Predicting the exposure and antibacterial activity of fluoroquinolones based on physicochemical properties

European Journal of Pharmaceutical Sciences

Volumn 47, Issue 1, 2012, Pages 21-27

  Völgyi, Gergely ^a   Vizserálek, Gábor ^a   Takács Novák, Krisztina ^a   Avdeef, Alex ^b   Tam, Kin Y ^c  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b In ADME Research   (United States)

^c ASTRAZENECA   (United Kingdom)

Author keywords

Antimicrobial activity; Fluoroquinolones; MIC; PAMPA; Protonation microconstants; True partition coefficients

Indexed keywords

AMIFLOXACIN; CIPROFLOXACIN; ENOXACIN; GATIFLOXACIN; LOMEFLOXACIN; MOXIFLOXACIN; NORFLOXACIN; OFLOXACIN; PEFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SPARFLOXACIN; TROVAFLOXACIN;

ANALYTIC METHOD; ANTIBACTERIAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; DRUG EXPOSURE; DRUG PENETRATION; MAXIMUM PLASMA CONCENTRATION; METHICILLIN SUSCEPTIBLE STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PARALLEL ARTIFICIAL MEMBRANE PERMEABILITY ASSAY; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; POTENTIOMETRY; PRIORITY JOURNAL; PROTON TRANSPORT; SPECTROPHOTOMETRY; STREPTOCOCCUS PNEUMONIAE;

1-OCTANOL; ANTI-BACTERIAL AGENTS; AREA UNDER CURVE; AZA COMPOUNDS; FLUOROQUINOLONES; HUMANS; HYDROGEN-ION CONCENTRATION; MEMBRANES, ARTIFICIAL; MICROBIAL SENSITIVITY TESTS; PERMEABILITY; PHYSICOCHEMICAL PHENOMENA; QUINOLINES; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; WATER;

EID: 84861334473     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.04.022     Document Type: Article

References (43)

1. V.T. Andriole The quinolones: past, present, and future Clinical Infectious Diseases 41 2005 S113 S119
2. A. Avdeef, and K.Y. Tam How well can the Caco-2/Madin-Darby Canine kidney models predict effective human jejunal permeability? Journal of Medicinal Chemistry 53 2010 3566 3584
3. K. Bush, and M.J. Pucci New antimicrobial agents on the horizon Biochemical Pharmacology 82 2011 1528 1539
4. P. Collignon, and J. Turnidge Fusidic acid in vitro activity International Journal of Antimicrobial Agents 12 1999 S45 S58
5. J.A. Cook, M.H. Silverman, D.J. Schelling, D.E. Nix, J.J. Schentag, R.R. Brown, and R.M. Stroshane Multiple-dose pharmacokinetics and safety of oral amifloxacin in healthy volunteers Antimicrobial Agents and Chemotherapy 34 1990 974 979
6. A. Dalhoff, and F.J. Schmitz In vitro antibacterial activity and pharmacodynamics of new quinolones European Journal of Clinical Microbiology & Infectious Diseases 22 2003 203 221
7. R.J. Fass In vitro activity of Bay 12-8039, a new 8-methoxy quinolone Antimicrobial Agents and Chemotherapy 41 1997 1818 1824
8. D. Felmingham, M.J. Robbins, K. Ingley, I. Mathiasa, H. Bhogala, A. Leakeya, G.L. Ridgway, and R.N. Grüneberg In vitro activity of trovafloxacin, a new fluoroquinolone, against recent clinical isolates The Journal of Antimicrobial Chemotherapy 39 Suppl. B 1997 43 49
9. FDA, 2011. Drug Information Online. < www.drugs.com >.
10. A. Forrest, D.E. Nix, C.H. Ballow, T.F. Goss, M.C. Birmingham, and J.J. Schentag Pharmacodynamics of intravenous ciprofloxacin in seriously ill patients Antimicrobial Agents and Chemotherapy 37 1993 1073 1081
11. T. Hou, J. Wang, W. Zhang, and X. Xu ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? The Journal of Chemical Information and Modeling 47 2007 460 463
12. D. Israel, G.J. Gillurn, M. Turik, K. Harvey, J. Ford, H. Dalton, M. Towle, R. Echols, A.H. Heller, and R. Polk Pharmacokinetics and serum bactericidal titers of ciprofloxacin and ofloxacin following multiple oral doses in healthy volunteers Antimicrobial Agents and Chemotherapy 37 1993 2193 2199
13. U. Jaehde, F. Sörgel, U. Stephan, and W. Schunack Effect of an antacid containing magnesium and aluminium on absorption, metabolism, and mechanism of renal elimination of pefloxacin in humans Antimicrobial Agents and Chemotherapy 38 1994 1129 1133
14. D.M. Johnson, R.N. Jones, and M.E. Erwin In vitro antimicrobial activity of CP-99433 compared with other fluoroquinolones Diagnostic Microbiology and Infectious Disease 17 1993 79 83
15. K.T. Kivistö, P. Ojala-KarIsson, and P.J. Neuvonen Inhibition of norfloxacin absorption by dairy products Antimicrobial Agents and Chemotherapy 36 1992 489 491
16. P.A. Lambert Cellular impermeability and uptake of biocides and antibiotics in Gram-positive bacteria and mycobacteria Journal of Applied Microbiology Symposium Supplement 92 2002 46S 54S
17. I. Laponogov, M.K. Sohi, D.A. Veselkov, X.S. Pan, R. Sawhney, A.W. Thompson, K.E. McAuley, L.M. Fisher, and M.R. Sanderson Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases Nature Structural & Molecular Biology 16 2009 667 669
18. I. Laponogov, X.S. Pan, D.A. Veselkov, K.E. McAuley, L.M. Fisher, and M.R. Sanderson Structural basis of gate-DNA breakage and resealing by type II topoisomerases PLoS One 5 2010 e11338
19. M.E. Lebsack, D. Nix, B. Ryerson, R.D. Totheraker, L. Welage, A.M. Norman, J.J. Schentag, and A.J. Sedman Effect of gastric acidity on enoxacin absorption Clinical Pharmacology & Therapeutics 52 1992 252 256
20. P. Lehto, and K.T. Kivistö Effect of sucralfate on absorption of norfloxacin and ofloxacin Antimicrobial Agents and Chemotherapy 38 1994 248 251
21. G.Y. Lesher, E.J. Froelich, M.D. Gruett, J.H. Bailey, and R.P. Brundage 1,8-naphthyridine derivatives: a new class of chemotherapeutic agents Journal of Medicinal Chemistry 5 1962 1063 1065
22. H. Lode, G. Hoffken, P. Olschewski, B. Sievers, A. Kirch, K. Borner, and P. Koeppe Pharmacokinetics of ofloxacin after parenteral and oral administration Antimicrobial Agents and Chemotherapy 31 1987 1338 1342
23. M.A. Mitscher Bacterial topoisomerase inhibitors: quinolone and pyridone antibacterial agents Chemical Review 105 2005 559 592
24. D.M. Morens, G.K. Folkers, and A.S. Fauci The challenge of emerging and re-emerging infectious diseases Nature 430 2004 242 249
25. H. Nikaido Prevention of drug access to bacterial targets: permeability barriers and active efflux Science 264 1994 382 388
26. M. Nakashima, T. Uematsu, K. Kosuge, H. Kusajima, T. Ooie, Y. Masuda, R. Ishida, and H. Uchida Single- and multiple dose pharmacokinetics on AM-1155, a new 6-fluoro-8-methoxy quinolone, in humans Antimicrobial Agents and Chemotherapy 39 1995 2635 2640
27. H.C. Neu, and P. Labthavikul Antibacterial activity of amifloxacin (WIN 49, 375), a new quinolone agent Diagnostic Microbiology and Infectious Disease 3 1985 469 478
28. D.E. Nix, and J.J. Schentag The quinolones: an overview and comparative appraisal of their pharmacokinetics and pharmacodynamics Journal of Clinical Pharmacology 28 1988 169 178
29. J.I. Oh, K.S. Paek, M.J. Ahn, M.Y. Kim, C.Y. Hong, I.C. Kim, and J.H. Kwak In vitro and in vivo evaluations of LB20304, a new fluoronaphthyridone Antimicrobial Agents and Chemotherapy 40 1996 1564 1568
30. R. O'Shea, and H.E. Moser Physicochemical properties of antibacterial compounds: implications for drug discovery Journal of Medicinal Chemistry 51 2008 2871 2878
31. M. Ritz, H. Lode, M. Fassbender, K. Borner, P. Koeppe, and C.E. Nord Multiple-dose pharmacokinetics of sparfloxacin and its influence in fecal flora Antimicrobial Agents and Chemotherapy 38 1994 455 459
32. T.J. Silhavy, D. Kahne, and S. Walker The bacterial cell envelope Cold Spring Harbour Perspectives in Biology 2 2010 a000414
33. L.L. Silver Challenges of antibacterial discovery Clinical Microbiology Reviews 24 2011 71 109
34. H. Stass, A. Dalhoff, D. Kubitza, and U. Schühly Pharmacokinetics, safety, and tolerability of ascending single doses of moxifloxacin, a new 8-methoxy quinolone, administered to healthy subjects Antimicrobial Agents and Chemotherapy 42 1998 2060 2065
35. H. Stuht, H. Lode, P. Koeppe, K.L. Rost, and T. Schaberg Interaction of lomefloxacin and ciprofloxacin with omeprazole and comparative pharmacokinetics Antimicrobial Agents and Chemotherapy 39 1995 1045 1049
36. K. Takács-Novák, B. Noszál, I. Hermecz, G. Keresztúri, B. Podányi, and G. Szász Protonation equilibria of quinolone antibacterials Journal of Pharmaceutical Sciences 79 1990 1023 1028
37. K. Takács-Novák, M. Józan, I. Hermecz, and G. Szász Lipophilicity of antibacterial fluoroquinolones International Journal of Pharmaceutics 79 1992 89 96
38. K. Takács-Novák, and K.Y. Tam Multiwavelength spectrophotometric determination of acid dissociation constants part V: microconstants and tautomeric ratios of diprotic amphoteric drugs Journal of Pharmaceutical and Biomedical Analysis 21 2001 1171 1182
39. R. Taléns-Visconti, T.M. Garrigues, E. Cantón, J. Freixas, A. Martín-Villodre, and J.M. Plá-Delfina Activity-bioavailability balance in oral drug development for a selected group of 6-fluoroquinolones Journal of Pharmaceutical Sciences 91 2002 2452 2464
40. K.Y. Tam, A. Avdeef, O. Tsinman, and N. Sun The permeation of amphoteric drugs through artificial membranes - an in combo absorption model based on paracellular and transmembrane permeability Journal of Medicinal Chemistry 53 2010 392 401
41. R. Teng, L.C. Dogolo, S.A. Willavize, H.L. Friedman, and J. Vincent Oral bioavailability of trovafloxacin with and without food in healthy volunteers Journal of Antimicrobial Chemotherapy 39 Suppl. B 1997 87 92
42. E. Wakabayashi, and S. Mitsuhashi In vitro antibacterial activity of AM-1155, a novel 6-fluoro 8-methoxy quinolone Antimicrobial Agents and Chemotherapy 38 1994 594 601
43. J.S. Wolfson, and D.C. Hooper Fluoroquinolone antimicrobial agents Clinical Microbiology Reviews 2 1989 378 424