Macrolides: Structures and microbial targets

International Journal of Antimicrobial Agents

Volumn 18, Issue SUPPL.1, 2001, Pages 3-

  Retsema, J ^a   Fu, Wenchi ^a,b  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b NONE   (United States)

Author keywords

Azithromycin; Erythromycin; Ketolides; Macrolides; Mode of action; Protein synthesis; Structure activity relationships

Indexed keywords

ANTIINFECTIVE AGENT; MACROLIDE;

ANTIBIOTIC RESISTANCE; BACTERIAL INFECTION; BACTERIUM; CHEMISTRY; CLASSIFICATION; DRUG EFFECT; GENETICS; GROWTH, DEVELOPMENT AND AGING; HUMAN; IC 50; METABOLISM; MICROBIOLOGY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW;

ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; DRUG RESISTANCE, BACTERIAL; HUMANS; INHIBITORY CONCENTRATION 50; MACROLIDES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0002226377     PISSN: 09248579     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0924-8579(01)00401-0     Document Type: Article

References (50)

1. Bryskier A. New research in macrolides and ketolides since, 1997. Exp Opin Invest Drugs 1999;8:1171-94.
2. Peters DH, Friedel HA, McTavish D. Azithromycin, A review of its antimicrobial activity, pharmacokinetic properties and clinical efficacy. Drugs 1992;44:750-99.
3. McFarland JW, Berger CM, Froshauer SA, et al. Quantitative structure-activity relationships among macrolide antibacterial agents: in vitro and in vivo potency against Pasteurella multocida. J Med Chem 1997;25:1340-6.
4. Vazquez D. Inhibitors of Protein Synthesis. Berlin: Springer, 1979:1-307.
5. 14C-erythromycin to Escherichia coli ribosomes. Antimicrob Agents Chemother 1974;6:479-88.
6. Dunne MW. Azalides: basic and clinical research. In: Zinner SH, Young LS, Acar FJ, Neu HC, editors. Expanding Indications for the New Macrolides, Azalides and Streptogramins. New York: Marcel Dekker, 1997:67-73.
7. Bright GM, Nagel AA, Bordner J, et al. Synthesis, in vitro and in vivo activity of novel 9-dioxo-9a-homoerythromycin A derivative; a new class of macrolide antibiotics, the azalides. J Antibiot 1988;XLI:1029-47.
8. Finch RG. Overview of the clinical use of macrolides and streptogramins. In: Zinner SH, Young LS, Acar FJ, Neu HC, editors. Expanding Indications for the New Macrolides, Azalides and Streptogramins. New York: Marcel Dekker, 1997.
9. Fiese EF, Steffen SH. Comparison of the acid stability of azithromycin and erythromycin A. J Antimicrob Chemother (Suppl. A) 1990;25:39-47.
10. Denis A, Agouridas C, Auger JM, et al. Synthesis and antibacterial activity of HMR 3647 a new ketolide highly potent against erythromycin-resistant and -susceptible pathogens. Bioorg Med Chem Lett 1999;9:3075-80.
11. Chu DT. Recent developments in macrolides and ketolides. Curr Opin Microbiol 1999;2:467-74.
12. Cocito C, Di Giambattista M, Nyssen E, Vannuffel P. Inhibition of protein synthesis by streptogramins and related antibiotics. J Antimicrob Chemother (Suppl. A) 1997;39:7-13.
13. Vannuffel P, Cocito C. Mechanism of action of streptogramins and macrolides. Drugs 1996:51(Suppl. 1):20-30.
14. Hansen LH, Mauvais P, Douthwaite S. The macrolide-ketolide binding site is formed by structures in domains II and V of 23S ribosomal rRNA. Mol Microbiol 1999;31:623-31.
15. Klita S, Szafranski P. Comparison of the mechanism of action of cyclic 11,12-erythromycin A carbonate and erythromycin A. Acta Biochim Pol 1980;27:213-20.
16. Fish SA, Cundliffe E. Structure-activity studies of tylosin-related macrolides. J Antibiot (Tokyo) 1996;49:1044-8.
17. English AR, Retsema JA, Girard AE, Schelkly W, Lynch JE. Evaluation of three 4″-deoxy-4″-sulfonamido-oleandomycin derivatives with erythromycin-like antibacterial potency. Antimicrob Agents Chemother 1984;25:118-22.
18. Retsema J, Girard A, Schelkly W, et al. Spectrum and mode of action of azithromycin (CP-62993), a new 15-membered-ring macrolide with improved potency against Gram-negative organisms. Antimicrob Agents Chemother 1987;31:1939-47.
19. Clancy J, Petitpas J, Dib-Hajj F, et al. Molecular cloning and functional analysis of a novel macrolide-resistance determinant, mefA, from Streptococcus pyogenes. Mol Microbiol 1996;22:867-79.
20. Bann N, Nissen P, Hansen J, et al. Placement of protein and RNA structures into a 5 Å-resolution map of the 50S ribosomal unit. Nature 1999;400:841-7.
21. Sutcliffe J, Tait-Kamradt A, Wondrack L. Streptococcus pneumoniae and Streptococcus pyogenes resistant to macrolides but sensitive to clindamycin: a common resistance pattern mediated by an efflux system. Antimicrob Agents Chemother 1996;40:1817-24.
22. Tait-Kamradt A, Clancy J, Cronan M, et al. mefE is necessary for the erythromycin-resistant M phenotype in Streptococcus pneumoniae. Antimicrob Agents Chemother 1997;41:2251-5.
23. Clancy J, Petitpas J, Dib-Hajj F, et al. Molecular cloning and functional analysis of a novel macrolide-resistance determinant, mefA, from Streptococcus pyogens. Mol Microbiol 1996;22:867-79.
24. Shortridge VD, Flamm RK, Rames N, Beyer J, Tanaka SK Novel mechanism of macrolide resistance in Streptococcus pneumoniae. Diagn Microb Infect Dis 1996;26:73-8.
25. Gay K, Baughman W, Miller Y, et al. The emergence of Streptococcus pneumoniae resistant to macrolide antimicrobial agents: a 6-year population-based assessment. J Infect Dis 2000;182:1417-24.
26. Shortridge D, Doern G, Bayer J, Brueggemann A, Flamm RK. Prevalence of macrolide resistance mechanisms in Streptococcus pneumoniae isolates from a multicenter antibiotic resistance surveillance study conducted in the United States in 1994-1995. Clin Infect Dis 1999;29:1186-8.
27. Gasc AM, Kauc L, Barraille P, Sicard M, Goodgal S. Gene localization, size and physical map of the chromosome of Streptococcus pneumoniae. J Bacteriol 1991;173:7361-7.
28. Sander P, Meier A, Bottger EC. Ribosomal drug resistance in mycobacteria. Res Microbiol 1996;147:59-67.
29. Deschmaeker P, Chapelle S, Lammens C, et al. Macrolide resistance and erythromycin resistance determinants among Belgian Streptococcus pyogenes and Streptococcus pneumoniae isolates. J Antimicrob Chemother 2000;45:167-73.
30. Oster P, Zanchi A, Cresti S, et al. Patterns of macrolide resistance determinants among community-acquired Streptococcus pneumoniae isolates over a 5-year period of decreased macrolide susceptibility states. Antimicrob Agents Chemother 1999;43:2510-2.
31. Nishijima T, Saito Y, Aoki A, Toriya M, Toyonaga Y, Fujii R. Distribution of mefE and ermB genes in macrolide-resistant strains of Streptococcus pneumoniae and their variable susceptibility to various antibiotics. J Antimicrob Chemother 1999;43:637-43.
32. Giovanetti E, Montanari MP, Mingoia M, Varaldo PE. Phenotypes and genotypes of erythromcyin-resistant Streptococcus pyogenes strains in Italy and heterogeneity of inducibly resistant strains. Antimicrob Agents Chemother 1999;43:1935-40.
33. Alos JI, Aracil B, Oteo J, Torres C, Gomez-Graces JL. High prevalence of erythromycin-resistant, clindamycin/miocamycin-susceptible (M phenotype) Streptococcus pyogenes: result of a Spanish multicentre study in 1998. J Antimicrob Chemother 2000;45:605-9.
34. Lina G, Ouagilia A, Reverdy ME, Leclercq R, Vandenesch F, Etienne J. Distribution of genes encoding resistance to macrolides, lincosamides and streptogramins among staphylococci. Antimicrob Infect Dis 1996;26:73-8.
35. Zarantonelli L, Borthagaray G, Lee EH, Shafer W. Decreased azithromycin susceptibility of Neisseria gonorrhoeae due to mtrR mutations. Antimicrob Agents Chemother 1999;43:2468-72.
36. Versalovic J, Shortridge D, Kibler K, et al. Mutations in 23S rRNA are associated with clarithromycin resistance in Helicobacter pylori. Antimicrob Agents Chemother 1996;40:477-80.
37. Tait-Kamradt A, Davies T, Cronan M, Jacobs MR, Appelbaum PC, Sutcliffe J. Mutations in 23S rRNA and ribosomal protein L4 account for resistance in pneumoccal strains selected in vitro by macrolide passage. Antimicrob Agents Chemother 2000;44:2118-25.
38. Davies TA, Bonifacio EO, Jacobs MR, Appelbaum PC. In vitro development of resistance to telithromycin (HMR3647), four macrolides, clindamycin and pristinamycin on Streptococcus pneumoniae. Antimicrob Agents Chemother 2000;44:414-7.
39. Rosato A, Vicarini H, Bonnefoy A, Chantot JF, Leclercq R. A new ketolide, HMR 3004, active against streptococci inducibly resistant to erythromycin. Antimicrob Agents Chemother 1998;42:1392-6.
40. Zhong P, Cao Z, Hammond R, et al. Induction of ribosome methylation in MLS-resistant Streptococcus pneumoniae by macrolides and ketolides. Microb Drug Resist 1999;5:183-8.
41. Bemer-Melchior P, Juvin ME, Tassin S, et al. In vitro activity of the new ketolide telithromycin compared with those of macrolides against Streptococcus pyogenes: influences of resistance mechanisms and methodological factors. Antimicrob Agents Chemother 2000;44:2999-3002.
42. Carbon C, Poole MD. The role of newer macrolides in the treatment of community-acquired respiratory tract infection. A review of experimental and clinical data. J Chemother 1999;11:107-18.
43. Vergis EN, Yu VL. Macrolides are ideal for empiric therapy of community-acquired pneumonia in the immunocompetent host. Semin Respir Infect 1997;12:322-8.
44. Honeybourne D. Community-acquired pneumonia in ambulatory patients: relative importance of atypical pathogens. Int J Antimicrob Agents 2001.
45. Mulazimoglu L. Treatment of community-acquired pneumonia in hospitalized patients. Int J Antimicrob Agents 2000.
46. Akalin HE. The place of antibiotic therapy in the management of chronic acute exacerbations of chronic bronchitis. Int J Antimicrob Agents 2001;18(Suppl. 1):49-55.
47. Dalhoff K. Worldwide guidelines for respiratory tract infections: community-acquired pneumonia. Int J Antimicrob Agents 2001;18(Suppl. 1)39-44.
48. Yanagihara K, Kohno S, Matsumima T. Japanese guidelines for the management of community-acquired pneumonia. Int J Antimicrob Agents 2001;18(Suppl. 1):45-8.
49. Williams JD. Non-antimicrobial activities of macrolides. Int J Antimicrob Agents 2001;1(Suppl. 1):89-91.
50. Pechère J-C. New perspectives on macrolide antibiotics. Int J Antimicrob Agents 2001;18(Suppl. 1).