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Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 7
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Research Article

Metabolism of artelinic acid to dihydroqinghaosu by human liver cytochrome P4503A

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Pages 703-717 | Published online: 22 Sep 2008

References

  • BASCO, L. K. and LEBRAS, J., 1993, In vitro activity of artemisinin derivatives against African isolates and clones of Plasmodium falciparum. American Journal of Tropical Medicine and Hygiene, 49, 301–307.
  • BANGCHANG, K. N., KARBWANG, J. and BACK, D. J., 1992, Mefloquine metabolism by human liver microsomes: effect of other antimalarial drugs. Biochemical Pharmacology, 43, 1957–1961.
  • BREWER, T. G., GRATE, S. J., PEGGINS, J. 0., WEINA, P. J., PETRAS, J. M., LEVI NE, B. S., HEIFFER, M. H. and SCHUSTER, B. G., 1994a, Fatal neurotoxicity of arteether and artemether. American Journal of Tropical Medicine and Hygiene, 51, 251–259.
  • BREWER, T. G., PEGGINS, J. 0., GRATE, S. J., PETRAS, J. M., LEVINE, B. S., WEINA, P. J., SWEARENGEN J., HEIFFER, M. H. and SCHUSTER, B. G., 1994b, Neurotoxicity in animals due to arteether and artemether. Transactions of the Royal Society of Tropical Medicine and Hygiene, 88, 33–36.
  • BREWER, T. G., PETRAS, J. M., PEGGINS, J. 0., Li, Q., LIN, A. J., SPERRY, M., FIGUEROA, L., AGUILAR, A. and SCHUSTER, B. S., 1993, Differential neurotoxicity of artemisinin analogues in an in vivo model. American Journal of Tropical Medicine and Hygiene, 49, 292.
  • BRUECKNER, R. P., COSTER, T., WESCHE, D. L., SHMUKLARSKY, M. and SCHUSTER, B. G., 1998, Prophylaxis of Plasmodium falciparum infection in a human challenge model with WR238605, a new 8-aminoquinoline antimalarial. Antimicrobial Agents and Chemotherapy, 42, 1293–1294.
  • BURKE, M. D., THOMPSON, S., HALPERT, J., HAAPARANTA, T. and MAYER, R. T., 1985, Ethoxy-, pentoxy-, and benzyloxyphenoxazone and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochemical Pharmacology, 34, 3337–3345.
  • BUTERS, J. T. M., SCHILLER, C. D. and Cuou, R. C., 1993, A high sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man: direct fluorescence monitoring of the deethylation of 7-ethoxy-4-trifluoroethylcoumarin. Biochemical Pharmacology, 46, 1577–1584.
  • GRACE, J. M., SKANCHY D. J., IDowu, R. O., ROTH, N. A. and AGUILAR, A. J., 1997, The debenzylation of artelinic acid by human liver cytochrome P-450 3A4. Paper presented at the 8th North American International Society for the Study of Xenobiotics Meeting, 26–30 October, Hilton Head, SC.
  • GRACE, J. M., AGUILAR, A. J., TROTMAN, K. M. and BREWER, T. G., 1998, Metabolism of fl-arteether to dihydroqinghaosu by human liver microsomes and recombinant cytochrome P450. Drug Metabolism and Disposition, 26, 313–317.
  • GUENGERICH, F. P., MULLER -ENOCH D. and BLAIR, I., 1986, Oxidation of quinidine by human liver cytochrome P-450. Molecular Pharmacology, 30, 287–295.
  • HALLIDAY, R. C., JONES, B. C., SMITH, D. A., KITTERINGHAM, N. R. and PARK, B. K., 1995, An investigation of the interaction between halofantrine, CYP2D6 and CYP3A4: studies with human liver microsomes and heterologous enzyme expression systems. British Journal of Clinical Pharmacology, 40, 369–378.
  • HELLGREN, U., ANGEL, V. H., BERGQVIST, Y., FORERO -GOMEZ, J. S. and ROMBO L, 1991, Plasma concentrations of sulfadoxine pyrimethamine, mefloquine and its main metabolite after regular malaria prophylaxis for two years. Transactions of the Royal Society of Tropical Medicine and Hygiene, 85, 356–357.
  • HIEN, T. T. and WHITE, N. J., 1993, Qinghaosu. Lancet, 341,603–608.
  • IRSHAID, Y., BRANCH, R. A. and ADEDOYIN, A., 1996, Metabolic interaction of putative cytochrome P4503A substrates with alternative pathways of dapsone metabolism in human liver microsomes. Drug Metabolism and Disposition, 24, 164–171.
  • ISLAM, S. A., WOLF, C. R., LENNARD, M. S. and STERNBERG, M. J. E., 1991, A three-dimensional template for substrates of human cytochrome P450 involved in debrisoquine 4-hydroxylase. Carcinogenesis, 12, 2211–2219.
  • KLAYMANN, D. L., 1985, Qinghaosu (Artemisinin): an antimalarial drug from China. Science, 228, 1049–1055.
  • KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAvws, D. S. and BOOBIS, A. R., 1989, The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine is the inverse of that in man. Biochemical Pharmacology, 38, 2795–2799.
  • KOYMANS, L., VERMEULEN, N. P. E., VAN ACKER, S., KOPPELE, J. M., HEYKANTS, J. P., LAVIRIJSEN, K., MEULDERMANS W. and DONNE -0 P DEN KELDER, G. M., 1992, A predictive model for substrates of cytochrome P450-desbrisoquine (2D6). Chemical Research in Toxicology, 5, 211–219.
  • LEEMANN, T., TRANSON, C. and DAYER, P., 1993, Cytochrome P450tb (CYP2C): a major monooxygenase catalyzing diclofenac 4'-hydroxylation in human liver. Life Sciences, 52, 29–34.
  • LESKOVAC, V. and PEGGINS, J. 0., 1992, Hepatic metabolism of artemisinin drugs. III. Induction of hydrogen peroxide production in rat liver microsomes by artemisinin drugs. Comparative Biochemistry and Physiology C, 101, 203–208.
  • Li, Q.-G., PEGGINS J. 0., FLECKENSTEIN, L. L., MASONIC, K., HEIFFER, M. H. and BREWER, T. G., 1998a, The pharmacokinetics and bioavailability of dihydroartemisinin, arteether, atremether, artesunic acid, and artelinic acid in rats. Journal of Pharmacy and Pharmacology, 50, 1–11.
  • LI, Q.-G., PEGGINS, J. 0., LIN, A. J., MASONIC, K., TROTMAN, K. M. and BREWER, T. G., 1998b, Pharmacology and toxicology of artelinic acid: preclinical investigations on pharmacokinetics, metabolism, protein, and red blood cell binding, and acute and anorectic toxicities. Transactions of the Royal Society of Tropical Medicine and Hygiene, 92, 332–340.
  • LIN, A. J., KLAYMAN, D. L. and MILHOUS, W. K., 1987, Antimalarial activity of new water-soluble dihydroartemisinin derivatives. Journal of Medicinal Chemistry, 30, 2147–2150.
  • LOOAREESUWAN, S., 1994, Overview of clinical studies on artemisinin derivatives in Thailand.
  • Transactions of the Royal Society of Tropical Medicine and Hygiene, 88 (Suppl. 1), S9-11. LOWRY, 0. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
  • MEIER, U., KRONBACH, T. and MEYER, U., 1985, Assay of mephenytoin metabolism in human liver microsomes by high-performance liquid chromatography. Analytical Biochemistry, 151, 286–291.
  • MELENDEZ V., PEGGINS J. 0., BREWER, T. G. and THEOHARIDES, A. D., 1991, Determination of the antimalarial arteether and its deethylated metabolite dihydroartemisinin in plasma by high-performance liquid chromatography with reductive electrochemical detection. Journal of Pharmaceutical Sciences, 80, 132–138.
  • Mucus, G., 1986, Pharmacokinetics and metabolism of quinidine in extensive and poor metabolisers of sparteine. European Journal of Clinical Pharmacology, 31, 69–72.
  • MILLER, L. G. and PANOSLkN, C. B., 1997, Ataxia and slurred speech after artesunate treatment for Falciparum malaria. New England Journal of Medicine, 336, 1328.
  • NELSON D. R., KAMATAKI, T., WAXMAN, D. J., GUENGERICH, F. P., ESTABROOK, R. W., FEYEREISEN, R., GONZALEZ, F. J., COON, M. J., GUNSALUS I. C., GOTOH, 0., OKUDA, K. and NEBERT, D. W., 1993, The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA and Cellular Biology, 12, 1–51.
  • NEWTON, D. J., WANG, R. W. and Lu, A. Y. H., 1995, Cytochrome P450 inhibitors: evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metabolism and Disposition, 23, 154–158.
  • OBACH, R. S., 1997, Predictions of human pharmacokinetics from liver microsomal metabolism data: experimental design and data interpretation. Paper presented at the 8th North American International Society for the Study of Xenobiotics Meeting, 26 October, Hilton Head, SC.
  • OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370–2378.
  • PEARCE, R., GREENWAY, D. and PARKINSON, A., 1992, Species differences and interindividual variation in liver microsomal cytochrome P450 2A enzymes: effects on coumarin, dicumarol, and testosterone oxidation. Archives of Biochemistry and Biophysics, 298, 211–225.
  • SENANAYAKE, N. and DE SILVA, H., 1994, Delayed cerebellar ataxia complicating Falciparum malaria: a clinical study of 74 patients. Journal of Neurology, 241, 456–459.
  • SHIMADA, T., YAMAZAKI, H., MIMURA, M., Nu', Y. and GUENGERICH, F. P., 1994, Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics, 270, 414–423.
  • SHOU, M., GROGAN, J., MANCEWICZ, J. A., KRAUSZ, K. W., GONZALEZ, F. J., GELBOIN, H. V. and KORZEKWA, K. R., 1994, Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry, 33, 6450–6455.
  • SHWE, T., MYINT, P. T., HTUT, Y., MYINT, W. and SOE, L., 1988, The effect of mefloquine-artemether compared with quinine on patients with complicated Falciparum malaria. Transactions of the Royal Society of Tropical Medicine and Hygiene, 82, 665–666.
  • SONDERFAN, A. J., ARLOTTO, M. P., DUTTON, D. R., MCMILLEN, S. K. and PARKINSON, A., 1987, Regulation of testosterone hydroxylation by rat liver microsomal cytochrome P-450. Archives of Biochemistry and Biophysics, 255, 27–41.
  • STROBL, G. R., KRUEDENER, S., STOCKIGT J., GUENGERICH, F. P. and WOLFF, T., 1993, Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies. Journal of Medicinal Chemistry, 36, 1136–1145.
  • TEIA-ISAVADHARM, P., NOSTEN, F., KYLE, D., LUXEMBURGER, C., TER KUILE, F., PEGGINS J. 0., BREWER, T. G. and WHITE, N. J., 1996, Comparative bioavailability of oral, rectal and intramuscular artemether in healthy subjects: use of simultaneous measurement by high performance liquid chromatography and bioassay. British Journal of Clinical Pharmacology, 42, 599–604.
  • TITULAER, H. A., ELING, W. M. and ZUIDEMA, J., 1993, Pharmacokinetic and pharmaco dynamic aspects of artelinic acid in rodents. Journal of Pharmacy and Pharmacology, 45, 830–835.
  • VAN HENSBROEK, M. B., ONYIORAH, E., JAFFAR, S., SCHNEIDER, G., PALMER, A., FRENKEL, J., ENWERE G., FORCK, S., NUSMEUER, A., BENNETT, S., GREENWOOD, B. and KWIATKOWSKI, D., 1996, A trial of artemether or quinine in children with cerebral malaria. New England Journal of Medicine, 335, 69–75.
  • VERME, C. N., LUDDEN, T. M., CLEMENTI, W. A. and HARRIS, S. C ., 1992, Pharmacokinetics of quinidine in male patients: a population analysis. Clinical Pharmacokinetks, 22, 468–480.
  • WANG, P. P., BEAUNE, P., KAMINSKY, L. S., DANNAN, GA., KADLUBAR, F. F., LARREY, D. and GUENGERICH, F. P., 1983, Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes. Biochemistry, 22, 5375–5383.
  • WESCHE, D. L., DECOSTER, M. A., TORTELLA, F. C. and BREWER, T. G., 1994, Neurotoxicity of artemisinin analogues in vitro. Antimicrobial Agents and Chemotherapy, 38, 1813-1819. WHITE, N. J., 1985, Clinical pharmacokinetics of antimalarial drugs. Clinical Pharmacokinetks, 10, 187–215.
  • WHITE, N. J., 1996, The treatment of malaria. New England Journal of Medicine, 335, 800-806. WRIGHTON, S. A., RING, B. J., WATKINS, P. B. and VANDENBRANDEN, M., 1989, Identification of a polymorphically expressed member of the human cytochrome P-450III family. Molecular Pharmacology, 36, 97–105.
  • WRIGHTON, S. A., BRIAN, W. R., MARIE -ANGES, S., IWASAKI, M., GUENGERICH, F. P., RAUCY, J. L., MOLOWA, D. T. and VANDENBRANDEN, M., 1990, Studies on the expression and metabolic capabilities of human liver capabilities of human liver cytochrome P450IIIA5 (HLp3). Molecular Pharmacology, 38, 207–213.
  • ZANNONI, D., 1985, Mefloquine: an antimalarial drug interacting with the b/c region of bacterial respiratory chains. FEBS Letters, 183, 340–344.
  • ZHAO, X.-J. and Ismzmu, T., 1997, The in vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 283, 1168–1176.

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