Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 11-12
112
Views
50
CrossRef citations to date
0
Altmetric
Research Article

Triclabendazole biotransformation and comparative diffusion of the parent drug and its oxidized metabolites into Fasciola hepatica

, , , , &
Pages 1043-1057 | Received 14 May 2004, Published online: 22 Sep 2008

Reference

  • ALVAREZ, L., IMPERIALE, F., SANCHEZ, S., MURNO, G. and LANUSSE, C., 2000, Uptake of albendazole and albendazole sulphoxide by Haemonchus contortus and Fasciola hepatica in sheep. Veterinary Parasitology, 94, 75–89.
  • ALVAREZ, L., MOTTIER, L. and LANUSSE, C., 2004, Comparative assessment of the access of albendazole, fenbendazole and triclabendazole to Fasciola hepatica: effect of bile in the incubation medium. Parasitology, 128, 73–81.
  • ALVAREZ, L., MOTTIER, L., SANCHEZ, S. and LANUSSE, C., 2001, Ex vivo diffusion of albendazole and its sulphoxide metabolite into Ascaris suum and Fasciola hepatica. Parasitology Research, 87, 929–934.
  • ALVAREZ, L., SANCHEZ, S. and LANUSSE, C., 1999, In vivo and ex vivo uptake of albendazole and its sulphoxide metabolite by cestode parasites: relationship with their kinetics behaviour in sheep. Journal of Veterinary Pharmacology and Therapeutics, 22, 77–86.
  • ALVINERIE, M. and GALTIER, P., 1986, Assay of triclabendazole and its main metabolites in plasma by high-performance liquid chromatography. Journal of Chromatography, 374, 409–414.
  • AVMA, 2001, Report of the AVMA panel on euthanasia. Journal of the American Veterinary Medical Association, 218, 669–696.
  • BENNETT, J. and KOHLER, P., 1987, Fasciola hepatica: action in vitro of triclabendazole on immature and adult species. Experimental Parasitology, 63, 49–57.
  • BOGAN, J., KINABO, L., STRONG, M., FORMICA, C., GALTIER, P. and ALVINERIE, M., 1988, Pharmacokinetics of triclabendazole in cattle, sheep, goats, horses, ponies, donkeys, pigs and man. In Proceedings of the 4th Congress of the European Association for Veterinary Pharmacology and Toxicology, Budapest, Hungary, pp. 159–163.
  • BORAY, J., CROWFOOT, P., STRONG, M., ALLISON, J., SCHELLENBAUM, M., VON ORELLI, M. and SARASIN, G., 1983, Treatment of immature and mature Fasciola hepatica infections in sheep with triclabendazole. Veterinary Record, 113, 315–317.
  • BeSCHER, G., BOWEN, F., STRONG, M. and CROWFOOT, P., 1999, Efficacy of triclabendazole, its metabolites and other compounds in sheep. In Proceedings of the International Conference of the World Association for the Advancement of Veterinary Parasitology, abstract c.7.40.
  • COLES, G., 1986, Anthelmintic activity of triclabendazole. Journal of Helminthology, 60, 210–212.
  • COURTNEY, C. and ROBERSON, E., 1995, Anticestodal and antinematodal drugs. In R. Adams (ed.), Veterinary Pharmacology and Therapeutics (Ames: Iowa State University Press), pp. 940–952.
  • CROSS, H., RENZ, A. and TREES, A., 1998, In vitro uptake of ivermectin by adult male Onchocerca ochengi. Annals of Tropical Medicine and Parasitology, 92, 711–720.
  • DIXIT, A. and ROCHE, T., 1984, Spetrophotometric assay of the flavin-containing mono-oxigenase and changes in its activity in female mouse liver with nutritional and diurnal conditions. Archives of Biochemistry and Biophysics, 233, 50–63.
  • DoucH, P. and BUCHANAN, L., 1979, Some properties of the sulphoxidases and sulphoxide reductases of the cestode Moniezia expansa, the nematode Ascaris suum and mouse liver. Xenobiotica, 9, 675–679.
  • FETTERER, R. and REW, R., 1984, Interaction of Fasciola hepatica with albendazole and its metabolites. Journal of Veterinary Pharmacology and Therapeutics, 7, 113–118.
  • GALTIER, P., LARRIEU, G. and BEAUNE, P., 1986, Characterization of the microsomal cytochrome P-450 species inhibited in rat liver in the course of fascioliasis. Biochemical Pharmacology, 35, 4345–4347.
  • GIBALDI, M. and PERRIER, D., 1982, Pharmacokinetics (New York: Marcel Dekker), pp. 45-109. GOTTSCHALL, D., THEODORIDES, V. and WANG, R., 1990, The metabolism of benzimidazole anthelmintics. Parasitology Today, 6, 118–124.
  • GROTHUSEN, A., HARDT, J., BRAUTIGAM, L., LANG, D. and BoCKE R., 1996, A convenient method to discriminate between cytochrome P450 enzymes and fiavin-containing mono-oxygenases in human liver microsomes. Archives of Toxicology, 71, 64–71.
  • HENNESSY, D., LACEY, E., STEEL, J. and PRICHARD, R., 1987, The kinetics of triclabendazole disposition in sheep. Journal of Veterinary Pharmacology and Therapeutics, 10, 64–72.
  • HENNESSY, D., PRICHARD, R. and STEEL, J., 1993, Biliary secretion and enterohepatic recycling of fenbendazole metabolites in sheep. Journal of Veterinary Pharmacology and Therapeutics, 16, 132–140.
  • Ho, N., GEARY, T., RAUB, T., BARSHUM, C. and THOMPSON, D., 1990, Biophysical transport properties of the cuticle of Ascaris suum. Molecular and Biochemical Parasitology, 41, 153–166.
  • LANUSSE, C., NARE, B. and PRICHARD, R., 1993, Comparative sulphoxidation of albendazole by sheep and cattle liver microsomes and the inhibitory effect of methimazole. Xenobiotica, 23, 285-295. LANUSSE, C. and PRICHARD, R., 1993, Clinical pharmacokinetics and metabolism of benzimidazole anthelmintics in ruminants. Drug Metabolism Reviews, 25, 235–279.
  • MAs-COMA, M., ESTEBAN, J. and BARGUES, M., 1999, Epidemiology of human fascioliasis: a review and proposed new classification. WHO Bulletin, 77, 340–346.
  • MCCRAKEN, R. and LIPKOWITZ, K., 1990, Structure—activity relationship of benzimidazole anthelmintics: a molecular modeling approach to in vivo drug efficacy. Journal of Parasitology, 76, 853–864.
  • McMANus, M., STUPANS, I., BURGESS, W., KOENIG, J., HALL, P. and BIRKETT, D., 1987, Flavin-containing mono-oxygenase activity in human liver microsomes. Drug Metabolism and Disposition, 15, 256–261.
  • MORONI, P., BURONFOSSE, T., LONGIN-SAUVAGEON, C., DELATOUR, P. and BENOIT, E., 1995, Chiral sulfoxidation of albendazole by the fiavin adenine dinucleotide-containing and cytochrome P450-dependent mono-oxygenases from rat liver microsomes. Drug Metabolism and Disposition, 23, 160–165.
  • MOTTIER, L., ALVAREZ, L., PIS, A. and LANUSSE, C., 2003, Transtegumental diffusion of benzimidazole anthelmintics into Moniezia benedeni: correlation with their octanol—water partition coefficients. Experimental Parasitology, 103, 1–7.
  • MOTTIER, L., MORENO, L., ALVAREZ, L., VIRKEL, G. and LANUSSE, C., 2004, Measurement of triclabendazole and its metabolites in liver flukes: method development and full validation. Journal of Pharmaceutical and Biomedical Analysis, 35, 991–999.
  • PtHouRco, F., THOMAS, J. and JARRY, C., 2000, A microscale HPLC method for the evaluation of octanol—water partition coefficients in a series of new 2-amino-2-oxazolines. Journal of Liquid Chromatography and Research Technology, 23, 443–453.
  • PRECIOUS, W. and BARRET, J., 1989, Xenobiotic metabolism in helminths. Parasitology Today, 5, 156–160.
  • RAWDEN, H., KOKWARO, G., WARD, S. and EDWARDS, G., 2000, Relative contribution of cytochromes P-450 and fiavin-containing mono-oxygenases to the metabolism of albendazole by human liver microsomes. British Journal of Clinical Pharmacology, 49, 313–322.
  • ROBINSON, M., LAWSON, J., TRUDGETT, A., HOEY, E. and FAIRWEATHER, I., 2004, The comparative metabolism of triclabendazole sulphoxide by triclabendazole-susceptible and triclabendazole-resistant Fasciola hepatica. Parasitology Research, 92, 205–210.
  • ROTHWELL, J. and SANGSTER, N., 1997, Haemonchus contortus: the uptake and metabolism of closantel. International Journal for Parasitology, 27, 313–319.
  • SMITH, P., KROHN, R., HERMANSON, G., MALLIA, A., GARTNER, F., PROVENZANO, M., FUJIMOTO, E., GOEKE, N., OLSON, B. and KLENK, D., 1985, Measurement of protein using bicinchoninic acid. Analytical Biochemistry, 150, 76–85.
  • SOLANA, H., RODRIGUEZ, J. and LANUSSE, C., 2001, Comparative metabolism of albendazole and albendazole sulphoxide by different helminth parasites. Parasitology Research, 87, 275–280.
  • SOUHAILI EL AMRI H., FARGETTON, X., DELATOUR, P. and BATT, A., 1987, Sulphoxidation of albendazole by the FAD-containing and cytochrome P-450 dependent mono-oxygenases from pig liver microsomes. Xenobiotica, 17, 1159–1168.
  • VIRKEL, G., LIFSCHITZ, A., SALLOVITZ, J., Pis, A. and LANUSSE, C., 2004, Comparative hepatic and extra-hepatic enantioselective sulphoxidation of albendazole and fenbendazole in sheep and cattle. Drug Metabolism and Disposition (in press).

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.