Significant breakthroughs in search for anti-infectious agents derived from erythromycin A

Current Medicinal Chemistry

Volumn 18, Issue 13, 2011, Pages 1993-2015

  Ma, Xiaodong ^a   Ma, Shutao ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Anti infectious agents; Bacterial resistance; Breakthroughs; Erythromycin A; Macrolide antibiotics; Structural modifications

Indexed keywords

ANTIINFECTIVE AGENT; AZITHROMYCIN; CETHROMYCIN; CLARITHROMYCIN; CP 544372; DIRITHROMYCIN; ERYTHROMYCIN; FLURITHROMYCIN; MODITHROMYCIN; PIKROMYCIN; ROXITHROMYCIN; TEA 0777; TEA 0929; TELITHROMYCIN; UNCLASSIFIED DRUG;

ARTICLE; COMMUNITY ACQUIRED PNEUMONIA; DOSE RESPONSE; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG METABOLISM; DRUG POTENCY; DRUG SAFETY; DRUG SYNTHESIS; DRUG TOLERABILITY; GASTROINTESTINAL SYMPTOM; HUMAN; LOBAR PNEUMONIA; LOWER RESPIRATORY TRACT INFECTION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SINGLE DRUG DOSE; UPPER RESPIRATORY TRACT INFECTION;

ANIMALS; ANTI-INFECTIVE AGENTS; BACTERIA; DRUG DISCOVERY; DRUG RESISTANCE, BACTERIAL; ERYTHROMYCIN; HUMANS;

EID: 79957939023     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986711795590075     Document Type: Article

References (110)

1. Wu, Y.J.; Su, W.G. Recent developments on ketolides and macrolides. Curr. Med. Chem., 2001, 8, 1727-1758.
2. Brisson-Noel, A.; Trieu-Cuot, P.; Courvalin, P. Mechanism of action of spiramycin and other macrolides. J. Antimicrob. Chemother., 1988, 22 Suppl B, 13-23.
3. Washington, J.A.; Wilson, W.R. Erythromycin: a microbial and clinical perspective after 30 years of clinical use (1). Mayo. Clin. Proc., 1985, 60, 189-203. (Pubitemid 15139126)
4. Washington, J.A.; Wilson, W.R. Erythromycin: a microbial and clinical perspective after 30 years of clinical use (2). Mayo. Clin. Proc., 1985, 60, 271-278. (Pubitemid 15091416)
5. Bryskier, A. Novelties in the field of macrolides. Expert Opin. Investig. Drugs, 1997, 6, 1697-1709. (Pubitemid 27488034)
6. Bryskier, A. New research in macrolides and ketolides since 1997. Expert Opin. Investig. Drugs, 1999, 8, 1171-1194. (Pubitemid 29410575)
7. Chu, D.T. Recent progress in novel macrolides, quinolones, and 2-pyridones to overcome bacterial resistance. Med. Res. Rev., 1999, 19, 497-520. (Pubitemid 29521754)
8. Morimoto, S.; Takahashi, Y.; Watanabe, Y.; Omura, S. Chemical modification of erythromycins. I. Synthesis and antibacterial activity of 6-Omethylerythromycins A. J. Antibiot., 1984, 37, 187-189. (Pubitemid 14195348)
9. Morimoto, S.; Misawa, Y.; Adachi, T.; Nagate, T.; Watanabe, Y.; Omura, S. Chemical modification of erythromycins. II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A. J. Antibiot., 1990, 43, 286-294. (Pubitemid 20106392)
10. Watanabe, Y.; Morimoto, S.; Adachi, T.; Kashimura, M.; Asaka, T. Chemical modification of erythromycins. IX. Selective methylation at the C6 hydroxyl group of erythromycin A oxime derivatives and preparation of clarithromycin. J. Antibiot., 1993, 46, 647-660. (Pubitemid 23173210)
11. Watanabe, Y.; Adachi, T.; Asaka, T.; Kashimura, M.; Matsunaga, T.; Morimoto, S. Chemical modification of erythromycins. XII. A facile synthesis of clarithromycin (6-O-methylerythromycin A) via 2'-silylethers of erythromycin A derivatives. J. Antibiot., 1993, 46, 1163-1167. (Pubitemid 23254160)
12. Djokic, S.; Kobrehel, G.; Lazarevski, G. Erythromycin series. XII. Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11- azaerythromycin A: synthesis and structure-activity relationship of its acyl derivatives. J. Antibiot., 1987, 40, 1006-1015. (Pubitemid 17103088)
13. Bright, G.M.; Nagel, A.A.; Bordner, J.; Desai, K.A.; Dibrino, J.N.; Nowakowska, J.; Vincent, L.; Watrous, R.M.; Sciavolino, F.C.; English, A.R. Synthesis, in vitro and in vivo activity of novel 9-deoxo-9a-AZA- 9ahomoerythromycin A derivatives; a new class of macrolide antibiotics, the azalides. J. Antibiot., 1988, 41, 1029-1047.
14. Cohen, M.L. Epidemiology of drug resistance: implications for a postantimicrobial era. Science, 1992, 257, 1050-1055.
15. Neu, H.C. The crisis in antibiotic resistance. Science, 1992, 257, 1064-1073.
16. Mylotte, J.M.; Karuza, J.; Bentley, D.W. Methicillin-resistant Staphylococcus aureus: a questionnaire survey of 75 long-term care facilities in western New York. Infect. Control Hosp. Epidemiol., 1992, 13, 711-718.
17. Baquero, F.; Martinez-Beltran, J.; Loza, E. A review of antibiotic resistance patterns of Streptococcus pneumoniae in Europe. J. Antimicrob. Chemother., 1991, 28 Suppl C, 31-38.
18. Lonks, J.R.; Medeiros, A.A. High rate of erythromycin and clarithromycin resistance among Streptococcus pneumoniae isolates from blood cultures from Providence, R.I. Antimicrob. Agents Chemother., 1993, 37, 1742-1745. (Pubitemid 23265523)
19. Yoshida, R.; Kaku, M.; Kohno, S.; Ishida, K.; Mizukane, R.; Takemura, H.; Tanaka, H.; Usui, T.; Tomono, K.; Koga, H. Trends in antimicrobial resistance of Streptococcus pneumoniae in Japan. Antimicrob. Agents Chemother., 1995, 39, 1196-1198.
20. Denis, A.; Agouridas, C.; Auger, J.M.; Benedetti, Y.; Bonnefoy, A.; Bretin, F.; Chantot, J.F.; Dussarat, A.; Fromentin, C.; D'Ambrieres, S.G.; Lachaud, S.; Laurin, P.; Le Martret, O.; Loyau, V.; Tessot, N.; Pejac, J.M.; Perron, S. 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. (Pubitemid 29515385)
21. Or, Y.S.; Clark, R.F.; Wang, S.; Chu, D.T.; Nilius, A.M.; Flamm, R.K.; 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. (Pubitemid 30173730)
22. Ma, Z.; Clark, R.F.; Brazzale, A.; Wang, S.; Rupp, M.J.; Li, L.; Griesgraber, G.; Zhang, S.; Yong, H.; Phan, L.T.; Nemoto, P.A.; Chu, D.T.; Plattner, J.J.; Zhang, X.; Zhong, P.; Cao, Z.; Nilius, A.M.; Shortridge, V.D.; Flamm, R.; Mitten, M.; Meulbroek, J.; Ewing, P.; Alder, J.; Or, Y.S. 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. (Pubitemid 33095321)
23. Cethromycin: A-195773, A-195773-0, A-1957730, Abbott-195773, ABT 773. Drugs R. D., 2007, 8, 95-102
24. Revill, P.; Bolos, J.; Serradelli, J. EDP-420: ketolide antibiotic. Drugs Future, 2006, 31, 479-483. (Pubitemid 44406094)
25. Ma, C.; Ma, S. Various novel erythromycin derivatives obtained by different modifications: recent advance in macrolide antibiotics. Mini. Rev. Med. Chem., 2010, 10, 272-286.
26. Tanikawa, T.; Asaka, T.; Kashimura, M.; Misawa, Y.; Suzuki, K.; Sato, M.; Kameo, K.; Morimoto, S.; Nishida, A. Synthesis and antibacterial activity of acylides (3-O-acyl-erythromycin derivatives): a novel class of macrolide antibiotics. J. Med. Chem., 2001, 44, 4027-4030. (Pubitemid 33095310)
27. Itoh, Z.; Nakaya, M.; Suzuki, T.; Arai, H.; Wakabayashi, K. Erythromycin mimics exogenous motilin in gastrointestinal contractile activity in the dog. Am. J. Physiol., 1984, 247, G688-694. (Pubitemid 15155590)
28. Wu, Y.J. Highlights of semi-synthetic developments from erythromycin A. Curr. Pharm. Des., 2000, 6, 181-223.
29. Kurath, P.; Jones, P.H.; Egan, R.S.; Perun, T.J. Acid degradation of erythromycin A and erythromycin B. Experientia, 1971, 27, 362.
30. Fernandes, P.B.; Bailer, R.; Swanson, R.; Hanson, C.W.; McDonald, E.; Ramer, N.; Hardy, D.; Shipkowitz, N.; Bower, R.R.; Gade, E. In vitro and in vivo evaluation of A-56268 (TE-031), a new macrolide. Antimicrob. Agents Chemother., 1986, 30, 865-873. (Pubitemid 17209139)
31. Hardy, D.J.; Hensey, D.M.; Beyer, J.M.; Vojtko, C.; McDonald, E.J.; Fernandes, P.B. Comparative in vitro activities of new 14-, 15-, and 16- membered macrolides. Antimicrob. Agents Chemother., 1988, 32, 1710-1719. (Pubitemid 18267620)
32. Chin, N.X.; Neu, N.M.; Labthavikul, P.; Saha, G.; Neu, H.C. Activity of A- 56268 compared with that of erythromycin and other oral agents against aerobic and anaerobic bacteria. Antimicrob. Agents Chemother., 1987, 31, 463-466. (Pubitemid 17027142)
33. Jansson, L.; Kalin, M. Comparative in vitro activity of A-56268 against respiratory tract pathogens. Eur. J. Clin. Microbiol., 1987, 6, 494-496. (Pubitemid 18074772)
34. Floyd-Reising, S.; Hindler, J.A.; Young, L.S. In vitro activity of A-56268 (TE-031), a new macrolide antibiotic, compared with that of erythromycin and other antimicrobial agents. Antimicrob. Agents Chemother., 1987, 31, 640-642. (Pubitemid 17054357)
35. Jones, R.N.; Barry, A.L. The antimicrobial activity of A-56268 (TE-031) and roxithromycin (RU965) against Legionella using broth microdilution method. J. Antimicrob. Chemother., 1987, 19, 841-842. (Pubitemid 17092073)
36. Liebers, D.M.; Baltch, A.L.; Smith, R.P.; Hammer, M.C.; Conroy, J.V. Susceptibility of Legionella pneumophila to eight antimicrobial agents including four macrolides under different assay conditions. J. Antimicrob. Chemother., 1989, 23, 37-41. (Pubitemid 19054100)
37. Adachi, T.; Morimoto, S.; Kondoh, H.; Nagate, T.; Watanabe, Y.; Sota, K. 14-Hydroxy-6-O-methylerythromycins A, active metabolites of 6- Omethylerythromycin A in human. J. Antibiot., 1988, 41, 966-975.
38. Chu, D.T.; Plattner, J.J.; Katz, L. New directions in antibacterial research. J. Med. Chem., 1996, 39, 3853-3874. (Pubitemid 26327422)
39. Brunet, E.; Munoz, D.M.; Parra, F.; Mantecon, S.; Juanes, O.; Rodriguez- Ubis, J.C.; Cruzado, M.C.; Asensio, R. Preparation of clarithromycin. Selective 6-O-methylation of the novel erythromycin A 9-O-(2- pyrimidyl)oxime. Tetrahedron Letters, 2007, 48, 1321-1324. (Pubitemid 46136415)
40. Mutak, S. Azalides from azithromycin to new azalide derivatives. J. Antibiot., 2007, 60, 85-122.
41. Retsema, J.; Girard, A.; Schelkly, W.; Manousos, M.; Anderson, M.; Bright, G.; Borovoy, R.; Brennan, L.; Mason, R. Spectrum and mode of action of azithromycin (CP-62,993), a new 15-membered-ring macrolide with improved potency against gram-negative organisms. Antimicrob. Agents Chemother., 1987, 31, 1939-1947. (Pubitemid 18009566)
42. Ferwerda, A.; Moll, H.A.; Hop, W.C.; Kouwenberg, J.M.; Tjon Pian Gi, C.V.; Robben, S.G.; de Groot, R. Efficacy, safety and tolerability of 3 day azithromycin versus 10 day co-amoxiclav in the treatment of children with acute lower respiratory tract infections. J. Antimicrob. Chemother., 2001, 47, 441-446. (Pubitemid 32303410)
43. Foulds, G.; Shepard, R.M.; Johnson, R.B. The pharmacokinetics of azithromycin in human serum and tissues. J. Antimicrob. Chemother., 1990, 25 Suppl A, 73-82. (Pubitemid 20043952)
44. Retsema, J.A.; Girard, A.E.; Girard, D.; Milisen, W.B. Relationship of high tissue concentrations of azithromycin to bactericidal activity and efficacy in vivo. J. Antimicrob. Chemother., 1990, 25 Suppl A, 83-89. (Pubitemid 20043953)
45. Girard, A.E.; Girard, D.; English, A.R.; Gootz, T.D.; Cimochowski, C.R.; Faiella, J.A.; Haskell, S.L.; Retsema, J.A. Pharmacokinetic and in vivo studies with azithromycin (CP-62,993), a new macrolide with an extended half-life and excellent tissue distribution. Antimicrob. Agents Chemother., 1987, 31, 1948-1954. (Pubitemid 18009567)
46. Asaka, T.; Manaka, A.; Sugiyama, H. Recent developments in macrolide antimicrobial research. Curr. Top. Med. Chem., 2003, 3, 961-989.
47. Yang, B.W.V.; Goldsmith, M.; Rizzi, J.P. A Novel Product from Beckmann Rearrangement of Erythromycin-a 9(E)Oxime. Tetrahedron Letters, 1994, 35, 3025-3028. (Pubitemid 24162663)
48. Bayod-Jasanada, M.; Carbajo, R.J.; Lopez-Ortiz, F. Synthesis of 9-deoxo-9aaza- 9a-homoerythromycin A 11,12-Hydrogen Borate and Azithromycin 11,12-Hydrogen Borate. A New Procedure to Obtain Azithromycin Dihydrate. J. Org. Chem., 1997, 62, 7479-7481. (Pubitemid 27463085)
49. Weisblum, B. Erythromycin resistance by ribosome modification. Antimicrob. Agents Chemother., 1995, 39, 577-585.
50. Leclercq, R.; Courvalin, P. Bacterial resistance to macrolide, lincosamide, and streptogramin antibiotics by target modification. Antimicrob. Agents Chemother., 1991, 35, 1267-1272.
51. Leclercq, R.; Courvalin, P. Intrinsic and unusual resistance to macrolide, lincosamide, and streptogramin antibiotics in bacteria. Antimicrob. Agents Chemother., 1991, 35, 1273-1276.
52. Weisblum, B. Inducible erythromycin resistance in bacteria. Br. Med. Bull., 1984, 40, 47-53. (Pubitemid 14219017)
53. Clancy, J.; Petitpas, J.; Dib-Hajj, F.; Yuan, W.; Cronan, M.; Kamath, A.V.; Bergeron, J.; Retsema, J.A. Molecular cloning and functional analysis of a novel macrolide-resistance determinant, mefA, from Streptococcus pyogenes. Mol. Microbiol., 1996, 22, 867-879. (Pubitemid 26411332)
54. 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. (Pubitemid 27422221)
55. Wondrack, L.; Massa, M.; Yang, B.V.; Sutcliffe, J. Clinical strain of Staphylococcus aureus inactivates and causes efflux of macrolides. Antimicrob. Agents Chemother., 1996, 40, 992-998. (Pubitemid 26117529)
56. 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, 1817-1824. (Pubitemid 26277799)
57. Pestka, S.; Vince, R.; LeMahieu, R.; Weiss, F.; Fern, L.; Unowsky, J. Induction of erythromycin resistance in Staphyloccus aureus by erythromycin derivatives. Antimicrob. Agents Chemother., 1976, 9, 128-130.
58. Allen, N.E. Macrolide resistance in Staphylococcus aureus: inducers of macrolide resistance. Antimicrob. Agents Chemother., 1977, 11, 669-674. (Pubitemid 8093326)
59. LeMahieu, R.A.; Carson, M.; Kierstead, R.W.; Fern, L.M.; Grunberg, E. Glycoside cleavage reactions on erythromycin A. Preparation of erythronolide A. J. Med. Chem., 1974, 17, 953-956.
60. Agouridas, C.; Denis, A.; Auger, J.M.; Benedetti, Y.; Bonnefoy, A.; Bretin, F.; Chantot, J.F.; Dussarat, A.; Fromentin, C.; D'Ambrieres, S.G.; Lachaud, S.; Laurin, P.; Le Martret, O.; Loyau, V.; Tessot, N. Synthesis and antibacterial activity of ketolides (6-O-methyl-3-oxoerythromycinderivatives): a new class of antibacterials highly potent against macrolideresistant and -susceptible respiratory pathogens. J. Med. Chem., 1998, 41, 4080-4100. (Pubitemid 28483484)
61. Keyes, R.F.; Carter, J.J.; Englund, E.E.; Daly, M.M.; Stone, G.G.; Nilius, A.M.; Ma, Z. Synthesis and antibacterial activity of 6-O-arylbutynyl ketolides with improved activity against some key erythromycin-resistant pathogens. J. Med. Chem., 2003, 46, 1795-1798. (Pubitemid 36532221)
62. Henninger, T.C.; Xu, X.; Abbanat, D.; Baum, E.Z.; Foleno, B.D.; Hilliard, J.J.; Bush, K.; Hlasta, D.J.; Macielag, M.J. Synthesis and antibacterial activity of C-6 carbamate ketolides, a novel series of orally active ketolide antibiotics. Bioorg. Med. Chem. Lett., 2004, 14, 4495-4499. (Pubitemid 39043972)
63. Tennakoon, M.A.; Henninger, T.C.; Abbanat, D.; Foleno, B.D.; Hilliard, J.J.; Bush, K.; Macielag, M.J. Synthesis and antibacterial activity of C6-carbazate ketolides. Bioorg. Med. Chem. Lett., 2006, 16, 6231-6235. (Pubitemid 44780977)
64. Kucukbasmaci, O.; Gonullu, N.; Aktas, Z.; Gurol, D.; Berkiten, R. In vitro activity of telithromycin compared with macrolides and fluoroquinolones against Streptococcus pneumoniae, Haemophilus influenzae and Moraxella catarrhalis. Int. J. Antimicrob. Agents, 2003, 22, 497-501. (Pubitemid 37356950)
65. Stratton, C.W.; Brown, S.D. Comparative in vitro activity of telithromycin and beta-lactam antimicrobials against community-acquired bacterial respiratory tract pathogens in the United States: findings from the PROTEKT US study, 2000-2001. Clin. Ther., 2004, 26, 522-530. (Pubitemid 38586453)
66. Low, D.E.; Felmingham, D.; Brown, S.D.; Rangaraju, M.; Nusrat, R. Activity of telithromycin against key pathogens associated with communityacquired respiratory tract infections. J. Infect., 2004, 49, 115-125. (Pubitemid 38967346)
67. Walsh, F.; Carnegy, F.; Willcock, J.; Amyes, S. Comparative in vitro activity of telithromycin against macrolide-resistant and -susceptible Streptococcus pneumoniae, Moraxella catarrhalis and Haemophilus influenzae. J. Antimicrob. Chemother., 2004, 53, 793-796. (Pubitemid 38660280)
68. Kozlov, R.S.; Bogdanovitch, T.M.; Appelbaum, P.C.; Ednie, L.; Stratchounski, L.S.; Jacobs, M.R.; Bozdogan, B. Antistreptococcal activity of telithromycin compared with seven other drugs in relation to macrolide resistance mechanisms in Russia. Antimicrob. Agents Chemother., 2002, 46, 2963-2968.
69. Shain, C.S.; Amsden, G.W. Telithromycin: the first of the ketolides. Ann. Pharmacother., 2002, 36, 452-464. (Pubitemid 34205321)
70. Wellington, K.; Noble, S. Telithromycin. Drugs, 2004, 64, 1683-1694; discussion 1695-1686. (Pubitemid 39128005)
71. Bertho, G.; Gharbi-Benarous, J.; Delaforge, M.; Lang, C.; Parent, A.; Girault, J.P. Conformational analysis of ketolide, conformations of RU 004 in solution and bound to bacterial ribosomes. J. Med. Chem., 1998, 41, 3373-3386. (Pubitemid 28406545)
72. Evrard-Todeschi, N.; Gharbi-Benarous, J.; Gaillet, C.; Verdier, L.; Bertho, G.; Lang, C.; Parent, A.; Girault, J.P. Conformations in solution and bound to bacterial ribosomes of ketolides, HMR 3647 (telithromycin) and RU 72366: a new class of highly potent antibacterials. Bioorg. Med. Chem., 2000, 8, 1579-1597. (Pubitemid 30428064)
73. Bertho, G.; Ladam, P.; Gharbi-Benarous, J.; Delaforge, M.; Girault, J.P. Solution conformation of methylated macrolide antibiotics roxithromycin and erythromycin using NMR and molecular modelling. Ribosome-bound conformation determined by TRNOE and formation of cytochrome P450- metabolite complex. Int. J. Biol. Macromol., 1998, 22, 103-127. (Pubitemid 28190588)
74. Bertho, G.; Gharbi-Benarous, J.; Delaforge, M.; Girault, J.P. Transferred nuclear Overhauser effect study of macrolide-ribosome interactions: correlation between antibiotic activities and bound conformations. Bioorg. Med. Chem., 1998, 6, 209-221. (Pubitemid 28260936)
75. Capobianco, J.O.; Cao, Z.; Shortridge, V.D.; Ma, Z.; Flamm, R.K.; 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. (Pubitemid 30340795)
76. Mason, E.O., Jr.; Lamberth, L.B.; Wald, E.R.; Bradley, J.S.; Barson, W.J.; Kaplan, S.L. In vitro activities of cethromycin (ABT-773), a new ketolide, against Streptococcus pneumoniae strains that are not susceptible to penicillin or macrolides. Antimicrob. Agents Chemother., 2003, 47, 166-169. (Pubitemid 36070359)
77. Nilius, A.M.; Bui, M.H.; Almer, L.; Hensey-Rudloff, D.; Beyer, J.; Ma, Z.; Or, Y.S.; Flamm, R.K. Comparative in vitro activity of ABT-773, a novel antibacterial ketolide. Antimicrob. Agents Chemother., 2001, 45, 2163-2168. (Pubitemid 32591721)
78. Strigl, S.; Roblin, P.M.; Reznik, T.; Hammerschlag, M.R. In vitro activity of ABT 773, a new ketolide antibiotic, against Chlamydia pneumoniae. Antimicrob. Agents Chemother., 2000, 44, 1112-1113. (Pubitemid 30165305)
79. Hammerschlag, M.R.; Reznik, T.; Roblin, P.M.; Ramirez, J.; Summersgill, J.; Bukofzer, S. Microbiological efficacy of ABT-773 (cethromycin) for the treatment of community-acquired pneumonia due to Chlamydia pneumoniae. J. Antimicrob. Chemother., 2003, 51, 1025-1028. (Pubitemid 36503440)
80. Miyashita, N.; Fukano, H.; Yoshida, K.; Niki, Y.; Matsushima, T. In vitro activity of cethromycin, a novel antibacterial ketolide, against Chlamydia pneumoniae. J. Antimicrob. Chemother., 2003, 52, 497-499. (Pubitemid 37120735)
81. Waites, K.B.; Crabb, D.M.; Duffy, L.B. In vitro activities of ABT-773 and other antimicrobials against human mycoplasmas. Antimicrob. Agents Chemother., 2003, 47, 39-42. (Pubitemid 36070339)
82. Credito, K.L.; Lin, G.; Pankuch, G.A.; Bajaksouzian, S.; Jacobs, M.R.; Appelbaum, P.C. Susceptibilities of Haemophilus influenzae and Moraxella catarrhalis to ABT-773 compared to their susceptibilities to 11 other agents. Antimicrob. Agents Chemother., 2001, 45, 67-72. (Pubitemid 32039095)
83. Goldstein, E.J.; Conrads, G.; Citron, D.M.; Merriam, C.V.; Warren, Y.; Tyrrell, K. In vitro activities of ABT-773, a new ketolide, against aerobic and anaerobic pathogens isolated from antral sinus puncture specimens from patients with sinusitis. Antimicrob. Agents Chemother., 2001, 45, 2363-2367. (Pubitemid 32666201)
84. Zhanel, G.G.; Hisanaga, T.; Nichol, K.; Wierzbowski, A.; Hoban, D.J. Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae. Expert Opin. Emerg. Drugs, 2003, 8, 297-321. (Pubitemid 37522653)
85. Kim, M.K.; Zhou, W.; Tessier, P.R.; Xuan, D.; Ye, M.; Nightingale, C.H.; Nicolau, D.P. Bactericidal effect and pharmacodynamics of cethromycin (ABT-773) in a murine pneumococcal pneumonia model. Antimicrob. Agents Chemother., 2002, 46, 3185-3192.
86. Mitten, M.J.; Meulbroek, J.; Nukkala, M.; Paige, L.; Jarvis, K.; Oleksijew, A.; Tovcimak, A.; Hernandez, L.; Alder, J.D.; Ewing, P.; Or, Y.S.; Ma, Z.; Nilius, A.M.; Mollison, K.; Flamm, R.K. Efficacies of ABT-773, a new ketolide, against experimental bacterial infections. Antimicrob. Agents Chemother., 2001, 45, 2585-2593. (Pubitemid 32801914)
87. Capitano, B.; Maglio, D.; Banevicius, M.A.; Nightingale, C.H.; Nicolau, D.P. Bactericidal effect of cethromycin (ABT-773) in an immunocompetent murine pneumococcal pneumonia model. Int. J. Antimicrob. Agents, 2003, 22, 588-593. (Pubitemid 37494994)
88. Azoulay-Dupuis, E.; Mohler, J.; Bedos, J.P.; Barau, C.; Fantin, B. Efficacy of cethromycin, a new ketolide, against Streptococcus pneumoniae susceptible or resistant to erythromycin in a murine pneumonia model. Antimicrob. Agents Chemother., 2006, 50, 3033-3038. (Pubitemid 44396409)
89. Rios, A.M.; Mejias, A.; Chavez-Bueno, S.; Fonseca-Aten, M.; Katz, K.; Hatfield, J.; Gomez, A.M.; Jafri, H.S.; McCracken, G.H., Jr.; Ramilo, O.; Hardy, R.D. Impact of cethromycin (ABT-773) therapy on microbiological, histologic, immunologic, and respiratory indices in a murine model of Mycoplasma pneumoniae lower respiratory infection. Antimicrob. Agents Chemother., 2004, 48, 2897-2904. (Pubitemid 38989153)
90. Hammerschlag, M.R.; Sharma, R. Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections. Expert Opin. Investig. Drugs, 2008, 17, 387-400. (Pubitemid 351578190)
91. Clark, R.F.; Ma, Z.; Wang, S.; Griesgraber, G.; Tufano, M.; Yong, H.; Li, L.; Zhang, X.; Nilius, A.M.; Chu, D.T.; Or, Y.S. Synthesis and antibacterial activity of novel 6-O-substituted erythromycin A derivatives. Bioorg. Med. Chem. Lett., 2000, 10, 815-819. (Pubitemid 30215891)
92. Hsu, M.C.; Junia, A.J.; Haight, A.R.; Zhang, W. Synthesis of erythromycin derivatives via the olefin cross-metathesis reaction. J. Org. Chem., 2004, 69, 3907-3911. (Pubitemid 38668251)
93. Plata, D.J.; Leanna, M.R. The synthesis of ketolide antibiotic ABT-773 (cethromycin). Tetrahedron, 2004, 60, 10171-10180. (Pubitemid 39303967)
94. Ban, N.; Nissen, P.; Hansen, J.; Moore, P.B.; Steitz, T.A. The complete atomic structure of the large ribosomal subunit at 2.4 A resolution. Science, 2000, 289, 905-920. (Pubitemid 30659939)
95. Nissen, P.; Hansen, J.; Ban, N.; Moore, P.B.; Steitz, T.A. The structural basis of ribosome activity in peptide bond synthesis. Science, 2000, 289, 920-930. (Pubitemid 30659940)
96. Schlunzen, F.; Zarivach, R.; Harms, J.; Bashan, A.; Tocilj, A.; Albrecht, R.; Yonath, A.; Franceschi, F. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature, 2001, 413, 814-821. (Pubitemid 33026843)
97. Douthwaite, S.; Hansen, L.H.; Mauvais, P. Macrolide-ketolide inhibition of MLS-resistant ribosomes is improved by alternative drug interaction with domain II of 23S rRNA. Mol. Microbiol., 2000, 36, 183-193.
98. Ma, Z.; Li, L.; Rupp, M.; Zhang, S.; Zhang, X. Regioselective synthesis of bifunctional macrolides for probing ribosomal binding. Org. Lett., 2002, 4, 987-990.
99. Wang, G.; Niu, D.; Qiu, Y.L.; Phan, L.T.; Chen, Z.; Polemeropoulos, A.; Or, Y.S. Synthesis of novel 6,11-O-bridged bicyclic ketolides via a palladiumcatalyzed bis-allylation. Org. Lett., 2004, 6, 4455-4458. (Pubitemid 39611786)
100. Kirst, H.A. New macrolide, lincosaminide and streptogramin B antibiotics. Expert Opin. Ther. Pat., 2010, 20, 1343-1357.
101. Poce, G.; Cesare Porretta, G.; Biava, M. C-9 Alkenylidine bridged macrolides: WO2008061189. Enanta Pharmaceuticals, Inc. Expert Opin. Ther. Pat., 2009, 19, 901-906.
102. Van Bambeke, F.; Harms, J.M.; Van Laethem, Y.; Tulkens, P.M. Ketolides: pharmacological profile and rational positioning in the treatment of respiratory tract infections. Expert Opin. Pharmacother., 2008, 9, 267-283. (Pubitemid 351233734)
103. Xiong, L.; Korkhin, Y.; Mankin, A.S. Binding site of the bridged macrolides in the Escherichia coli ribosome. Antimicrob. Agents Chemother., 2005, 49, 281-288. (Pubitemid 40065804)
104. Stucki, A.; Gerber, P.; Acosta, F.; Cottagnoud, M.; Cottagnoud, P.; Jiang, L.; Nguyen, P.; Wachtel, D.; Wang, G.; Phan, L.T. Effects of EDP-420 on penicillin-resistant and quinolone- and penicillin-resistant pneumococci in the rabbit meningitis model. J. Antimicrob. Chemother., 2008, 61, 665-669. (Pubitemid 351321144)
105. Abbanat, D.; Morrow, B.; Bush, K. New agents in development for the treatment of bacterial infections. Curr. Opin. Pharmacol., 2008, 8, 582-592.
106. Fernandes, P.B.; Baker, W.R.; Freiberg, L.A.; Hardy, D.J.; McDonald, E.J. New macrolides active against Streptococcus pyogenes with inducible or constitutive type of macrolide-lincosamide-streptogramin B resistance. Antimicrob. Agents Chemother., 1989, 33, 78-81. (Pubitemid 19015769)
107. Ma, S.; Jiao, B.; Liu, Z.; Wang, H.; Xian, R.; Zheng, M.; Lou, H. Synthesis and antibacterial activity of 4",11-di-O-arylalkylcarbamoyl azithromycin derivatives. Bioorg. Med. Chem. Lett., 2009, 19, 1698-1701.
108. Tanikawa, T.; Asaka, T.; Kashimura, M.; Suzuki, K.; Sugiyama, H.; Sato, M.; Kameo, K.; Morimoto, S.; Nishida, A. Synthesis and antibacterial activity of a novel series of acylides: 3-O-(3-pyridyl)acetylerythromycin A derivatives. J. Med. Chem., 2003, 46, 2706-2715. (Pubitemid 36702539)
109. Nikaido, H. Multidrug efflux pumps of gram-negative bacteria. J. Bacteriol., 1996, 178, 5853-5859. (Pubitemid 26337766)
110. Hansen, J.L.; Ippolito, J.A.; Ban, N.; Nissen, P.; Moore, P.B.; Steitz, T.A. The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol. Cell, 2002, 10, 117-128. (Pubitemid 34876566)