Transport of gemifloxacin, a 4th generation quinolone antibiotic, in the Caco-2 and engineered MDCKII cells, and potential involvement of efflux transporters in the intestinal absorption of the drug

Xenobiotica

Volumn 43, Issue 4, 2013, Pages 355-367

  Jin, Hyo Eon ^a   Song, Boran ^a   Shim, Won Sik ^b   Kim, Dae Duk ^a   Chong, Saeho ^a   Chung, Suk Jae ^a   Shim, Chang Koo ^a  

^a Seoul National University   (South Korea)

^b Gachon University   (South Korea)

Author keywords

BCRP; Bioavailability; Gemifloxacin; MRP2; P gp

Indexed keywords

1,2,3,4,6,7,12,12A OCTAHYDRO 6 ISOBUTYL 9 METHOXY 1,4 DIOXOPYRAZINO[1',2':1,6]PYRIDO[3,4 B]INDOLE 3 PROPANOIC ACID TERT BUTYL ESTER; GEMIFLOXACIN; VERAPAMIL; VERLUKAST;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE ABSORPTION; MALE; MDCK CELL; NONHUMAN; RAT;

ADMINISTRATION, ORAL; ANIMALS; ANTI-BACTERIAL AGENTS; BIOLOGICAL TRANSPORT; CACO-2 CELLS; DOGS; FLUOROQUINOLONES; HUMANS; INHIBITORY CONCENTRATION 50; INTESTINAL ABSORPTION; KINETICS; MADIN DARBY CANINE KIDNEY CELLS; MALE; MEMBRANE TRANSPORT PROTEINS; NAPHTHYRIDINES; QUINOLONES; RATS; RATS, SPRAGUE-DAWLEY; VERAPAMIL;

RATTUS;

EID: 84879511957     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2012.720740     Document Type: Article

References (63)

1. Allen JD, van Loevezijn A, Lakhai JM, van der Valk M, van Tellingen O, Reid G, Schellens JH, Koomen GJ, Schinkel AH. (2002). Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C. Mol Cancer Ther 1:417-425
2. Alvarez AI, Pérez M, Prieto JG, Molina AJ, Real R, Merino G. (2008). Fluoroquinolone efflux mediated by ABC transporters. J Pharm Sci 97:3483-3493
3. Artursson P, Karlsson J. (1991). Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-885
4. Balaji V, Poongothai S, Madhavi B, Reddy R, Naidu PY, Karrunakaran CM, Ilavarasan R. (2010). Development and validation of a dissolution test with spectrophotometric analysis for gemifloxacin in tablet dosage form. Pharma science monitor, An international journal of pharmaceutical sciences Online Published 581-594
5. Ball P. (2000). Quinolone generations: Natural history or natural selection? J Antimicrob Chemother 46 Suppl T1:17-24 (Pubitemid 30468444)
6. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB. (1999). OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos 27:866-871 (Pubitemid 29347585)
7. de Lannoy IA, Silverman M. (1992). The MDR1 gene product, P-glycoprotein, mediates the transport of the cardiac glycoside, digoxin. Biochem Biophys Res Commun 189:551-557 (Pubitemid 23030076)
8. Drlica K, Malik M. (2003). Fluoroquinolones: Action and resistance. Curr Top Med Chem 3:249-282
9. Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J. (1986). Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother 30:444-446 (Pubitemid 16017326)
10. Fish DN, Chow AT. (1997). The clinical pharmacokinetics of levofloxacin. Clin Pharmacokinet 32:101-119 (Pubitemid 27104410)
11. Giacomini KM, Huang SM, Tweedie DJ, Benet LZ, Brouwer KL, Chu X, Dahlin A, Evers R, Fischer V, Hillgren KM, Hoffmaster KA, Ishikawa T, Keppler D, Kim RB, Lee CA, Niemi M, Polli JW, Sugiyama Y, Swaan PW, Ware JA, Wright SH, Yee SW, Zamek-Gliszczynski MJ, Zhang L; International Transporter Consortium. (2010). Membrane transporters in drug development. Nat Rev Drug Discov 9:215-236
12. Grasela DM. (2000). Clinical pharmacology of gatifloxacin, a new fluoroquinolone. Clin Infect Dis 31 Suppl2:S51-S58 (Pubitemid 32269610)
13. Griffiths NM, Hirst BH, Simmons NL. (1993). Active secretion of the fluoroquinolone ciprofloxacin by human intestinal epithelial Caco-2 cell layers. Br J Pharmacol 108:575-576 (Pubitemid 23067919)
14. Hong CY. (2001). Discovery of gemifloxacin (Factive, LB20304a): A quinolone of a new generation. Farmaco 56:41-44 (Pubitemid 32372581)
15. Hooper DC. (2002). Fluoroquinolone resistance among Gram-positive cocci. Lancet Infect Dis 2:530-538 (Pubitemid 34966356)
16. Horibe S, Takara K, Minegaki T, Ohnishi N, Yokoyama T. (2009). Distribution of Abcg2 (BCRP) and Abcc2 (MRP2) mRNAs in rat small intestine and liver. EXCLI Journal 8:12-19
17. Horikawa M, Kato Y, Tyson CA, Sugiyama Y. (2002). The potential for an interaction between MRP2 (ABCC2) and various therapeutic agents: Probenecid as a candidate inhibitor of the biliary excretion of irinotecan metabolites. Drug Metab Pharmacokinet 17:23-33
18. Jacobs MR, Felmingham D, Appelbaum PC, Grüneberg RN; Alexander Project Group. (2003). The Alexander Project 1998-2000: Susceptibility of pathogens isolated from community-Acquired respiratory tract infection to commonly used antimicrobial agents. J Antimicrob Chemother 52:229-246 (Pubitemid 36986885)
19. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H. (1999). The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther 290:672-677 (Pubitemid 29344561)
20. Katneni K, Charman SA, Porter CJ. (2008). An evaluation of the relative roles of the unstirred water layer and receptor sink in limiting the in-vitro intestinal permeability of drug compounds of varying lipophilicity. J Pharm Pharmacol 60:1311-1319
21. Lamp KC, Bailey EM, Rybak MJ. (1992). Ofloxacin clinical pharmacokinetics. Clin Pharmacokinet 22:32-46
22. Landersdorfer CB, Kirkpatrick CM, Kinzig M, Bulitta JB, Holzgrabe U, Drusano GL, Sörgel F. (2009). Competitive inhibition of renal tubular secretion of gemifloxacin by probenecid. Antimicrob Agents Chemother 53:3902-3907
23. Letschert K, Faulstich H, Keller D, Keppler D. (2006). Molecular characterization and inhibition of amanitin uptake into human hepatocytes. Toxicol Sci 91:140-149
24. LG Life Sciences LPIGP. (2003). Factive (Gemifloxacin) for the treatment of acute exacerbations of chronic bronchitis and communityacquired pneumonia NDA #21-158 Briefing Document
25. Li H, Chung SJ, Kim DC, Kim HS, Lee JW, Shim CK. (2001). The transport of a reversible proton pump antagonist, 5, 6-dimethyl-2-(4-Fluorophenylamino)-4- (1-methyl-1,2,3, 4-tetrahydroisoquinoline-2-yl) pyrimidine hydrochloride (YH1885), across caco-2 cell monolayers. Drug Metab Dispos 29:54-59 (Pubitemid 32041680)
26. Li H, Jin HE, Kim W, Han YH, Kim DD, Chung SJ, Shim CK. (2008a). Involvement of P-glycoprotein, multidrug resistance protein 2 and breast cancer resistance protein in the transport of belotecan and topotecan in Caco-2 and MDCKII cells. Pharm Res 25:2601-2612
27. Li M, Yuan H, Li N, Song G, Zheng Y, Baratta M, Hua F, Thurston A, Wang J, Lai Y. (2008b). Identification of interspecies difference in efflux transporters of hepatocytes from dog, rat, monkey and human. Eur J Pharm Sci 35:114-126
28. Lowes S, Simmons NL. (2002). Multiple pathways for fluoroquinolone secretion by human intestinal epithelial (Caco-2) cells. Br J Pharmacol 135:1263-1275 (Pubitemid 34259129)
29. Lüders AK, Saborowski R, Bickmeyer U. (2009). Inhibition of multidrug/xenobiotic resistance transporter by MK571 improves dye (Fura 2) accumulation in crustacean tissues from lobster, shrimp, and isopod. Comp Biochem Physiol C Toxicol Pharmacol 150:368-371
30. MacLean C, Moenning U, Reichel A, Fricker G. (2008). Closing the gaps: A full scan of the intestinal expression of p-glycoprotein, breast cancer resistance protein, and multidrug resistanceassociated protein 2 in male and female rats. Drug Metab Dispos 36:1249-1254 (Pubitemid 351929307)
31. Madgula VL, Avula B, Choi YW, Pullela SV, Khan IA, Walker LA, Khan SI. (2008). Transport of Schisandra chinensis extract and its biologically-Active constituents across Caco-2 cell monolayers-An in-vitro model of intestinal transport. J Pharm Pharmacol 60:363-370 (Pubitemid 351269824)
32. Maeda T, Takahashi K, Ohtsu N, Oguma T, Ohnishi T, Atsumi R, Tamai I. (2007). Identification of influx transporter for the quinolone antibacterial agent levofloxacin. Mol Pharm 4:85-94
33. Makhey VD, Guo A, Norris DA, Hu P, Yan J, Sinko PJ. (1998). Characterization of the regional intestinal kinetics of drug efflux in rat and human intestine and in Caco-2 cells. Pharm Res 15:1160-1167 (Pubitemid 28401704)
34. Matsson P, Pedersen JM, Norinder U, Bergström CA, Artursson P. (2009). Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharm Res 26:1816-1831
35. Merino G, Alvarez AI, Pulido MM, Molina AJ, Schinkel AH, Prieto JG. (2006). Breast cancer resistance protein (BCRP/ABCG2) transports fluoroquinolone antibiotics and affects their oral availability, pharmacokinetics, and milk secretion. Drug Metab Dispos 34:690-695
36. Naruhashi K, Tamai I, Inoue N, Muraoka H, Sai Y, Suzuki N, Tsuji A. (2002). Involvement of multidrug resistance-Associated protein 2 in intestinal secretion of grepafloxacin in rats. Antimicrob Agents Chemother 46:344-349 (Pubitemid 34087178)
37. Park MS, Okochi H, Benet LZ. (2011). Is Ciprofloxacin a Substrate of P-glycoprotein? Arch Drug Inf 4:1-9.
38. Rabbaa L, Dautrey S, Colas-Linhart N, Carbon C, Farinotti R. (1996). Intestinal elimination of ofloxacin enantiomers in the rat: Evidence of a carrier-mediated process. Antimicrob Agents Chemother 40:2126-2130 (Pubitemid 26296259)
39. Ramji JV, Austin NE, Boyle GW, Chalker MH, Duncan G, Fairless AJ, Hollis FJ, McDonnell DF, Musick TJ, Shardlow PC. (2001). The disposition of gemifloxacin, a new fluoroquinolone antibiotic, in rats and dogs. Drug Metab Dispos 29:435-442 (Pubitemid 32275558)
40. Ranjane PN, Gandhi SV, Kadukar SS, Bothara KG. (2010). Stability indicating RP-LC method for the determination of gemifloxacin mesylate. Chromatographia 71:1113-1117
41. Rohwedder RW, Bergan T, Thorsteinsson SB, Scholl H. (1990). Transintestinal elimination of ciprofloxacin. Diagn Microbiol Infect Dis 13:127-133 (Pubitemid 20191254)
42. Sasabe H, Kato Y, Suzuki T, Itose M, Miyamoto G, Sugiyama Y. (2004). Differential involvement of multidrug resistance-Associated protein 1 and P-glycoprotein in tissue distribution and excretion of grepafloxacin in mice. J Pharmacol Exp Ther 310:648-655 (Pubitemid 38988910)
43. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y. (2002). Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res 19:147-153 (Pubitemid 34165399)
44. Silbermann MH, Boersma AW, Janssen AL, Scheper RJ, Herweijer H, Nooter K. (1989). Effects of cyclosporin A and verapamil on the intracellular daunorubicin accumulation in Chinese hamster ovary cells with increasing levels of drug-resistance. Int J Cancer 44:722-726 (Pubitemid 19258751)
45. Soldner A, Benet LZ, Mutschler E, Christians U. (2000). Active transport of the angiotensin-II antagonist losartan and its main metabolite EXP 3174 across MDCK-MDR1 and caco-2 cell monolayers. Br J Pharmacol 129:1235-1243 (Pubitemid 30153981)
46. Sörgel F, Jaehde U, Naber K, Stephan U. (1989). Pharmacokinetic disposition of quinolones in human body fluids and tissues. Clin Pharmacokinet 16 Suppl 1:5-24 (Pubitemid 19112890)
47. Stephens RH, O'Neill CA, Warhurst A, Carlson GL, Rowland M, Warhurst G. (2001). Kinetic profiling of P-glycoprotein-mediated drug efflux in rat and human intestinal epithelia. J Pharmacol Exp Ther 296:584-591 (Pubitemid 32112489)
48. Taipalensuu J, Törnblom H, Lindberg G, Einarsson C, Sjöqvist F, Melhus H, Garberg P, Sjöström B, Lundgren B, Artursson P. (2001). Correlation of gene expression of ten drug efflux proteins of the ATP-binding cassette transporter family in normal human jejunum and in human intestinal epithelial Caco-2 cell monolayers. J Pharmacol Exp Ther 299:164-170 (Pubitemid 32905131)
49. Tamai I, Yamashita J, Kido Y, Ohnari A, Sai Y, Shima Y, Naruhashi K, Koizumi S, Tsuji A. (2000). Limited distribution of new quinolone antibacterial agents into brain caused by multiple efflux transporters at the blood-brain barrier. J Pharmacol Exp Ther 295:146-152
50. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K. (2002). cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol 13:1703-1710 (Pubitemid 34700594)
51. Uwai Y, Okuda M, Takami K, Hashimoto Y, Inui K. (1998). Functional characterization of the rat multispecific organic anion transporter OAT1 mediating basolateral uptake of anionic drugs in the kidney. FEBS Lett 438:321-324 (Pubitemid 28529298)
52. Vadlapatla RK, Vadlapudi AD, Kwatra D, Pal D, Mitra AK. (2011). Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin. Int J Pharm 420:26-33
53. van Loevezijn A, Allen JD, Schinkel AH, Koomen GJ. (2001). Inhibition of BCRP-mediated drug efflux by fumitremorgin-type indolyl diketopiperazines. Bioorg Med Chem Lett 11:29-32 (Pubitemid 32006117)
54. Vance-Bryan K, Guay DR, Rotschafer JC. (1990). Clinical pharmacokinetics of ciprofloxacin. Clin Pharmacokinet 19:434-461
55. Vanwert AL, Srimaroeng C, Sweet DH. (2008). Organic anion transporter 3 (oat3/slc22a8) interacts with carboxyfluoroquinolones, and deletion increases systemic exposure to ciprofloxacin. Mol Pharmacol 74:122-131 (Pubitemid 351872164)
56. Vousden M, Allen A, Lewis A, Ehren N. (1999). Lack of pharmacokinetic interaction between gemifloxacin and digoxin in healthy elderly volunteers. Chemotherapy 45:485-490 (Pubitemid 29531420)
57. Yague G, Morris JE, Pan XS, Gould KA, Fisher LM. (2002). Cleavable-complex formation by wild-type and quinolone-resistant Streptococcus pneumoniae type II topoisomerases mediated by gemifloxacin and other fluoroquinolones. Antimicrob Agents Chemother 46:413-419 (Pubitemid 34087189)
58. Yamaguchi H, Yano I, Hashimoto Y, Inui KI. (2000). Secretory mechanisms of grepafloxacin and levofloxacin in the human intestinal cell line caco-2. J Pharmacol Exp Ther 295:360-366
59. Yamaguchi H, Yano I, Saito H, Inui K. (2002). Pharmacokinetic role of P-glycoprotein in oral bioavailability and intestinal secretion of grepafloxacin in vivo. J Pharmacol Exp Ther 300:1063-1069 (Pubitemid 34165013)
60. Yasui-Furukori N, Uno T, Sugawara K, Tateishi T. (2005). Different effects of three transporting inhibitors, verapamil, cimetidine, and probenecid, on fexofenadine pharmacokinetics. Clin Pharmacol Ther 77:17-23 (Pubitemid 40075385)
61. Yuk JH, Nightingale CH, Quintiliani R, Sweeney KR. (1991). Bioavailability and pharmacokinetics of ofloxacin in healthy volunteers. Antimicrob Agents Chemother 35:384-386
62. Zhanel GG, Noreddin AM. (2001). Pharmacokinetics and pharmacodynamics of the new fluoroquinolones: Focus on respiratory infections. Curr Opin Pharmacol 1:459-463 (Pubitemid 33593833)
63. Zhang L, Strong JM, Qiu W, Lesko LJ, Huang SM. (2006). Scientific perspectives on drug transporters and their role in drug interactions. Mol Pharm 3:62-69 (Pubitemid 43331752)