Effects of carbamazepine and two of its metabolites on the non-biting midge Chironomus riparius in a sediment full life cycle toxicity test

Water Research

Volumn 98, Issue , 2016, Pages 19-27

  Heye, Katharina ^a   Becker, Dennis ^a   Lütke Eversloh, Christian ^b   Durmaz, Vedat ^c   Ternes, Thomas A ^b   Oetken, Matthias ^a   Oehlmann, Jörg ^a  

^a GOETHE UNIVERSITY   (Germany)

^b FEDERAL INSTITUTE OF HYDROLOGY   (Germany)

^c ZUSE INSTITUTE BERLIN   (Germany)

Author keywords

10,11 dihydro 10,11 dihydroxy carbamazepine; Carbamazepine 10,11 epoxide; Ecdysone receptor; Pharmaceutical; Reproduction

Indexed keywords

AMIDES; ANIMALS; DRUG PRODUCTS; HORMONES; METABOLITES; MOLECULAR DYNAMICS; POPULATION STATISTICS; RISK ASSESSMENT; SEDIMENTS; TOXICITY;

10,11-DIHYDRO-10,11-DIHYDROXY-CARBAMAZEPINE; CARBAMAZEPINE 10 ,11 EPOXIDES; CHIRONOMUS RIPARIUS; CLASSICAL MOLECULAR DYNAMICS; ECDYSONE RECEPTOR; FULL LIFE-CYCLE TESTS; POPULATION GROWTH RATES; REPRODUCTION;

BIOMOLECULES;

CARBAMAZEPINE; ECDYSONE RECEPTOR; ANTICONVULSIVE AGENT;

CONCENTRATION (COMPOSITION); DRUG; FLY; GROWTH RATE; LIFE CYCLE ANALYSIS; METABOLITE; MOLECULAR ANALYSIS; OECD; POPULATION GROWTH; RISK ASSESSMENT; TOXICITY TEST;

ARTICLE; CHIRONOMUS RIPARIUS; CLUTCH SIZE; CONTROLLED STUDY; FEMALE; LC50; LIFE CYCLE; MALE; MICROBIAL DEGRADATION; MOLECULAR DYNAMICS; MORTALITY; NONHUMAN; POPULATION GROWTH; PRIORITY JOURNAL; RISK ASSESSMENT; SEDIMENT; TOXICITY TESTING; ANIMAL; CHEMISTRY; CHIRONOMIDAE; LIFE CYCLE STAGE;

CERATOPOGONIDAE; CHIRONOMUS RIPARIUS;

ANIMALS; ANTICONVULSANTS; CARBAMAZEPINE; CHIRONOMIDAE; LIFE CYCLE STAGES; TOXICITY TESTS;

EID: 84962662555     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2016.03.071     Document Type: Article

References (62)

1. Almeida Â., Freitas R., Calisto V., Esteves V.I., Schneider R.J., Soares A.M.V.M., Figueira E. Chronic toxicity of the antiepileptic carbamazepine on the clam Ruditapes philippinarum. Comp. Biochem. Physiol. Part C 2015, 172-173:26-35.
2. Åqvist J., Medina C., Samuelsson J.E. A new method for predicting binding affinity in computer-aided drug design. Protein Eng. 1994, 7(3):385-391.
3. Armitage P.D., Cranston P.S., Pinder L.C.V. The Chironomidae. Biology and Ecology of Non-biting midges 1995, Chapman & Hall, London.
4. Bahlmann A., Brack W., Schneider R.J., Krauss M. Carbamazepine and its metabolites in wastewater: analytical pitfalls and occurrence in Germany and Portugal. Water Res. 2014, 57:104-114.
5. Bennett G.D., Amore B.M., Finnell R.H., Wlodarczyk B., Kalhorn T.F., Skiles G.L., Nelson S.D., Slattery J.T. Teratogenicity of carbamazepine-10, 11-epoxide and oxcarbazepine in the SWV mouse. J. Pharmacol. Exp. Ther. 1996, 279(3):1237-1242.
6. Benoit D.A., Sibley P.K., Juenemann J.L., Ankley G.T. Chironomus tentans life-cycle test: design and evaluation for use in assessing toxicity of contaminated sediments. Environ. Toxicol. Chem. 1997, 16(6):1165-1176.
7. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., Bourne P.E. The protein data bank. Nucleic Acids Res. 2000, 28(1):235-242.
8. Billas I.M.L., Iwema T., Garnier J.M., Mitschler A., Rochel N., Moras D. Structural adaptability in the ligand-binding pocket of the ecdysone hormone receptor. Nature 2003, 426:91-96.
9. Bourgeois B.F., Wad N. Individual and combined antiepileptic and neurotoxic activity of carbamazepine and carbamazepine-10,11-epoxide in mice. J. Pharmacol. Exp. Ther. 1984, 231(2):411-415.
10. Bu H.-Z., Kang P., Deese A.J., Zhao P., Pool W.F. Human in vitro glutathionyl and protein adducts of carbamazepine-10,11-epoxide, a stable and pharmacologically active metabolite of carbamazepine. Drug Metab. Dispos. 2005, 33(12):1920-1924.
11. de Jongh C.M., Kooij P.J.F., de Voogt P., ter Laak T.L. Screening and human health risk assessment of pharmaceuticals and their transformation products in Dutch surface waters and drinking water. Sci. Total Environ. 2012, 427-428:70-77.
12. Durmaz V., Schmidt S., Sabri P., Piechotta C., Weber M. Hands-off linear interaction energy approach to binding mode and affinity estimation of estrogens. J. Chem. Inf. Model. 2013, 53(10):2681-2688.
13. Elendt B.P., Bias W.R. Trace nutrient deficiency in Daphnia magna cultured in standard medium for toxicity testing. Effects of the optimization of culture conditions on life history parameters of D. magna. Water Res. 1990, 24(9):1157-1167.
14. Fenet H., Arpin-Pont L., Vanhoutte-Brunier A., Munaron D., Fiandrino A., Martínez Bueno M.-J., Boillot C., Casellas C., Mathieu O., Gomez E. Reducing PEC uncertainty in coastal zones: a case study on carbamazepine, oxcarbazepine and their metabolites. Environ. Int. 2014, 68:177-184.
15. Ferrari B., Paxéus N., Giudice R.L., Pollio A., Garric J. Ecotoxicological impact of pharmaceuticals found in treated wastewaters: study of carbamazepine, clofibric acid, and diclofenac. Ecotoxicol. Environ. Saf. 2003, 55(3):359-370.
16. Forbes V.E., Cold A. Effects of the pyrethroid esfenvalerate on life-cycle traits and population dynamics of Chironomus riparius - importance of exposure scenario. Environ. Toxicol. Chem. 2005, 24(1). 78-78.
17. Galus M., Kirischian N., Higgins S., Purdy J., Chow J., Rangaranjan S., Li H., Metcalfe C., Wilson J.Y. Chronic, low concentration exposure to pharmaceuticals impacts multiple organ systems in zebrafish. Aquat. Toxicol. 2013, 132-133:200-211.
18. Gillham R.A., Williams N., Wiedmann K., Butler E., Larkin J.G., Brodie M.J. Concentration-effect relationships with carbamazepine and its epoxide on psychomotor and cognitive function in epileptic patients. J. Neurol. Neurosurg. Psychiatry 1988, 51(7):929-933.
19. Gilroy È.A.M., Balakrishnan V.K., Solomon K.R., Sverko E., Sibley P.K. Behaviour of pharmaceuticals in spiked lake sediments - effects and interactions with benthic invertebrates. Chemosphere 2012, 86(6):578-584.
20. Gower A.M., Buckland P.J. Water quality and the occurrence of Chironomus riparius Meigen (Diptera: Chironomidae) in a stream receiving sewage effluent. Freshw. Biol. 1978, 8(2):153-164.
21. Gros M., Petrović M., Ginebreda A., Barceló D. Removal of pharmaceuticals during wastewater treatment and environmental risk assessment using hazard indexes. Environ. Int. 2010, 36(1):15-26.
22. Hess B., Kutzner C., van ver Spoel D., Lindahl E. GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation. J. Chem. Theory Comput. J. Chem. Theory Comput. 2008, 4(3):435-447.
23. Hornak V., Abel R., Okur A., Strockbine B., Roitberg A., Simmerling C. Comparison of multiple Amber force fields and development of improved protein backbone parameters. PROT Proteins Struct. Funct. Bioinforma. 2006, 65(3):712-725.
24. Jakalian A., Bush B.L., Jack D.B., Bayly C.I. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method. J. Comput. Chem. 2000, 21(2):132-146.
25. Jelic A., Gros M., Ginebreda A., Cespedes-Sánchez R., Ventura F., Petrovic M., Barcelo D. Occurrence, partition and removal of pharmaceuticals in sewage water and sludge during wastewater treatment. Water Res. 2011, 45(3):1165-1176.
26. Jurado A., López-Serna R., Vázquez-Suné E., Carrera J., Pujades E., Petrovic M., Barceló D. Occurrence of carbamazepine and five metabolites in an urban aquifer. Chemosphere 2014, 115:47-53.
27. Kaiser E., Prasse C., Wagner M., Bröder K., Ternes T.A. Transformation of oxcarbazepine and human metabolites of carbamazepine and oxcarbazepine in wastewater treatment and sand filters. Environ. Sci. Technol. 2014, 48(17):10208-10216.
28. Klopman G., Wang S., Balthasar D.M. Estimation of aqueous solubility of organic molecules by the group contribution approach. Application to the study of biodegradation. J. Chem. Inf. Model. 1992, 32(5):474-482.
29. Lamichhane K., Garcia S.N., Huggett D.B., DeAngelis D.L., La Point T.W. Chronic effects of carbamazepine on life-history strategies of Ceriodaphnia dubia in three successive generations. Arch. Environ. Contam. Toxicol. 2013, 64(3):427-438.
30. Langford K., Thomas K.V. Input of selected human pharmaceutical metabolites into the Norwegian aquatic environment. J. Environ. Monit. 2011, 13(2):416-421.
31. Lertratanangkoon K., Horning M.G. Metabolism of carbamazepine. Drug Metab. Dispos. 1982, 10(1):1-10.
32. Li Z.-H., Zlabek V., Grabic R., Velisek J., Machova J., Randak T. Enzymatic alterations and RNA/DNA ratio in intestine of rainbow trout, Oncorhynchus mykiss, induced by chronic exposure to carbamazepine. Ecotoxicology 2010, 19(5):872-878.
33. Löffler D., Römbke J., Meller M., Ternes T.A. Environmental fate of pharmaceuticals in water/sediment systems. Environ. Sci. Technol. 2005, 39(14):5209-5218.
34. López-Serna R., Petrović M., Barceló D. Occurrence and distribution of multi-class pharmaceuticals and their active metabolites and transformation products in the Ebro river basin (NE Spain). Sci. Total Environ. 2012, 440:280-289.
35. Luo Y., Guo W., Ngo H.H., Nghiem L.D., Hai F.I., Zhang J., Liang S., Wang X.C. A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment. Sci. Total Environ. 2014, 473-474:619-641.
36. Martín J., Camacho-Muñoz D., Santos J.L., Aparicio I., Alonso E. 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. 2012, 239-240:40-47.
37. McLean M.J., Macdonald R.L. Carbamazepine and 10,11-epoxycarbamazepine produce use- and voltage-dependent limitation of rapidly firing action potentials of mouse central neurons in cell culture. J. Pharmacol. Exp. Ther. 1986, 238(2):727-738.
38. Miao X.-S., Metcalfe C.D. Determination of carbamazepine and its metabolites in aqueous samples using liquid chromatography-electrospray tandem mass spectrometry. Anal. Chem. 2003, 75(15):3731-3738.
39. Miao X.-S., Yang J.-J., Metcalfe C.D. Carbamazepine and its metabolites in wastewater and in biosolids in a municipal wastewater treatment plant. Environ. Sci. Technol. 2005, 39(19):7469-7475.
40. OECD OECD Guidelines for the Testing of Chemicals No. 211: Daphnia magna Reproduction Test 1998, Organisation of Economic Co-Cooperation and Development, Paris.
41. OECD OECD Guideline for the Testing of Chemicals No. 233: Sediment-water Chironomid Life-cycle Toxicity Test Using Spiked Water or Spiked Sediment 2010, Organisation of Economic Co-Cooperation and Development, Paris.
42. Oetken M., Nentwig G., Loffler D., Ternes T., Oehlmann J. Effects of pharmaceuticals on aquatic invertebrates. Part I. The antiepileptic drug carbamazepine. Arch. Environ. Contam. Toxicol. 2005, 49(3):353-361.
43. Patsalos P.N., Stephenson T.J., Krishna S., Elyas A.A., Lascelles P.T., Wiles C.M. Side-effects induced by carbamazepine-10,11-epoxide. Lancet 1985, 326(8453). 496-496.
44. Pirmohamed M., Graham A., Roberts P., Smith D., Chadwick D., Breckenridge A.M., Park B.K. Carbamazepine-hypersensitivity: assessment of clinical and in vitro chemical cross-reactivity with phenytoin and oxcarbazepine. Br. J. Clin. Pharmacol. 1991, 32(6):741-749.
45. Pirmohamed M., Kitteringham N.R., Breckenridge A.M., Park B.K. The effect of enzyme induction on the cytochrome P450-mediated bioactivation of carbamazepine by mouse liver microsomes. Biochem. Pharmacol. 1992, 44(12):2307-2314.
46. Rasmussen J.B. The life-history, distribution, and production of Chironomus riparius and Glyptotendipes paripes in a prairie pond. Hydrobiologia 1984, 119(1):65-72.
47. Riddiford L.M., Truman J.W. Hormone receptors and the regulation of insect metamorphosis. Integr. Comp. Biol. 1993, 33(3):340-347.
48. Riley R.J., Kitteringham N.R., Park B.K. Structural requirements for bioactivation of anticonvulsants to cytotoxic metabolites in vitro. Br. J. Clin. Pharmacol. 1989, 28(4):482-487.
49. Santos N.A.G., Medina W.S.G., Martins N.M., Mingatto F.E., Curti C., Santos A.C. Aromatic antiepileptic drugs and mitochondrial toxicity: effects on mitochondria isolated from rat liver. Toxicol. in Vitro 2008, 22(5):1143-1152.
50. Shear N.H., Spielberg S.P. Anticonvulsant hypersensitivity syndrome. In vitro assessment of risk. J. Clin. Investig. 1988, 82(6):1826-1832.
51. Sibley P.K., Benoit D.A., Ankley G.T. The significance of growth in Chironomus tentans sediment toxicity tests: relationship to reproduction and demographic endpoints. Environ. Toxicol. Chem. 1997, 16(2):336-345.
52. Sildanchandra W., Crane M. Influence of sexual dimorphism in Chironomus riparius Meigen on toxic effects of cadmium. Environ. Toxicol. Chem. 2000, 19(9):2309-2313.
53. Stein K., Ramil M., Fink G., Sander M., Ternes T.A. Analysis and sorption of psychoactive drugs onto sediment. Environ. Sci. Technol. 2008, 42(17):6415-6423.
54. Stief P. Enhanced exoenzyme activities in sediments in the presence of deposit-feeding Chironomus riparius larvae. Freshw. Biol. 2007, 52(9):1807-1819.
55. Suarez S., Lema J.M., Omil F. Removal of pharmaceutical and personal care products (PPCPs) under nitrifying and denitrifying conditions. Water Res. 2010, 44(10):3214-3224.
56. Ternes T.A. Occurrence of drugs in German sewage treatment plants and rivers. Water Res. 1998, 32(11):3245-3260.
57. Vaishnav D.D., Boethling R.S., Babeu L. Quantitative structure - biodegradability relationships for alcohols, ketones and alicyclic compounds. Chemosphere 1987, 16(4):695-703.
58. Vulliet E., Berlioz-Barbier A., Lafay F., Baudot R., Wiest L., Vauchez A., Lestremau F., Botta F., Cren-Olivé C. A national reconnaissance for selected organic micropollutants in sediments on French territory. Environ. Sci. Pollut. Res. Int. 2014, 21(19):11370-11379.
59. Wang J., Wolf R.M., Caldwell J.W., Kollman P.A., Case D.A. Development and testing of a general amber force field. J. Comput. Chem. 2004, 25(9):1157-1174.
60. Wiklund C., Fagerström T. Why do males emerge before females? A hypothesis to explain the incidence of protandry in butterflies. Oecologia 1977, 31:153-158.
61. Writer J.H., Antweiler R.C., Ferrer I., Ryan J.N., Thurman E.M. In-stream attenuation of neuro-active pharmaceuticals and their metabolites. Environ. Sci. Technol. 2013, 47(17):9781-9790.
62. Yang Y.-Y., Toor G.S., Williams C.F. Pharmaceuticals and organochlorine pesticides in sediments of an urban river in Florida, USA. J. Soils Sediments 2015, 15(4):993-1004.