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Xenobiotica
the fate of foreign compounds in biological systems
Volume 48, 2018 - Issue 2
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General Xenobiochemistry

Predictions of bisphenol A hepatic clearance in the isolated perfused rat liver (IPRL): impact of albumin binding and of co-administration with naproxen

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Pages 135-147 | Received 15 Nov 2016, Accepted 08 Feb 2017, Published online: 03 Mar 2017

References

  • Acevedo N, Davis B, Schaeberle CM, et al. (2013). Perinatally administered bisphenol a as a potential mammary gland carcinogen in rats. Environ Health Perspect 121:1040–6
  • Andersen ME. (1983). C. H. I. Pharmacokinetic interaction of mixtures. Proceedings of the fourteenth annual Conference on Environmental Toxicology, November 1983 OH. AFAMRL, pp. 226–238
  • Banerjee T, Singh SK, Kishore N. (2006). Binding of naproxen and amitriptyline to bovine serum albumin: biophysical aspects. J Phys Chem B 110:24147–56
  • Bessems M, T Hart NA, Tolba R, et al. (2006). The isolated perfused rat liver: standardization of a time-honoured model. Lab Anim 40:236–46
  • Borrirukwisitsak S, Keenan HE, Gauchoote-Lindsay C. (2012). Effects of salinity, ph and temperature on the octanol-water partition coefficient of bisphenol A. IJESD 3:460–4
  • Brede C, Fjeldal P, Skjevrak I, H H. (2003). Increased migration levels of bisphenol A from polycarbonate baby bottles after dishwashing, boiling and brushing. Food Addit Contam 20:684–9
  • Camenisch G, Umehara K. (2012). Predicting human hepatic clearance from in vitro drug metabolism and transport data: a scientific and pharmaceutical perspective for assessing drug-drug interactions. Biopharm Drug Dispos 33:179–94
  • Cheikh Rouhou M, Rheault I, Haddad S. (2013). Modulation of trichloroethylene in vitro metabolism by different drugs in rats. Toxicol in Vitro 27:34–43
  • Chen MY, Ike M, Fujita M. (2002). Acute toxicity, mutagenicity, and estrogenicity of bisphenol-A and other bisphenols. Environ Toxicol 17:80–6
  • Chiba M, Ishii Y, Sugiyama Y. (2009). Prediction of hepatic clearance in human from in vitro data for successful drug development. AAPS J 11:262–76
  • Csanady GA, Oberste-Frielinghaus HR, Semder B, et al. (2002). Distribution and unspecific protein binding of the xenoestrogens bisphenol A and daidzein. Arch Toxicol 76:299–305
  • DE Bandt JP, Cynober L, Lim SK, et al. (2007). Metabolism of ornithine, α-ketoglutarate and arginine in isolated perfused rat liver. Br J Nutr 73:227
  • Fanali G, DI Masi A, Trezza V, et al. (2012). Human serum albumin: from bench to bedside. Mol Aspects Med 33:209–90
  • Ferrigno A, Richelmi P, Vairetti M. (2013). Troubleshooting and improving the mouse and rat isolated perfused liver preparation. J Pharmacol Toxicol Methods 67:107–14
  • Sudlow G, B DJ, Wade DN. (1976). Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 12: 1052–61
  • Geens T, Roosens L, Neels H, Covaci A. (2009). Assessment of human exposure to Bisphenol-A, Triclosan and Tetrabromobisphenol-A through indoor dust intake in Belgium. Chemosphere 76:755–60
  • Godoy P, Hewitt NJ, Albrecht U, et al. (2013). Recent advances in 2D and 3D in vitro systems using primary hepatocytes, alternative hepatocyte sources and non-parenchymal liver cells and their use in investigating mechanisms of hepatotoxicity, cell signaling and ADME. Arch Toxicol 87:1315–530
  • Gonzalez-Bejar M, Alarcon E, Poblete H, et al. (2010). Stereoselective interaction of epimeric naproxen-RGD peptides with human serum albumin. Biomacromolecules 11:2255–60
  • Gores GJ, K L, Larusso NF. (1986). The isolated perfused rat liver: conceptual and practical considerations. Hepatology 6:511–17
  • Gradolatto A, Canivenc-Lavier MC, Basly JP, et al. (2004). Metabolism of apigenin by rat liver phase I and phase ii enzymes and by isolated perfused rat liver. Drug Metab Dispos 32:58–65
  • Haddad S. (1999). A modeling approach to account for toxicokinetic interactions in the calculation of biological hazard index for chemical mixtures. Toxicol Lett 108:303–8
  • Haddad S, Beliveau M, Tardif R, Krishnan K. (2001). A PBPK modeling-based approach to account for interactions in the health risk assessment of chemical mixtures. Toxicol Sci 63:125–31
  • Haddad S, Charest-Tardif G, Tardif R, Krishnan K. (2000). Validation of a physiological modeling framework for simulating the toxicokinetics of chemicals in mixtures. Toxicol Appl Pharmacol 167:199–209
  • Haddad S, Krishnan K. (1998). Physiological modeling of toxicokinetic interactions: implications for mixture risk assessment. Environ Health Perspect 106(Suppl 6):1377–84
  • Haddad S, Poulin P, Funk C. (2010). Extrapolating in vitro metabolic interactions to isolated perfused liver: predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine. J Pharm Sci 99:4406–26
  • Hanioka N, Naito T, Narimatsu S. (2008). Human UDP-glucuronosyltransferase isoforms involved in bisphenol A glucuronidation. Chemosphere 74:33–6
  • Hoekstra EJ, Simoneau C. (2013). Release of bisphenol A from polycarbonate: a review. Crit Rev Food Sci Nutr 53:386–402
  • Houston J. (1994). The utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochem Pharmacol 47:1469–79
  • Houston J, Galetin A. (2008). Methods for predicting in vivo pharmacokinetics using data from in vitro assays. Curr Drug Metab 9:940–51
  • Houston JB, Carlile DJ. (1997). Incorporation of in vitro drug metabolism data into physiologically-based pharmacokinetic models. Toxicol In Vitro 11:473–8
  • Hoyer PB. (2001). Reproductive toxicology: current and future directions. Biochem Pharmacol 62:1557–64
  • Ito K, Brown HS, Houston JB. (2004). Database analyses for the prediction of in vivo drug-drug interactions from in vitro data. Br J Clin Pharmacol 57:473–86
  • Ito K, Iwatsubo T, Kanamitsu S, et al. (1998). Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver. Pharmacol Rev 50:387–412
  • Judson R, Houck K, Martin M, et al. (2014). In vitro and modelling approaches to risk assessment from the U.S. Environmental Protection Agency ToxCast programme. Basic Clin Pharmacol Toxicol 115:69–76
  • Kang JH, Katayama Y, Kondo F. (2006). Biodegradation or metabolism of bisphenol A: from microorganisms to mammals. Toxicology 217:81–90
  • Kiang TK, Ensom MH, Chang TK. (2005). UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106:97–132
  • Kim HS, Han S-Y, Yoo SD, et al. (2001). Potential oestrogenic effects of bisphenol-A estimated by in vitro and in vivo combination assays. J Toxicol Sci 26:111–18
  • Krebs H, Henseleit K. (1932). Untersuchungen über die harnstoffbildung imtierkörper. Hoppe-Seylers Zeitschrift für Physiologische. Chemie 210:33–66
  • Krishnan K, Clewell HJ III, Andersen ME. (1994). Physiologically based pharmacokinetic analyses of simple mixtures. Environ Health Perspect 102(Suppl 9):151–5
  • Krishnan K, Haddad S, Beliveau M, Tardif R. (2002). Physiological modeling and extrapolation of pharmacokinetic interactions from binary to more complex chemical mixtures. Environ Health Perspect 110(Suppl 6):989–94
  • Le HH, Carlson EM, Chua JP, Belcher SM. (2008). Bisphenol A is released from polycarbonate drinking bottles and mimics the neurotoxic actions of estrogen in developing cerebellar neurons. Toxicol Lett 176:149–56
  • Manevski N, Moreolo PS, Yli-Kauhaluoma J, Finel M. (2011). Bovine serum albumin decreases Km values of human UDP-glucuronosyltransferases 1A9 and 2B7 and increases Vmax values of UGT1A9. Drug Metab Dispos 39:2117–29
  • Mao J, Tay S, Khojasteh CS, et al. (2016). Evaluation of time dependent inhibition assays for marketed oncology drugs: comparison of human hepatocytes and liver microsomes in the presence and absence of human plasma. Pharm Res 33:1204–19
  • Maruthamuthu M, Kishore S. (1987). Binding of naproxen to bovine serum albumin and tryptophan-modified bovine serum albumin. Proc Indian Acad Sci – Chem Sci 99:273–9
  • Matthews JB, Twomey K, Zacharewski TR. (2001). In vitro and in vivo interactions of bisphenol A and its metabolite, Bisphenol A Glucuronide, with estrogen receptors α and β. Chem Res Toxicol 14:149–57
  • Meek ME, Lipscomb JC. (2015). Gaining acceptance for the use of in-vitro toxicity assays and QIVIVE in regulatory risk assessment. Toxicology 332:112–23
  • Michalowicz J. (2014). Bisphenol A–sources, toxicity and biotransformation. Environ Toxicol Pharmacol 37:738–58
  • Mischinger HJ, Walsh TR, Liu T, et al. (1992). An improved technique for isolated perfusion of rat livers and an evaluation of perfusates. J Surg Res 53:158–65
  • Mitchell SJ, Huizer-Pajkos A, Cogger VC, et al. (2011). Poloxamer 407 increases the recovery of paracetamol in the isolated perfused rat liver. J Pharm Sci 100:334–40
  • Obach RS. (1999). Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metab Dispos 27:1350–9
  • Obach RS, Walsky RL, Venkatakrishnan K, et al. (2006). The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J Pharmacol Exp Ther 316:336–48
  • Peters JRT. (1985). Serum albumin. Adv Protein Chem 37:161–245
  • Pottenger LH. (2000). The relative bioavailability and metabolism of Bisphenol A in rats is dependent upon the route of administration. Toxicol Sci 54:3–18
  • Poulin P, Burczynsky FJ, Haddad S. (2016). The role of extracellular binding proteins in the cellular uptake of drugs: impact on quantitative in vitro-to-in vivo extrapolations of toxicity and efficacy in physiologically based pharmacokinetic-pharmacodynamic research. J Pharm Sci 105:497–508
  • Poulin P, Haddad S. (2011). Microsome composition-based model as a mechanistic tool to predict nonspecific binding of drugs in liver microsomes. J Pharm Sci 100:4501–17
  • Poulin P, Haddad S. (2015). Albumin and uptake of drugs in cells: additional validation exercises of a recently published equation that quantifies the albumin-facilitated uptake mechanism(s) in physiologically based pharmacokinetic and pharmacodynamic modeling research. J Pharm Sci 104:4448–58
  • Poulin P, Hop CE, Ho Q, et al. (2012). Comparative assessment of In Vitro-In Vivo extrapolation methods used for predicting hepatic metabolic clearance of drugs. J Pharm Sci 101:4308–26
  • Poulin P, Theil FP. (2009). Development of a novel method for predicting human volume of distribution at steady-state of basic drugs and comparative assessment with existing methods. J Pharm Sci 98:4941–61
  • Ring BJ, Chien JY, Adkison KK, et al. (2011). PhRMA CPCDC initiative on predictive models of human pharmacokinetics, part 3: comparative assessement of prediction methods of human clearance. J Pharm Sci 100:4090–110
  • Rowland A, Gaganis P, Elliot DJ, et al. (2007). Binding of inhibitory fatty acids is responsible for the enhancement of UDP-glucuronosyltransferase 2B7 activity by albumin: implications for in vitro-in vivo extrapolation. J Pharmacol Exp Ther 321:137–47
  • Rowland A, Knights KM, Mackenzie PI, Miners JO. (2008). The “albumin effect” and drug glucuronidation: bovine serum albumin and fatty acid-free human serum albumin enhance the glucuronidation of UDP-glucuronosyltransferase (UGT) 1A9 substrates but not UGT1A1 and UGT1A6 activities. Drug. Metab Dispos 36:1056–62
  • Snyder RW, Maness SC, Gaido KW, et al. (2000). Metabolism and disposition of bisphenol A in female rats. Toxicol Appl Pharmacol 168:225–34
  • Tardif R, Charest-Tardif G, Brodeur J, Krishnan K. (1997). Physiologically based pharmacokinetic modeling of a ternary mixture of alkyl benzenes in rats and humans. Toxicol Appl Pharmacol 144:120–34
  • Tardif R, Lapare S, Krishnan K, Brodeur J. (1993). Physiologically based modeling of the toxicokinetic interaction between toluene and m-xylene in the rat. Toxicol Appl Pharmacol 120:266–73
  • Toothaker RD, Barker SH, Gillen MV, et al. (2000). Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride. Biopharm Drug Dispos 21:229–33
  • Uchaipichat V, Winner LK, Mackenzie PI, et al. (2006). Quantitative prediction of in vivo inhibitory interactions involving glucuronidated drugs from in vitro data: the effect of fluconazole on zidovudine glucuronidation. Br J Clin Pharmacol 61:427–39
  • U.S. Environmental Protection Agency 1986. Guidelines for the health risk assessment of chemical mixtures. Washington, DC: EPA
  • Upmeier A, Degen GH, Diel P, et al. (2000). Toxicokinetics of bisphenol A in female DA/Han rats after a single i.v. and oral administration. Arch Toxicol 74:431–6
  • Verbeeck RK, Blackburn JL, Loewen GR. (1983). Clinical pharmacokinetics of non-steroidal anti-inflammatory drugs. Clin Pharmacokinet 8:297–331
  • Verner MA, Magher T, Haddad S. (2010). High concentrations of commonly used drugs can inhibit the in vitro glucuronidation of bisphenol A and nonylphenol in rats. Xenobiotica 40:83–92
  • Vom Saal FS, Hughes C. (2005). An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment. Environ Health Perspect 113:926–33
  • Wilkinson GR. (1987). Clearance approaches in pharmacology. Pharmacol Rev 39:1–47
  • Xie X, Wang X, Xu X, et al. (2010). Investigation of the interaction between endocrine disruptor bisphenol A and human serum albumin. Chemosphere 80:1075–80
  • Yokota H, Iwano H, Endo M, et al. (1999). Glucuronidation of the environmental oestrogen bisphenol A by an isoform of UDP-glucuronosyltransferase, UGT2B1, in the rat liver. Biochem J 340:405–9
  • Yoon M, Blaauboer BJ, Clewell HJ. (2015). Quantitative in vitro to in vivo extrapolation (QIVIVE): an essential element for in vitro-based risk assessment. Toxicology 332:1–3

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