Metabolic pathways of anthelmintic drug monepantel in sheep and in its parasite (Haemonchus contortus)

Drug Testing and Analysis

Volumn 6, Issue 10, 2014, Pages 1055-1062

  Stuchlíková, Lucie ^a   Jirásko, Robert ^b   Vokřál, Ivan ^a   Valát, Martin ^a   Lamka, Jiří ^a   Szotáková, Barbora ^a   Holčapek, Michal ^b   Skálová, Lenka ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

Amino acetonitrile derivatives; Biotransformation; Mass spectrometry; Nematodes; UHPLC MS

Indexed keywords

BIOCONVERSION; BIOMOLECULES; DISEASE CONTROL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; METABOLITES; STRAIN;

AMINO-ACETONITRILE DERIVATIVE; BIOTRANSFORMATION; EX-VIVO; GASTROINTESTINAL; IN-VIVO; METABOLIC PATHWAYS; NEMATODE; PARASITE-; U-HPLC-MS; ULTRA-HIGH PERFORMANCE LIQUID CHROMATOGRAPHIES;

MASS SPECTROMETRY;

MONEPANTEL; AMINOACETONITRILE; ANTHELMINTIC AGENT;

ARTICLE; COMPARATIVE STUDY; DRUG HYDROLYSIS; DRUG METABOLISM; DRUG STRUCTURE; DRUG TRANSFORMATION; EX VIVO STUDY; EXPERIMENTAL SHEEP; FECES ANALYSIS; HAEMONCHUS CONTORTUS; IN VIVO STUDY; METABOLISM; NONHUMAN; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; URINALYSIS; ANALOGS AND DERIVATIVES; ANIMAL; DRUG EFFECTS; HAEMONCHUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; PROCEDURES; SHEEP;

AMINOACETONITRILE; ANIMALS; ANTHELMINTICS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HAEMONCHUS; MALE; SHEEP; TANDEM MASS SPECTROMETRY;

EID: 84916895223     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1630     Document Type: Article

References (33)

1. R. Kaminsky, P. Ducray, M. Jung, R. Clover, L. Rufener, J. Bouvier, S.S. Weber, A. Wenger, W. Wieland-Berghausen, T. Goebel, N. Gauvry, F. Pautrat, T. Skripsky, O. Froelich, C. Komoin-Oka, B. Westlund, A. Sluder, P. Mäser. A new class of anthelmintics effective against drug-resistant nematodes. Nature 2008, 452, 176.
2. L. Rufener, P. Mäser, I. Roditi, R. Kaminsky. Haemonchus contortus Acetylcholine receptors of the DEG-3 subfamily and their role in sensitivity to monepantel. Pathogens 2009, 5, e1000380.
3. G.C. Coles. The future of veterinary parasitology. Vet. Parasitol. 2001, 98, 31.
4. R. Kaminsky, N. Gauvry, S.S. Weber, T. Skripsky, J. Bouvier, A. Wenger, F. Schroeder, Y. Desaules, R. Hotz, T. Goebel, B.C. Hosking, S. Pautrat, S. Wieland-Berghausen, P. Ducray. Identification of the amino-acetonitrile derivative monepantel (AAD 1566) as a new anthelmintic drug development candidate. Parasitol. Res. 2008, 103, 931.
5. Australian Pesticides and Veterinary Medicines Authority. Public Release Summary on the Evaluation of the New Active Monepantel in the Product Zolvix Monepantel Broad Spectrum Oral Anthelmintic for Sheep. 2010, APVMA product number 62752, 1-79.
6. D. Karadzovska, W. Seewald, A. Browning, M. Smal, J. Bouvier, J.M. Giraudel. Pharmacokinetics of monepantel and its sulfone metabolite, monepantel sulfone, after intravenous and oral administration in sheep. J. Vet. Pharmacol. Therap. 2009, 32, 359.
7. B. Kinsella, P. Byrne, H. Cantwell, M. McCormack, A. Furey, M. Danaher. Determination of the new anthelmintic monepantel and its sulfone metabolite in milk and muscle using a UHPLC-MS/MS and QuEChERS method. J. Chromatogr. B 2011, 879, 3707.
8. L. Stuchlíková, R. Jirásko, I. Vokřál, J. Lamka, M. Špulák, M. Holčapek, B. Szotáková, H. Bártíková, M. Pour, L. Skálová. Investigation of the metabolism of monepantel in ovine hepatocytes by UHPLC/MS/MS. Anal. Bioanal. Chem. 2013, 405, 1705.
9. V. Cvilink, J. Lamka, L. Skálová. Xenobiotic metabolizing enzymes and metabolism of anthelmintics in helminths. Drug Metab. Rev. 2009, 41, 8.
10. S.T. Laing, A. Ivens, R. Laing, S. Ravikumar, V. Butler, D.J. Woods, J.S. Gilleard. Characterization of the xenobiotic response of Caenorhabditis elegans to the anthelmintic drug albendazole and the identification of novel drug glucoside metabolites. Biochem. J. 2010, 432, 505.
11. G.P. Brennan, I. Fairweather, A. Trudgett, E. McCoy Hoey, M. McConville, M. Meaney, M. Robinson, N. McFerran, L. Ryan, C. Lanusse, L. Mottier, L. Alvarez, H. Solana, G. Virkel, P.M. Brophy. Understanding triclabendazole resistance. Exp. Mol. Pathol. 2007, 82, 104.
12. K.S. Hakala, M. Link, B. Szotáková, L. Skálová, R. Kostiainen, R.A. Ketola. Characterization of metabolites of sibutramine in primary cultures of rat hepatocytes by liquid chromatography-ion trap mass spectrometry. Anal. Bioanal. Chem. 2008, 393, 1327.
13. M. Holčapek, L. Kolářová, M. Nobilis. High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites. Anal. Bioanal. Chem. 2008, 391, 59.
14. A.W.T. Bristow, K.S. Webb. Intercomparison study on accurate mass measurement of small molecules in mass spectrometry. J. Am. Soc. Mass Spectrom. 2003, 14, 1086.
15. R. Jirásko, M. Holčapek, M. Nobilis. Identification of phase I and phase II metabolites of benfluron and dimefluron in rat urine using high-performance liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2011, 25, 2153.
16. R. Kučera, M. Nobilis, L. Skálová, B. Szotáková, P. Císař, T. Jira, J. Klimeš, V. Wsól. Use of chiral liquid chromatography for the evaluation of stereospecifity in the carbonyl reduction of potential benzo[c]fluorine antineoplastics benfluron and dimefluron in various species. J. Pharm. Biomed. Anal. 2005, 37, 1049.
17. M. Nicklasson, S. Björkman, B. Roth, M. Jönsson, P. Höglund. Stereoselective metabolism of pentoxifylline in vitroand in vivo in humans. Chirality 2002, 14, 643.
18. M.H. Roos, M. Otsen, R. Hoekstra, J.G. Veenstra, J.A. Lenstra. Genetic analysis of inbreeding of two strains of the parasitic nematode Haemonchus contortus. Int. J. Parasitol. 2004, 34, 109.
19. J.A. van Wyk, F.S. Malan. Resistance of field strains of Haemonchus contortus to ivermectin, closantel, rafoxanide and the benzimidazoles in South Africa. Vet. Rec. 1988, 123, 226.
20. J.A. van Wyk, H.M. Gerber, H.T. Groeneveld. A technique for the recovery of nematodes from ruminants by migration from gastro-intestinal ingesta gelled in agar: large-scale application. Onderstepoort J. Vet. Res. 1980, 47, 147.
21. M. Holčapek, R. Jirásko, M. Lísa. Basic rules for the interpretation of atmospheric pressure ionization mass spectra of small molecules. J. Chromatogr. A 2010, 25, 3908.
22. G.G. Gibson, P. Skett. Introduction to drug metabolism. Nelson Thornes Publishers: Cheltenham, UK, 2001.
23. A. Parkinson. Biotransformation of xenobiotics. In Klaassen CD (ed) Casarett & Doull's Toxicology - The Basic Science of Poisons. (Ed.: C.D. Klaassen). McGraw-Hill: New York, 2001, pp. 133-219.
24. B. Testa, J.M. Mayer. Hydrolysis in Drug and Prodrug Metabolism. University of Lausanne: Switzerland, 2003.
25. J. Barrett. Helminth detoxification mechanism. J. Helminthol. 1997, 71, 85.
26. J. Barrett. Cytochrome P450 in parasitic protozoa and helminths. Comp. Biochem. Physiol. C 1998, 121, 181.
27. M. Alvinerie, J. Dupuy, C. Eeckhoutte, J.F. Sutra, D. Kerboeuf. In vitro metabolism of moxidectin in Haemonchus contortus adult stages. Parasitol. Res. 2001, 87, 702.
28. J. Rothwell, N. Sangster. Haemonchus contortus: the uptake and metabolism of closantel. Int. J. Parasitol. 1997, 27, 313.
29. I. Vokřál, V. Jedličková, R. Jirásko, L. Stuchlíková, H. Bártíková, L. Skálová, J. Lamka, M. Holčapek, B. Szotáková. The metabolic fate of ivermectine in host (Ovis aries) and parasite (Haemonchus contortus). Parasitology 2013, 140, 361.
30. V. Cvilink, V. Kubíček, M. Nobilis, V. Křížová, B. Szotáková, J. Lamka, M. Várady, M. Kuběnová, R. Novotná, M. Gavelová, L. Skálová. Biotransformation of flubendazole and selected model xenobiotics in Haemonchus contortus. Vet. Parasitol. 2008, 151, 242.
31. V. Cvilink, L. Skálová, B. Szotáková, J. Lamka, R. Kostiainen, R.A. Ketola. LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. Anal. Bioanal. Chem. 2008, 391, 337.
32. I. Vokřál, H. Bártíková, L. Prchal, L. Stuchlíková, L. Skálová, B. Szotáková, J. Lamka, M. Várady, V. Kubíček. The metabolism of flubendazole and the activities of selected biotransformation enzymes in Haemonchus contortus strains susceptible and resistant to anthelmintics. Parasitology 2012, 139, 1309.
33. I. Vokřál, R. Jirásko, L. Stuchlíková, H. Bártíková, B. Szotáková, J. Lamka, M. Várady, L. Skálová. Biotransformation of albendazole and activities of selected detoxification enzymes in Haemonchus contortus strains susceptible and resistant to anthelmintics. Vet. Parasitol. 2013, 196, 373.