Ketolides: The future of the macrolides?

Current Opinion in Pharmacology

Volumn 2, Issue 5, 2002, Pages 493-500

  Nilius, Angela M ^a   Ma, Zhenkun ^b  

^a ABBOTT LABORATORIES   (United States)

^b Cumbre Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMOXICILLIN; AMOXICILLIN PLUS CLAVULANIC ACID; ANTIBIOTIC AGENT; AZITHROMYCIN; BETA LACTAM; CEFUROXIME AXETIL; CETHROMYCIN; CLARITHROMYCIN; CLINDAMYCIN; ERYTHROMYCIN; ERYTHROMYCIN DERIVATIVE; HMR 3004; JOSAMYCIN; KETOLIDE; LINCOSAMIDE; MACROLIDE; METHYLTRANSFERASE; MIKAMYCIN B; PENICILLIN G; PIKROMYCIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; RNA 23S; ROXITHROMYCIN; TELITHROMYCIN; TROVAFLOXACIN; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; DRUG DERIVATIVE; ERMGT PROTEIN, LACTOBACILLUS REUTERI;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; CLINICAL TRIAL; COMMUNICABLE DISEASE; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; HUMAN; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PATHOGENESIS; PREVALENCE; PRIORITY JOURNAL; RESPIRATORY TRACT INFECTION; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION; BACTERIAL INFECTION; BACTERIUM; CHEMISTRY; DRUG EFFECT; GENETICS; METABOLISM; MICROBIOLOGY; RIBOSOME;

ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; BACTERIAL PROTEINS; DRUG RESISTANCE, MICROBIAL; ERYTHROMYCIN; HUMANS; KETOLIDES; MACROLIDES; METHYLTRANSFERASES; RIBOSOMES;

EID: 0036782870     PISSN: 14714892     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1471-4892(02)00198-4     Document Type: Review

References (59)

1. Doern GV, Heilmann KP, Huynh HK, Rhomberg PR, Coffman SL, Brueggemann AB: Antimicrobial resistance among clinical isolates of Streptococcus pneumoniae in the United States during 1999-2000, including a comparison of resistance rates since 1994-1995. Antimicrob Agents Chemother 2001, 45:1721-1729.
2. Hoban DJ, Doern GV, Fluit AC, Roussel-Delvallez M, Jones RN: Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999. Clin Infect Dis 2001, 32:S81-S93.
3. Doern GV, Brueggemann AB, Pierce G, Hogan T, Holley HP Jr, Rauch AM: Prevalence of antimicrobial resistance among 723 outpatient clinical isolates of Moraxella catarrhalis in the United States in 1994 and 1995: results of a 30 center national surveillance study. Antimicrob Agents Chemother 1996, 40:2884-2886.
4. Doern GV, Brueggemann AB, Pierce G, Holley HP Jr, Rauch AM: Antibiotic resistance among clinical isolates of Haemophilus influenzae in the United States in 1994 to 1995 and detection of β-lactamase positive strains resistant to amoxicillin-clavulanate: results of a 30 center national surveillance study. Antimicrob Agents Chemother 1996, 41:292-297
5. Almer LS, Shortridge VD, Nilius AM, Soni NB, Beyer JM, Stone GG, Flamm RK: Antimicrobial susceptibility and molecular characterization of community-acquired methicillin-resistant Staphylococcus aureus. Diag Microbiol Infect Dis 2002, in press.
6. American Thoracic Society: Guidelines for the initial management of adults with community acquired pneumonia: diagnosis, assessment of severity; and initial antimicrobial therapy. Am Rev Respir Dis 1993, 148:1418-1426.
7. Bartlett JG, Dowell SF, Mandel LA, File TM Jr, Musher DM, Fine MJ: Practice guidelines for the management of community-acquired pneumonia in adults. Clin Infect Dis 2000, 31:347-382.
8. Ban N, Nissen P, Hansen J, Moore PB, Steitz TA: The complete atomic structure of the large ribosomal subunit at 2.4 Å resolution. Science 2000, 289:905-920.
9. Nissen P, Hansen J, Ban N, Moore PB, Steitz TA: The structural basis of ribosome activity in peptide bond synthesis. Science 2000, 289:920-930.
10. Harms J, Schluenzen F, Zarivach R, Bashan A, Gat S, Agmon I, Bartels H, Fransceschi F, Yonath A: High resolution structure of the large ribosomal subunit from a mesophilic eubacterium. Cell 2001, 107:679-688.
11. Schlünzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Fransceschi F: Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 2001, 413:814-821.
12. Leclercq R, Courvalin P: Bacterial resistance to macrolide, lincosamide, and streptogramin antibiotics by target modification. Antimicrob Agents Chemother 1991, 35:1267-1272.
13. Weisblum B: Macrolide resistance. Drug Resist Update 1998, 1:29-41.
14. Roberts MC, Sutcliffe J, Courvalin P, Jensen LB, Rood J, Seppala H: Nomenclature for macrolide and macrolide-lincosamide-streptogramin B resistance determinants. Antimicrob Agents Chemother 1999, 43:2823-2830.
15. Johnston NJ, de Azavedo JC, Kellner JD, Low DE: Prevalence and characterization of the mechanisms of macrolide, lincosamide, and streptogramin resistance in isolates of Streptococcus pneumoniae. Antimicrob Agents Chemother 1998, 42:2425-2426.
16. Baquero F, Garcia-Rodriguez JA, Garcia de Lomas J, Aguilar L and the Spanish Surveillance Group for Respiratory Pathogens: Antimicrobial resistance of 1,113 Streptococcus pneumoniae isolates from patients with respiratory tract infections in Spain: results of a 1-year (1996-1997) multicenter surveillance study. Antimicrob Agents Chemother 1999, 43:357-359.
17. de Azavedo JC, Yeung RH, Bast DJ, Duncan CL, Borgia SB, Low DE: Prevalence and mechanisms of macrolide resistance in isolates of group A streptococci from Ontario, Canada. Antimicrob Agents Chemother 1999, 43:2144-2147.
18. Lina G, Quaglia, A, Reverdy M-E, Leclercq R, Vandenesch F, Etienne J: Distribution of genes encoding resistance to macrolide, lincosamide, and streptogramin resistance among staphylococci. Antimicrob Agents Chemother 1999, 43:1062-1066.
19. Shortridge VD, Doern GV, Brueggemann AB, Beyer JB, 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, 29:1186-1188.
20. Tait-Kamradt A, Davies T, Appelbaum PC, Depardieu F, Courvalin P, Petitpas J, Wondrak L, Walker A, Jacobs MR, Sutcliffe J: Two new mechanisms of macrolide resistance in clinical strains of Streptococcus pneumoniae from eastern Europe and North America. Antimicrob Agents Chemother 2000, 44:3395-3401.
21. Pihlajamäki M, Kataja J, Seppälä H, Elliot J, Leinonen M, Huovinen P, Jalava J: Ribosomal mutations in Streptococcus pneumoniae clinical isolates. Antimicrob Agents Chemother 2002, 46:654-658.
22. Shortridge VD, Zhong P, Cao Z, Beyer JM, Almer LS, Ramer NC, Doktor SZ, Flamm RK: Comparison of in vitro activities of ABT-773 and telithromycin against macrolide-susceptible and -resistant streptococci and staphylococci. Antimicrob Agents Chemother 2002, 46:783-786.
23. Clancy J, Petitpas J, Dib-Hajj F, Yuan W, Cronan M, Kamath AV, Bergeron J, Retsema JA: Molecular cloning and functional analysis of a novel macrolide-resistance determinant, mefA, from Streptococcus pyogenes. Mol Microbiol 1996, 22:867-879.
24. Tait-Kamradt A, Clancy J, Cronan M, Dib-Hajj F, Wondrack L, Yuan W, Sutcliffe J: mefE is necessary for the erythromycin-resistant M phenotype in Streptococcus pneumoniae. Antimicrob Agents Chemother 1997, 41:2251-2255.
25. Goldman R, Capobianco J: Role of an energy-dependent efflux pump in plasmid pNE24-mediated resistance to 14- and 15-membered macrolides in Staphylococcus epidermidis. Antimicrob Agents Chemother 1990, 34:1973-1980.
26. Singh K, Malathum K, Murray BE: Disruption of an Enterococcus faecium species-specific gene, a homologue of acquired resistance genes of staphylococci, is associated with an increased in macrolide susceptibility. Antimicrob Agents Chemother 2001, 45:263-266.
27. Brockmann H, Hencke, W: Picromycin, a new antibiotic from actinomycetes. Naturwissenschaften 1950, 37:138-139.
28. Allen NE: Macrolide resistance in Staphylococcus aureus: inducers of macrolide resistance. Antimicrob Agents Chemother 1977, 11:669-674.
29. Pestka S, Vince R, LeMahieu R, Weiss F, Fern L, Unowsky J: Induction of erythromycin resistance in Staphylococcus aureus by erythromycin derivatives. Antimicrob Agents Chemother 1976, 9:128-130.
30. Agouridas C, Benedetti Y, Denis A, Le Martret O, Chantot J-F: Ketolide: a new distinct class of macrolide antibacterials. synthesis and structure characterization of RU-004. Abstract 157 of the 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1995 September 17-20, San Francisco.
31. Agouridas C, Denis A, Auger J-M, Benedetti Y, Bonnefoy A, Bretin F, Chantot J-F, Dussarat A, Fromentin C, D'Ambrieres SG et al.: Synthesis and antibacterial activity of ketolides (6-O-methyl-3-oxoerythromycin derivatives): a new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens. J Med Chem 1998, 41:4080-4100.
32. Denis A, Agouridas C, Auger J-M, Benedetti Y, Bonnefoy A, Bretin F, Chantot J-F, Dussarat A, Fromentin C, D'Ambrieres SG 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, 9:3075-3080.
33. Asaka T, Kashimura M, Misawa Y, Ono T, Suzuki K, Yoshida H, Yoshida T, Akashi T, Yokoo C, Nagate T, Morimoto S: New macrolide antibiotics, TE-802: synthesis and biological properties. Abstract F176 of the 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1995 September 17-20, San Francisco.
34. Phan LT, Or YS, Chen Y, Chu DTW, Ewing P, Nilius AM, Bui MH, Raney PM, Hensey-Rudloff D, Mitten M et al.: 2-Substituted tricyclic ketolides: new antibacterial macrolides-synthesis and biological activity. Abstract F127 of the 38th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1998 September 24-27, San Diego.
35. Ma Z, Clark RF, Wang S, Nilius AM, Flamm RK, Or YS: Design, synthesis and characterization of ABT-773: a novel ketolide highly active against multidrug-resistant pathogens. Abstract F2133 of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1999 September 26-29, San Francisco.
36. Or YS, Clark RF, Wang S, Chu DTW, Nilius AM, Flamm RK, Mitten M, Ewing P, Alder J, Ma Z: Design, synthesis, and antimicrobial activity of 6-O-substituted ketolides active against resistant respiratory tract pathogens. J Med Chem 2000, 43:1045-1049.
37. Ma Z, Clark RF, Brazzale A, Wang S, Rupp MJ, Li L, Griesgraber G, Zhang S, Yong H, Phan LT et al.: Novel erythromycin derivatives with aryl groups tethered to the C-6 position are potent protein synthesis inhibitors and active against multidrug-resistant respiratory pathogens. J Med Chem 2001, 44:4137-4156.
38. Denis A, Agouridas C, Bonnefoy A, Bretin F, Fromentin C, Bonnett A: Synthesis and antibacterial activity of 2-halogeno, 2-methyl, and 2,3 enol-ether ketolides using β-keto-ester chemistry. Abstract F2152 of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1999 September 26-29, San Francisco.
39. Denis A, Bretin F, Fromentin C, Bonnet A, Piltan G, Bonnefoy A, Agouridas C: Beta-keto-ester chemistry and ketolides. Synthesis and antibacterial activity of 2-halogeno, 2-methyl and 2,3 enol-ether ketolides. Bioorg Med Chem Lett 2000, 10:2019-2022.
40. Bush K, Abbanat D, Ashley G, Baum E, Carney J, Fardis M, Foleno B, Grant E, Henninger T, Hilliard et al.: In vitro and in vivo SAR of ketolides derived from R13-modified erythromycin A and picromycin core structures. Abstract F1821 of the 40th Interscience Conference on Antimicrobial Agents and Chemotherapy, 2000 September 17-20, Toronto.
41. B resistance. J Antimicrob Chemother 1997, 40:85-90.
42. Xioang L, Shah S, Mauvais P, Mankin AS: A ketolide resistance mutation in domain II of 23S rRNA reveals the proximity of hairpin 35 to the peptidyl transferase centre. Mol Microbiol 1999, 31:633-639.
43. Garza-Ramos G, Xiong L, Zhong P, Mankin A: Binding site of macrolide antibiotics on the ribosome: new resistance mutation identifies a specific interaction of ketolides with rRNA. J Bacteriol 2001, 183:6898-6907.
44. Capobianco JO, Cao Z, Shortridge VD, Ma Z, Flamm RK, Zhong P: Studies of the novel ketolide ABT-773: transport, binding to ribosomes, and inhibition of protein synthesis in Streptococcus pneumoniae. Antimicrob Agents Chemother 2000, 44:1562-1567.
45. Zhong P, Hammond R, Cao Z, Chen Y, Shortridge D, Nilius A, Flamm RK, Or YS: Molecular basis of ABT-773 activity against erm-containing macrolide resistant S. pneumoniae. Abstract 2134 of the 39th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1999 September 26-29, San Francisco.
46. Almer L, Nilius A, Beyer J, Meulbroek J, Mitten M, Flamm R: The in vitro and in vivo activity of ABT-773 against fluoroquinolone resistant S. pneumoniae. Abstract 2136 of the 40th Interscience Conference on Antimicrobial Agents and Chemotherapy, 2000 September 17-20, Toronto, Canada.
47. Nilius AM, Bui MH, Almer L, Hensey-Rudloff D, Beyer J, Ma Z, Or YS, Flamm RK: Comparative in vitro activity of ABT-773, a novel antibacterial ketolide. Antimicrob Agents Chemother 2001, 45:2163-2168.
48. + Streptococcus pneumoniae. Abstract 3.16 of the 6th International Conference on the Macrolides, Azalides, Streptogramins, Ketolides, and Oxazolidinones, 2002 January 23-25, Bologna, Italy.
49. Andrews JM, Weller TMA, Ashby JP, Walker RM, Wise R: The in vitro activity of ABT-773, a new ketolide antibacterial agent. J Antimicrob Chemother 2000, 46:1017-1022.
50. Stringl S, Roblin PM, Reznik T, Hammerschlag MR: The in vitro activity of ABT-773, a new ketolide antibiotic, against C. pneumoniae. Antimicrob Agents Chemother 2000, 44:1112-1113.
51. Davies TA, Ednie LM, Hoellman DM, Pankuch GA, Jacobs MR, Appelbaum PC: Antipneumococcal activity of ABT-773 compared to those of 10 other agents. Antimicrob Agents Chemother 2000, 44:1894-1899.
52. Credito KL, Lin G, Pankuch GA, Bajaksouzian S, Jacobs MR, Appelbaum PC: Susceptibilities of Haemophilus influenzae and Moraxella catarrhalis to ABT-773 compared to their susceptibilities to 11 other agents. Antimicrob Agents Chemother 2001, 45:67-92.
53. Boswell FJ, Andrews JM, Wise R: Pharmacodynamic properties of HMR 3647, a novel ketolide, on respiratory tract pathogens, enterococci, and Bacteroides fragilis demonstrated by studies of time-kill kinetics and postantibiotic effect. J Antimicrob Chemother 1998, 41:149-153.
54. Mitten MJ, Meulbroek J, Nukkala M, Paige L, Jarvis K, Oleksijew A, Tovcimak A, Hernandez L, Alder JD, Ewing P et al.: Efficacies of ABT-773, a new ketolide, against experimental bacterial infections. Antimicrob Agents Chemother 2001, 45:2585-2593.
55. Barman Balfour JA, Figgett DP: Telithromycin. Drugs 2001, 61:815-829.
56. Hagberg L, Pullman J, Rangaraju M, Leroy B: Telithromycin is effective in the treatment of pneumococcal bacteremia associated with community-acquired pneumonia. Abstract 861 of the 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, 2001 December 16-19, Chicago.
57. Zervos M, Aubier M, Rangaraju M, Leroy B: Five day telithromycin, a new ketolide, is as effective as standard 10 day comparators in the treatment of acute exacerbation of chronic bronchitis. Abstract 916 of the 41st Interscience Conference on Antimicrobial Agents and Chemotherapy, 2001 December 16-19, Chicago.
58. Aubier M, Baz M, Rangaraju M, Leroy B: Telithromycin is highly effective in the treatment of community-acquired respiratory tract infections caused by Streptococcus pneumoniae with reduced penicillin and/or macrolide susceptibility. Abstract 860 of the 41st Interscience Conference of Antimicrobial Agents and Chemotherapy, 2001 December 16-19, Chicago.
59. Anon.: Aventis begins to roll out Ketek. Scrip 2002, 2719:23.