Danofloxacin-mesylate is a substrate for ATP-dependent efflux transporters

British Journal of Pharmacology

Volumn 150, Issue 4, 2007, Pages 463-469

  Schrickx, J A ^a   Fink Gremmels, J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

ABC; ABCB1; ABCC2; ABCG2; Danofloxacin; Fluoroquinolones; Mesylate; Transport

Indexed keywords

ABC TRANSPORTER; ADENOSINE TRIPHOSPHATE; BREAST CANCER RESISTANCE PROTEIN; CIPROFLOXACIN; DANOFLOXACIN; ELACRIDAR; GLYCOPROTEIN P; GREPAFLOXACIN; KO 143; MULTIDRUG RESISTANCE PROTEIN 2; PROTEIN INHIBITOR; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG; VALSPODAR; VERLUKAST;

ANIMAL CELL; ARTICLE; CELL COMPARTMENTALIZATION; CELL CULTURE; CELL GROWTH; CELL MEMBRANE; CELL STRAIN CACO 2; CONCENTRATION (PARAMETERS); CULTURE MEDIUM; DEVICE; DRUG ABSORPTION; DRUG ELIMINATION; DRUG EXCRETION; DRUG STRUCTURE; DRUG TRANSPORT; EVALUATION; FLUOROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MONOLAYER CULTURE; NONHUMAN; POROSITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FAMILY; PROTEIN FUNCTION; PROTEIN SECRETION; PROTEIN TRANSPORT; TARGET ORGAN;

ACRIDINES; ADENOSINE TRIPHOSPHATE; ANTI-BACTERIAL AGENTS; ATP-BINDING CASSETTE TRANSPORTERS; CACO-2 CELLS; CARRIER PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CULTURE MEDIA; CYCLOSPORINS; DIFFUSION CHAMBERS, CULTURE; FLUOROMETRY; FLUOROQUINOLONES; HUMANS; MEMBRANE TRANSPORT PROTEINS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NEOPLASM PROTEINS; P-GLYCOPROTEIN; PROPIONATES; QUINOLINES; TETRAHYDROISOQUINOLINES;

EID: 33847165756     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0706974     Document Type: Article

References (53)

1. Allen JD, Van Loevezijn A, Lakhai JM, Van Der Valk M, Van Tellingen O, Reid G et al. (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. Andrews J, Honeybourne D, Jevons G, Brenwald N, Cunningham B, Wise R (1997). Concentrations of levofloxacin (HR 355) in the respiratory tract following a single oral dose in patients undergoing fibre-optic bronchoscopy. J Antimicrob Chemother 40: 573-577.
3. Aouali N, Eddabra L, Macadre J, Morjani H (2005). Immunosuppressors and reversion of multidrug-resistance. Crit Rev Oncol/Hematol Immunosuppressive Treatment Induction Cancer 56: 61-70.
4. Braish TF, Fox DE (1990). Synthesis of (S,S)- and (R,R)-2-alkyl-2,5-diazabicyclo[2.2.1]heptanes. J Org Chem 55: 1684-1687.
5. Campbell L, Abulrob a-NG, Kandalaft LE, Plummer S, Hollins aJ, Gibbs A et al. (2003). Constitutive expression of P-glycoprotein in normal lung alveolar epithelium and functionality in primary alveolar epithelial cultures. J Pharmacol Exp Ther 304: 441-452.
6. Cormet-Boyaka E, Huneau JF, Mordrelle A, Boyaka PN, Carbon C, Rubinstein E et al. (1998). Secretion of sparfloxacin from the human intestinal Caco-2 cell line is altered by P-glycoprotein inhibitors. Antimicrob Agents Chemother 42: 2607-2611.
7. De Bruin M, Miyake K, Litman T, Robey R, Bates SE (1999). Reversal of resistance by GF120918 in cell lines expressing the ABC half-transporter, MXR. Cancer Lett 146: 117-126.
8. De Lange EC, Marchand S, Van Den Berg D, Van Der Sandt IC, De Boer aG, Delon A et al. (2000). In vitro and in vivo investigations on fluoroquinolones; effects of the P-glycoprotein efflux transporter on brain distribution of sparfloxacin. Eur J Pharm Sci 12: 85-93.
9. Deguchi Y, Sun J, Tauchi Y, Sakai S, Morimoto K (2003). Distribution characteristics of grepafloxacin, a fluoroquinolone antibiotic, in lung epithelial lining fluid and alveolar macrophage. Drug Metab Pharmacokinet 18: 319-326.
10. Eloranta JJ, Meier PJ, Kullak U, Gerd A (2005). Coordinate transcriptional regulation of transport and metabolism. Methods in enzymology. In: Helmut Sies aLP (ed.) Phase II Conjugation Enzymes and Transport Systems. Academic Press: New York, pp. 511-530.
11. Fernandez C, Buyse M, German-Fattal M, Gimenez F (2004). Influence of the pro-inflammatory cytokines on P-glycoprotein expression and functionality. J Pharm Pharm Sci 7: 359-371.
12. Fernandez-Teruel C, Gonzalez-Alvarez I, Casabo VG, Ruiz-Garcia A, Bermejo M (2005). Kinetic modelling of the intestinal transport of sarafloxacin. Studies in situ in rat and in vitro in Caco-2 cells. J Drug Target 13: 199-212.
13. Fernandez-Varon E, Ayala I, Marin P, Carrion A, Martos N, Escudero E et al. (2006). Pharmacokinetics of danofloxacin in horses after intravenous, intramuscular and intragastric administration. Equine Vet J 38: 342-346.
14. Friis C (1993a). Penetration of danofloxacin into the respiratory tract tissues and secretions in calves. Am J Vet Res 54: 1122-1127.
15. Friis C (1993b). Penetration of danofloxacin into the respiratory tract tissues and secretions in calves. Am J Vet Res 54: 1122-1127.
16. Friis C, Nielsen JP (1997). Penetration of danofloxacin into the respiratory tract tissues and secretions in healthy and Actinobacillus pleuropneumoniae infected pigs. J Vet Pharmacol Ther 20: 87-109.
17. Garcia MA, Solans C, Aramayona JJ, Rueda S, Bregante MA (2000). Development of a method for the determination of danofloxacin in plasma by HPLC with fluorescence detection. Biomed Chromatogr 14: 89-92.
18. Gekeler V, Ise W, Sanders KH, Ulrich WR, Beck J (1995). The leukotriene LTD4 receptor antagonist MK571 specifically modulates MRP associated multidrug resistance. Biochem Biophys Res Commun 208: 345-352.
19. Griffiths NM, Hirst BH, Simmons NL (1994). Active intestinal secretion of the fluoroquinolone antibacterials ciprofloxacin, norfloxacin and pefloxacin; a common secretory pathway? J Pharmacol Exp Ther 269: 496-502.
20. Ito T, Yano I, Tanaka K, Inui K-I (1997). Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther 282: 955-960.
21. Jonker JW, Merino G, Musters S, Van Herwaarden aE, Bolscher E, Wagenaar E et al. (2005). The breast cancer resistance protein BCRP (ABCG2) concentrates drugs and carcinogenic xenotoxins into milk. Nat Med 11: 127-129.
22. Kalitsky-Szirtes J, Shayeganpour A, Brocks DR, Piquette-Miller M (2004). Suppression of drug-metabolizing enzymes and efflux transporters in the intestine of endooxin-treated rats. Drug Metab Dispos 32: 20-27.
23. Knoll U, Glunder G, Kietzmann M (1999). Comparative study of the plasma pharmacokinetics and tissue concentrations of danofloxacin and enrofloxacin in broiler chickens. J Vet Pharmacol Ther 22: 239-246.
24. Langmann T, Mauerer R, Zahn A, Moehle C, Probst M, Stremmel W et al. (2003). Real-time reverse transcription-PCR expression profiling of the complete human ATP-binding cassette transporter superfamily in various tissues. Clin Chem 49: 230-238.
25. Lindecrona RH, Friis C, Nielsen JP (2000). Pharmacokinetics and penetration of danofloxacin into the gastrointestinal tract in healthy and in Salmonella typhimurium infected pigs. Res Vet Sci 68: 211-216.
26. Lowes S, Simmons NL (2002). Multiple pathways for fluoroquinolone secretion by human intestinal epithelial (Caco-2) cells. Br J Pharmacol 135: 1263-1275.
27. Maliepaard M, Scheffer GL, Faneyte IF, Van Gastelen MA, Pijnenborg aCLM, Schinkel aH et al. (2001). Subcellular localization and distribution of the breast cancer resistance protein transporter in normal human tissues. Cancer Res 61: 3458-3464.
28. Mckellar Q, Gibson I, Monteiro A, Bregante M (1999). Pharmacokinetics of enrofloxacin and danofloxacin in plasma, inflammatory exudate, and bronchial secretions of calves following subcutaneous administration. Antimicrob Agents Chemother 43: 1988-1992.
29. Mckellar QA, Gibson IF, Mccormack RZ (1998). Pharmacokinetics and tissue disposition of danofloxacin in sheep. Biopharm Drug Dispos 19: 123-129.
30. 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.
31. Morris ME, Zhang S (2006). Flavonoid-drug interactions: effects of flavonoids on ABC transporters. Life Sci 78: 2116-2130.
32. Nakajima Y, Hattori K, Shinsei M, Matsunaga N, Iizasa H, Sasabe H et al. (2000). Physiologically-based pharmacokinetic analysis of grepafloxacin. Biol Pharm Bull 23: 1077-1083.
33. Naruhashi K, Tamai I, Inoue N, Muraoka H, Sai Y, Suzuki N et al. (2001). Active intestinal secretion of new quinolone antimicrobials and the partial contribution of P-glycoprotein. J Pharm Pharmacol 53: 699-709.
34. Naruhashi K, Tamai I, Inoue N, Muraoka H, Sai Y, Suzuki N et al. (2002). Involvement of multidrug resistance-associated protein 2 in intestinal secretion of grepafloxacin in rats. Antimicrob Agents Chemother 46: 344-349.
35. Prime-Chapman HM, Fearn RA, Cooper aE, Moore V, Hirst BH (2004). Differential MRP1-6 isoform expression and function in human intestinal epithelial Caco-2 cells. J Pharmacol Exp Ther 311: 476-484.
36. Pulido MM, Molina aJ, Merino G, Mendoza G, Prieto JG, Alvarez aI (2006). Interaction of enrofloxacin with breast cancer resistance protein (BCRP/ABCG2): influence of flavonoids and role in milk secretion in sheep. J Vet Pharmacol Ther 29: 279-287.
37. Rabbaa L, Dautrey S, Colas-Linhart N, Carbon C, Farinotti R (1995). Stereoselectivity of ofloxacin intestinal transport in the rat. Drugs 49 (Suppl 2): 333-334.
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.
39. Ruiz-Garc?́a A, Huimin L, Plá-Delfina JM, Ming Hu (2002). Kinetic characterization of secretory transport of a new ciprofloxacin derivative (CNV97100) across Caco-2 cell monolayers. J Pharm Sci 91: 2511-2519.
40. 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.
41. Scheffer GL, Pijnenborg aCLM, Smit EF, Muller M, Postma DS, Timens W et al. (2002). Multidrug resistance related molecules in human and murine lung. J Clin Pathol 55: 332-339.
42. Shem-Tov M, Rav-Hon O, Ziv G, Lavi E, Glickman A, Saran A (1998). Pharmacokinetics and penetration of danofloxacin from the blood into the milk of cows. J Vet Pharmacol Ther 21: 209-213.
43. Sorgel F, Naber KG, Jaehde U, Reiter A, Seelmann R, Sigl G (1989). Gastrointestinal secretion of ciprofloxacin. Evaluation of the charcoal model for investigations in healthy volunteers. Am J Med 87: 62S-65S.
44. Suzuki T, Kato Y, Sasabe H, Itose M, Miyamoto G, Sugiyama Y (2002). Mechanism for the tissue distribution of grepafloxacin, a fluoroquinolone antibiotic, in rats 10.1124/dmd.30.12.1393. Drug Metab Dispos 30: 1393-1399.
45. Taipalensuu J, Tornblom H, Lindberg G, Einarsson C, Sjoqvist F, Melhus H et al. (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.
46. Volpe DA (2004). Permeability classification of representative fluoroquinolones by a cell culture method. AAPS PharmSci 6: e13.
47. Von Traeder W, Kleinhaus S (2002). Konzentrationsabhängige dosierung von danofloxacin - ein beitrag zur optimierung der klinischen wirksamkeit und vermeidung der selektion resistenter kieme. Tierärztliche Umschau 57: 102-107.
48. Wise R, Honeybourne D (1996). A review of the penetration of sparfloxacin into the lower respiratory tract and sinuses. J Antimicrob Chemother 37 (Suppl A): 57-63.
49. Xia CQ, Liu N, Yang D, Miwa G, Gan LS (2005). Expression, localization, and functional characteristics of breast cancer resistance protein in Caco-2 cells. Drug Metab Dispos 33: 637-643.
50. 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.
51. Yamaguchi H, Yano I, Saito H, Inui K-I (2002). Pharmacokinetic role of P-glycoprotein in oral bioavailability and intestinal secretion of grepafloxacin in vivo. J Pharmacol Exp Ther 300: 1063-1069.
52. Zakelj S, Sturm K, Kristl A (2006). Ciprofloxacin permeability and its active secretion through rat small intestine in vitro. Int J Pharm 313: 175-180.
53. Zhao YL, Cai SH,Wang L, Kitaichi K, Tatsumi Y, Nadai M et al. (2002). Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin. Clin Exp Pharmacol Physiol 29: 167-172.