Pharmaceuticals and Personal Care Products in Soils and Sediments

Biophysico-Chemical Processes of Anthropogenic Organic Compounds in Environmental Systems

Volumn , Issue , 2011, Pages 185-213

  Pan, Bo ^a   Xing, Baoshan ^b  

^a KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Pharmaceuticals and personal care products (PPCPs) and occurrence; Pharmaceuticals and personal care products in soils and sediments; Sorption as affected by solution chemistry

Indexed keywords

EID: 84886330426     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470944479.ch7     Document Type: Chapter

References (155)

1. Accinelli, C., Koskinen, W. C., Becker, J. M., and Sadowsky, M. J. (2007), Environmental fate of two sulfonamide antimicrobial agents in soil, J. Agric. Food Chem. 55, 2677-2682.
2. Agarwal, S. P., Anwer, M. K., and Aqil, M. (2008), Complexationof furosemide with fulvic acid extracted from shilajit: A novel approach, Drug Dev. Ind. Pharm. 34, 506-511.
3. AHI (2002), Animal Health Institute; available from< http://www.ahi.org >
4. Akyuz, S. and Akyuz, T. (2003), FT-IR spectroscopic investigation of adsorption of pyrimidine on sepiolite and montmorillonite from Anatolia, J. Inclusion. Phenom. Macrocycl. Chem. 46, 51-55.
5. Al-Rajab, A. J., Sabourin, L., Scott, A., Lapen, D. R., and Topp, E. (2009), Impact of biosolids on the persistence and dissipation pathways of triclosan and triclocarban in an agricultural soil, Sci. Total Environ. 407, 5978-5985.
6. Alpuche, C., Garau, J., and Lim, V. (2006), Global and local variations in antimicrobial susceptibilities and resistance development in the major respiratory pathogens, Proc. Symp. Augmentin Heritage in Evolving Antibacterial Therapy, London, pp. S135-S138.
7. Andreozzi, R., Raffaele, M., and Nicklas, P. (2003), Pharmaceuticals in STP effluents and their solar photodegradation in aquatic environment, Chemosphere 50, 1319-1330.
8. Bai, Y., Wu, F., Liu, C., Guo, J., Fu, P., Li, W., and Xing, B. (2008), Interaction between carbamazepine and humic substances: A fluorescence spectroscopy study, Environ. Toxicol. Chem. 27, 95-102.
9. Barron, L., Havel, J., Purcell, M., Szpak, M., Kellehera, B., and Paull, B. (2009), Predicting sorption of pharmaceuticals and personal care products onto soil and digested sludge using artificial neural networks, Analyst 134, 663-670.
10. Belden, J. B., Maul, J. D., and Lydy, M. J. (2007), Partitioning and photo degradation of ciprofloxacin in aqueous systems in the presence of organic matter, Chemosphere 66, 1390-1395.
11. Bialk, H. M., Simpson, A. J., and Pedersen, J. A. (2005), Cross-coupling of sulfonamide antimicrobial agents with model humic constituents, Environ. Sci. Technol. 39, 4463-4473.
12. Bialk, H. M., Hedman, C., Castillo, A., and Pedersen, J. A. (2007), Laccase-mediated Michael addition of N-15-sulfapyridine to a model humic constituent, Environ. Sci. Technol. 41, 3593-3600.
13. Bialk, H. M. and Pedersen, J. A. (2008), NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances, Environ. Sci. Technol. 42, 106-112.
14. Bonin, J. L. and Simpson, M. J. (2007), Sorption of steroid estrogens to soil and soil constituents in single-and multi-sorbate systems, Environ. Toxicol. Chem. 26, 2604-2610.
15. Bowman, J. C., Zhou, J. L., and Readman, J. W. (2002), Sediment-water interactions of natural oestrogens under estuarine conditions, Mar. Chem. 77, 263-276.
16. Boxall, A. B. A., Fogg, L. A., Baird, D. J., Lewis, C., Telfer, T. C., Kolpin, D., and Gravell, A. (2005), Targeted Monitoring Study for Veterinary Medicines in the UK Environment, Final Report to the UK Environmental Agency
17. Boyd, S. A., Sheng, G. Y., Teppen, B. J., and Johnston, C. J. (2001), Mechanisms for the adsorption of substituted nitrobenzenes by smectite clays, Environ. Sci. Technol. 35, 4227-4234.
18. Calisto, V. and Esteves, V. I. (2009), Psychiatric pharmaceuticals in the environment, Chemosphere 77, 1257-1274.
19. Campbell, C. G., Borglin, S. E., Green, F. B., Grayson, A., Wozei, E., and Stringfellow, W. T. (2006), Biologically directed environmental monitoring, fate, and transport of estrogenic endocrine disrupting compounds in water: A review, Chemo-sphere 65, 1265-1280.
20. Carballa, M., Fink, G., Omil, F., Lema, J. M., and Ternes, T. (2008), Determination of the solid-water distribution coefficient (K-d) for pharmaceuticals, estrogens and musk fragrances in digested sludge,Water Res. 42, 287-295.
21. Carrasquillo, A. J., Bruland, G. L., Mackay, A. A., and Vasudevan, D. (2008), Sorption of ciprofloxacin and oxytetracycline zwitterions to soils and soil minerals: Influence of compound structure. Environ. Sci. Technol. 42, 7634-7642.
22. Casey, F. X. M, Larsen, G. L., Hakk, H., and Simunek, J. (2003), Fate and transport of 17 beta-estradiol in soil-water systems, Environ. Sci. Technol. 37, 2400-2409.
23. Casey, F. X. M., Hakk, H., Simunek, J., and Larsen, G. L. (2004), Fate and transport of testosterone in agricultural soils, Environ. Sci. Technol. 38, 790-798.
24. Chefetz, B., Illani, T., Schulz, E., Chorover, J. (2006), Wastewater dissolved organic matter: characteristics and sorptive capabilities, Water Sci. Technol. 53, 51-57.
25. Chander, Y., Kumar, K., Goyal, S. M., and Gupta, S. C. (2005), Antibacterial activity of soil-bound antibiotics, J. Environ. Qual. 34, 1952-1957.
26. Chee-Sanford, J. C., Mackie, R. I., Koike, S., Krapac, I. J., Lin, Y.F., Yannarell, A. C., Maxwell, S., and Aminov, R. I. (2009), Fate and transport of antibiotic residues and antibiotic resistance genes following land application of manure waste, J. Environ. Qual. 38, 1086-1108.
27. Chen, J. Y., Zhu, D. Q., and Sun, C. (2007), Effect of heavy metals on the sorption of hydrophobic organic compounds to wood charcoal, Environ. Sci. Technol. 41, 2536-2541.
28. Chiou, C. T., Peters, L. J., and Freed, V. H. (1979), Physical concept of soil-water equilibria from non-ionic organic-compounds, Science 206, 831-832.
29. Colucci, M. S., Bork, H., and Topp, E. (2001), Persistence of estrogenic hormones in agricultural soils: I. 17 beta-estradiol and estrone, J. Environ. Qual. 30, 2070-2076.
30. Colucci, M. S. and Topp, E. (2002), Dissipation of part-per-trillion concentrations of estrogenic hormones from agricultural soils, Can. J. Soil Sci. 82, 335-340.
31. Cousins, I. T., Staples, C. A., Klecka, G. M., andMacKay, D. (2002), A multimedia assessment of the environmental fate of bisphenol A, Hum. Ecol. Risk Assess. 8, 1107-1135.
32. Daughton, C. G. and Ternes, T. A. (1999), Pharmaceuticals and personal care products in the environment: Agents of subtle change? Environ. Health Perspect. 107, 907-938.
33. During, R. A., Krahe, S., and Gath, S. (2002), Sorption behavior of nonylphenol in terrestrial soils, Environ. Sci. Technol. 36, 40524057.
34. Elmund, G. K., Morrison, S. M., Grant, D. W., and Nevins, M. P. (1971), Role of excreted chlortetracycline in modifying decomposition process in feedlot waste, Bull. Environ. Contam. Toxicol. 6, 129-132.
35. Ericson, J. F. (2007), An evaluation of the OECD 308 water/ sediment systems for investigating the biodegradation of pharmaceuticals, Environ. Sci. Technol. 41, 5803-5811.
36. Eschenbach, A., Wienberg, R., and Mahro, B. (1998), Fate and stability of nonextractable residues of [C-14]PAH in contaminated soils under environmental stress conditions, Environ. Sci. Technol. 32, 2585-2590.
37. Fan, Z. S., Casey, F. X. M., Larsen, G. L., and Hakk, H. (2006), Fate and transport of 1278-TCDD, 1378-TCDD, and 1478-TCDD in soil-water systems, Sci. Total Environ. 371, 323-333.
38. Fan, Z. S., Casey, F. X. M., Hakk, H., and Larsen, G. L. (2007), Persistence and fate of 17 beta-estradiol and testosterone in agricultural soils, Chemosphere 67, 886-895.
39. Figueroa, R. A., Leonard, A., and Mackay, A. A. (2004), Modeling tetracycline antibiotic sorption to clays, Environ. Sci. Technol. 38, 476-483.
40. Forster, M., Laabs, V., Lamshft, M., Groeneweg, J., Zhlke, S., Spiteller, M., Krauss, M., Kaupenjohann, M., and Amelung, W. (2009), Sequestration of manure-applied sulfadiazine residues in soils, Environ. Sci. Technol. 43, 1824-1830.
41. Gao, J. A. and Pedersen, J. A. (2005), Adsorption of sulfonamide antimicrobial agents to clay minerals, Environ. Sci. Technol. 39, 9509-9516.
42. Gevao, B., Semple, K. T., and Jones, K. C. (2000), Bound pesticide residues in soils: A review, Environ. Pollut. 108, 3-14.
43. Golet, E. M., Strehler, A., Alder, A. C., and Giger, W. (2002), Determination of fluoroquinolone antibacterial agents in sewage sludge and sludge-treated soil using accelerated solvent extraction followed by solid-phase extraction, Anal. Chem. 74, 5455-5462.
44. Gonsalves, D. and Tucker, D. P. H. (1977), Behavior of oxytetra-cycline in Florida citrus and soils, Arch. Environ. Contam. Toxicol. 6, 515-523.
45. Gu, C. and Karthikeyan, K. G. (2005a), Interaction of tetracycline with aluminum and iron hydrous oxides, Environ. Sci. Technol. 39, 2660-2667.
46. Gu, C. and Karthikeyan, K. G. (2005b), Sorption of the antimicrobial ciprofloxacin to aluminum and iron hydrous oxides, Environ. Sci. Technol. 39, 9166-9173.
47. Gu, C. Karthikeyan, K. G., Sibley, S. D., and Pedersen, J. A. (2007), Complexation of the antibiotic tetracycline with humic acid, Chemosphere 66, 1494-1501.
48. Hamscher, G., Sczesny, S., Hoper, H., and Nau, H. (2002), Determination of persistent tetracycline residues in soil fertilized with liquid manure by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry, Anal. Chem. 74, 1509-1518.
49. Hamscher, G., Pawelzick, H. T., Hoper, H., and Nau, H. (2005), Different behavior of tetracyclines and sulfonamides in sandy soils after repeated fertilization with liquid manure, Environ. Toxicol. Chem. 24, 861-868.
50. Health, I. (2004), IMS World Review, IMS, Fairfield, CT.
51. Hildebrand, C., Londry, K. L., and Farenhorst, A. (2006), Sorption and desorption of three endocrine disrupters in soils, J. Environ. Sci. Health Pt. B-Pesticide Contam. Agric. Wastes 41, 907921.
52. Hirsch, R., Ternes, T., Haberer, K., and Kratz, K. L. (1999), Occurrence of antibiotics in the aquatic environment, Sci. Total Environ. 225, 109-118.
53. Holbrook, R. D., Love, N. G., and Novak, J. T. (2004), Sorption of 17-beta-estradiol and 17 alpha-ethinylestradiol by colloidal organic carbon derived from biological wastewater treatment systems, Environ. Sci. Technol. 38, 3322-3329.
54. Holthaus, K. I. E., Johnson, A. C., Jurgens, M. D., Williams, R. J., Smith, J. J. L., and Carter, J. E. (2002), The potential for estradiol and ethinylestradiol to sorb to suspended and bed sediments in some English rivers, Environ. Toxicol. Chem. 21, 2526-2535.
55. Huschek, G., Hollmann, D., Kurowski, N., Kaupenjohann, M., and Vereecken, H. (2008), Re-evaluation of the conformational structure of sulfadiazine species using NMR and ab initio DFT studies and its implication on sorption and degradation, Chemo-sphere 72, 1448-1454.
56. Ilani, T., Schulz, E., Chefetz, B. (2005), Interactions of organic compounds with wastewater dissolved organic matter: Role of hydrophohic fractions, J. Environ. Qual. 34, 552-562.
57. Jacobsen, A. M., Halling-Sorensen, B., Ingerslev, F., and Hansen, S. H. (2004), Simultaneous extraction of tetracycline, macrolide and sulfonamide antibiotics from agricultural soils using pressurised liquid extraction, followed by solid-phase extraction and liquid chromatography-tandem mass spectrometry, J. Chroma-togr. A 1038, 157-170.
58. Jacobsen, A. M., Lorenzen, A., Chapman, R., and Topp, E. (2005), Persistence of testosterone and 17 beta-estradiol in soils receiving swine manure or municipal biosolids, J. Environ. Qual. 34, 861-871.
59. Jaynes, W. F. and Boyd, S. A. (1991), Clay mineral type andorganic-compound sorption by hexadecyltrimethlyammonium-ex-changed clays, Soil Sci. Soc. Am. J. 55, 43-48.
60. Jia, D. A., Zhou, D. M., Wang, Y. J., Zhu, H. W., and Chen, J. L. (2008), Adsorption and cosorption of Cu(II) and tetracycline on two soils with different characteristics, Geoderma 146, 224230.
61. Jones, A. D., Bruland, G. L., Agrawal, S. G., and Vasudevan, D. (2005), Factors influencing the sorption of oxytetracycline to soils, Environ. Toxicol. Chem. 24, 761-770.
62. Kahle, M. and Stamm, C. (2007), Sorption of the veterinary antimicrobial sulfathiazole to organic materials of different origin, Environ. Sci. Technol. 41, 132-138.
63. Kang, S. H. and Xing, B. S. (2008), Humic acid fractionation upon sequential adsorption onto goethite, Langmuir 24, 2525-2531.
64. Kay, P., Blackwell, P. A., and Boxall, A. B. A. (2005), A lysimeter experiment to investigate the leaching of veterinary antibiotics through a clay soil and comparison with field data, Environ. Pollut. 134, 333-341.
65. Kazpard, V., Lartiges, B. S., Frochot, C., de la Caillerie, J. B. D., Viriot, M. L., Portal, J. M., Gorner, T., and Bersillon, J. L. (2006), Fate of coagulant species and conformational effects during the aggregation of a model of a humic substance with Al-13 poly-cations, Water Res. 40, 1965-1974.
66. Kemper, N. (2008), Veterinary antibiotics in the aquatic and terrestrial environment, Ecol. Indic. 8, 1-13.
67. Kesimli, B. and Topacli, A. (2001), Infrared studies on Co and Cd complexes of sulfamethoxazole, Spectrochim. Acta Pt. A-Molec. Biomolec. Spectrosc 57, 1031-1036.
68. Kim, S. C. and Carlson, K. (2005), LC-MS2 for quantifying trace amounts of pharmaceutical compounds in soil and sediment matrices, Trends Anal. Chem. 24, 635-644.
69. Klecka, G. M., Gonsior, S. J., West, R. J., Goodwin, P. A., and Markham, D. A. (2001), Biodegradation of bisphenol a in aquatic environments: River die-away, Environ. Toxicol. Chem. 20, 2725-2735.
70. Kulshrestha, P., Giese, R. F., and Aga, D. S. (2004), Investigating the molecular interactions of oxytetracycline in clay and organic matter: Insights on factors affecting its mobility in soil, Environ. Sci. Technol. 38, 4097-4105.
71. Kunkel, U. and Radke, M. (2008), Biodegradation of acidic pharmaceuticals in bed sediments: Insight from a laboratory experiment, Environ. Sci. Technol. 42, 7273-7279.
72. Kwon, J. W. and Armbrust, K. L. (2005), Degradation of citalopram by simulated sunlight, Environ. Toxicol. Chem. 24, 1618-1623.
73. Lai, K. M., Johnson, K. L., Scrimshaw, M. D., and Lester, J. N. (2000), Binding of waterborne steroid estrogens to solid phases in river and estuarine systems, Environ. Sci. Technol. 34, 3890-3894.
74. Lalumera, G. M., Calamari, D., Galli, P., Castiglioni, S., Crosa, G., and Fanelli, R. (2004), Preliminary investigation on the environmental occurrence and effects of antibiotics used in aqua-culture in Italy, Chemosphere 54, 661-668.
75. Lam, M. W. and Mabury, S. A. (2005), Photodegradation of the pharmaceuticals atorvastatin, carbamazepine, levofloxacin, and sulfamethoxazole in natural waters, Aquatic Sci. 67, 177188.
76. Laor, Y. and Rebhun, M. (2002), Evidence for nonlinear binding of PAHs to dissolved humic acids, Environ. Sci. Technol. 36, 955961.
77. Lee, C. L., Kuo, L. J., Wang, H. L., and Hsieh, P. C. (2003), Effects of ionic strength on the binding of phenanthrene and pyrene to humic substances: Three-stage variation model, Water Res. 37, 4250-4258.
78. Li, H. and Lee, L. S. (1999), Sorption and abiotic transformation of aniline and alpha-naphthylamine by surface soils, Environ. Sci. Technol. 33, 1864-1870.
79. Li, J. H., Zhou, B. X., Shao, J. H., Yang, Q. F., Liu, Y. Q., and Cai, W. M. (2007), Influence of the presence of heavy metals and surface-active compounds on the sorption of bisphenol A to sediment, Chemosphere 68, 1298-1303.
80. Lindberg, R. H., Bjorklund, K., Rendahl, P., Johansson, M. I., Tysklind, M., and Andersson, B. A. V. (2007), Environmental risk assessment of antibiotics in the Swedish environment with emphasis on sewage treatment plants, Water Res. 41, 613-619.
81. Liu, R. X., Wilding, A., Hibberd, A., and Zhou, J. L. (2005), Partition of endocrine-disrupting chemicals between colloids and dissolved phase as determined by cross-flow ultrafiltration, Environ. Sci. Technol. 39, 2753-2761.
82. Loffler, D., Rombke, J., Meller, M., and Ternes, T. A. (2005), Environmental fate of pharmaceuticals in water/sediment systems, Environ. Sci. Technol. 39, 5209-5218.
83. Loffredo, E. and Senesi, N. (2006), Fate of anthropogenic organic pollutants in soils with emphasis on adsorption/desorption processes of endocrine disruptor compounds, Pure Appl. Chem. 78, 947-961.
84. Lucas, S. D. and Jones, D. L. (2006), Biodegradation of estrone and 17 beta-estradiol in grassland soils amended with animal wastes, Soil Biol. Biochem. 38, 2803-2815.
85. MacKay, A. A. and Canterbury, B. (2005), Oxytetracycline sorption to organic matter by metal-bridging, J. Environ. Qual. 34, 19641971.
86. MacKay, A. A. and Seremet, D. E. (2008), Probe compounds to quantify cation exchange and complexation interactions of ciprofloxacin with soils, Environ. Sci. Technol. 42, 8270-8276.
87. MacKay, D. and Paterson, S. (1991), Evaluating the multimedia fate of organic-chemicals. A level-III fugacity model, Environ. Sci. Technol. 25, 427-436.
88. Makkar, R. S. and Rockne, K. J. (2003), Comparison of synthetic surfactants and biosurfactants in enhancing biodegradation of polycyclic aromatic hydrocarbons, Environ. Toxicol. Chem. 22, 2280-2292.
89. Maskaoui, K., Hibberd., A., and Zhou, J. L. (2007), Assessment of the interaction between aquatic colloids and pharmaceuticals facilitated by cross-flow ultrafiltration, Environ. Sci. Technol. 41, 8038-8043.
90. Matamoros, V., Caselles-Osorio, A., Garcia, J., and Bayona, J. M. (2008), Behaviour of pharmaceutical products and biodegradation intermediates in horizontal subsurface flow constructed wetland. A microcosm experiment, Sci. Total Environ. 394, 171-176.
91. McClellan, K. and Halden, R. U. (2010), Pharmaceuticals and personal care products in archived US biosolids from the 2001 EPA national sewage sludge survey, Water Res. 44, 658-668.
92. Monteiro, S. C. and Boxall, A. B. A. (2010), Occurrence and fate of human pharmaceuticals in the environment, Rev. Environ. Con-tam. Toxicol. 202, 53-154.
93. Nikolaou, A., Meric, S., andFatta, D. (2007), Occurrence patterns of pharmaceuticals in water and wastewater environments, Anal. Bioanal. Chem. 387, 1225-1234.
94. Oppel, J., Broll, G., Loffler, D., Meller, M., Rombke, J., and Ternes, T. (2004), Leaching behaviour of pharmaceuticals in soil-testing-systems: A part of an environmental risk assessment for groundwater protection, Sci. Total Environ. 328, 265273.
95. Ottmar, K. J., Colosi, L. M., and Smith, J. A. (2010), Sorption of statin pharmaceuticals to wastewater-treatment biosolids, terrestrial soils, and freshwater sediment. J. Environ. Eng. [Am. Soc. Civil Eng. (ASCE)] 136, 256-264.
96. Pan, B., Ghosh, S., and Xing, B. S. (2007), Nonideal binding between dissolved humic acids and polyaromatic hydrocarbons, Environ. Sci. Technol. 41, 6472-6478.
97. Pan, B., Ning, P., and Xing, B. S. (2009), Humic substances. Part V: Sorption of pharmaceuticals and personal care products, Environ. Sci. Pollut. Res. 16, 106-116.
98. Patrolecco, L., Capri, S., De Angelis, S., Pagnotta, R., Polesello, S., and Valsecchi, S. (2006), Partition of nonylphenol and related compounds among different aquatic compartments in Tiber River (central Italy), Water Air Soil Pollut. 172, 151-166.
99. Petruzzelli, L., Celi, L., Cignetti, A., and Marsan, F. A. (2002), Influence of soil organic matter on the leaching of polycyclic aromatic hydrocarbons in soil, J. Environ. Sci. Health Pt. B- Pesticide Contam. Agric. Wastes 37, 187-199.
100. Pignatello, J. J. andXing, B. S. (1996), Mechanisms of slow sorption of organic chemicals to natural particles, Environ. Sci. Technol. 30, 1-11.
101. Pils, J. R. V. and Laird, D. A. (2007), Sorption of tetracycline and chlortetracycline on K-and Ca-saturated soil clays, humic substances, and clay-humic complexes, Environ. Sci. Technol. 41, 1928-1933.
102. Polubesova, T., Sherman-Nakache, M., and Chefetz, B. (2007), Binding of pyrene to hydrophobic fractions of dissolved organic matter: Effect of polyvalent metal complexation, Environ. Sci. Technol. 41, 5389-5394.
103. Rabolle, M. and Spliid, N. H. (2000), Sorption and mobility of metronidazole, olaquindox, oxytetracycline and tylosin in soil, Chemosphere 40, 715-722.
104. Roberts, T. R. (1984), IUPAC reports on pesticides. 17. Non-extractable pesticide-residues in soils and plants, Pure Appl. Chem. 56, 945-956.
105. Rubert, K. F. and Pedersen, J. A. (2006), Kinetics of oxytetracycline reaction with a hydrous manganese oxide, Environ. Sci. Technol. 40, 7216-7221.
106. Rubinfeld, S. A. and Luthy, R. G. (2008), Nitromusk compounds in San Francisco Bay sediments, Chemosphere 73, 873-879.
107. Samuelsen, O. B., Torsvik, V., and Ervik, A. (1992), Long-range changes in oxytetracycline concentration and bacterial-resistance towards oxytetracycline in a fish farm sediment after medication, Sci. Total Environ. 114, 25-36.
108. Sarmah, A. K., Meyer, M. T., and Boxall, A. B. A. (2006), A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment, Chemosphere 65, 725-759.
109. Schafer, A. I., Mastrup, M., and Jensen, R. L. (2002), Particle interactions and removal of trace contaminants from water and wastewaters, Desalination 147, 243-250.
110. Scheytt, T. J., Mersmann, P., Rejman-Rasinski, E., and These, A. (2007), Tracing pharmaceuticals in the unsaturated zone, J. Soils Sediments 7, 75-84.
111. Schlusener, M. P., Spiteller, M., and Bester, K. (2003), Determination of antibiotics from soil by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry, J. Chro-matogr. A 1003, 21-28.
112. Seget, S. and Pharma, D. (2008), Pharmaceutical Market Trends, 2008-2012: Key Market Forecasts and Growth Opportunities, URCH Publishing.
113. Seveno, N. A., Kallifidas, D., Smalla, K., van Elsas, J. D., Collard, J. M., Karagouni, A. D., and Wellington, E. M. H. (2002), Occurrence and reservoirs of antibiotic resistance genes in the environment, Rev. Med. Microbiol. 13, 15-27.
114. Shareef, A., Angove, M. J., Wells, J. D., and Johnson, B. B. (2006), Sorption of bisphenol A, 17 alpha-ethynylestradiol and estrone to mineral surfaces, J. Colloid Interface Sci. 297, 62-69.
115. Sibley, S.D. and Pedersen, J. A. (2008), Interaction of the macrolide antimicrobial clarithromycin with dissolved humic acid, Environ. Sci. Technol. 42, 422-428.
116. Sparks, D. L. (2003), Environmental Soil Chemistry, Elsevier, San Diego.
117. Stein, K., Ramil, M., Fink, G., Sander, M., and Ternes, T. A. (2008), Analysis and sorption of psychoactive drugs onto sediment, Environ. Sci. Technol. 42, 6415-6423.
118. Strock, T. J., Sassman, S. A., and Lee, L. S. (2005), Sorption and related properties of the swine antibiotic carbadox and associated N-oxide reduced metabolites, Environ. Sci. Technol. 39, 3134-3142.
119. Stumpe, B. and Marschner, B. (2007), Long-term sewage sludge application and wastewater irrigation on the mineralization and sorption of 17 beta-estradiol and testosterone in soils, Sci. Total Environ. 374, 282-291.
120. Sun, W. L., Ni, J. R., Xu, N., and Sun, L. Y. (2007), Fluorescence of sediment humic substance and its effect on the sorption of selected endocrine disruptors, Chemosphere 66, 700-707.
121. Suntisukaseam, U., Weschayanwiwat, P., and Sabatini, D. A. (2007), Sorption of amphiphile pharmaceutical compounds onto polar and nonpolar adsorbents, Environ. Eng. Sci. 24, 14571465.
122. Tao, S., Cao, H. Y., Liu, W. X., Li, B. G., Cao, J., Xu, F. L., Wang, X. J., Coveney, R. M., Shen, W. R., Qin, B. P., and Sun, R. (2003), Fate modeling of phenanthrene with regional variation in Tian-jin, China, Environ. Sci. Technol. 37, 2453-2459.
123. ter Laak, T. L., Gebbink, W. A., and Tolls, J. (2006a), Estimation of soil sorption coefficients of veterinary pharmaceuticals from soil properties, Environ. Toxicol. Chem. 25, 933-941.
124. ter Laak, T. L., Gebbink, W. A., and Tolls, J. (2006b), The effect of pH and ionic strength on the sorption of sulfachloropyridazine, tylosin, and oxytetracycline to soil, Environ. Toxicol. Chem. 25, 904-911.
125. Thiele, S. (2000), Adsorption of the antibiotic pharmaceutical compound sulfapyridine by a long-term differently fertilized loess Chernozem, J. Plant Nutr. Soil Sci.-Z. Pflanzenernahr. Bodenkd. 163, 589-594.
126. Thiele-Bruhn, S. (2003), Pharmaceutical antibiotic compounds in soils-a review, J. Plant Nutr. Soil Sci.-Z. Pflanzenernahr. Bodenkd. 166, 145-167.
127. Thiele-Bruhn, S., Seibicke, T., Schulten, H. R., and Leinweber, P. (2004), Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions, J. Environ. Qual. 33, 1331-1342.
128. Tolls, J. (2001), Sorption of veterinary pharmaceuticals in soils: A review, Environ. Sci. Technol. 35, 3397-3406.
129. Topp, E., Hendel, J. G., Lapen, D. R., and Chapman, R. (2008a), Fate of the nonsteroidal anti-inflammatory drug naproxen in agricultural soil receiving liquid municipal biosolids, Environ. Toxicol. Chem. 27, 2005-2010.
130. Topp, E., Monteiro, S. C., Beck, A., Coelho, B. B., Boxall, A. B. A., Duenk, P. W., Kleywegt, S., Lapen, D. R., Payne, M., Sabourin, L., Li, H. X., and Metcalfe, C. D. (2008b), Runoff of pharmaceuticals and personal care products following application of biosolids to an agricultural field, Sci. Total Environ. 396, 52-59.
131. Uslu, M. O., Yediler, A., Balcioglu, I. A., and Schulte-Hostede, S. (2008), Analysis and sorption behavior of fluoroquinolones in solid matrices, Water Air Soil Pollut. 190, 55-63.
132. Van Emmerik, T., Angove, M. J., Johnson, B. B., Wells, J. D., and Fernandes, M. B. (2003), Sorption of 17 beta-estradiol onto selected soil minerals, J. Colloid Interface Sci. 266, 33-39.
133. van Olphen, H., ed. (1977), An Introduction to Clay Colloid Chemistry. Wiley-Interscience, New York.
134. Wehrhan, A., Kasteel, R., Simunek, J., Groeneweg, J., and Vereeck-en, H. (2007), Transport of sulfadiazine in soil columns- Experiments and modelling approaches, J. Contam. Hydrol. 89, 107-135.
135. Weissmahr, K. W., Haderlein, S. B., and Schwarzenbach, R. P. (1998), Complex formation of soil minerals with nitroaromatic explosives and other pi-acceptors, Soil Sci. Soc. Am. J. 62, 369378.
136. Werner, J. J., McNeill, K., and Arnold, W. A. (2005), Environmental photodegradation of mefenamic acid, Chemosphere 58, 13391346.
137. Werner, J. J., Arnold, W. A., and McNeill, K. (2006), Water hardness as a photochemical parameter: Tetracycline photolysis as a function of calcium concentration, magnesium concentration, and pH, Environ. Sci. Technol. 40, 7236-7241.
138. WHO (2005), World Health Report. available at www.who.int/whr/2005/annexesen.pdf.
139. Wilga, J., Kot-Wasik, A., and Namiesnik, J. (2008), Studies of human and veterinary drugs' fate in environmental solid samples-Analytical problems. J. Chromatogr. Sci. 46, 601-608.
140. Willert, P. L. (2007), Assessment of the pharmaceutical market in Poland after accession to the European Union, Eur. J. Health Econ. 8, 347-357.
141. Williams, C. F., Williams, C. E., and Adamsen, E. J. (2006), Sorption-desorption of carbamazepine from irrigated soils, J. Environ. Qual. 35, 1779-1783.
142. Xu, J., Chen, W. P., Wu, L. S., Green, R., and Chang, A. C. (2009), Leachability of some emerging contaminants in reclaimed municipal wastewater-irrigated turf grass fields, Environ. Toxicol. Chem. 28, 1842-1850.
143. Yamamoto, H., Liljestrand, H. M., Shimizu, Y., and Morita, M. (2003), Effects of physical-chemical characteristics on the sorption of selected endocrine disrnptors by dissolved organic matter surrogates, Environ. Sci. Technol. 37, 26462657.
144. Yeager, R. L. and Halley, B. A. (1990), Sorption-desorption of [C-14] efrotomycin with soils, J. Agric. Food Chem. 38, 883-886.
145. Ying, G. G., Kookana, R. S., and Dillon, P. (2004), Attenuation of two estrogen compounds in aquifer materials supplemented with sewage effluent, Ground Water Monit. Remediat. 24, 102-107.
146. Ying, G. G., and Kookana, R. S. (2005), Sorption and degradation of estrogen-like-endocrine disrupting chemicals in soil, Environ. Toxicol. Chem. 24, 2640-2645.
147. Yu, X. Y., Ying, G. G., and Kookana, R. S. (2006), Sorption and desorption behaviors of diuron in soils amended with charcoal, J. Agric. Food Chem. 54, 8545-8550.
148. Yu, Z. Q., Xiao, B. H., Huang, W. L., and Peng, P. (2004), Sorption of steroid estrogens to soils and sediments, Environ. Toxicol. Chem. 23, 531-539.
149. Yu, Z. Q. and Huang, W. L. (2005), Competitive sorption between 17a-ethinyl estradiol and naphthalene/phenanthrene by sediments, Environ. Sci. Technol. 39, 4878-4885.
150. Zeng, G. M., Zhang, C., Huang, G. H., Yu, J., Wang, Q., Li, J. B., Xi, B. D., and Liu, H. L. (2006), Adsorption behavior of bisphenol A on sediments in Xiangjiang River, central-south China, Chemo-sphere 65, 1490-1499.
151. Zhang, D., Pan, B., Zhang, H., Ning, P., and Xing, B. (2010), Contribution of different sulfamethoxazole species to their overall adsorption on functionalized carbon nanotubes, Environ. Sci. Technol. 44, 3806-3811.
152. Zhou, J. L. and Liu, Y. P. (2000), Kinetics and equilibria of the interactions between diethylhexyl phthalate and sediment particles in simulated estuarine systems, Mar. Chem. 71, 165-176.
153. Zhou, J. L. (2006), Sorption and remobilization behavior of 4-tert-octylphenol in aquatic systems, Environ. Sci. Technol. 40, 2225-2234.
154. Zhou, J. L., Liu, R., Wilding, A., and Hibberd, A. (2007), Sorption of selected endocrine disrupting chemicals to different aquatic colloids, Environ. Sci. Technol. 41, 206-213.
155. Zukowska, B., Breivik, K., and Wania, F. (2006), Evaluating the environmental fate of pharmaceuticals using a level III model based on poly-parameter linear free energy relationships, Sci. Total Environ. 359, 177-187.