Diclofenac and its transformation products: Environmental occurrence and toxicity - A review

Environment International - Tập 96 - Trang 127-138 - 2016
Linson Lonappan1, Satinder Kaur Brar1, Ratul Kumar Das1, Mausam Verma2, Rao Y. Surampalli3
1INRS-ETE, Université du Québec, 490, Rue de la Couronne, Québec, G1K 9A9, Canada
2CO(2) Solutions Inc., 2300, Rue Jean-Perrin, Québec, Québec, G2C 1T9, Canada.
3Department of Civil Engineering, University of Nebraska-Lincoln, N104 SEC PO Box 886105, Lincoln, NE 68588-6105, USA

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Acuña, 2015, Balancing the health benefits and environmental risks of pharmaceuticals: diclofenac as an example, Environ. Int., 85, 327, 10.1016/j.envint.2015.09.023

Agüera, 2005, Application of time-of-flight mass spectrometry to the analysis of phototransformation products of diclofenac in water under natural sunlight, J. Mass Spectrom., 40, 908, 10.1002/jms.867

Ahrer, 2001, Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry, J. Chromatogr. A, 910, 69, 10.1016/S0021-9673(00)01187-0

Alder, 2006, Consumption and occurrence

Al-Rajab, 2010, The non-steroidal anti-inflammatory drug diclofenac is readily biodegradable in agricultural soils, Sci. Total Environ., 409, 78, 10.1016/j.scitotenv.2010.09.020

Anumol, 2016, Occurrence and fate of emerging trace organic chemicals in wastewater plants in Chennai, India, Environ. Int., 92–93, 33, 10.1016/j.envint.2016.03.022

Aristi, 2016, Nutrients versus emerging contaminants–or a dynamic match between subsidy and stress effects on stream biofilms, Environ. Pollut., 212, 208, 10.1016/j.envpol.2016.01.067

Backhaus, 2014, Medicines, shaken and stirred: a critical review on the ecotoxicology of pharmaceutical mixtures, Philos. Trans. R. Soc. Lond. Ser. B Biol. Sci., 369

Barakat, 2011, New trends in removing heavy metals from industrial wastewater, Arab. J. Chem., 4, 361, 10.1016/j.arabjc.2010.07.019

Behera, 2011, Occurrence and removal of antibiotics, hormones and several other pharmaceuticals in wastewater treatment plants of the largest industrial city of Korea, Sci. Total Environ., 409, 4351, 10.1016/j.scitotenv.2011.07.015

Beltran, 2009, Diclofenac removal from water with ozone and activated carbon, J. Hazard. Mater., 163, 768, 10.1016/j.jhazmat.2008.07.033

Bendz, 2005, Occurrence and fate of pharmaceutically active compounds in the environment, a case study: Hoje River in Sweden, J. Hazard. Mater., 122, 195, 10.1016/j.jhazmat.2005.03.012

Benotti, 2008, Pharmaceuticals and endocrine disrupting compounds in U.S. drinking water, Environ. Sci. Technol., 43, 597, 10.1021/es801845a

BirdLife

Boettcher, 1991, Pharmacological properties of five diclofenac metabolites identified in human plasma, Agents Actions, 34, 135, 10.1007/BF01993259

Buser, 1998, Occurrence and fate of the pharmaceutical drug diclofenac in surface waters: rapid photodegradation in a Lake, Environ. Sci. Technol., 32, 3449, 10.1021/es980301x

Carballa, 2005, Removal of cosmetic ingredients and pharmaceuticals in sewage primary treatment, Water Res., 39, 4790, 10.1016/j.watres.2005.09.018

Carmona, 2014, Occurrence of acidic pharmaceuticals and personal care products in Turia River Basin: from waste to drinking water, Sci. Total Environ., 484, 53, 10.1016/j.scitotenv.2014.02.085

Carter, 2014, Fate and uptake of pharmaceuticals in soil-earthworm systems, Environ. Sci. Technol., 48, 5955, 10.1021/es500567w

Carter, 2014, Fate and uptake of pharmaceuticals in soil-plant systems, J. Agric. Food Chem., 62, 816, 10.1021/jf404282y

Chefetz, 2008, Sorption and mobility of pharmaceutical compounds in soil irrigated with reclaimed wastewater, Chemosphere, 73, 1335, 10.1016/j.chemosphere.2008.06.070

Clara, 2005, Removal of selected pharmaceuticals, fragrances and endocrine disrupting compounds in a membrane bioreactor and conventional wastewater treatment plants, Water Res., 39, 4797, 10.1016/j.watres.2005.09.015

Cleuvers, 2003, Aquatic ecotoxicity of pharmaceuticals including the assessment of combination effects, Toxicol. Lett., 142, 185, 10.1016/S0378-4274(03)00068-7

Cleuvers, 2004, Mixture toxicity of the anti-inflammatory drugs diclofenac, ibuprofen, naproxen, and acetylsalicylic acid, Ecotoxicol. Environ. Saf., 59, 309, 10.1016/S0147-6513(03)00141-6

Cleuvers, 2008, Chronic mixture toxicity of pharmaceuticals to daphnia – the example of nonsteroidal anti-inflammatory drugs, 277

da Silva Oliveira, 2007, Heavy metals in untreated/treated urban effluent and sludge from a biological wastewater treatment plant, Environ. Sci. Pollut. Res. Int., 14, 483, 10.1065/espr2006.10.355

Dai, 2015, Occurrence and source apportionment of pharmaceuticals and personal care products in the Beiyun River of Beijing, China, Chemosphere, 119, 1033, 10.1016/j.chemosphere.2014.08.056

Das, 2010, Diclofenac is toxic to the Himalayan vulture Gyps himalayensis, Bird Conserv. Int., 21, 72, 10.1017/S0959270910000171

Drillia, 2005, Fate and mobility of pharmaceuticals in solid matrices, Chemosphere, 60, 1034, 10.1016/j.chemosphere.2005.01.032

Ericson, 2010, Physiological effects of diclofenac, ibuprofen and propranolol on Baltic Sea blue mussels, Aquat. Toxicol., 99, 223, 10.1016/j.aquatox.2010.04.017

Eriksson, 2010, A photochemical study of diclofenac and its major transformation products, Photochem. Photobiol., 86, 528, 10.1111/j.1751-1097.2009.00703.x

Fatta-Kassinos, 2011, Existence of pharmaceutical compounds in tertiary treated urban wastewater that is utilized for reuse applications, Water Resour. Manag., 25, 1183, 10.1007/s11269-010-9646-4

Fent, 2006, Ecotoxicology of human pharmaceuticals, Aquat. Toxicol., 76, 122, 10.1016/j.aquatox.2005.09.009

Ferrari, 2003, Ecotoxicological impact of pharmaceuticals found in treated wastewaters: study of carbamazepine, clofibric acid, and diclofenac, Ecotoxicol. Environ. Saf., 55, 359, 10.1016/S0147-6513(02)00082-9

Ferrari, 2004, Environmental risk assessment of six human pharmaceuticals: are the current environmental risk assessment procedures sufficient for the protection of the aquatic environment?, Environ. Toxicol. Chem., 23, 1344, 10.1897/03-246

Gomez, 2007, Pilot survey monitoring pharmaceuticals and related compounds in a sewage treatment plant located on the Mediterranean coast, Chemosphere, 66, 993, 10.1016/j.chemosphere.2006.07.051

Gonzalez-Rey, 2014, Effects of non-steroidal anti-inflammatory drug (NSAID) diclofenac exposure in mussel Mytilus galloprovincialis, Aquat. Toxicol., 148, 221, 10.1016/j.aquatox.2014.01.011

Gros, 2010, Removal of pharmaceuticals during wastewater treatment and environmental risk assessment using hazard indexes, Environ. Int., 36, 15, 10.1016/j.envint.2009.09.002

Haap, 2008, Acute effects of diclofenac and DMSO to Daphnia magna: immobilisation and hsp70-induction, Chemosphere, 73, 353, 10.1016/j.chemosphere.2008.05.062

Hallare, 2004, Developmental toxicity and stress protein responses in zebrafish embryos after exposure to diclofenac and its solvent, DMSO, Chemosphere, 56, 659, 10.1016/j.chemosphere.2004.04.007

Halling-Sørensen, 1998, Occurrence, fate and effects of pharmaceutical substances in the environment - a review, Chemosphere, 36, 357, 10.1016/S0045-6535(97)00354-8

Hao, 2007, Liquid chromatography–tandem mass spectrometry of bioactive pharmaceutical compounds in the aquatic environment—a decade's activities, Anal. Bioanal. Chem., 387, 1247, 10.1007/s00216-006-0956-6

Heberer, 2002, Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data, Toxicol. Lett., 131, 5, 10.1016/S0378-4274(02)00041-3

Heberer, 2002, Tracking persistent pharmaceutical residues from municipal sewage to drinking water, J. Hydrol., 266, 175, 10.1016/S0022-1694(02)00165-8

Heberer, 1998, Occurrence and distribution of organic contaminants in the aquatic system in Berlin. Part I: Drug residues and other polar contaminants in Berlin surface and groundwater, Acta Hydrochim. Hydrobiol., 26, 272, 10.1002/(SICI)1521-401X(199809)26:5<272::AID-AHEH272>3.0.CO;2-O

Henry, 2013

Hernando, 2006, Environmental risk assessment of pharmaceutical residues in wastewater effluents, surface waters and sediments, Talanta, 69, 334, 10.1016/j.talanta.2005.09.037

Hilton, 2003, Determination of selected human pharmaceutical compounds in effluent and surface water samples by high-performance liquid chromatography–electrospray tandem mass spectrometry, J. Chromatogr. A, 1015, 129, 10.1016/S0021-9673(03)01213-5

Hoeger, 2005, Water-borne diclofenac affects kidney and gill integrity and selected immune parameters in brown trout (Salmo trutta f. fario), Aquat. Toxicol., 75, 53, 10.1016/j.aquatox.2005.07.006

Hoeger, 2008, Distribution of intraperitoneally injected diclofenac in brown trout (Salmo trutta f. fario), Ecotoxicol. Environ. Saf., 71, 412, 10.1016/j.ecoenv.2007.10.020

Huschek, 2004, Environmental risk assessment of medicinal products for human use according to European Commission recommendations, Environ. Toxicol., 19, 226, 10.1002/tox.20015

Johnson, 2013, Do concentrations of ethinylestradiol, estradiol, and diclofenac in European rivers exceed proposed EU environmental quality standards?, Environ. Sci. Technol., 47, 12297, 10.1021/es4030035

Jones, 2002, Aquatic environmental assessment of the top 25 English prescription pharmaceuticals, Water Res., 36, 5013, 10.1016/S0043-1354(02)00227-0

Kallio, 2010, Metabolites of the aquatic pollutant diclofenac in fish bile, Environ. Sci. Technol., 44, 7213, 10.1021/es903402c

Karvelas, 2003, Occurrence and fate of heavy metals in the wastewater treatment process, Chemosphere, 53, 1201, 10.1016/S0045-6535(03)00591-5

Kasprzyk-Hordern, 2008, The occurrence of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs in surface water in South Wales, UK, Water Res., 42, 3498, 10.1016/j.watres.2008.04.026

Khadka, 2013, Understanding the efficacy of diclofenac use-ban and its aftermath effect on Gyps vulture in Koshi Tappu Wildlife Reserve, Nepal, J. Entomol. Zool., 1, 20

Khan, 2004, Modelling of pharmaceutical residues in Australian sewage by quantities of use and fugacity calculations, Chemosphere, 54, 355, 10.1016/j.chemosphere.2003.07.001

Khetan, 2007, Human pharmaceuticals in the aquatic environment: a challenge to green chemistry, Chem. Rev., 107, 2319, 10.1021/cr020441w

Kim, 2007, Occurrence and removal of pharmaceuticals and endocrine disruptors in South Korean surface, drinking, and waste waters, Water Res., 41, 1013, 10.1016/j.watres.2006.06.034

Kimura, 2005, Removal of pharmaceutical compounds by submerged membrane bioreactors (MBRs), Desalination, 178, 135, 10.1016/j.desal.2004.11.033

Kosjek, 2005, Determination of non-steroidal anti-inflammatory drug (NSAIDs) residues in water samples, Environ. Int., 31, 679, 10.1016/j.envint.2004.12.001

Kovala-Demertzi, 2000, Transition metal complexes of diclofenac with potentially interesting anti-inflammatory activity, J. Inorg. Biochem., 79, 153, 10.1016/S0162-0134(99)00175-0

Kummerer, 2004, Pharmaceuticals in the environment – a brief summary

Kunkel, 2012, Fate of pharmaceuticals in rivers: deriving a benchmark dataset at favorable attenuation conditions, Water Res., 46, 5551, 10.1016/j.watres.2012.07.033

Langford, 2011, Multi-residue screening of prioritised human pharmaceuticals, illicit drugs and bactericides in sediments and sludge, J. Environ. Monit., 13, 2284, 10.1039/c1em10260e

Larsson, 2013, Sludge removal of nonsteroidal anti-inflammatory drugs during wastewater treatment studied by direct hollow fiber liquid phase microextraction, J. Environ. Prot., Vol. 04, 10, 10.4236/jep.2013.49109

Lawrence, 2007, Structural and functional responses of river biofilm communities to the nonsteroidal anti-inflammatory diclofenac, Environ. Toxicol. Chem., 26, 573, 10.1897/06-340R.1

Lee, 2011, Chronic exposure to diclofenac on two freshwater cladocerans and Japanese medaka, Ecotoxicol. Environ. Saf., 74, 1216, 10.1016/j.ecoenv.2011.03.014

Letzel, 2009, Exposure assessment of the pharmaceutical diclofenac based on long-term measurements of the aquatic input, Environ. Int., 35, 363, 10.1016/j.envint.2008.09.002

Lindqvist, 2005, Occurrence of acidic pharmaceuticals in raw and treated sewages and in receiving waters, Water Res., 39, 2219, 10.1016/j.watres.2005.04.003

Lonappan, 2016, J. Chromatogr. A, 1433, 106, 10.1016/j.chroma.2016.01.030

Loos, 2010, Pan-European survey on the occurrence of selected polar organic persistent pollutants in ground water, Water Res., 44, 4115, 10.1016/j.watres.2010.05.032

López-Serna, 2012, Occurrence and distribution of multi-class pharmaceuticals and their active metabolites and transformation products in the Ebro River basin (NE Spain), Sci. Total Environ., 440, 280, 10.1016/j.scitotenv.2012.06.027

Lopez-Serna, 2013, Occurrence of 95 pharmaceuticals and transformation products in urban groundwaters underlying the metropolis of Barcelona, Spain, Environ. Pollut., 174, 305, 10.1016/j.envpol.2012.11.022

Ma, 2016, Characterization of pharmaceutically active compounds in Dongting Lake, China: occurrence, chiral profiling and environmental risk, Sci. Total Environ., 557–558, 268, 10.1016/j.scitotenv.2016.03.053

Marco-Urrea, 2010, Degradation of the drug sodium diclofenac by Trametes versicolor pellets and identification of some intermediates by NMR, J. Hazard. Mater., 176, 836, 10.1016/j.jhazmat.2009.11.112

Markandya, 2008, Counting the cost of vulture decline—an appraisal of the human health and other benefits of vultures in India, Ecol. Econ., 67, 194, 10.1016/j.ecolecon.2008.04.020

Martín, 2012, Occurrence of pharmaceutical compounds in wastewater and sludge from wastewater treatment plants: removal and ecotoxicological impact of wastewater discharges and sludge disposal, J. Hazard. Mater., 239–240, 40, 10.1016/j.jhazmat.2012.04.068

McGettigan, 2013, Use of non-steroidal anti-inflammatory drugs that elevate cardiovascular risk: an examination of sales and essential medicines lists in low-, middle-, and high-income countries, PLoS Med., 10, e1001388, 10.1371/journal.pmed.1001388

Mehinto, 2010, Uptake and biological effects of environmentally relevant concentrations of the nonsteroidal anti-inflammatory pharmaceutical diclofenac in rainbow trout (Oncorhynchus mykiss), Environ. Sci. Technol., 44, 2176, 10.1021/es903702m

Memmert, 2013, Diclofenac: new data on chronic toxicity and bioconcentration in fish, Environ. Toxicol. Chem., 32, 442, 10.1002/etc.2085

Metcalfe, 2003, Distribution of acidic and neutral drugs in surface waters near sewage treatment plants in the lower great lakes, Canada, Environ. Toxicol. Chem., 22, 2881, 10.1897/02-627

Moore, 1990, Photochemical studies on the antiinflammatory drug diclofenac, Photochem. Photobiol., 52, 685, 10.1111/j.1751-1097.1990.tb08667.x

Naidoo, 2009, Diclofenac toxicity in Gyps vulture is associated with decreased uric acid excretion and not renal portal vasoconstriction, Comp. Biochem. Physiol., Part C: Toxicol. Pharmacol., 149, 269

Naidoo, 2009, Veterinary diclofenac threatens Africa's endangered vulture species, Regul. Toxicol. Pharmacol., 53, 205, 10.1016/j.yrtph.2009.01.010

Naisbitt, 2007, Investigation of the immunogenicity of diclofenac and diclofenac metabolites, Toxicol. Lett., 168, 45, 10.1016/j.toxlet.2006.10.014

Oaks, 2004, Diclofenac residues as the cause of vulture population decline in Pakistan, Nature, 427, 630, 10.1038/nature02317

Öllers, 2001, Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water, J. Chromatogr. A, 911, 225, 10.1016/S0021-9673(01)00514-3

Osorio, 2016, Investigating the formation and toxicity of nitrogen transformation products of diclofenac and sulfamethoxazole in wastewater treatment plants, J. Hazard. Mater., 309, 157, 10.1016/j.jhazmat.2016.02.013

Palmer

Pereira, 2015, Environmental impact of pharmaceuticals from Portuguese wastewaters: geographical and seasonal occurrence, removal and risk assessment, Environ. Res., 136, 108, 10.1016/j.envres.2014.09.041

Pereira, 2016, Occurrence of pharmaceuticals and cocaine in a Brazilian coastal zone, Sci. Total Environ., 548–549, 148, 10.1016/j.scitotenv.2016.01.051

Petrović, 2003, Analysis and removal of emerging contaminants in wastewater and drinking water, TrAC Trends Anal. Chem., 22, 685, 10.1016/S0165-9936(03)01105-1

Prakash, 2003, Catastrophic collapse of Indian white-backed Gyps bengalensis and long-billed Gyps indicus vulture populations, Biol. Conserv., 109, 381, 10.1016/S0006-3207(02)00164-7

Prakash, 2012, The population decline of Gyps vultures in India and Nepal has slowed since veterinary use of diclofenac was banned, PLoS One, 7, e49118, 10.1371/journal.pone.0049118

Qin, 2012, Photochemical characteristics of diclofenac and its photodegradation of inclusion complexes with β-cyclodextrins, Quim Nova, 35, 559, 10.1590/S0100-40422012000300022

Rabiet, 2006, Consequences of treated water recycling as regards pharmaceuticals and drugs in surface and ground waters of a medium-sized Mediterranean catchment, Environ. Sci. Technol., 40, 5282, 10.1021/es060528p

Refat, 2014, Synthesis and characterization of coordination behavior of diclofenac sodium drug toward Hg(II), Pb(II), and Sn(II) metal ions: chelation effect on their thermal stability and biological activity, Synth. React. Inorg., Met.-Org., Nano-Met. Chem., 44, 161, 10.1080/15533174.2012.752009

Sacher, 2001, Pharmaceuticals in groundwaters: analytical methods and results of a monitoring program in Baden-Württemberg, Germany, J. Chromatogr. A, 938, 199, 10.1016/S0021-9673(01)01266-3

Samaras, 2013, Fate of selected pharmaceuticals and synthetic endocrine disrupting compounds during wastewater treatment and sludge anaerobic digestion, J. Hazard. Mater., 244–245, 259, 10.1016/j.jhazmat.2012.11.039

Scheurell, 2009, Occurrence of diclofenac and its metabolites in surface water and effluent samples from Karachi, Pakistan, Chemosphere, 77, 870, 10.1016/j.chemosphere.2009.07.066

Scheytt, 2005, Determination of sorption coefficients of pharmaceutically active substances carbamazepine, diclofenac, and ibuprofen, in sandy sediments, Chemosphere, 60, 245, 10.1016/j.chemosphere.2004.12.042

Schmidt, 2011, Effects of the pharmaceuticals gemfibrozil and diclofenac on the marine mussel (Mytilus spp.) and their comparison with standardized toxicity tests, Mar. Pollut. Bull., 62, 1389, 10.1016/j.marpolbul.2011.04.043

Schmitt-Jansen, 2007, Phytotoxicity assessment of diclofenac and its phototransformation products, Anal. Bioanal. Chem., 387, 1389, 10.1007/s00216-006-0825-3

Schulze, 2010, Identification of a phytotoxic photo-transformation product of diclofenac using effect-directed analysis, Environ. Pollut., 158, 1461, 10.1016/j.envpol.2009.12.032

Schwaiger, 2004, Toxic effects of the non-steroidal anti-inflammatory drug diclofenac. Part I: histopathological alterations and bioaccumulation in rainbow trout, Aquat. Toxicol., 68, 141, 10.1016/j.aquatox.2004.03.014

Sharma, 2014, Diclofenac is toxic to the Steppe Eagle Aquila nipalensis: widening the diversity of raptors threatened by NSAID misuse in South Asia, Bird Conserv. Int., 1

Sosiak, 2005

Sotelo, 2012, Removal of caffeine and diclofenac on activated carbon in fixed bed column, Chem. Eng. Res. Des., 90, 967, 10.1016/j.cherd.2011.10.012

Sotelo, 2014, Competitive adsorption studies of caffeine and diclofenac aqueous solutions by activated carbon, Chem. Eng. J., 240, 443, 10.1016/j.cej.2013.11.094

Stierlin, 1979, Biotransformation of diclofenac sodium (Voltaren®) in animals and in man, Xenobiotica, 9, 601, 10.3109/00498257909042327

Strenn, 2004, Carbamazepine, diclofenac, ibuprofen and bezafibrate - investigations on the behaviour of selected pharmaceuticals during wastewater treatment, Water Sci. Technol., 50, 269, 10.2166/wst.2004.0337

Stulten, 2008, Isolation and characterization of a new human urinary metabolite of diclofenac applying LC–NMR–MS and high-resolution mass analyses, J. Pharm. Biomed. Anal., 47, 371, 10.1016/j.jpba.2008.01.024

Stulten, 2008, Occurrence of diclofenac and selected metabolites in sewage effluents, Sci. Total Environ., 405, 310, 10.1016/j.scitotenv.2008.05.036

Suriyanon, 2013, Mechanistic study of diclofenac and carbamazepine adsorption on functionalized silica-based porous materials, Chem. Eng. J., 214, 208, 10.1016/j.cej.2012.10.052

Swan, 2006, Toxicity of diclofenac to Gyps vultures, Biol. Lett., 2, 279, 10.1098/rsbl.2005.0425

Taggart, 2007, Diclofenac disposition in Indian cow and goat with reference to Gyps vulture population declines, Environ. Pollut., 147, 60, 10.1016/j.envpol.2006.08.017

Taggart, 2007, Diclofenac residues in carcasses of domestic ungulates available to vultures in India, Environ. Int., 33, 759, 10.1016/j.envint.2007.02.010

Tavares

Tavares, 2014

The Drug controller General, 2006, I. Diclofenac for veterinary use: regarding

Theodorou, 1999, Copper(II) complexes of diclofenac: spectroscopic studies and DNA strand breakage, Biometals, 12, 167, 10.1023/A:1009246122577

Thomas, 2004, The occurrence of selected human pharmaceutical compounds in UK estuaries, Mar. Pollut. Bull., 49, 436, 10.1016/j.marpolbul.2004.02.028

Triebskorn, 2004, Toxic effects of the non-steroidal anti-inflammatory drug diclofenac. Part II: cytological effects in liver, kidney, gills and intestine of rainbow trout (Oncorhynchus mykiss), Aquat. Toxicol., 68, 151, 10.1016/j.aquatox.2004.03.015

Valdés, 2014, Occurrence and bioaccumulation of pharmaceuticals in a fish species inhabiting the Suquía River basin (Córdoba, Argentina), Sci. Total Environ., 472, 389, 10.1016/j.scitotenv.2013.10.124

Venkateshwarlu, 2011

Verlicchi, 2015, Pharmaceuticals and personal care products in untreated and treated sewage sludge: occurrence and environmental risk in the case of application on soil — a critical review, Sci. Total Environ., 538, 750, 10.1016/j.scitotenv.2015.08.108

Vieno, 2014, Fate of diclofenac in municipal wastewater treatment plant — a review, Environ. Int., 69, 28, 10.1016/j.envint.2014.03.021

Virani, 2011, Major declines in the abundance of vultures and other scavenging raptors in and around the Masai Mara ecosystem, Kenya, Biol. Conserv., 144, 746, 10.1016/j.biocon.2010.10.024

Weigel, 2002, Drugs and personal care products as ubiquitous pollutants: occurrence and distribution of clofibric acid, caffeine and DEET in the North Sea, Sci. Total Environ., 295, 131, 10.1016/S0048-9697(02)00064-5

Willis, 1979, The pharmacokinetics of diclofenac sodium following intravenous and oral administration, Eur. J. Clin. Pharmacol., 16, 405, 10.1007/BF00568201

Xu, 2009, Degradation and adsorption of selected pharmaceuticals and personal care products (PPCPs) in agricultural soils, Chemosphere, 77, 1299, 10.1016/j.chemosphere.2009.09.063

Yamada, 1990, Reactivity of surface hydroxyl groups with metal complex compounds, J. Electron Spectrosc. Relat. Phenom., 54–55, 845, 10.1016/0368-2048(90)80277-H

Yoon, 2010, Occurrence of endocrine disrupting compounds, pharmaceuticals, and personal care products in the Han River (Seoul, South Korea), Sci. Total Environ., 408, 636, 10.1016/j.scitotenv.2009.10.049

Zhang, 2008, Carbamazepine and diclofenac: removal in wastewater treatment plants and occurrence in water bodies, Chemosphere, 73, 1151, 10.1016/j.chemosphere.2008.07.086

Ziółkowska, 2014, Biomarkers of leguminous plant viability in response to soil contamination with diclofenac, Pol. J. Environ. Stud., 23, 263

Zorita, 2009, Occurrence and removal of pharmaceuticals in a municipal sewage treatment system in the south of Sweden, Sci. Total Environ., 407, 2760, 10.1016/j.scitotenv.2008.12.030