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The effect of oral lipids and circulating lipoproteins on the metabolism of drugs

& , PhD (Professor)
Pages 1385-1398 | Published online: 10 Aug 2009

Bibliography

  • Yengi LG, Leung L, Kao J. The evolving role of drug metabolism in drug discovery and development. Pharm Res 2007;24(5):842-58
  • Danielson PB. The cytochrome P450 superfamily: biochemistry, evolution and drug metabolism in humans. Curr Drug Metab 2002;3(6):561-97
  • Pikuleva IA. Cytochrome P450s and cholesterol homeostasis. Pharmacol Ther 2006;112(3):761-73
  • Brocks DR, Wasan KM. The influence of lipids on stereoselective pharmacokinetics of halofantrine: important implications in food-effect studies involving drugs that bind to lipoproteins. J Pharm Sci 2002;91(8):1817-26
  • Brocks DR, Ala S, Aliabadi HM. The effect of increased lipoprotein levels on the pharmacokinetics of cyclosporine A in the laboratory rat. Biopharm Drug Dispos 2006;27(1):7-16
  • Shayeganpour A, Jun AS, Brocks DR. Pharmacokinetics of Amiodarone in hyperlipidemic and simulated high fat-meal rat models. Biopharm Drug Dispos 2005;26(6):249-57
  • Shayeganpour A, Hamdy DA, Brocks DR. Effects of intestinal constituents and lipids on intestinal formation and pharmacokinetics of desethylamiodarone formed from amiodarone. J Pharm Pharmacol 2008;60(12):1625-32
  • Yang CS, Brady JF, Hong JY. Dietary effects on cytochromes P450, xenobiotic metabolism, and toxicity. Faseb J 1992;6(2):737-44
  • Patel JP, Korashy HM, El-Kadi AO, Brocks DR. Effect of bile and lipids on the stereoselective metabolism of halofantrine by rat everted-intestinal sacs. Chirality 2009 [E-pub ahead of print]
  • Porter CJ, Charman WN. Lipid-based formulations for oral administration: opportunities for bioavailability enhancement and lipoprotein targeting of lipophilic drugs. J Recept Signal Transduct Res 2001;21(2-3):215-57
  • Shen H, Howles P, Tso P. From interaction of lipidic vehicles with intestinal epithelial cell membranes to the formation and secretion of chylomicrons. Adv Drug Deliv Rev 2001;50(Suppl 1):S103-25
  • Lutz M, Bonilla S, Concha J, Effect of dietary oils, cholesterol and antioxidant vitamin supplementation on liver microsomal fluidity and xenobiotic-metabolizing enzymes in rats. Ann Nutr Metab 1998;42(6):350-9
  • van de Waterbeemd H, Smith DA, Jones BC. Lipophilicity in PK design: methyl, ethyl, futile. J Comput Aided Mol Des 2001;15(3):273-86
  • Hegele RA. Plasma lipoproteins: genetic influences and clinical implications. Nat Rev Genet 2009;10(2):109-21
  • Pollex RL, Hegele RA. Genetic determinants of plasma lipoproteins. Nat Clin Pract Cardiovasc Med 2007;4(11):600-9
  • Kris-Etherton PM, Krummel D, Russell ME, The effect of diet on plasma lipids, lipoproteins, and coronary heart disease. J Am Diet Assoc 1988;88(11):1373-400
  • Lichtenstein AH, Kennedy E, Barrier P, Dietary fat consumption and health. Nutr Rev 1998;56(5 Pt 2):S3-19; discussion S-28
  • Rakic V, Puddey IB, Dimmitt SB, A controlled trial of the effects of pattern of alcohol intake on serum lipid levels in regular drinkers. Atherosclerosis 1998;137(2):243-52
  • Wanner C, Quaschning T. Dyslipidemia and renal disease: pathogenesis and clinical consequences. Curr Opin Nephrol Hypertens 2001;10(2):195-201
  • Wanner C, Krane V. Uremia-specific alterations in lipid metabolism. Blood Purif 2002;20(5):451-3
  • Panza F, D'Introno A, Colacicco AM, Lipid metabolism in cognitive decline and dementia. Brain Res Rev 2006;51(2):275-92
  • Duntas LH, Wartofsky L. Cardiovascular risk and subclinical hypothyroidism: focus on lipids and new emerging risk factors. What is the evidence? Thyroid 2007;17(11):1075-84
  • Adibhatla RM, Hatcher JF. Altered lipid metabolism in brain injury and disorders. Subcell Biochem 2008;49:241-68
  • Kreisberg RA. Diabetic dyslipidemia. Am J Cardiol 1998;82(12A):67U-73U; discussion 85U-6U
  • Mantel-Teeuwisse AK, Kloosterman JM, Maitland-van der Zee AH, Drug-Induced lipid changes: a review of the unintended effects of some commonly used drugs on serum lipid levels. Drug Saf 2001;24(6):443-56
  • Wasan KM, Brocks DR, Lee SD, Impact of lipoproteins on the biological activity and disposition of hydrophobic drugs: implications for drug discovery. Nat Rev Drug Discov 2008;7(1):84-99
  • Salter AM, Brindley DN. The biochemistry of lipoproteins. J Inherit Metab Dis 1988;11(Suppl 1):4-17
  • Chung NS, Wasan KM. Potential role of the low-density lipoprotein receptor family as mediators of cellular drug uptake. Adv Drug Deliv Rev 2004;56(9):1315-34
  • Ros E. Intestinal absorption of triglyceride and cholesterol. Dietary and pharmacological inhibition to reduce cardiovascular risk. Atherosclerosis 2000;151(2):357-79
  • Storch J, Thumser AE. The fatty acid transport function of fatty acid-binding proteins. Biochim Biophys Acta 2000;1486(1):28-44
  • Field FJ. Intestinal cholesterol esterase: intracellular enzyme or contamination of cytosol by pancreatic enzymes? J Lipid Res 1984;25(4):389-99
  • Nordskog BK, Phan CT, Nutting DF, Tso P. An examination of the factors affecting intestinal lymphatic transport of dietary lipids. Adv Drug Deliv Rev 2001;50(1-2):21-44
  • Levy E, Menard D. Developmental aspects of lipid and lipoprotein synthesis and secretion in human gut. Microsc Res Tech 2000;49(4):363-73
  • Olson RE. Discovery of the lipoproteins, their role in fat transport and their significance as risk factors. J Nutr 1998;128(2 Suppl):439S-43S
  • Kaminsky LS, Zhang QY. The small intestine as a xenobiotic-metabolizing organ. Drug Metab Dispos 2003;31(12):1520-5
  • Custodio J, Benet LZ. Intestinal transporter function may be decreased following high fat ingestion. AAPS J 2005;7: Abstract R6234
  • Sachs-Barrable K, Lee SD, Wasan EK, Enhancing drug absorption using lipids: a case study presenting the development and pharmacological evaluation of a novel lipid-based oral amphotericin B formulation for the treatment of systemic fungal infections. Adv Drug Deliv Rev 2008;60(6):692-701
  • Barta CA, Sachs-Barrable K, Feng F, Wasan KM. Effects of monoglycerides on P-glycoprotein: modulation of the activity and expression in Caco-2 cell monolayers. Mol Pharm 2008;5(5):863-75
  • Yoshinari K, Takagi S, Yoshimasa T, Hepatic CYP3A expression is attenuated in obese mice fed a high-fat diet. Pharm Res 2006;23(6):1188-200
  • Caliph SM, Charman WN, Porter CJ. Effect of short-, medium-, and long-chain fatty acid-based vehicles on the absolute oral bioavailability and intestinal lymphatic transport of halofantrine and assessment of mass balance in lymph-cannulated and non-cannulated rats. J Pharm Sci 2000;89(8):1073-84
  • Fernandez S, Rodier JD, Ritter N, Lipolysis of the semi-solid self-emulsifying excipient Gelucire 44/14 by digestive lipases. Biochim Biophys Acta 2008;1781(8):367-75
  • Larsen A, Holm R, Pedersen ML, Mullertz A. Lipid-based formulations for danazol containing a digestible surfactant, Labrafil M2125CS: in vivo bioavailability and dynamic in vitro lipolysis. Pharm Res 2008;25(12):2769-77
  • Cuine JF, Charman WN, Pouton CW, Increasing the proportional content of surfactant (Cremophor EL) relative to lipid in self-emulsifying lipid-based formulations of danazol reduces oral bioavailability in beagle dogs. Pharm Res 2007;24(4):748-57
  • Sek L, Boyd BJ, Charman WN, Porter CJ. Examination of the impact of a range of Pluronic surfactants on the in-vitro solubilisation behaviour and oral bioavailability of lipidic formulations of atovaquone. J Pharm Pharmacol 2006;58(6):809-20
  • Brocks DR, Mehvar R. Stereoselectivity in the pharmacodynamics and pharmacokinetics of the chiral antimalarial drugs. Clin Pharmacokinet 2003;42(15):1359-82
  • Gharavi N, Sattari S, Shayeganpour A, The stereoselective metabolism of halofantrine to desbutylhalofantrine in the rat: evidence of tissue-specific enantioselectivity in microsomal metabolism. Chirality 2007;19(1):22-33
  • Milton KA, Edwards G, Ward SA, Pharmacokinetics of halofantrine in man: effects of food and dose size. Br J Clin Pharmacol 1989;28(1):71-7
  • Humberstone AJ, Porter CJ, Charman WN. A physicochemical basis for the effect of food on the absolute oral bioavailability of halofantrine. J Pharm Sci 1996;85(5):525-9
  • Trevaskis NL, Porter CJ, Charman WN. An examination of the interplay between enterocyte-based metabolism and lymphatic drug transport in the rat. Drug Metab Dispos 2006;34(5):729-33
  • Brunner LJ, Bai S. Effect of dietary oil intake on hepatic cytochrome P450 activity in the rat. J Pharm Sci 2000;89(8):1022-7
  • Yao HT, Chang YW, Lan SJ, The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci 2006;79(26):2432-40
  • Levy E, Spahis S, Sinnett D, Intestinal cholesterol transport proteins: an update and beyond. Curr Opin Lipidol 2007;18(3):310-8
  • Wang E, Casciano CN, Clement RP, Johnson WW. Cholesterol interaction with the daunorubicin binding site of P-glycoprotein. Biochem Biophys Res Commun 2000;276(3):909-16
  • Sidhu AB, Uhlemann AC, Valderramos SG, Decreasing pfmdr1 copy number in plasmodium falciparum malaria heightens susceptibility to mefloquine, lumefantrine, halofantrine, quinine, and artemisinin. J Infect Dis 2006;194(4):528-35
  • Bodin K, Bretillon L, Aden Y, Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome P450 3A4. J Biol Chem 2001;276(42):38685-9
  • Vassallo P, Trohman RG. Prescribing amiodarone: an evidence-based review of clinical indications. JAMA 2007;298(11):1312-22
  • Meng X, Mojaverian P, Doedee M, Bioavailability of amiodarone tablets administered with and without food in healthy subjects. Am J Cardiol 2001;87(4):432-5
  • Shayeganpour A, El-Kadi AO, Brocks DR. Determination of the enzyme(s) involved in the metabolism of amiodarone in liver and intestine of rat: the contribution of cytochrome P450 3A isoforms. Drug Metab Dispos 2006;34(1):43-50
  • Elsherbiny ME, El-Kadi AO, Brocks DR. The metabolism of amiodarone by various CYP isoenzymes of human and rat, and the inhibitory influence of ketoconazole. J Pharm Sci 2008;11(1):147-59
  • Hirunpanich V, Sato H. Docosahexaenoic acid (DHA) inhibits saquinavir metabolism in-vitro and enhances its bioavailability in rats. J Pharm Pharmacol 2006;58(5):651-8
  • Hirunpanich V, Katagi J, Sethabouppha B, Sato H. Demonstration of docosahexaenoic acid as a bioavailability enhancer for CYP3A substrates: in vitro and in vivo evidence using cyclosporin in rats. Drug Metab Dispos 2006;34(2):305-10
  • Hirunpanich V, Murakoso K, Sato H. Inhibitory effect of docosahexaenoic acid (DHA) on the intestinal metabolism of midazolam: in vitro and in vivo studies in rats. Int J Pharm 2008;351(1-2):133-43
  • Horrocks LA, Yeo YK. Health benefits of docosahexaenoic acid (DHA). Pharmacol Res 1999;40(3):211-25
  • Noble S, Faulds D. Saquinavir. A review of its pharmacology and clinical potential in the management of HIV infection. Drugs 1996;52(1):93-112
  • Gupta SK, Benet LZ. High-fat meals increase the clearance of cyclosporine. Pharm Res 1990;7(1):46-8
  • Gupta SK, Manfro RC, Tomlanovich SJ, Effect of food on the pharmacokinetics of cyclosporine in healthy subjects following oral and intravenous administration. J Clin Pharmacol 1990;30(7):643-53
  • Thakkar RR, Wang OL, Zerouga M, Docosahexaenoic acid reverses cyclosporin A-induced changes in membrane structure and function. Biochim Biophys Acta 2000;1474(2):183-95
  • Busnach G, Stragliotto E, Minetti E, Effect of n-3 polyunsaturated fatty acids on cyclosporine pharmacokinetics in kidney graft recipients: a randomized placebo-controlled study. J Nephrol 1998;11(2):87-93
  • McKenney JM, Swearingen D, Di Spirito M, Study of the pharmacokinetic interaction between simvastatin and prescription omega-3-acid ethyl esters. J Clin Pharmacol 2006;46(7):785-91
  • Xu L, Liu Y, Wang T, Development and validation of a sensitive and rapid non-aqueous LC-ESI-MS/MS method for measurement of diosgenin in the plasma of normal and hyperlipidemic rats: a comparative study. J Chromatogr B Analyt Technol Biomed Life Sci 2009;877(14-15):1530-6
  • Hirunpanich V, Sethabouppha B, Sato H. Inhibitory effects of saturated and polyunsaturated fatty acids on the cytochrome P450 3A activity in rat liver microsomes. Biol Pharm Bull 2007;30(8):1586-8
  • Yamazaki H, Shimada T. Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human CYP450 enzymes. Xenobiotica 1999;29(3):231-41
  • Di Augustine RP, Fouts JR. The effects of unsaturated fatty acids on hepatic microsomal drug metabolism and cytochrome P-450. Biochem J 1969;115(3):547-54
  • Yoo JS, Ning SM, Pantuck CB, Regulation of hepatic microsomal cytochrome P450IIE1 level by dietary lipids and carbohydrates in rats. J Nutr 1991;121(7):959-65
  • Yoo JS, Smith TJ, Ning SM, Modulation of the levels of cytochromes P450 in rat liver and lung by dietary lipid. Biochem Pharmacol 1992;43(12):2535-42
  • Rushmore TH, Kong AN. Pharmacogenomics, regulation and signaling pathways of Phase I and II drug metabolizing enzymes. Curr Drug Metab 2002;3(5):481-90
  • Li CC, Lii CK, Liu KL, n-6 and n-3 polyunsaturated fatty acids down-regulate cytochrome P-450 2B1 gene expression induced by phenobarbital in primary rat hepatocytes. J Nutr Biochem 2006;17(10):707-15
  • Li CC, Lii CK, Liu KL, DHA down-regulates phenobarbital-induced cytochrome P450 2B1 gene expression in rat primary hepatocytes by attenuating CAR translocation. Toxicol Appl Pharmacol 2007;225(3):329-36
  • Kamiyama Y, Matsubara T, Yoshinari K, Role of human hepatocyte nuclear factor 4alpha in the expression of drug-metabolizing enzymes and transporters in human hepatocytes assessed by use of small interfering RNA. Drug Metab Pharmacokinet 2007;22(4):287-98
  • Hertz R, Magenheim J, Berman I, Bar-Tana J. Fatty acyl-CoA thioesters are ligands of hepatic nuclear factor-4alpha. Nature 1998;392(6675):512-6
  • Patel JP, Fleischer JG, Wasan KM, Brocks DR. The effect of experimental hyperlipidemia on the stereoselective tissue distribution, lipoprotein association and microsomal metabolism of (+/-)-halofantrine. J Pharm Sci 2009;98(7):2516-28
  • Brocks DR, Ramaswamy M, MacInnes AI, Wasan KM. The stereoselective distribution of halofantrine enantiomers within human, dog, and rat plasma lipoproteins. Pharm Res 2000;17(4):427-31
  • Sugioka N, Haraya K, Maeda Y, Pharmacokinetics of human immunodeficiency virus protease inhibitor, nelfinavir, in poloxamer 407-induced hyperlipidemic model rats. Biol Pharm Bull 2009;32(2):269-75
  • Fukushima K, Shibata M, Mizuhara K, Effect of serum lipids on the pharmacokinetics of atazanavir in hyperlipidemic rats. Biomed Pharmacother 2009 [E-pub ahead of print]
  • Gershkovich P, Hoffman A. Effect of a high-fat meal on absorption and disposition of lipophilic compounds: the importance of degree of association with triglyceride-rich lipoproteins. Eur J Pharm Sci 2007;32(1):24-32
  • Hussain MM, Strickland DK, Bakillah A. The mammalian low-density lipoprotein receptor family. Annu Rev Nutr 1999;19:141-72
  • Havel RJ. Functional activities of hepatic lipoprotein receptors. Annu Rev Physiol 1986;48:119-34
  • Shayeganpour A, Korashy H, Patel JP, The impact of experimental hyperlipidemia on the distribution and metabolism of amiodarone in rat. Int J Pharm 2008;361(1-2):78-86
  • Kim MS, Wang S, Shen Z, Differences in the pharmacokinetics of peroxisome proliferator-activated receptor agonists in genetically obese Zucker and sprague-dawley rats: implications of decreased glucuronidation in obese Zucker rats. Drug Metab Dispos 2004;32(9):909-14
  • Xiong H, Yoshinari K, Brouwer KL, Negishi M. Role of constitutive androstane receptor in the in vivo induction of Mrp3 and CYP2B1/2 by phenobarbital. Drug Metab Dispos 2002;30(8):918-23
  • Pascussi JM, Gerbal-Chaloin S, Drocourt L, The expression of CYP2B6, CYP2C9 and CYP3A4 genes: a tangle of networks of nuclear and steroid receptors. Biochim Biophys Acta 2003;1619(3):243-53
  • Kishida T, Muto S, Hayashi M, Strain differences in hepatic cytochrome P450 1A and 3A expression between Sprague-Dawley and Wistar rats. J Toxicol Sci 2008;33(4):447-57
  • Humberstone AJ, Porter CJ, Edwards GA, Charman WN. Association of halofantrine with postprandially derived plasma lipoproteins decreases its clearance relative to administration in the fasted state. J Pharm Sci 1998;87(8):936-42
  • Prueksaritanont T, Koike M, Hoener BA, Benet LZ. Transport and metabolism of cyclosporine in isolated rat hepatocytes. The effects of lipids. Biochem Pharmacol 1992;43(9):1997-2006
  • Prueksaritanont T, Hoener BA, Benet LZ. Effects of low-density lipoprotein and ethinyl estradiol on cyclosporine metabolism in isolated rat liver perfusions. Drug Metab Dispos 1992;20(4):547-52
  • Aliabadi HM, Spencer TJ, Mahdipoor P, Insights into the effects of hyperlipoproteinemia on cyclosporine A biodistribution and relationship to renal function. AAPS J 2006;8(4):E672-81
  • Chao YS, Windler EE, Chen GC, Havel RJ. Hepatic catabolism of rat and human lipoproteins in rats treated with 17 alpha-ethinyl estradiol. J Biol Chem 1979;254(22):11360-6
  • Venkatachalam M, Sathe SK. Chemical composition of selected edible nut seeds. J Agric Food Chem 2006;54(13):4705-14

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