Relation between structure, activity and adverse effects of quinolones;Relación entre estructura, actividad y efectos adversos de las quinolonas

Revista Espanola de Quimioterapia

Volumn 17, Issue 3, 2004, Pages 232-243

  Gutierrez Zufiaurre N ^a  

^a HOSPITAL UNIVERSITARIO DE SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 QUINOLONE DERIVATIVE; 8 (3 AMINO 1 PYRROLIDINYL) 1 CYCLOPROPYL 7 FLUORO 9 METHYL 4 OXO 3 QUINOLIZINECARBOXYLIC ACID; CIPROFLOXACIN; CLINAFLOXACIN; ENOXACIN; FLEROXACIN; GARENOXACIN; GATIFLOXACIN; GEMIFLOXACIN; GREPAFLOXACIN; LOMEFLOXACIN; MOXIFLOXACIN; NALIDIXIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT; NORFLOXACIN; PEFLOXACIN; PGE 4175997; PGE 9262932; PGE 9509924; PIPERACILLIN; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; QUINOLIZINE DERIVATIVE; QUINOLONE DERIVATIVE; SITAFLOXACIN; SPARFLOXACIN; TEMAFLOXACIN; TOSUFLOXACIN; TROVAFLOXACIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTHROPATHY; CRYSTALLURIA; DRUG ACTIVITY; DRUG ERUPTION; DRUG STRUCTURE; ERYTHEMA; GENOTOXICITY; HEMOLYTIC UREMIC SYNDROME; HUMAN; NEUROTOXICITY; PHOTOTOXICITY; PRURITUS; REVIEW; STRUCTURE ACTIVITY RELATION; URTICARIA;

HUMANS; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9644303068     PISSN: 02143429     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (68)

1. Albrecht, R. Development of antibacterial agents of the nalidixic acid type. Prog Drug Res 1977; 21: 9-104.
2. Lesher, G.Y., Forelich, E.D., Gruet, M.D., Bailey, J.H., Brundage, R.P. 1,8-Naphthyridine derivaties. A new class of chemotherapeutic agents. J Med Pharm Chem 1962; 5: 1063-1068.
3. Ronald, A.R., Turck, M., Petersdorf, R.G. A critical evaluation of nalidixic acid in urinary-tract infections. N Engl J Med 1966; 275: 1081-1089.
4. Read, R.C., Morrissey, I., Ambler, J.E. Clinicians manual on respiratory tract infections and fluoroquinolones. Science Press, London UK 2000.
5. Koga, H., Itoh, A., Murayama, S., Suzue, S., Irikura, T. Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. J Med Chem 1980; 23: 1358-1363.
6. Li, Q., Chu, D.T., Claiborne, A. y cols. Synthesis and structure-activity relationships of 2-pyridones: A novel series of potent DNA gyrase inhibitors as antibacterial agents. J Med Chem 1996; 39; 3070-3088.
7. Domagala, J.M. Structure-activity and structure-side-effect relationships for the quinolone antibacterials. J Antimicrob Chemother 1994; 33: 685-706.
8. Stein, G.E. The 4-quinolone antibiotics: Past, present and future. Pharmacotherapy 1988; 8: 301-314.
9. Tillotson, G.S. Quinolones: Structure-activity relationships and future predictions. J Med Microbiol 1996; 44: 320-324.
10. Lipsky, B.A., Baker, C.A. Fluoroquinolone toxicity profiles: A review focusing on newer agents. Clin Infect Dis 1999; 28: 352-364.
11. Hooper, D.C. Mechanisms of fluoroquinolone resistance. Drug Resis Updates 1999; 2: 38-55.
12. Ledoussal, B., Almstead, J.K., Flaim, C.P. Novel fluoroquinolone, structure-activity and design of new potent and safe agents. 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco 1999; F-544.
13. Hayashi, K., Todo, Y., Hamamoto, S., Ojima, K., Yamada, M., Kito, T. T-3811, a novel des-F(6)-quinolone: Synthesis and in vitro activity of 7-(isoindolin-5-yl) derivaties. 37th Interscience Conference on Antimicrobial Agents and Chemotherapy, Toronto 1997; F-158.
14. Fix, A.M., Pfaller, M.A., Biedenbach, D.J., Beach, M.L., Jones, R.N. Comparative antimicrobial spectrum and activity of BMS284756 (T-3811, a desfluoroquinolone) tested against 656 Enterobacteriaceae, including preliminary in vitro susceptibility test comparisons and development. Int J Antimicrob Agents 2001; 18: 141-145.
15. Takahata, M., Mitsuyama, J., Yamashiro, Y. y cols. In vitro and in vivo antimicrobial activities of T-3811ME, a novel des-F(6)-quinolone. Antimicrob Agents Chemother 1999; 43: 1077-1084.
16. Pankuch, G.A., Nagai, K., Davies, T.A., Jacobs, M.R., Appelbaum, P.C. Antipneumococcal activity of BMS 284756 compared to six other agents. Antimicrob Agents Chemother 2002; 46: 251-254.
17. Fung-Tomc, J.C., Minassian, B., Kolek, B. y cols. Antibacterial spectrum of a novel des-fluoro(6)-quinolone, BMS284756. Antimicrob Agents Chemother 2000; 44: 3351-3356.
18. Barry, A.L., Fuchs, P.C., Brown, S.D. In vitro activities of three non-fluorinated quinolones against representatives bacterial isolates. Antimicrob Agents Chemother 2001; 45: 1923-1927.
19. Lawrence, L.E., Wu, P., Fan, L. y cols. The inhibition and selectivity of bacterial topoisomerases by BMS-284756 and its analogues. J Antimicrob Chemother 2001; 48: 195-201.
20. Yamakawa, T., Mitsuyama, J., Hayashi, K. In vitro and in vivo antibacterial activity of T-3912, a novel non-fluorinated topical quinolone. J Antimicrob Chemother 2002; 49: 455-465.
21. Cecchetti, V., Fravolini, A., Lorenzini, M.C., Tabarrini, O., Terni, P., Xin, T. Studies on 6-aminoquinolones: Synthesis and antibacterial evaluation of 6-amino-8-methylquinolones. J Med Chem 1996; 39: 436-445.
22. Cecchetti, V., Fravolini, A., Lorenzini, M.C. y cols. Chemometric methodologies in a quantitative structure-activity relationship study: The antibacterial activity of 6-aminoquinolones. J Med Chem 1997; 40: 1698-1706.
23. Llorente, B., Leclerc, F., Cedergren, R. Using SAR and QSAR analysis to model the activity and structure of the quinolone-DNA complex. Bio Med Chem 1996; 4: 61-71.
24. Yoshida, T., Yamamoto, Y., Orita, H. y cols. Studies on quinolone antibacterials. IV. Structure-activity relationships of antibacterial activity and side effects for 5- and 8-substitued and 5,8-disubstitued-7(3-amino-1- pyrrolidinyl)-1-cyclopropil-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. Chem Pharm Bull (Tokyo) 1996; 44: 1074-1085.
25. Kahn, A.A., Araujo, F.G., Brightly, K.E., Gootz, T.D., Remington, J.S. Anti-Toxoplasma gondii activities and structure-activity relationships of novel fluoroquinolones related to trovafloxacin. Antimicrob Agents Chemother 1999; 43: 1783-1787.
26. Zhao, B.Y, Pine, R., Domagala, J., Drlica, K. Fluoroquinolone action against clinical isolates of Mycobacterium tuberculosis: Effects of a C-8 methoxy group on survival in liquid media and in human macrophages. Antimicrob Agents Chemother 1999; 43: 661-666.
27. Jorgensen, J.H., Weigel, L.M., Ferraro, M.J., Swenson, J.M., Tenover, F.C. Activities of newer fluoroquinolones against Streptococcus pneumoniae clinical isolates including those with mutations in the gyrA, parC, and parE loci. Antimicrob Agents Chemother 1999; 43: 329-334.
28. Pan, X.S., Fisher, M.L. Targeting of DNA gyrase in Streptococcus pneumoniae by sparfloxacin: Selective targeting of gyrase or topoisomerase IV by quinolones. Antimicrob Agents Chemother 1997; 41: 471-474.
29. Davies, T.A., Pankuch, G.A., Dewasse, B.E., Jacobs, M.R., Appelbaum, P.C. In vitro development of resistance to five quinolones and amoxicillin clavunate in Streptococcus pneumoniae. Antimicrob Agents Chemother 1999; 43: 1177-1782.
30. Pestova, E., Beyer, R., Cianciotto, N.P., Noskin, G.A., Peterson, L.R. Contribution of topoisomerase IV and DNA gyrase mutation in Streptococcus pneumoniae for resistance to novel fluoroquinolones. Antimicrob Agents Chemother 1999; 43: 2000-2004.
31. Fukuda, H., Kishii, R., Takei, M., Hosaka, M. Contribution of the 8-methoxy group of gatifloxacin to resistance selectivity, target preference, and antibacterial activity against Streptococcus pneumoniae. Antimicrob Agents Chemother 2001; 45: 1649-1453.
32. Dalhoff, A. Comparative in vitro and in vivo activity of the C-8 methoxy quinolone moxifloxacin and the C-8 chlorine quinolone BAY y-3118. Clin Infect Dis 2001; 32 (Suppl. 1): S16-S22.
33. Dalhoff, A. The C-8 methoxy group of moxifloxacin decreases the propensity for quinolone resistance development in Staphylococcus aureus. 37th Annual Meeting of the Infectious Diseases Society of America, Philadelphia 1999; Abstr. 102.
34. Nakane, T., Iyobe, S., Sato, K., Mitsuhashi, S. In vitro antibacterial activity of DU-6859a, a new fluoroquinolone, Antimicrob Agents Chemother 1995; 39: 2822-2826.
35. Mitsuyama, J. Structures of existing and new quinolones and relationship to bactericidal activity against Streptococcus pneumoniae, J Antimicrob Chemother 1999; 44: 201-207.
36. Morrissey, I., Hoshino, K., Sato, K. y cols. Mechanism of differential activities of ofloxacin enantiomers. Antimicrob Agents Chemother 1996; 40: 1775-1784.
37. Renau, T.E., Gage, J.W., Dever, J.A. y cols. Structure-activity relationships of quinolone agents against mycobacteria: Effect of structural modifications at the 8 position. Antimicrob Agents Chemother 1996; 40: 2363-2368.
38. Peterson, L.R. Quinolone molecular structure-activity relationships: What we have learned about improving antimicrobial activity? Clin Infect Dis 2001; 33 (Supl. 3): S180-S186.
39. Piddock, L.J., Jonhson, M., Ricci, V., Hill, S.L. Activities of new fluoroquinolones against fluoroquinolone-resistant pathogens of the lower respiratory tract. Antimicrob Agents Chemother 1998; 42: 2956-2960.
40. Boswell, F.J., Wise R. Advances in the macrolides and quinolones. Infect Dis Clin North Am 1998; 12: 647-670.
41. Hong, C.Y., Kim, Y.K., Nam, D.-H. y cols. SB-265805 (LB20304a): Structure-activity relationship of the oxime-derivatized pyrrolidine. The importance of the oximinoalkyl group on in vitro antibacterial activity and pharmacokinetics. 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego 1998; F-095.
42. Hong, C.Y., Kim, Y.K., Jang, J.H., Kim, M.Y. SB-265805 (LB20304a): The synergistic effect of the methyloxime and aminomethyl groups of the C7-pyrrolidine on in vitro activity. 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego 1998; F-096.
43. Appelbaum, P.C., Hunter, P.A. The fluoroquinolones antibacterials: Past, present and future perspectives. Int J Antimicrb Agents 2000; 16: 5-15.
44. Pestova, E., Millichap, J.J., Noskin, G.A., Peterson, L.R. Intracellular targets of moxifloxacin: A comparison with other fluoroquinolones. J Antimicrob Chemother 2000; 45: 583-590.
45. Beyer, R., Pestova, E., Millichap, J.J., Noskin, G.A., Peterson, L.R. A convenient assay for estimating the possible involvement of efflux of fluoroquinolones by Streptococcus pneumoniae and Staphylococcus aureus: Evidence for disminished moxifloxacin, sparfloxacin and trovafloxacin efflux. Antimicrob Agents Chemother 2000; 44: 798-801.
46. Davies, T.A., Kelly, L.M., Pankuch, G.A., Credito, K.L., Jacobs, M.R., Appelbaum, P.C. Antipneumococcal activities of gemifloxacin compared to those of nine other agents. Antimicrob Agents Chemother 2000; 44: 304-310.
47. Alovero, F.L., Pan, X.S., Morris, J.A., Manzo, R.H., Fisher, L.M. Engineering the specifity of antibacterial fluoroquinolones: Benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase. Antimicrob Agents Chemother 2000; 44: 320-325.
48. Lister, P.D., Sanders, C.C. Pharmacodynamics of levofloxacin and ciprofloxacin against Streptococcus pneumoniae. J Antimicrob Chemother 1999; 43: 79-86.
49. Ma, Z., Chu, D.T., Cooper, C.S. y cols. Synthesis and antimicrobial activity oh 4-H-4-oxoquinolizines derivaties: Consequences of structural modifications at the C-8 position. J Med Chem 1999; 42: 4203-4213.
50. Li, Q., Mitscher, L.A., Shen, L.L. The 2-pyridone antibacterial agents: Bacterial topoisomerase inhibitors. Med Res Rev 2000; 20: 231-293.
51. Blanche, F., Cameron, B., Bernard, F.X. y cols. Differential behaviors of Staphylococcus aureus and Escherichia coli type II DNA topoisomerases. Antimicrob Agents Chemother 1996; 40: 2714-2720.
52. Nilius, A.M., Hensey-Rudloff, D.M., Almer, L.S. y cols. Comparative in vitro antibacterial activity of A-170568.1, a novel 2-pyridone antibacterial agent. 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego 1998; F-79.
53. Amiger, Y-L., Chu, D.T.W., Fung, A.K.L. y cols. The discovery of A-165753 and A-170568, two potent broad-spectrum antimicrobial agents. 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego 1998; F-86.
54. Flamm, R.K., Vojtko, C., Ramer, N. y cols. Comparative in vitro activity of A-86719.1, a novel bacterial DNA gyrase inhibitor. 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Washington DC 1994; F-45.
55. Ball, P., Tillotson, G. Tolerability of fluoroquinolone antibiotics: Past, present and future. Drug Safety 1995; 13: 343-358.
56. Ribard, P., Kahn, M.F. Rheumatological side-effects of quinolones. En: Kahn, M.F. (Ed.). Baillière's clinical rheumatology: Drug induced rheumatic diseases. Baillière Tindall, London 1991; 175-191.
57. Bryskier, A., Chantot, J.F. Classification and structure-activity relationships of fluoroquinolones. Drug 1995; 49 (Suppl. 2): 16-28.
58. Lomaestro, B.M., Bailie, G.R. Quinolone-cation interactions: A review. DICP. Ann Pharmacother 1991; 25: 1249-1258.
59. Shentag, J.J., Nix, D.E. Pharmacokinetics and tissue penetration of fluoroquinolones. En: Sanders, E.W., Sanders, C.C. (Eds.). Fluoroquinolones in the treatment of infectious diseases. Physicians and Scientist Publ. Co., Glenview, IL 1990; 29-44.
60. Wolfson, J.S., Hooper, D.C. Overview of fluoroquinolone safety. Am J Med 1991; 91 (Suppl. 6A): 153S-161S.
61. Wagstaff, A.J., Balfour, J.A. Grepafloxacin. Drugs 1997; 53: 817-824.
62. Trovafloxacin (Trovan) package insert. Pfizer, New York 1998.
63. Fort, F.L. Mutagenicity of quinolone antibacterials. Drug Safety 1992; 7: 214-222.
64. Norrby, S.R. Side effects of quinolones: Comparison between quinolones and other antibiotics. Eur J Clin Microbiol Infect Dis 1991; 10: 378-383.
65. Rosen, T., Chu, D.T.W., Lico, I.M., Fernandes, P.B., Marsh, K., Shen, L. Design, synthesis, and properties of (4S)-7-(4-amino-2-substitued-pyrrolinyl) quinolone-3-carboxylic acids. J Med Chem 1988; 31: 1598-1611.
66. Christ, W., Lehnert, T., Ulbrich, B. Specific toxicologic aspects of the quinolones. Rev Infect Dis 1988; 10 (Suppl. 1): S141-S146.
67. Grepafloxacin (Raxar) package insert. Glaxo Welcome, North Carolina 1997.
68. Halkin, H. Advers effects of the fluoroquinolones. Rev Infect Dis 1988; 10 (Suppl. 1): S258-S261.