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Xenobiotica
the fate of foreign compounds in biological systems
Volume 21, 1991 - Issue 11
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Research Article

Thebaine O-demethylation to oripavine: Genetic differences between two rat strains

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Pages 1501-1509 | Received 03 Jan 1991, Accepted 05 Jun 1991, Published online: 22 Sep 2008

References

  • Al-Dabbagh S. G., Idle J. R., Smith R. L. Animal modelling of human polymorphic oxidation—the metabolism of debrisoquine and phenacetin in rat inbred strains. Journal of Pharmacy and Pharmacology 1981; 33: 161–164
  • Boobis A. R., Seddon C. E., Davies D. S. Bufuralol 1′-hydroxylase activity of the rat—strain differences and the effects of inhibitors. Biochemical Pharmacology 1986; 35: 2961–2965
  • Brochmann-Hanssen E. A second pathway for the terminal steps in the biosynthesis of morphine. Planta Medica 1984; 51: 343–345
  • Brochmann-Hanssen E. Biosynthesis of morphinan alkaloids. The Chemistry and Biology of Isoquinoline Alkaloids, J. D. Phillipson, M. F. Roberts, M. H. Zenk. Springer-Verlag, Berlin. Heidelberg, New York, Tokyo 1985; 229–239
  • Cardinale G. J., Donnerer J., Finck A. D., Kantrowitz J. D., Oka K., Spector S. Morphine and codeine are endogenous components of human cerebrospinal fluid. Life Sciences 1987; 40: 301–306
  • Chen Z. R., Somogyi A. A., Reynolds G., Bochner F. Disposition and metabolism of codeine after single and chronic doses in one poor and seven extensive metabolisers. British Journal of Clinical Pharmacology 1991; 31: 381–390
  • Chen Z. R., Somogyi A. A., Bochner F. Polymorphic O-demethylation of codeine. Lancet 1988; ii: 914–915
  • Dayer P., Desmeules J., Leemann T., Striberni R. Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalysing debrisoquine 4-hydroxylation (cytochrome P-450 db1/bufI). Biochemical and Biophysical Research Communications 1988; 152: 411–416
  • Donnerer J., Cardinale G., Coffey J., Lissek C. A., Jardine I., Spector S. Chemical characterization and regulation of endogenous morphine and codeine in the rat. Journal of Pharmacology and Experimental Therapeutics 1987; 242: 583–587
  • Donnerer J., Oka K., Brossi A., Rice K. C., Spector S. Presence and formation of codeine and morphine in the rat. Proceedings of the National Academy of Sciences 1986; 83: 4566–4567
  • Eichelbaum M., Gross A. S. The genetic polymorphism of debrisoquine/sparteine metabolism—clinical aspects. Pharmacology and Therapeutics 1990; 46: 377–394
  • Goldstein A., Barrett R. W., James I. F., Lowney L. I., Weitz C. J., Knipmeyer L. L., Rapoport H. Morphine and other opiates from beef brain and adrenal. Proceedings of the National Academy of Sciences 1985; 82: 5203–5207
  • Gonzalez F. J., Skoda R. C., Kimura S., Umeno M., Zanger U. M., Nebert D. W., Gelboin H. V., Hardwick J. P., Meyer U. A. Characterization of the common genetic defect in human deficient debrisoquine metabolism. Nature 1988; 331: 442–446
  • Jaffe J. H., Martin W. R. Opioid analgesics and antagonists. The Pharmacological Basis of Therapeutics, A. Goodman Gilman, T. W. Rall, A. S. Nies, P. Taylor. Pergamon Press, New York 1990; 498
  • Kahn G. C., Rubenfield M., Davies D. S., Murray S., Boobis A. R. Sex and strain differences in hepatic debrisoquine 4-hydroxylase activity of the rat. Drug Metabolism and Disposition 1985; 13: 510–516
  • Kobayashi S., Murray S., Watson D., Sesardic D., Davies D. S., Boobis A. R. The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochemical Pharmacology 1989; 38: 2795–2799
  • Kodaira H., Spector S. Transformation of thebaine to oripavine, codeine, and morphine by rat liver, kidney, and brain microsomes. Proceedings of the National Academy of Sciences 1988; 85: 1267–1271
  • Kodaira H., Lisek C. A., Jardine I., Arimura A., Spector S. Identification of the convulsant opiate thebaine in mammalian brain. Proceedings of the National Academy of Sciences 1989; 86: 716–719
  • Kroemer H. K., Mikus G., Kronbach T., Meyer U. A., Eichelbaum M. In vitro characterization of the human cytochrome P-450 involved in the polymorphic oxidation of propafenone. Clinical Pharmacology and Therapeutics 1989; 45: 28–33
  • Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
  • Matsunaga E., Zanger U. M., Hardwick J. P., Gelboin H. V., Meyer U. A., Gonzalez F. J. The CYP2D gene subfamily: analysis of the molecular basis of the debrisoquine 4-hydroxylase deficiency in DA rats. Biochemistry 1989; 28: 7394–7355
  • Meier P. J., Müller H. K., Dick B., Meyer U. A. Hepatic monooxygenase activities in subjects with a genetic defect in drug oxidation. Gastroenterology 1983; 85: 682–692
  • Mikus G., Somogyi A. A., Bochner F., Eichelbaum M. Codeine O-demethylation: rat strain differences and the effects of inhibitors. Biochemical Pharmacology 1991; 41: 757–762
  • Misra A. L., Pontani R. B., Mule S. J. Pharmacokinetics and metabolism of [3H]thebaine. Xenobiotica 1974; 4: 17–32
  • Nichols A. I., Peck C. C. LSNLR: A general weighted least squares nonlinear regression program. USUHS version 1.0. Division of Clinical Pharmacology and Medicine, Uniformed Services University for the Health Sciences. 1981, Technical Report No. 5.0
  • Oguri K., Hanioka N., Yoshimura H. Species differences in metabolism of codeine: urinary excretion of codeine glucuronide, morphine-3-glucuronide and morphine-6-glucuronide in mice, rats, guine pigs and rabbits. Xenobiotica 1990; 20: 683–688
  • Oka K., Kantrowitz J. D., Spector S. Isolation of morphine from toad skin. Proceedings of the National Academy of Sciences 1985; 82: 1852–1854
  • Stadler R., Zenk M. H. A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline. Liebigs Annalen der Chemie 1990; 555–562
  • Todd R. D., Muldoon S. M., Watson R. L. Determination of morphine in cerebrospinal fluid and plasma by high-performance liquid chromatography with electrochemical detection. Journal of Chromatography 1982; 232: 101–110
  • Weitz C. J., Lowney L. I., Faull K. F., Feistner G., Goldstein A. Morphine and codeine from mammalian brain. Proceedings of the National Academy of Sciences 1986; 83: 9784–9788
  • Yeh S. Y. Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat. Archives of International Pharmacodynamics 1981; 254: 223–240
  • Yue Q. Y., Svensson J.-O., Alm C., Sjöqvist F., Säwe J. Codeine O-demethylation cosegregates with polymorphic debrisoquine hydroxylation. British Journal of Clinical Pharmacology 1989; 28: 639–645
  • Zysset T., Zeugin T., Küpfer A. In-vivo and in-vitro dextromethorphan metabolism in SD and DA rat: an animal model of the debrisoquine-type polymorphic oxidation in man. Biochemical Pharmacology 1988; 37: 3155–3160

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