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Fate of febantel in the aquatic environment—the role of abiotic elimination processes


Febantel is widely used anthelmintic drug active against a range of gastrointestinal parasites in animals. Despite the fact that it has been detected in the aquatic environment, there is no information on its environmental fate. Therefore, abiotic elimination processes of febantel in the aquatic environment have been studied. The results of direct and indirect photodegradation experiments showed that febantel was persistent against solar radiation. Kinetics of hydrolytic elimination was pH and temperature dependent with half-lives in the range from 210 min to 99 days. Febantel metabolites, fenbendazole and fenbendazole sulfone, were found as major degradation products using high-resolution mass spectrometry. The proposed hydrolytic degradation pathway consisted of the base catalyzed hydrolysis followed by consecutive oxidative cyclization to the five-membered ring of the benzo-imidazole derivative. Aquatic toxicity of febantel and its hydrolytic mixture were evaluated toward the luminescence bacteria Vibrio fischeri. Investigation of febantel sorption onto river sediments showed that the best agreement was obtained with the linear model (R2 > 0.99), while the rate of sorption is the best described with the kinetic model of pseudo-second order. The organic carbon-normalized sorption coefficient, KOC, ranged from 1490 to 3894 L kg−1 for five sediment samples. The results of this research demonstrate that febantel persist in the natural waters and potentially could travel far from the source.

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  • Babić S, Periša M, Škorić I (2013) Photolytic degradation of norfloxacin, enrofloxacin and ciprofloxacin in various aqueous media. Chemosphere 91:1635–1642

    Article  Google Scholar 

  • Bártíková H, Podlipná R, Skálová L (2016) Veterinary drugs in the environment and their toxicity to plants. Chemosphere 144:2290–2301

    Article  Google Scholar 

  • Biošić M, Mitrevski M, Babić S (2017a) Environmental behavior of sulfadiazine, sulfamethazine and their metabolites. Environ Sci Poll Res 24:9802–9812

    Article  Google Scholar 

  • Biošić M, Škorić I, Beganović J, Babić S (2017b) Nitrofurantoin hydrolytic degradation in the environment. Chemosphere 186:660–668

    Article  Google Scholar 

  • Blum KM, Andersson PL, Ahrens L, Wiberg K, Haglund P (2018) Persistence, mobility and bioavailability of emerging organic contaminants discharged from sewage treatment plants. Sci Total Environ 612:1532–1542

    CAS  Article  Google Scholar 

  • Boxall ABA, Fogg L, Blackwell PA, Kay P, Pemberton EJ (2002) Review of veterinary medicines in the environment. R&D technical report P6-012/8/TR, environment agency, Bristol

  • Carlssona G, Patring J, Kreuger J, Norrgren L, Oskarsson A (2013) Toxicity of 15 veterinary pharmaceuticals in zebrafish (Danio rerio) embryos. Aquat Toxicol 126:30–41

    Article  Google Scholar 

  • Danaher M, De Ruyck H, Crooks SRH, Dowling G, O’Keeffe M (2007) Review of methodology for the determination of benzimidazole residues in biological matrices. J Chromatogr B 845:1–37

    CAS  Article  Google Scholar 

  • ECHA (2003) European Commission—Joint Research Centre, technical guidance document on risk Assessment, Part II Accessed 1 March 2018

  • ECHA (2017) European chemicals agency, guidance on information requirements and chemical safety assessment. Chapter R.11: PBT/vPvB assessment. Version 3.0. Accessed 1 March 2018

  • EPISuite (2017) US EPA Estimation Programs Interface Suite™ for Microsoft® Windows, v 4.11, United States Environmental Protection Agency, Washington, DC, USA

  • Farre M, Ašperger D, Kantiani L, Gonzalez S, Petrović M, Barcelo D (2008) Assessment of the acute toxicity of triclosan and methyl triclosan in wastewater based on the bioluminescence inhibition of Vibrio fischeri. Anal Bioanal Chem 390(8):1999–2007

    CAS  Article  Google Scholar 

  • Horvat AJM, Petrović M, Babić S, Mutavdžić Pavlović D, Ašperger D, Pelko S, Mance AD, Kaštelan-Macan M (2012) Analysis, occurrence and fate of anthelmintics and their transformation products in the environment. TrAC-Trend Anal Chem 31:61–84

    CAS  Article  Google Scholar 

  • Hulett JR (1964) Deviations from Arrhenius equation. Q Rev Chem Soc 18(3):227–242

    CAS  Article  Google Scholar 

  • Janz JM, Farrens DL (2003) Assessing structural elements that influence Schiff base stability: mutants E113Q and D190N destabilize rhodopsin through different mechanisms. Vis Res 43:2991–3002

    CAS  Article  Google Scholar 

  • Kalberlah F, Oltmanns J, Schwarz M (2014) Guidance for the precautionary protection of raw water destined for drinking water extraction from contaminants regulated under REACH, project (UFOPLAN) FKZ 371265416

  • Kim H-Y, Lee I-S, Oh J-E (2017) Human and veterinary pharmaceuticals in the marine environment including fish farms in Korea. Sci Total Environ 579:940–949

    CAS  Article  Google Scholar 

  • Kümmerer K (2009) Antibiotics in the aquatic environment. A review Part I. Chemosphere 75:417–434

    Article  Google Scholar 

  • Kurwadkar ST, Adams CD, Meyer MT, Kolpin DW (2007) Effects of Sorbate speciation on sorption of selected sulfonamides in three loamy soils. J Agric Food Chem 55:1370–1376

    CAS  Article  Google Scholar 

  • Lagergren S (1898) Zur theorie der sogenannten adsorption gelöster stoffe. K. Sven. Vetenskapsakad. Handl. 24:1–39

  • Li WC (2014) Occurrence, sources and fate of pharmaceuticals in aquatic environment and soil. Environ Poll 187:193–201

    CAS  Article  Google Scholar 

  • McKay G, Ho YS (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465

    Article  Google Scholar 

  • Mitchell SM, Ullman JL, Teel AL, Watts RJ (2015) Hydrolysis of amphenicol and macrolide antibiotics: chloramphenicol, florfenicol, spiramycin, and tylosin. Chemosphere 134:504–511

    CAS  Article  Google Scholar 

  • Mutavdžić Pavlović D, Ćurković L, Blažek D, Župan J (2014) The sorption of sulfamethazine on soil samples: isotherms and error analysis. Sci Total Environ 497–498:543–552

    Article  Google Scholar 

  • OECD (2000) Test no. 106: adsorption-desorption using a batch equilibrium method

  • OECD (2004) Test no. 111: hydrolysis as a function of pH

  • Oh SJ, Park J, Lee MJ, Park SY, Lee J-H, Choi K (2006) Ecological hazard assessment of major veterinary benzimidazoles: acute and chronis toxicities to aquatic microbes and invertebrates. Environ Toxicol Chem 25(8):2221–2226

    CAS  Article  Google Scholar 

  • Schwarzenbach RP, Gschwend PM, Imboden DM (2003) Environmental organic chemistry, 2nd edn. Willey, Hoboken

    Google Scholar 

  • Sim W-J, Kim H-Y, Choi S-D, Kwon J-H, Oh J-E (2013) Evaluation of pharmaceuticals and personal care products with emphasis on anthelmintics in human sanitary waste, sewage, hospital wastewater, livestock wastewater and receiving water. J Hazard Mater 248–249:219–227

    Article  Google Scholar 

  • Thiele-Bruhn S (2003) Pharmacutical antibiotic compounds in soils—a review. J Plant Nutr Soil Sci 166:145–167

    CAS  Article  Google Scholar 

  • Wagil M, Maszkowska J, Białk-Bielińska A, Stepnowski P, Kumirska J (2015) A comprehensive approach to the determination of two benzimidazoles in environmental samples. Chemosphere 119:S35–S41

    CAS  Article  Google Scholar 

  • Yamamoto H, Nakamura Y, Moriguchi S, Nakamura Y, Honda Y, Tamura I, Hirata Y, Hayashi A, Sekizawa J (2009) Persistence and partitioning of eight selected pharmaceuticals in the aquatic environment: laboratory photolysis, biodegradation, and sorption experiments. Water Res 43:351–362

    CAS  Article  Google Scholar 

  • Zrnčić M, Gross M, Babić S, Kaštelan-Macan M, Barcelo D, Petrović M (2014) Analysis of anthelmintics in surface water by ultra high performance liquid chromatography coupled to quadrupole linear ion trap tandem mass spectrometry. Chemosphere 99:224–232

    Article  Google Scholar 

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This study has been fully supported by the Croatian Science Foundation under the project Fate of pharmaceuticals in the environment and during advanced wastewater treatment (PharmaFate) (IP-09-2014-2353).

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Correspondence to Sandra Babić.

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Responsible editor: Hongwen Sun

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Babić, S., Pavlović, D.M., Biošić, M. et al. Fate of febantel in the aquatic environment—the role of abiotic elimination processes. Environ Sci Pollut Res 25, 28917–28927 (2018).

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  • Anthelmintic
  • Hydrolysis
  • Sorption
  • Degradation products
  • Toxicity