 72079, USA; Department of Drug Metabolism, Schering-Plough Research Institute, Kenilworth, NJ, 07033-0539, USA
&
Carl E. Cerniglia Divisions of Microbiology, National Center for Toxicological Research, Jefferson, AR, 72079, USA
Pages 1081-1092 | Received 01 Apr 1995, Published online: 22 Sep 2008

References

  • Cashman J. R. A convenient radiometric assay for flavin-containing monooxygenase activity. Analytical Biochemistry 1987; 160: 295–300
  • Cashman J. R., Celestial J. R., Leach A., Newdoll J., Park S. B. Tertiary amines related to brompheniramine: preferred conformations for N-oxygenation by the hog liver flavin-containing monooxygenase. Pharmaceutical Research 1993; 10: 1097–1105
  • Cashman J. R., Yang Z. Analysis of amine metabolites by high-performance liquid chromatography on silica gel with a non-aqueous ionic eluent. Journal of Chromatography 1990; 532: 404–410
  • Cerniglia C. E., Hansen F. B., Jr, Lambert K. J., Korfmacher W. A., Miller D. W. Fungal transformations of antihistamines: metabolism of methapyrilene, thenyldiamine, and tripelennamine to N-oxide and N-demethylated derivatives. Xenobiotica 1988; 18: 301–312
  • Davis P. J., Yang W., Hezari M., Campos J., Reddy C. G. Applications of whole cell fungal systems as models of mammalian xenobiotic/drug metabolism. Secondary-Metabolite Biosynthesis and Metabolism, R. J. Petroski, S. P. McCormick. Plenum, New York 1992; 197–207
  • Doerge R. F. Histamine and antihistamine agents. Textbook of Organic Medicinal and Pharmaceutical Chemistry, C. O. Wilson, O. Gisvold, R. F. Doerge. J. B. Lippincott, Phildelphia 1977; 648–670
  • Foster B. C., Coutts R. T., Pasutto F. M. Biotransformation of aryl alkylamines by Cunninghamella bainieri. Xenobiotica 1989; 19: 531–538
  • Hansen E. B., Jr., Cerniglia C. E., Korfmacher W. A., Miller D. W., Heflich R. H. Microbial transformation of the antihistamine pyrilamine maleate. Formation of potential mammalian metabolites. Drug Metabolism and Disposition 1987; 15: 9–106
  • Hansen E. B., Jr, Heflich R. H., Korfmacher W. A., Miller D. W., Cerniglia C. E. Microbial transformation of the antihistaminic drug tripolidine hydrochloride. Journal of Pharmaceutical Sciences 1988; 77: 259–264
  • Kabasakalian P., Taggart M., Townley E. Urinary excretion of pheniramine and its N-demethylated metabolites in man—comparison with chlorpheniramine and brompheniramine data. Journal of Pharmaceutical Sciences 1968a; 57: 621–623
  • Kabasakalian P., Taggart M., Townley E. Urinary excretion of pheniramine and its N-demethylated metabolites in man. Journal of Pharmaceutical Sciences 1968b; 57: 856–858
  • Kamm J. J., Ferullo C. R., Miller D., Van Loon E. J. Metabolism of chlorpheniramine-3H by the rat and dog. Biochemical Pharmacology 1969; 18: 659–671
  • Kasuya F., Igarashi K., Fukui M. Metabolism of chlorpheniramine in rat and human by use of stable isotopes. Xenobiotica 1991; 21: 97–109
  • Korfmacher W. A., Holder C. L., Cerniglia C. E., Miller D. W., Hansen E. B., Jr, Lambert K. J., Gosnell A. B., Slikker W., Jr, Rushing L. G., Thompson H. C., Jr. Desorption chemical ionization mass spectrometry of nine antihistamines and some of their metabolites. Spectrocpy International Journal 1985; 4: 181–192
  • Lijinsky W., Reuber M. D., Blackwell B. M. Liver tumors induced in rats by oral administration of the antihistamine methapyrilene hydrochloride. Science 1980; 209: 817–819
  • Lai C. M., Stoll R. G., Look Z. M., Yacobi A. Urinary excretion of chlorpheniramine and pseudoephedrine in humans. Journal of Pharmaceutical Sciences 1979; 68: 1243–1246
  • Luo H., Hawes E. M., McKay G., Korchinski E. D., Midha K. K. N+-glucuronicdation of aliphatic tertiary amines, a general phenomenon in the metabolism of H1-antihistamines in humans. Xenobiotica 1991; 21: 1281–1288
  • Maurer H. H. Chromatography of histamine H1- and H2-receptor blockers in biosamples. Journal of Chromatography 1990; 531: 369–404
  • Osterloh J. D., Karakaya A., Carter D. E. Isolation and identification of the polar metabolites of chlorpheniramine in the dog. Drug Metabolism and Disposition 1990; 8: 12–15
  • Peets E. A., Jackson M., Symohowicz S. J. Metabolism of chlorpheniramine maleate in man. Journal of Pharmacology and Experimental Therapeutics 1972; 180: 464–474
  • Yang W., Jiang T., Acosta D., Davis P. J. Microbial models of mammalian metabolism: involvement of cytochrome P450 in the N-demethylation of N-methylcarbazole by Cunninghamella echinulata. Xenobiotica 1993; 23: 973–982

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