Abstract
Laboratory studies were conducted to characterize the 1-octanol/water partition coefficients of pharmaceutically active substances carbamazepine, clofibric acid, diclofenac, ibuprofen, and propyphenazone. Partition coefficients determined by shake flask experiments (OECD guideline 107) varied between log KOW 1.51 for carbamazepine, 2.88 for clofibric acid, 1.90 for diclofenac, 2.48 for ibuprofen, and 2.02 for propyphenazone. Comparison of these values with the literature values revealed rather significant differences for most of the compounds. The partitioning coefficients of the acidic compounds diclofenac and ibuprofen agreed much better with sorption and mobility data from previously conducted experiments, whereas KOW values for carbamazepine were lower and for clofibric acid higher than expected from experiments. Only KOW values for propyphenazone were in the same range as reported in the literature and expected from column experiments.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Avdeef, A., Box, K. J., Comer, J. E. A., Hibbert, C. and Tam, K. Y. 1998, ‘pH-metric logP10. Determination of liposomal membrane-water partitioning coefficients of ionizable drugs’, Pharmaceutical Res. 15(2), 209–215.
Buser, H.-R., Poiger, T. and Müller, M. D.: 1999, ‘Occurrence and environmental behaviour of the chiral pharmaceutical drug ibuprofen in surface waters and in wastewater’, Environ. Sci. Technol. 33, 2529–2535.
Fini, A., Fazio, G. and Rabasco, A. M. 1993, ‘1-octanol/water partitioning of Diclofenac salts’, Acta Technol. Legis Med. 4, 33–34.
Hanna, M., de Biasi, V., Bond, B., Salter, C., Hutt, A. J. and Camilleri, P. 1998, ‘Estimation of the partitioning characteristics of drugs: A comparison of a large and diverse drug series utilizing chromatographic and electrophoretic methodology’, Anal. Chem. 70, 2092–2099.
Hansch, C., Hoekmann, D., Leo, A., Zhang, L. T. and Li, P. 1995, ‘The expanding role of quantitative structures-activity-relationships (QSAR) in toxicology’, Toxicol. Lett. 79(1–3), 45–53.
Heberer, Th. 2002, ‘Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: A review of recent research data’, Toxicol. Lett. 131, 5–17.
Heberer, Th., Schmidt-Bäumler, K. and Stan, H.-J.: 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(5), 272–278.
Henschel, K.-P., Wenzel, A., Diedrich, M. and Fliedner, A.: 1997, ‘Environmental hazard assessment of Pharmaceuticals’, Regulatory Toxicology and Pharmacology 25, 220–225.
Holm, J. V., Rügge, K., Bjerg, P. L. and Christensen, T. H.: 1995, ‘Occurrence and distribution of pharmaceutical compounds in the groundwater downgradient of a landfill (Grindsted, Denmark)’, Environ. Sci. Technol. 29, 1415–1420.
Karickhoff, S. W., Brown, D. S. and Scott, T. A. 1979, ‘Sorption of hydrophobic pollutants on natural sediments’, Wat. Res. 13, 241–248.
Lützhoft, H.-C. H., Vaes, W. H. J., Freidig, A. P., Halling-Sorensen, B. and Hermens, J. L. M.: 2000a, ‘Influence of pH and other modifying factors on the distribution of 4-Quinolones to solid phases and humic acids studied by ‘Negligible-Depletion’ SPME-HPLC’, Env. Sci. Technol. 34, 4989–4994.
Lützhoft, H.-C. H., Vaes, W. H. J., Freidig, A. P., Halling-Sorensen, B. and Hermens, J. L. M.: 2000b, ‘1-Octanol/water distribution coefficient of oxolinic acid: Influence of pH and its relation to the interaction with dissolved organic carbon’, Chemosphere 40, 759–765.
Mersmann, P., Scheytt, T. and Heberer, Th.: 2002, ‘Column experiments on the transport behavior of pharmaceutically active substances in the saturated zone’, Acta hydrochim. hydrobiol. 30, 275–284.
Meylan, W. M., Howard, P. H. and Boethling, R. S.: 1996, ‘Improved method for estimating water solubility from octanol water partition coefficient’, Environ. Toxicol. Chem. 15(2), 100–106.
Merck Index: 2001, An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th edn., Merck Research Laboratories, Whitehouse Station, NJ.
Mutschler, E., Geisslinger, G., Kroemer, H. K. and Schäfer-Korting, M.: 2001, Arzneimittelwirkungen. — Lehrbuch der Pharmakologie und Toxikologie (Textbook of Pharmacology and Toxicology), Wissenschaftliche Verlagsgesellschaft, Stuttgart, 8th edn, pp. 1211.
Neely, W. B. and Blau, G. E.: 1985, Environmental Exposure from Chemicals, CRC Press, Boca Raton, FL, USA.
OECD, Organisation for Economic Cooperation and Development: 1995, Guideline for the Testing of Chemicals 107 — Partition Coefficient (n-Octanol/water): Shake Flask Method, Paris.
Rafols, C., Roses, M. and Bosch, E.: 1997, ‘A comparison between different approaches to estimate the aqueous pKa of several non-steroidal anti-inflammatory drugs’, Analytica Chim. Acta 338, 127–134.
Reddersen, K. and Heberer, Th.: 2003, ‘Multi-methods for the trace-level determination of pharmaceutical residues in sewage, surface and ground water samples applying GC-MS’, J. Sep. Sci. 26, 1443–1450.
Scheytt, T., Mersmann, P., Leidig, M., Pekdeger, A. and Heberer, Th.: 2004, ‘Transport of pharmaceutically active compounds in saturated laboratory columns’, Ground Water 42, 767–773.
Scheytt, T., Mersmann, P., Lindstädt, R. and Heberer, Th.: in press, ‘Determination of sorption coefficients of pharmaceutically active substances carbamazepine, diclofenac, and ibuprofen in sandy sediments’, Chemosphere.
Scheytt, T.: 2002, ‘Pharmaceuticals in groundwater — Input, degradation, and transport (In German)’, Habilitation Thesis, Technical University Berlin, pp. 148
Scheytt, T., Grams, S. and Fell, H.: 1998, ‘Occurrence and behaviour of drugs in groundwater’, in J.V. Brahana, Y. Eckstein, L. K. Ongley, R. Schneider and I. E. Moore (eds), IAH/AIH Proceedings Gambling with Groundwater — Physical, Chemical, and Biological Aspects of Aquifer-Stream Relations, Las Vegas, NV, USA, October 1998, pp. 13–18.
Stuer-Lauridsen, F., Birkved, M., Hansen, L. P., Holten, Lützhøft, H.-C. and Halling-Sørensen, B.: 2000, ‘Environmental risk assessment of human pharmaceuticals in Denmark after normal therapeutic use’, Chemosphere 40, 783–793.
Syracuse Science Center: 2002, ‘Database of experimental octanol-water partition coefficients (Log P)’, http://esc-plaza.syrres.com/interkow/kowdemo.htm
Ternes, T. A.: 1998, ‘Occurrence of drugs in German sewage treatment plants and rivers’, Wat. Res. 32(11), 3245–3260.
Tixier, C., Singer, H. P., Oellers, S. and Müller, S. R.: 2003, ‘Occurrence and fate of Carbamazepine, Clofibric acid, Diclofenac, Ibuprofen, Ketoprofen, and Naproxen in Surface waters’, Environ. Sci. Technol. 37(6), 1061–1068.
Yalkowsky, S. H. and Dannenfelser, R. M.: 1992, Aquasol Database of Aqueous Solubility. — Version 5, College of Pharmacy, University of Arizona, Tucson, AZ.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Scheytt, T., Mersmann, P., Lindstädt, R. et al. 1-Octanol/Water Partition Coefficients of 5 Pharmaceuticals from Human Medical Care: Carbamazepine, Clofibric Acid, Diclofenac, Ibuprofen, and Propyphenazone. Water Air Soil Pollut 165, 3–11 (2005). https://doi.org/10.1007/s11270-005-3539-9
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11270-005-3539-9