An update on the clinical pharmacokinetics of fexofenadine enantiomers

References

• Simpson K, Jarvis B. Fexofenadine: a review of its use in the management of seasonal allergic rhinitis and chronic idiopathic urticaria. Drugs. 2000;59:301–321.
   PubMed Web of Science ®Google Scholar
• Russell T, Stoltz M, Weir S. Pharmacokinetics, pharmacodynamics, and tolerance of single- and multiple-dose fexofenadine hydrochloride in healthy male volunteers. Clin Pharmacol Ther. 1998;64:612–621.
   PubMed Web of Science ®Google Scholar
• Cvetkovic M, Leake B, Fromm MF, et al. OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999;27:866–871.
   PubMed Web of Science ®Google Scholar
• Tian X, Zamek-Gliszczynski MJ, Li J, et al. Multidrug resistance-associated protein 2 is primarily responsible for the biliary excretion of fexofenadine in mice. Drug Metab Dispos. 2008;36:61–64.
   PubMed Web of Science ®Google Scholar
• Tahara H, Kusuhara H, Fuse E, et al. P-glycoprotein plays a major role in the efflux of fexofenadine in the small intestine and blood-brain barrier, but only a limited role in its biliary excretion. Drug Metab Dispos. 2005;33:963–968.
   PubMed Web of Science ®Google Scholar
• Matsushima S, Maeda K, Inoue K, et al. The inhibition of human multidrug and toxin extrusion 1 is involved in the drug-drug interaction caused by cimetidine. Drug Metab Dispos. 2009;37:555–559.
   PubMed Web of Science ®Google Scholar
• Yamada S, Yasui-Furukori N, Akamine Y, et al. Effects of the P-glycoprotein inducer carbamazepine on fexofenadine pharmacokinetics. Ther Drug Monit. 2009;31:764–768.
   PubMed Web of Science ®Google Scholar
• Hamman MA, Bruce MA, Haehner-Daniels BD, et al. The effect of rifampin administration on the disposition of fexofenadine. Clin Pharmacol Ther. 2001;69:114–121.
   PubMed Web of Science ®Google Scholar
• Wang Z, Hamman MA, Huang SM, et al. Effect of St John’s wort on the pharmacokinetics of fexofenadine. Clin Pharmacol Ther. 2002;71:414–420.
   PubMed Web of Science ®Google Scholar
• Shimizu M, Uno T, Sugawara K, et al. Effects of itraconazole and diltiazem on the pharmacokinetics of fexofenadine, a substrate of P-glycoprotein. Br J Clin Pharmacol. 2006;61:538–544.
   PubMed Web of Science ®Google Scholar
• Shimizu M, Uno T, Sugawara K, et al. Effects of single and multiple doses of itraconazole on the pharmacokinetics of fexofenadine, a substrate of P-glycoprotein. Br J Clin Pharmacol. 2006;62:372–376.
   PubMed Web of Science ®Google Scholar
• Uno T, Shimizu M, Sugawara K, et al. Lack of dose-dependent effects of itraconazole on the pharmacokinetic interaction with fexofenadine. Drug Metab Dispos. 2006;34:1875–1879.
   PubMed Web of Science ®Google Scholar
• Yasui-Furukori N, Uno T, Sugawara K, et al. Different effects of three transporting inhibitors, verapamil, cimetidine, and probenecid, on fexofenadine pharmacokinetics. Clin Pharmacol Ther. 2005;7:17–23.
   Web of Science ®Google Scholar
• Perloff MD, Von Moltke LL, Greenblatt DJ. Fexofenadine transport in Caco-2 cells: inhibition with verapamil and ritonavir. J Clin Pharmacol. 2002;42:1269–1274.
   PubMed Web of Science ®Google Scholar
• Lemma GL, Wang Z, Hamman MA, et al. The effect of short- and long-term administration of verapamil on the disposition of cytochrome P450 3A and P-glycoprotein substrates. Clin Pharmacol Ther. 2006;79:218–230.
   PubMed Web of Science ®Google Scholar
• Dresser GK, Bailey DG, Leake BF, et al. Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. Clin Pharmacol Ther. 2002;71:11–20.
   PubMed Web of Science ®Google Scholar
• Robbins DK, Castles MA, Pack DJ, et al. Dose proportionality and comparison of single and multiple dose pharmacokinetics of fexofenadine (MDL 16455) and its enantiomers in healthy male volunteers. Biopharm Drug Dispos. 1998;19:455–463.
   PubMed Web of Science ®Google Scholar
• Miura M, Uno T, Tateishi T, et al. Determination of fexofenadine enantiomers in human plasma with high-performance liquid chromatography. J Pharm Biomed Anal. 2007;43:741–745.
   PubMed Web of Science ®Google Scholar
• Miura M, Uno T, Tateishi T, et al. Pharmacokinetics of fexofenadine enantiomers in healthy subjects. Chirality. 2007;19:223–227.
   PubMed Web of Science ®Google Scholar
• Kusuhara H, Miura M, Yasui-Furukori N, et al. Effect of coadministration of single and multiple doses of rifampicin on the pharmacokinetics of fexofenadine enantiomers in healthy subjects. Drug Metab Dispos. 2013;41:206–213.
   PubMed Web of Science ®Google Scholar
• Giacomini KM, Huang SM, Tweedie DJ, et al. Membrane transporters in drug development. Nat Rev Drug Discov. 2010;9:215–236.
   PubMed Web of Science ®Google Scholar
• Westphal K, Weinbrenner A, Giessmann T, et al. Oral bioavailability of digoxin is enhanced by talinolol: evidence for involvement of intestinal P-glycoprotein. Clin Pharmacol Ther. 2000;68:6–12.
   PubMed Web of Science ®Google Scholar
• Lee CA, Cook JA, Reyner EL, et al. P-glycoprotein related drug interactions: clinical importance and a consideration of disease states. Expert Opin Drug Metab Toxicol. 2010;6:603–619.
   PubMed Web of Science ®Google Scholar
• Lin JH. Transporter-mediated drug interactions: clinical implications and in vitro assessment. Expert Opin Drug Metab Toxicol. 2007;3:81–92.
   PubMed Web of Science ®Google Scholar
• Matheny CJ, Lamb MW, Brouwer KR, et al. Pharmacokinetic and pharmacodynamic implications of P-glycoprotein modulation. Pharmacotherapy. 2001;21:778–796.
   PubMed Web of Science ®Google Scholar
• Schrickx JA, Fink-Gremmels J. Implications of ABC transporters on the disposition of typical veterinary medicinal products. Eur J Pharmacol. 2008;585:510–519.
   PubMed Web of Science ®Google Scholar
• Drescher S, Schaeffeler E, Hitzl M, et al. MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine. Br J Clin Pharmacol. 2002;53:526–534.
   PubMed Web of Science ®Google Scholar
• Yi SY, Hong KS, Lim HS, et al. A variant 2677A allele of the MDR1 gene affects fexofenadine disposition. Clin Pharmacol Ther. 2004;76:418–427.
   PubMed Web of Science ®Google Scholar
• Akamine Y, Miura M, Sunagawa S, et al. Influence of drug-transporter polymorphisms on the pharmacokinetics of fexofenadine enantiomers. Xenobiotica. 2010;40:782–789.
   PubMed Web of Science ®Google Scholar
• Kalliokoski A, Niemi M. Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009;158:693–705.
   PubMed Web of Science ®Google Scholar
• Xiong H, Carr RA, Locke CS, et al. Dual effects of rifampin on the pharmacokinetics of atrasentan. J Clin Pharmacol. 2007;47:423–429.
   PubMed Web of Science ®Google Scholar
• van Giersbergen PL, Treiber A, Schneiter R, et al. Inhibitory and inductive effects of rifampin on the pharmacokinetics of bosentan in healthy subjects. Clin Pharmacol Ther. 2007;81:414–419.
   PubMed Web of Science ®Google Scholar
• Zheng HX, Huang Y, Frassetto LA, et al. Elucidating rifampin’s inducing and inhibiting effects on glyburide pharmacokinetics and blood glucose in healthy volunteers: unmasking the differential effects of enzyme induction and transporter inhibition for a drug and its primary metabolite. Clin Pharmacol Ther. 2009;85:78–85.
   PubMed Web of Science ®Google Scholar
• Bidstrup TB, Stilling N, Damkier P, et al. Rifampicin seems to act as both an inducer and an inhibitor of the metabolism of repaglinide. Eur J Clin Pharmacol. 2004;60:109–114.
   PubMed Web of Science ®Google Scholar
• Shitara Y. Clinical importance of OATP1B1 and OATP1B3 in drug-drug interactions. Drug Metab Pharmacokinet. 2011;26:220–227.
   PubMed Web of Science ®Google Scholar
• Vavricka SR, Van Montfoort J, Ha HR, et al. Interactions of rifamycin SV and rifampicin with organic anion uptake systems of human liver. Hepatology. 2002;36:164–172.
   PubMed Web of Science ®Google Scholar
• Tapaninen T, Neuvonen PJ, Niemi M. Orange and apple juice greatly reduce the plasma concentrations of the OATP2B1 substrate aliskiren. Br J Clin Pharmacol. 2011;71:718–726.
   PubMed Web of Science ®Google Scholar
• Neuhofel AL, Wilton JH, Victory JM, et al. Lack of bioequivalence of ciprofloxacin when administered with calcium-fortified orange juice: a new twist on an old interaction. J Clin Pharmacol. 2002;42:461–466.
   PubMed Web of Science ®Google Scholar
• Lilja JJ, Backman JT, Laitila J, et al. Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. Clin Pharmacol Ther. 2003;73:192–198.
   PubMed Web of Science ®Google Scholar
• Lilja JJ, Juntti-Patinen L, Neuvonen PJ. Orange juice substantially reduces the bioavailability of the beta-adrenergic-blocking agent celiprolol. Clin Pharmacol Ther. 2004;75:184–190.
   PubMed Web of Science ®Google Scholar
• Lilja JJ, Raaska K, Neuvonen PJ. Effects of orange juice on the pharmacokinetics of atenolol. Eur J Clin Pharmacol. 2005;61:337–340.
   PubMed Web of Science ®Google Scholar
• Schwarz UI, Seemann D, Oertel R, et al. Grapefruit juice ingestion significantly reduces talinolol bioavailability. Clin Pharmacol Ther. 2005;77:291–301.
   PubMed Web of Science ®Google Scholar
• Kullak-Ublick GA, Ismair MG, Stieger B, et al. Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001;120:525–533.
   PubMed Web of Science ®Google Scholar
• Shimizu M, Fuse K, Okudaira K, et al. Contribution of OATP (organic anion-transporting polypeptide) family transporters to the hepatic uptake of fexofenadine in humans. Drug Metab Dispos. 2005;33:1477–1481.
   PubMed Web of Science ®Google Scholar
• Matsushima S, Maeda K, Ishiguro N, et al. Investigation of the inhibitory effects of various drugs on the hepatic uptake of fexofenadine in humans. Drug Metab Dispos. 2008;36:663–669.
   PubMed Web of Science ®Google Scholar
• Glaeser H, Bailey DG, Dresser GK, et al. Intestinal drug transporter expression and the impact of grapefruit juice in humans. Clin Pharmacol Ther. 2007;81:362–370.
   PubMed Web of Science ®Google Scholar
• Nozawa T, Imai K, Nezu J, et al. Functional characterization of pHsensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004;308:438–445.
   PubMed Web of Science ®Google Scholar
• Imanaga J, Kotegawa T, Imai H, et al. The effects of the SLCO2B1 c.1457C > T polymorphism and apple juice on the pharmacokinetics of fexofenadine and midazolam in humans. Pharmacogenet Genomics. 2011;21:84–93.
   PubMed Web of Science ®Google Scholar
• Lee W, Glaeser H, Smith LH, et al. Polymorphisms in human organic anion-transporting polypeptide 1A2 (OATP1A2): implications for altered drug disposition and central nervous system drug entry. J Biol Chem. 2005;280:9610–9617.
   PubMed Web of Science ®Google Scholar
• Gröer C, Brück S, Lai Y, et al. LC-MS/MS based quantification of clinically relevant intestinal uptake and efflux transporter proteins. J Pharm Biomed Anal. 2013;85:253–261.
   PubMed Web of Science ®Google Scholar
• Tamai I. Oral drug delivery utilizing intestinal OATP transporters. Adv Drug Deliv Rev. 2012;64:508–514.
   PubMed Web of Science ®Google Scholar
• Nishimura M, Naito S. Tissue-specific mRNA expression profiles of human ATP-binding cassette and solute carrier transporter superfamilies. Drug Metab Pharmacokinet. 2005;20:452–477.
   PubMedGoogle Scholar
• Meier Y, Eloranta JJ, Darimont J, et al. Regional distribution of solute carrier mRNA expression along the human intestinal tract. Drug Metab Dispos. 2007;35:590–594.
   PubMed Web of Science ®Google Scholar
• Nozawa T, Nakajima M, Tamai I, et al. Genetic polymorphisms of human organic anion transporters OATP-C (SLC21A6) and OATP-B (SLC21A9): allele frequencies in the Japanese population and functional analysis. J Pharmacol Exp Ther. 2002;302:804–813.
   PubMed Web of Science ®Google Scholar
• Niemi M, Kivistö KT, Hofmann U, et al. Fexofenadine pharmacokinetics are associated with a polymorphism of the SLCO1B1 gene (encoding OATP1B1). Br J Clin Pharmacol. 2005;59:602–604.
   PubMed Web of Science ®Google Scholar
• Akamine Y, Yasui-Furukori N, Ieiri I, et al. Psychotropic drug-drug interactions involving P-glycoprotein. CNS Drugs. 2012;6:959–973.
   Google Scholar
• Owen A, Goldring C, Morgan P, et al. Induction of P-glycoprotein in lymphocytes by carbamazepine and rifampicin: the role of nuclear hormone response elements. Br J Clin Pharmacol. 2006;62:237–242.
   PubMed Web of Science ®Google Scholar
• Akamine Y, Miura M, Yasui-Furukori N, et al. Carbamazepine differentially affects the pharmacokinetics of fexofenadine enantiomers. Br J Clin Pharmacol. 2012;3:478–481.
   Google Scholar
• Tateishi T, Miura M, Suzuki T, et al. The different effects of itraconazole on the pharmacokinetics of fexofenadine enantiomers. Br J Clin Pharmacol. 2008;65:693–700.
   PubMed Web of Science ®Google Scholar
• Sakugawa T, Miura M, Hokama N, et al. Enantioselective disposition of fexofenadine with the P-glycoprotein inhibitor verapamil. Br J Clin Pharmacol. 2009;67:535–540.
   PubMed Web of Science ®Google Scholar
• Miura M, Uno T. Clinical pharmacokinetics of fexofenadine enantiomers. Expert Opin Drug Metab Toxicol. 2010;6:69–74.
   PubMed Web of Science ®Google Scholar
• Li F, Howard KD, Myers MJ. Influence of P-glycoprotein on the disposition of fexofenadine and its enantiomers. J Pharm Pharmacol. 2017;69:274–284.
   PubMed Web of Science ®Google Scholar
• Bailey DG. Fruit juice inhibition of uptake transport: a new type of food-drug interaction. Br J Clin Pharmacol. 2010;70:645–655.
   PubMed Web of Science ®Google Scholar
• Shirasaka Y, Shichiri M, Murata Y, et al. Long-lasting inhibitory effect of apple and orange juices, but not grapefruit juice, on OATP2B1-mediated drug absorption. Drug Metab Dispos. 2013;41:615–621.
   PubMed Web of Science ®Google Scholar
• Akamine Y, Miura M, Komori H, et al. Effects of one-time apple juice ingestion on the pharmacokinetics of fexofenadine enantiomers. Eur J Clin Pharmacol. 2014;70:1087–1095.
   PubMed Web of Science ®Google Scholar
• Togami K, Tosaki Y, Chono S, et al. Enantioselective uptake of fexofenadine by Caco-2 cells as model intestinal epithelial cells. J Pharm Pharmacol. 2013;65:22–29.
   PubMed Web of Science ®Google Scholar
• Bailey DG, Dresser GK, Leake BF, et al. Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruitjuice. Clin Pharmacol Ther. 2007;81:495–502.
   PubMed Web of Science ®Google Scholar
• Seden K, Dickinson L, Khoo S, et al. Grapefruit-drug interactions. Drugs. 2010;70:2373–2407.
   PubMed Web of Science ®Google Scholar
• Akamine Y, Miura M, Komori H, et al. The change of pharmacokinetics of fexofenadine enantiomers through the single and simultaneous grapefruit juice ingestion. Drug Metab Pharmacokinet. 2015;30:352–357.
   PubMed Web of Science ®Google Scholar