Investigation of the prerequisites for the optimization of specific plasma protein binding as a strategy for the reduction of first-pass hepatic metabolism

References

• Antila S, Sundberg S, Lehtonen LA. (2007). Clinical pharmacology of levosimendan. Clin Pharmacokinet 46:535–52
   PubMed Web of Science ®Google Scholar
• Balant LP, Dayer P, Fabre J. (1983). Consequences of renal insufficiency on the hepatic clearance of some drugs. Int J Clin Pharmacol Res 3:459–74
   PubMedGoogle Scholar
• Benet LZ, Hoener BA. (2002). Changes in plasma protein binding have little clinical relevance. Clin Pharmacol Ther 71:115–21
   PubMed Web of Science ®Google Scholar
• Benigni R. (2003). Quantitative structure-activity relationship (QSAR) models of mutagens and carcinogens. Boca Raton, FL: CRC Press
   Google Scholar
• Berezhkovskiy LM. (2010). On the influence of protein binding on pharmacological activity of drugs. J Pharm Sci 99:2153–65
   PubMed Web of Science ®Google Scholar
• Berezhkovskiy LM. (2011). The corrected traditional equations for calculation of hepatic clearance that account for the difference in drug ionization in extracellular and intracellular tissue water and the corresponding corrected PBPK equation. J Pharm Sci 100:1167–83
   PubMed Web of Science ®Google Scholar
• Carl P, Hogskilde S, Lang-Jensen T, et al. (1994). Pharmacokinetics and pharmacodynamics of eltanolone (pregnanolone), a new steroid intravenous anaesthetic, in humans. Acta Anaesthesiol Scand 38:734–41
   PubMedGoogle Scholar
• Chao P, Uss AS, Cheng K. (2010). Use of intrinsic clearance for prediction of human hepatic clearance. Expert Opin Drug Metab Toxicol 6:189–98
   PubMed Web of Science ®Google Scholar
• Colmenarejo G. (2003). In silico prediction of drug-binding strengths to human serum albumin. Med Res Rev 23:275–301
   PubMed Web of Science ®Google Scholar
• Colmenarejo G, Alvarez-Pedraglio A, Lavandera JL. (2001). Cheminformatic models to predict binding affinities to human serum albumin. J Med Chem 44:4370–8
   PubMed Web of Science ®Google Scholar
• Corey AE, Agnew JR, Valentine SN, et al. (1999). Azimilide pharmacokinetics following intravenous and oral administration of a solution and capsule formulation. J Clin Pharmacol 39:1272–6
   PubMed Web of Science ®Google Scholar
• Costigan MG, Gilchrist TL, Lindup WE. (1996). Synthesis and physicochemical properties of the furan dicarboxylic acid, 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid, an inhibitor of plasma protein binding in uraemia. J Pharm Pharmacol 48:635–40
   PubMedGoogle Scholar
• Curry S, Mandelkow H, Brick P, Franks N. (1998). Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat Struct Biol 5:827–35
   PubMed Web of Science ®Google Scholar
• Deeb O, Hemmateenejad B. (2007). ANN-QSAR model of drug-binding to human serum albumin. Chem Biol Drug Des 70:19–29
   PubMed Web of Science ®Google Scholar
• Determination of midazolam in serum by XLC-MS using symbiosis™ Pharma. Available from: http://ichrom.com/wp-content/uploads/2012/08/53066-Midazolam.pdf [last accessed 20 Jun 2014]
   Google Scholar
• Dingemanse J, Clozel M, van Giersbergen PL. (2002). Pharmacokinetics and pharmacodynamics of tezosentan, an intravenous dual endothelin receptor antagonist, following chronic infusion in healthy subjects. Br J Clin Pharmacol 53:355–62
   PubMedGoogle Scholar
• Dollery C. (1993). Therapeutic drugs. Edinburgh: Churchill Livingstone
   Google Scholar
• Dörwald FZ. (2012). Lead optimization for medicinal chemists. Hoboken (NJ): Wiley-VCH
   Google Scholar
• Enquist M, Hermansson J. (1989a). Comparison between two methods for the determination of the total and free (R)- and (S)-disopyramide in plasma using an alpha 1-acid glycoprotein column. J Chromatogr 494:143–56
   PubMedGoogle Scholar
• Enquist M, Hermansson J. (1989b). Separation and quantitation of (R)- and (S)-atenolol in human plasma and urine using an alpha 1-AGP column. Chirality 1:209–15
   PubMed Web of Science ®Google Scholar
• Enquist M, Hermansson J. (1990). Separation of the enantiomers of beta-receptor blocking agents and other cationic drugs using a CHIRAL-AGP column. Binding properties and characterization of immobilized alpha 1-acid glycoprotein. J Chromatogr 519:285–98
   PubMed Web of Science ®Google Scholar
• Fasano M, Curry S, Terreno E, et al. (2005). The extraordinary ligand binding properties of human serum albumin. IUBMB Life 57:787–96
   PubMed Web of Science ®Google Scholar
• Fehske KJ, Schlafer U, Wollert U, Muller WE. (1982). Characterization of an important drug binding area on human serum albumin including the high-affinity binding sites of warfarin and azapropazone. Mol Pharmacol 21:387–93
   PubMed Web of Science ®Google Scholar
• Fitos I, Visy J, Simonyi M, Hermansson J. (1992). Chiral high-performance liquid chromatographic separations of vinca alkaloid analogues on alpha 1-acid glycoprotein and human serum albumin columns. J Chromatogr 609:163–71
   PubMed Web of Science ®Google Scholar
• Fournier T, Medjoubi NN, Porquet D. (2000). Alpha-1-acid glycoprotein. Biochim Biophys Acta 18:1–2
   Google Scholar
• Gillette JR. (1971). Factors affecting drug metabolism. Ann NY Acad Sci 179:43–66
   PubMed Web of Science ®Google Scholar
• Gleeson MP. (2007). Plasma protein binding affinity and its relationship to molecular structure: an in-silico analysis. J Med Chem 50:101–12
   PubMed Web of Science ®Google Scholar
• Gordon SG, Miller MW, Saunders AB. (2006). Pimobendan in heart failure therapy – a silver bullet? J Am Anim Hosp Assoc 42:90–3
   PubMedGoogle Scholar
• Gugler R, Leschik M, Dengler HJ. (1975). Disposition of quercetin in man after single oral and intravenous doses. Eur J Clin Pharmacol 9:229–34
   PubMed Web of Science ®Google Scholar
• Hansch C, Lao A, Hoekman D. (1995a). Exploring QSAR. Hydrophobic, electronic and steric constants. Washington: American Chemical Society
   Google Scholar
• Hansch C, Telzer B, Zhang L. (1995b). Comparative QSAR in toxicology: examples from teratology and cancer chemotherapy of aniline mustards. Crit Rev Toxicol 25:67–89
   PubMed Web of Science ®Google Scholar
• Hermansson J, Eriksson M, Nyquist O. (1984). Determination of (R)- and (S)-disopyramide in human plasma using a chiral alpha 1-acid glycoprotein column. J Chromatogr 336:321–8
   PubMed Web of Science ®Google Scholar
• Hollmann M, Brode E, Hotz D, et al. (1983). Investigations on the pharmacokinetics of propafenone in man. Arzneimittelforschung 33:763–70
   PubMed Web of Science ®Google Scholar
• Hu M, Li X. (2011). Oral bioavailability: basic principles, advanced concepts, and applications. Hoboken: Wiley
   Google Scholar
• Ito K, Houston JB. (2004). Comparison of the use of liver models for predicting drug clearance using in vitro kinetic data from hepatic microsomes and isolated hepatocytes. Pharm Res 21:785–92
   PubMed Web of Science ®Google Scholar
• Karschner E, Schwilke E, Lowe R, et al. (2009). Implications of plasma delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers. J Anal Toxicol 33:469–77
   PubMed Web of Science ®Google Scholar
• Kragh-Hansen U. (1988). Evidence for a large and flexible region of human serum albumin possessing high affinity binding sites for salicylate, warfarin, and other ligands. Mol Pharmacol 34:160–71
   PubMed Web of Science ®Google Scholar
• Kratochwil NA, Huber W, Muller F, et al. (2002). Predicting plasma protein binding of drugs: a new approach. Biochem Pharmacol 64:1355–74
   PubMed Web of Science ®Google Scholar
• Kremer JM, Wilting J, Janssen LH. (1988). Drug binding to human alpha-1-acid glycoprotein in health and disease. Pharmacol Rev 40:1–47
   PubMed Web of Science ®Google Scholar
• Liu X, Wright M, Hop CE. (2014). Rational use of plasma protein and tissue binding data in drug design. J Med Chem 6:6
   Google Scholar
• Lobell M, Sivarajah V. (2003). In silico prediction of aqueous solubility, human plasma protein binding and volume of distribution of compounds from calculated pKa and AlogP 98 values. Mol Divers 7:69–87
   PubMed Web of Science ®Google Scholar
• Maryadele JON. (2001). Merck index. Merck
   Google Scholar
• Mendza M. (1998). Structure-activity relationships in environmental sciences. London: Chapman & Hall
   Google Scholar
• Obach RS, Lombardo F, Waters NJ. (2008). Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug Metab Dispos 36:1385–405
   PubMed Web of Science ®Google Scholar
• Pere PJ, Ekstrand A, Salonen M, et al. (2011). Pharmacokinetics of ropivacaine in patients with chronic renal failure. Br J Anaesth 106:512–21
   PubMedGoogle Scholar
• Petitpas I, Bhattacharya AA, Twine S, et al. (2001). Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I. J Biol Chem 276:22804–9
   PubMed Web of Science ®Google Scholar
• Ritch AE, Perera WN, Jones CJ. (1982). Pharmacokinetics of azapropazone in the elderly. Br J Clin Pharmacol 14:116–19
   PubMed Web of Science ®Google Scholar
• Roberts JA, Pea F, Lipman J. (2013). The clinical relevance of plasma protein binding changes. Clin Pharmacokinet 52:1–8
   PubMed Web of Science ®Google Scholar
• Rolan PE. (1994). Plasma protein binding displacement interactions – why are they still regarded as clinically important? Br J Clin Pharmacol 37:125–8
   PubMed Web of Science ®Google Scholar
• Rothwell JA, Day AJ, Morgan MRA. (2005). Experimental determination of octanol – water partition coefficients of quercetin and related flavonoids. J Agric Food Chem 53:4355–60
   PubMed Web of Science ®Google Scholar
• Saiakhov R, Stefan L, Klopman G. (2000). Multiple computer-automated structure evaluation model of the plasma protein binding affinity of diverse drugs. Perspect Drug Discov Des 19:133–55
   Google Scholar
• Sangster J. (1994). Octanol-water partition coefficients: fundamentals and physical chemistry. New York: Wiley
   Google Scholar
• Sarnatskaya VV, Lindup WE, Niwa T, et al. (2002). Effect of protein-bound uraemic toxins on the thermodynamic characteristics of human albumin. Biochem Pharmacol 63:1287–96
   PubMedGoogle Scholar
• Schill G, Wainer IW, Barkan SA. (1986). Chiral separations of cationic and anionic drugs on an alpha 1-acid glycoprotein-bonded stationary phase (EnantioPac). II. Influence of mobile phase additives and pH on chiral resolution and retention. J Chromatogr 365:73–88
   PubMed Web of Science ®Google Scholar
• Seydel JK, Schaper KJ. (1982). Quantitative structure-pharmacokinetic relationships and drug design. Pharmacol Ther 15:131–82
   Web of Science ®Google Scholar
• Smith DA, Di L, Kerns EH. (2010). The effect of plasma protein binding on in vivo efficacy: misconceptions in drug discovery. Nat Rev Drug Discov 9:929–39
   PubMed Web of Science ®Google Scholar
• Sudlow G, Birkett DJ, Wade DN. (1975). Characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11:824–32
   PubMed Web of Science ®Google Scholar
• Sudlow G, Birkett DJ, Wade DN. (1976). Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 12:1052–61
   PubMed Web of Science ®Google Scholar
• Svennebring A. (2014). Visualization of plasma and tissue binding using dose fractions parameter. Drug Dev Res 75:425–37
   PubMed Web of Science ®Google Scholar
• Takata K, Kurita T, Morishima Y, et al. (2008). Do the kidneys contribute to propofol elimination? Br J Anaesth 101:648–52
   PubMedGoogle Scholar
• Tang H, Mayersohn M. (2005). A novel model for prediction of human drug clearance by allometric scaling. Drug Metab Dispos 33:1297–303
   PubMed Web of Science ®Google Scholar
• Thomas VH, Bhattachar S, Hitchingham L, et al. (2006). The road map to oral bioavailability: an industrial perspective. Expert Opin Drug Metab Toxicol 2:591–608
   PubMed Web of Science ®Google Scholar
• Toon S, Rowland M. (1983). Structure-pharmacokinetic relationships among the barbiturates in the rat. J Pharmacol Exp Ther 225:752–63
   PubMed Web of Science ®Google Scholar
• Tsakovska I, Lessigiarska I, Netzeva T, Worth A. (2007). A mini review of mammalian toxicity (Q)SAR models. QSAR Comb Sci 27:41–8
   Google Scholar
• van de Waterbeemd H, Lennernäs H, Artursson P, et al. (2003). Drug bioavailability: estimation of solubility, permeability, absorption and bioavailability. Weinheim, Germany: Wiley-VCH
   Google Scholar
• van der Geest R, van Laar T, Kruger PP, et al. (1998). Pharmacokinetics, enantiomer interconversion, and metabolism of R-apomorphine in patients with idiopathic Parkinson's disease. Clin Neuropharmacol 21:159–68
   PubMed Web of Science ®Google Scholar
• Varma MVS, Feng B, Obach RS, et al. (2009). Physicochemical determinants of human renal clearance. J Med Chem 52:4844–52
   PubMed Web of Science ®Google Scholar
• Verbeeck R, Tjandramaga TB, Verberckmoes R, De Schepper PJ. (1976). Biotransformation and excretion of lorazepam in patients with chronic renal failure. Br J Clin Pharmacol 3:1033–9
   PubMed Web of Science ®Google Scholar
• Waters NJ, Lombardo F. (2010). Use of the Oie-Tozer model in understanding mechanisms and determinants of drug distribution. Drug Metab Dispos 38:1159–65
   PubMed Web of Science ®Google Scholar
• Wishart D, with staff. (2014). Drugbank version 4.1. Available at: www.drugbank.ca [last accessed 20 Jun 2014]
   Google Scholar
• Yamasaki K, Maruyama T, Kragh-Hansen U, Otagiri M. (1996). Characterization of site I on human serum albumin: concept about the structure of a drug binding site. Biochim Biophys Acta 18:147–57
   Google Scholar
• Yamazaki K, Kanaoka M. (2004). Computational prediction of the plasma protein-binding percent of diverse pharmaceutical compounds. J Pharm Sci 93:1480–94
   PubMed Web of Science ®Google Scholar
• Zhang D, Krishna R, Wang L, et al. (2005). Metabolism, pharmacokinetics, and protein covalent binding of radiolabeled MaxiPost (BMS-204352) in humans. Drug Metab Dispos 33:83–93
   PubMed Web of Science ®Google Scholar
• Zhivkova Z, Doytchinova I. (2012). Quantitative structure – plasma protein binding relationships of acidic drugs. J Pharm Sci 101:4627–41
   PubMed Web of Science ®Google Scholar
• Zlotos G, Bucker A, Kinzig-Schippers M, et al. (1998). Plasma protein binding of gyrase inhibitors. J Pharm Sci 87:215–20
   PubMed Web of Science ®Google Scholar