The effect of experimental hyperlipidemia on the stereoselective tissue distribution, lipoprotein association and microsomal metabolism of (±)-halofantrine

Journal of Pharmaceutical Sciences

Volumn 98, Issue 7, 2009, Pages 2516-2528

  Patel, Jigar P ^a   Fleischer, Jackie G ^b   Wasan, Kishor M ^b   Brocks, Dion R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Chirality; Disposition; Lipids lipoproteins; Metabolism; Pharamcokinetics

Indexed keywords

DEBUTYLHALOFANTRINE; HALOFANTRINE; HIGH DENSITY LIPOPROTEIN; IMIPRAMINE; LIPOPROTEIN; LOW DENSITY LIPOPROTEIN; QUINIDINE; TRIACYLGLYCEROL;

ADIPOSE TISSUE; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BRAIN TISSUE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG METABOLISM; ENANTIOMER; HEART; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYPERLIPIDEMIA; KIDNEY PARENCHYMA; LIVER; LIVER MICROSOME; LUNG PARENCHYMA; MALE; NONHUMAN; RAT; SPLEEN; STEREOCHEMISTRY; TISSUE DISTRIBUTION; TISSUE PERFUSION;

EID: 67650122778     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21607     Document Type: Article

References (36)

1. Brocks DR, Mehvar R. 2003. Stereoselectivity in the pharmacodynamics and pharmacokinetics of the chiral antimalarial drugs. Clin Pharmacokinet 42: 1359-1382. (Pubitemid 38045841)
2. Basco LK, Gillotin C, Gimenez F, Farinotti R, Le Bras J. 1992. In vitro activity of the enantiomers of mefloquine, halofantrine and enpiroline against Plasmodium falciparum. Br J Clin Pharmacol 33: 517-520.
3. Karle JM, Olmeda R, Gerena L, Milhous WK. 1993. Plasmodium falciparum: Role of absolute stereochemistry in the antimalarial activity of synthetic amino alcohol antimalarial agents. Exp Parasitol 76:345-351. (Pubitemid 23196039)
4. Brocks DR, Toni JW. 1999. Pharmacokinetics of halofantrine in the rat: Stereoselectivity and interspecies comparisons. Biopharm Drug Dispos 20: 165-169. (Pubitemid 29137675)
5. Gimenez F, Gillotin C, Basco LK, Bouchaud O, Aubry AF, Wainer IW, Le Bras J, Farinotti R. 1994. Plasma concentrations of the enantiomers of halofantrine and its main metabolite in malaria patients. Eur J Clin Pharmacol 46:561-562. (Pubitemid 24247934)
6. Wesche DL, Schuster BG, Wang WX, Woosley RL. 2000. Mechanism of cardiotoxicity of halofantrine. Clin Pharmacol Ther 67:521-529.
7. Bryson HM, Goa KL. 1992. Halofantrine. A review of its antimalarial activity, pharmacokinetic properties and therapeutic potential. Drugs 43:236-258.
8. Brocks DR. 2000. Stereoselective pharmacokinetics of desbutylhalofantrine, a metabolite of halofantrine, in the rat after administration of the racemic metabolite or parent drug. Biopharm Drug Dispos 21:365-371. (Pubitemid 32895586)
9. Brocks DR. 2002. Stereoselective halofantrine and desbutylhalofantrine disposition in the rat: Cardiac and plasma concentrations and plasma protein binding. Biopharm Drug Dispos 23:9-15. (Pubitemid 34256938)
10. McIntosh MP, Batey AJ, Porter CJ, Charman WN, Coker SJ. 2003. Desbutylhalofantrine: Evaluation of QT prolongation and other cardiovascular effects after intravenous administration in vivo. J Cardiovasc Pharmacol 41:406-413. (Pubitemid 36255300)
11. Humberstone AJ, Porter CJ, Edwards GA, Charman WN. 1998. Association of halofantrine with postprandially derived plasma lipoproteins decreases its clearance relative to administration in the fasted state. J Pharm Sci 87:936-942. (Pubitemid 28381250)
12. Brocks DR, Wasan KM. 2002. The influence of lipids on stereoselective pharmacokinetics of halofantrine: Important implications in food-effect studies involving drugs that bind to lipoproteins. J Pharm Sci 91:1817-1826. (Pubitemid 34810527)
13. Brocks DR, Ramaswamy M, MacInnes AI, Wasan KM. 2000. The stereoselective distribution of halofantrine enantiomers within human, dog, and rat plasma lipoproteins. Pharm Res 17:427-431. (Pubitemid 30395297)
14. Humberstone AJ, Cowman AF, Horton J, Charman WN. 1998. Effect of altered serum lipid concentrations on the IC50 of halofantrine against Plasmodium falciparum. J Pharm Sci 87:256-258. (Pubitemid 28081337)
15. McIntosh MP, Batey AJ, Coker SJ, Porter CJ, Charman WN. 2004. Evaluation of the impact of altered lipoprotein binding conditions on halofantrine induced QTc interval prolongation in an anaesthetized rabbit model. J Pharm Pharmacol 56:69-77. (Pubitemid 38195330)
16. Wasan KM, Brocks DR, Lee SD, Sachs-Barrable K, Thornton SJ. 2008. Impact of lipoproteins on the biological activity and disposition of hydrophobic drugs: Implications for drug discovery. Nat Rev Drug Discov 7:84-99.
17. Shayeganpour A, Korashy H, Patel JP, El-Kadi AO, Brocks DR. 2008. The impact of experimental hyperlipidemia on the distribution and metabolism of amiodarone in rat. Int J Pharm 361:78-86.
18. Aliabadi HM, Spencer TJ, Mahdipoor P, Lavasanifar A, Brocks DR. 2006. Insights into the effects of hyperlipoproteinemia on cyclosporine A biodistribution and relationship to renal function. AAPS J 8:E672-E681. (Pubitemid 44710305)
19. Barakat MM, El-Kadi AO, du Souich P. 2001. L-NAME prevents in vivo the inactivation but not the down-regulation of hepatic cytochrome P450 caused by an acute inflammatory reaction. Life Sci 69:1559-1571.
20. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. 1951. Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
21. Wasan KM, Ramaswamy M, McIntosh MP, Porter CJ, Charman WN. 1999. Differences in the lipoprotein distribution of halofantrine are regulated by lipoprotein apolar lipid and protein concentration and lipid transfer protein I activity: In vitro studies in normolipidemic and dyslipidemic human plasmas. J Pharm Sci 88:185-190.
22. Brocks DR. 2001. A high-performance liquid chromatographic assay for the determination of desbutylhalofantrine enantiomers in rat plasma. J Pharm Pharm Sci 4:24-31. (Pubitemid 34305613)
23. Brocks DR, Dennis MJ, Schaefer WH. 1995. A liquid chromatographic assay for the stereospecific quantitative analysis of halofantrine in human plasma. J Pharm Biomed Anal 13:911-918.
24. Wasan KM, Kennedy AL, Cassidy SM, Ramaswamy M, Holtorf L, Chou JW, Pritchard PH. 1998. Pharmacokinetics, distribution in serum lipoproteins and tissues, and renal toxicities of amphotericin B and amphotericin B lipid complex in a hypercholesterolemic rabbit model: Single-dose studies. Antimicrob Agents Chemother 42:3146-3152. (Pubitemid 28553733)
25. Gharavi N, Sattari S, Shayeganpour A, El-Kadi AO, Brocks DR. 2007. The stereoselective metabolism of halofantrine to desbutylhalofantrine in the rat: Evidence of tissue-specific enantioselectivity in microsomal metabolism. Chirality 19:22-33.
26. Bailer AJ. 1988. Testing for the equality of area under the curves when using destructive measurement techniques. J Pharmacokinet Biopharm 16:303-309. (Pubitemid 18192401)
27. Johnston TP, Palmer WK. 1993. Mechanism of poloxamer 407-induced hypertriglyceridemia in the rat. Biochem Pharmacol 46:1037-1042. (Pubitemid 23280545)
28. Wout ZG, Pec EA, Maggiore JA, Williams RH, Palicharla P, Johnston TP. 1992. Poloxamer 407-mediated changes in plasma cholesterol and triglycerides following intraperitoneal injection to rats. J Parenter Sci Technol 46:192-200. (Pubitemid 23052584)
29. Palmer WK, Emeson EE, Johnston TP. 1997. The poloxamer 407-induced hyperlipidemic atherogenic animal model. Med Sci Sports Exerc 29:1416-1421. (Pubitemid 27483984)
30. Shayeganpour A, Lee SD, Wasan KM, Brocks DR. 2007. The influence of hyperlipoproteinemia on in vitro distribution of amiodarone and desethylamiodarone in human and rat plasma. Pharm Res 24:672-678. (Pubitemid 46411956)
31. Koelz HR, Sherrill BC, Turley SD, Dietschy JM. 1982. Correlation of low and high density lipoprotein binding in vivo with rates of lipoprotein degradation in the rat. A. comparison of lipoproteins of rat and human origin. J Biol Chem 257:8061-8072. (Pubitemid 13241226)
32. Bilheimer DW, Watanabe Y, Kita T. 1982. Impaired receptor-mediated catabolism of low density lipoprotein in the WHHL rabbit, an animal model of familial hypercholesterolemia. Proc Natl Acad Sci USA 79:3305-3309.
33. Bilheimer DW, Stone NJ, Grundy SM. 1979. Metabolic studies in familial hypercholesterolemia. Evidence for a gene-dosage effect in vivo. J Clin Invest 64:524-533. (Pubitemid 9234998)
34. Hussain MM, Strickland DK, Bakillah A. 1999. The mammalian low-density lipoprotein receptor family. Annu Rev Nutr 19:141-172. (Pubitemid 29380600)
35. Kim C, Vaziri ND. 2005. Down-regulation of hepatic LDL receptor-related protein (LRP) in chronic renal failure. Kidney Int 67:1028-1032. (Pubitemid 41623326)
36. Hussain MM, Mahley RW, Boyles JK, Lindquist PA, Brecht WJ, Innerarity TL. 1989. Chylomicron metabolism. Chylomicron uptake by bone marrow in different animal species. J Biol Chem 264:17931-17938. (Pubitemid 19279260)