Predicting the ecotoxicological effects of transformation products

Handbook of Environmental Chemistry, Volume 2: Reactions and Processes

Volumn 2 P, Issue , 2009, Pages 205-244

  Escher, Beate I ^a   Baumgartner, Rebekka ^a,b   Lienert, Judit ^a   Fenner, Kathrin ^a,b  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

Baseline toxicity; Ecotoxicology; Environmental transformation products; Herbicides; Metabolites; Mode of toxic action; Pesticides; Pharmaceuticals; QSAR

Indexed keywords

ANIMALIA;

EID: 70249123490     PISSN: 14336839     EISSN: None     Source Type: Book Series    
DOI: 10.1007/698_2_015     Document Type: Article

References (70)

1. Boxall ABA, Sinclair CJ, Fenner K, Kolpin D, Maud SJ (2004) When synthetic chemicals degrade in the environment. Environ Sci Technol 38:368A-375A
2. Dewez D, Marchand M, Eullaffroy P, Popovic R (2002) Evaluation of the effects of diuron and its derivatives on Lemna gibba using a fluorescence toxicity index. Environ Toxicol 17:493-501
3. Liu WP, Gan JJ, Lee SJ, Werner I (2004) Isomer selectivity in aquatic toxicity and biodegradation of cypermethrin. J Agricultur Food Chem 52:6233-6238
4. Tixier C, Sancelme M, Bonnemoy F, Cuer A, Veschambre H (2001) Degradation products of a phenylurea herbicide, diuron: Synthesis, ecotoxicity, and biotransformation. Environ Toxicol Chem 20:1381-1389
5. Weyandt RG, Pressel J (2003) Strategies for detection of the ecotoxicological risks of degradation metabolites. Anal Bioanal Chem 375:188-189
6. Belfroid AC, van Drunen M, Beek MA, Schrap SM, van Gestel CAM, van Hattum B (1998) Relative risks of transformation products of pesticides for aquatic ecosystems. Sci Total Environ 222:167-183
7. Sinclair CJ, Boxall ABA (2003) Assessing the ecotoxicity of pesticide transformation products. Environ Sci Technol 37:4617-4625
8. Lee JH, Landrum PF (2006) Development of a multi-component damage assessment model (MDAM) for time-dependent mixture toxicity with toxicokinetic interactions. Environ Sci Technol 40:1341-1349
9. Lee JH, Landrum PF (2006) Application of multi-component damage assessment model (MDAM) for the toxicity of metabolized PAH in Hyalella azteca. Environ Sci Technol 40:1350-1357
10. Legierse KCHM, Verhaar HJM, Vaes WHJ, De Bruijn JHM, Hermens JLM (1999) Analysis of the time-dependent acute aquatic toxicity of organophosphorus pesticides: The critical target occupation model. Environ Sci Technol 33:917-925
11. Escher BI, Bramaz N, Richter M, Lienert J (2006) Comparative ecotoxicological hazard assessment of beta-blockers and their human metabolites using a mode-of-action based test battery and a QSAR approach. Environ Sci Technol 40:7402-7408
12. Lienert J, Güdel K, Escher BI (2007) Screening method for ecotoxicological hazard assessment of 42 pharmaceuticals considering human metabolism and excretory routes. Environ Sci Technol 41:4471-4478
13. Fenner K, Kooijman C, Scheringer M, Hungerbuhler K (2002) Including transformation products into the risk assessment for chemicals: The case of nonylphenol ethoxylate usage in Switzerland. Environ Sci Technol 36:1147-1154
14. Villeneuve D, Blankenship A, Giesy J (2000) Derivation and application of relative potency estimates based on in-vitro bioassays. Environ Sci Toxicol 19:2835-2843
15. Altenburger R, Backhaus T, Boedeker W, Faust M, Scholze M, Grimme LH (2000) Predictability of the toxicity of multiple chemical mixtures to Vibrio Fischeri: Mixtures composed of similarly acting chemicals. Environ Toxicol Chem 19:2341-2347
16. Backhaus T, Altenburger R, Boedeker W, Faust M, Scholze M, Grimme LH (2000) Predictability of the toxicity of multiple mixtures of dissimilarly acting chemicals to Vibrio Fischeri. Environ Toxicol Chem 19:2348-2356
17. Escher BI, Bramaz N, Eggen RIL, Richter M (2005) In-vitro assessment of modes of toxic action of pharmaceuticals in aquatic life. Environ Sci Technol 39:3090-3100
18. Altenburger R, Walter H, Grote M (2004) What contributes to the combined effect of a complex mixture? Environ Sci Technol 38:6353-6362
19. Junghans M, Backhaus T, Faust M, Scholze M, Grimme LH (2006) Application and validation of approaches for the predictive hazard assessment of realistic pesticide mixtures. Aqua Toxicol 76:93-110
20. McCarty LS, Hodson PV, Craig GR, Kaiser KLE (1985) The use of quantitative structure-activity relationships to predict the acute and chronic toxicities of organic chemicals to fish. Environ Tox Chem 4:595-606
21. Hermens JLM (1989) Quantitative structure-activity relationships of environmental pollutants. In The Handbook of Environmental Chemistry, Reaction and Processes; Hutzinger J (ed) Springer, Berlin, Germany, vol 2E, pp 111-162
22. Hansch C, Leo A (1995) Exploring QSAR Fundamentals and Applications in Chemistry and Biology. Am Chem Soc, Washington, DC
23. van Wezel AP, Opperhuizen A (1995) Narcosis due to environmental pollutants in aquatic organisms: Residue-based toxicity, mechanisms, and membrane burdens. Crit Rev Toxicol 25:255-279
24. Lipnick RL, Watson K, Strausz A (1987) A QSAR study of the acute toxicity of some industrial organic chemicals to goldfish. Narcosis, electrophile and proelectrophile mechanism. Xenobiotica 17:1011-1025
25. Verhaar HJM, Ramos EU, Hermens JLM (1996) Classifying environmental pollutants. 2: Separation of class 1 (baseline toxicity) and class 2 (polar narcosis) type compounds based on chemical descriptors. J Chemometrics 10:149-162
26. Maeder V, Escher BI, Scheringer M, Hungerbühler K (2004) Toxic ratio as an indicator of the intrinsic toxicity in the assessment of persistent, bioaccumulative, and toxic chemicals. Environ Sci Technol 38:3659-3666
27. Bradbury SP (1994) Predicting modes of toxic action from chemical structure. An overview. SAR and QSAR in Environ Res 2:89-104
28. Hermens JLM, Balaz S, Damborsky J, Karcher W, Müller M, Sabljic A, Sjöström M (1995) Assessment of QSARs for predicting fate and effects of chemicals in the environment: An international European project. SAR and QSAR Environ Res 3:223-236
29. Spycher S, Nendza M, Gasteiger J (2004) Comparison of different classification methods applied to a mode of toxic action data set. QSAR Comb Sci 23:779-791
30. von der Ohe PC, Kühne R, Ebert R-U, Altenburger R, Liess M, Schüürmann G (2005) Structural alerts- a new classification model to discriminate excess toxicity from narcotic effect levels of organic compounds in the acute daphnid assay. Chem Res Toxicol 18:536-555
31. European Commission Technical Guidance Document in Support of Commission Directive 93/67/EEC on Risk Assessment for New Notified Substances, Commission Regulation (EC) No 1488/94 on Risk Assessment for Existing Substances, and Directive 98/8/EC of the European Parliament and of the Council Concerning the Placing of Biocidal Products on the Market, Office for Official Publications of the European Communities, 2003. http://ecb.jrc.it/
32. Vaes WHM, Urrestarazu-Ramos E, Verhaar H, Hermens JLM (1998) Acute toxicity of nonpolar versus polar narcosis: Is there a difference? Environ Toxicol Chem 17:1380-1384
33. Vaes WHJ, Urrestarazu-Ramos E, Hamwick C, van Holstein I, Blaauboer BJ, Seinen W, Verhaar HJM, Hermens JLM (1997) Solid phase microextraction as a tool to determine membrane/water partition coefficients and bioavailable concentrations in in-vitro systems. Chem Res Toxicol 10:1067-1072
34. Vaes WHJ, Urrestarazu-Ramos E, Verhaar HJM, Cramer CJ, Hermens JLM (1998) Understanding and estimating membrane/water partition coefficients: Approaches to derive quantitative structure property relationships. Chem Res Toxicol 11:847-854
35. Escher BI, Sigg L (2004) Chemical Speciation of Organics and of Metals at Biological Interfaces. In: Van Leeuwen HP, Köster W (eds) Physicochemical Kinetics and Transport at Biointerfaces. Wiley, Chichester, vol 9, pp 205-271
36. Verhaar HJM, Mulder W, Hermens JLM (1995) QSARs for ecotoxicity, Report prepared within the framework of the project QSAR for Prediction of Fate and Effects of Chemicals in the Environment, an international project of the Environmental Technologies RTD Programme (DGXII/D-1) of the European Commission under Contract number EV5V-CT92_0211
37. Van Leeuwen CJ, van der Zandt PTJ, Aldenberg T, Verhaar HJM, Hermens JLM (1992) Application of QSARs, extrapolation and equilibrium partitioning in aquatic effect assessment. 1. Narcotic industrial pollutants. Environmental Toxicology and Chemistry 11:267-282
38. Hilal SH, Karickhoff SW, Carreira LA (2005) University of Georgia, Athens, GA
39. USEPA Exposure Assessment Tools and Models, United States Environmental Protection Agency, 2005. http://www.epa.gov/oppt/exposure/docs/ episuite.htm
40. Hansch C, Leo A, Hoekman D (1995) Exploring QSAR Hydrophobic, Electronic and Steric Constants; American Chemical Society: Washington, DC
41. Gasser L, Fenner K, Scheringer M (2007) Indicators for the exposure assessment of transformation products of organic micropollutants. Environ Sci Technol 41:2445-2451
42. Escher B, Schwarzenbach RP (2002) Mechanistic studies on baseline toxicity and uncoupling as a basis for modeling internal lethal concentrations in aquatic organisms. Aquat Sci 64:20-35
43. USEPA Reregistration Eligibility Decision for Diuron List A Case 0046, United States Environmental Protection Agency, Office of Prevention, Pesticides and Toxic Substances, 2003. http://www.epa.gov/REDs/ diuron_red.pdf
44. USEPA ECOTOX Database, United States Environmental Protection Agency, 2006. http://www.epa.gov/ecotox/ecotox_home.htm
45. Fernández-Alba AR, Hernando MD, Piedra L, Chisti Y (2002) Toxicity evaluation of single and mixed antifouling biocides measured with acute toxicity bioassays. Analytica Chimica Acta 456:303-312
46. Urrestarazu-Ramos E, Vaal MA, Hermens JLM (2002) Interspecies sensitivity in the aquatic toxicity of aromatic amines. Environ Toxicol Pharmacol 11:149-158
47. Solomon KR, Baker DB, Richards RP, Dixon DR, Klaine SJ, LaPoint TW, Kendall RJ, Weisskopf CP, Giddings JM, Giesy JP, Hall LW, Williams WM (1996) Ecological risk assessment of atrazine in North American surface waters. Environ Toxicol Chem 15:31-74
48. Stratton GW (1984) Effects of the Herbicide Atrazine and its Degradation Products, Alone and in Combination, on Phototrophic Microorganisms. Arch Environ Contam Toxicol 13:35-42
49. Fairchild JF, Ruessler DS, Haverland PS, Carlson AR (1997) Comparative Sensitivity of Selenastrum capricornutum and Lemna minor to Sixteen Herbicides. Arch Environ Contam Toxicol 32:353-357
50. EuropeanCommission Bromoxynil SANCO/4347/2000 - final, 2004. http://europa.eu.int/comm/food/plant/protection/evaluation/existactive/ list_bromoxynil.pdf
51. Escher BI, Hunziker RW, Schwarzenbach RP (2001) Interaction of phenolic uncouplers in binary mixtures: Concentration-additive and synergistic effects. Environ Sci Technol 35:3905-3914
52. Peterson HG, Boutin C, Martin PA, Freemark KE, Ruecker NJ, Moody MJ (1994) Aquatic phyto-toxicity of 23 pesticides applied at Expected Environmental Concentrations. Aquatic Toxicol 28:275-292
53. EMEA Guideline on the Environmental Risk Assessment of Medicinal Products for Human Use CHMP/SWP/4447/00, The European Agency for the Evaluation of Medicinal Products, 2006. http://www.emea.eu.int/pdfs/ human/swp/444700en.pdf
54. Crane M, Watts C, Boucard T (2006) Chronic aquatic environmental risks from exposure to human pharmaceuticals. Sci Tot Environ 367:23-41
55. Huschek G, Hansen PD (2006) Ecotoxicological classification of the Berlin river system using bioassays in respect to the European Water Framework Directive. Environmental Monitoring and Assessment 121:15-31
56. Joss A, Zabczynski S, Göbel A, Hoffmann B, Löffler D, McArdell CS, Ternes TA, Thomson A, Siegrist H (2006) Biological degradation of pharmaceuticals in municipal wastewater treatment: Proposing a classification scheme. Water Research 40:1686-1696
57. Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD (2002) Pharmaceuticals, hormones and other organic contaminants in U.S. streams, 1999-2000: A national reconnaissance. Environ Sci Technol 36:1201-1211
58. Davies MN (1998) Clinical pharmacokinetics of ibuprofen. Clinical Pharmacokinetics 34:101-154
59. Dollery C, Boobis AR, Burley D, Davies DM, Davies DS, Harrison PI, Orme MLE, Park BK, Goldberg LI (eds) (1991) Therapeutic drugs; Churchill Livingstone, New York, NY
60. Baselt RC, Cravey RH (2000) Disposition of Toxic Drugs and Chemicals in Man; fourth edition ed, Chemical Toxicology Institute: Foster City, CA, USA
61. Avdeef A, Box KJ, Comer JEA, Hibbert C, Yam KY (1998) PH-metric log P10. Determination of liposomal membrane-water partition coefficients of ionizable drugs. Pharm Res 15:209-215
62. Cleuvers M (2003) Aquatic ecotoxicity of pharmaceuticals including the assessment of combination effects. Toxicol Lett 142:185-194
63. Hanisch B, Abbas B, Kratz W (2002) Ökotoxikologische Bewertung von Humanarzneimitteln in aquatischen Ökosystemen, Landesumweltamt Brandenburg
64. Ferrari B, Mons R, Vollat B, Fraysse B, Paxeus N, Lo Giudice R, Pollio A, Garric J (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 23:1344-1354
65. Saller R (1983) Praktische Pharmakologie. Eigenschaften gebräuchlicher Medikamente; Schattauer: Stuttgart, Germany
66. Brooks BW, Foran CM, Richards SM, Weston J, Turner PK, Stanley JK, Solomon KR, Slattery JK, LaPoint TW (2003) Aquatic Ecotoxicology of fluoxetine. Toxicol Lett 142:169-183
67. Christensen AM, Faaborg-Andersen S, Ingerslev F, Baun A (2007) Mixture and single-substance toxicity of selective serotonin reuptake inhibitors toward algae and crustaceans. Environ Toxicol Chem 26:85-91
68. Berzas Nevado JJ, Villasenor Llenera MJ, Guiberteau Cabanillas C, Rodriguez Robledo V (2006) Screening of citalopram, fluoxetine and their metabolites in human urine samples by gas-chromatography-mass spectrometry. A global robustness/ruggedness study. J Chromatogr A 1123:130-133
69. Traboulsie A, Chemin J, Kupfer E, Nargeot J, Lory P (2006) T-Type calcium channels are inhibited by fluoxetine and its metabolite norfluoxetine. Mol Pharmacol 69:1963-1968
70. de Vane CL (1999) Metabolism and pharmacokinetics of selective serotonin reuptake inhibitors. Cell Mol Neurobiol 19:443-466