1887

Chapter 19 : Ketolides

MyBook is a cheap paperback edition of the original book and will be sold at uniform, low price.

Ebook: Choose a downloadable PDF or ePub file. Chapter is a downloadable PDF file. File must be downloaded within 48 hours of purchase

Buy this Chapter
Digital (?) $30.00

Preview this chapter:
Zoom in
Zoomout

Ketolides, Page 1 of 2

| /docserver/preview/fulltext/10.1128/9781555815929/9781555812379_Chap19-1.gif /docserver/preview/fulltext/10.1128/9781555815929/9781555812379_Chap19-2.gif

Abstract:

The ketolides belong to group II of the classification of macrolides. All ketolides are characterized structurally by the absence of an α-L-cladinose at position 3 of the erythronolide A and the presence of a 3-keto group. The affinity for ribosomes is higher for ketolides than for erythromycin A. The dissociation constants are summarized. Cethromycin binds tightly to ribosomes in comparison to erythromycin A. Blockade of the exit tunnel by ketolides induces premature dissociation of peptidyl-tRNAs from the ribosome. The available ketolides inhibit the assembly of 50S sub-units of and . Various ketolides have been shown not to be capable of inducing resistance to other macrolides. This phenomenon has been explored with strains of , , and in the presence of ketolides and their counterpart with an L-cladinose and with clarithromycin, erythromycin A, and azithromycin. Erythromycin A accumulation dropped about 70 to 80% after induction. Ketolides could accumulate in the bacterial cell to preinduction level, and the concentration remains high enough to interfere with the ribosome. The efflux mechanism of resistance of involves a Mef protein, which binds to macrolides and ketolides and extrudes them from the bacterial cell, resulting in reduced intracellular drug concentrations. The ability of sequential subcultures in subinhibitory concentrations of telithromycin, azithromycin, roxithromycin, clindamycin, and pristinamycin to select for resistance was investigated. Introduction of halogen at the C-2 position of the erythronolide A ring leads to the synthesis of HMR 3562 and HMR 3787.

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19

Key Concept Ranking

Antibacterial Agents
0.5602578
Lower Respiratory Tract Infections
0.4459685
0.5602578
Highlighted Text: Show | Hide
Loading full text...

Full text loading...

Figures

Image of Figure 1
Figure 1

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 2
Figure 2

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 3
Figure 3

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 4
Figure 4

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 5
Figure 5

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 6
Figure 6

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 7
Figure 7

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 8
Figure 8

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 9
Figure 9

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 10
Figure 10

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 11
Figure 11

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 12
Figure 12

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 13
Figure 13

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 14
Figure 14

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 15
Figure 15

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 16
Figure 16

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 17
Figure 17

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 18
Figure 18

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 19
Figure 19

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 20
Figure 20

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 21
Figure 21

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 22
Figure 22

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 23
Figure 23

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 24
Figure 24

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 25
Figure 25

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 26
Figure 26

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 27
Figure 27

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 28
Figure 28

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 29
Figure 29

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 30
Figure 30

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 31
Figure 31

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 32
Figure 32

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 33
Figure 33

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 34
Figure 34

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 35
Figure 35

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 36
Figure 36

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 37
Figure 37

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 38
Figure 38

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 39
Figure 39

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 40
Figure 40

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 41
Figure 41

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 42
Figure 42

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 43
Figure 43

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 44
Figure 44

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 45
Figure 45

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 46
Figure 46

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 47
Figure 47

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint
Image of Figure 48
Figure 48

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Permissions and Reprints Request Permissions
Download as Powerpoint

References

/content/book/10.1128/9781555815929.ch19
1. Abbanat D,, Ashley G,, Carney J,, Fardis M,, Foleno B,, Hilliard J,, Li Y,, Licari P,, Loeloff M,, Macielag M,, Melton J,, Stryker S,, Wira E,, Bush K, 2001, In vitro and in vivo activities of 15-methyl ketolide derivatives of erythromycin A, 41st Intersci Conf Antimicrob Agents Chemother, abstract F-1173.
2. Appelbaum PC,, Ednie L,, Kelly L,, Matic Y, 2004, Anti-pneumococcal activity of two novel macrolides, GW 773546 and GW 708408, compared with 5 other agents by MIC, 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1400.
3. Asaka T,, Kashimura M,, Ishi T, et al, 1997, New macrolide antibiotics, acylides (3-O-acyl-S-O desosaminyl erythronolides), synthesis and biological properties, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-262, p 190.
4. Asaka T,, Kashimura M,, Misawa Y, et al, 1995a, A new macrolide antibiotic, TE-810. Synthesis and biological properties, 35th Intersci Conf Antimicrob Agents Chemother, abstract F-177, p 144.
5. Asaka T,, Kashimura M,, Misawa Y, et al, 1995b, A new macrolide antibiotic, TE-802. Synthesis and biological properties, 35th Intersci Conf Antimicrob Agents Chemother, abstract E-176, p 143.
6. Ashley GW,, Li Y,, Liu G,, Ma W,, Myles D,, Shaw S,, Zhang D,, Zheng H, 2004, 15-Amido ketolides, a new class of ketolide antibacterial agents, 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1409.
7. Baker WR,, Clark JD,, Stephens RL,, Kim KH, 1988, Modification of macrolide antibiotics. Synthesis of 11-deoxy-11-(carboxyamino)-6-O-methyl erythromycin A 11,12-(cyclic esters) via an intramolecular Michael reaction of O-carbamate with an α,β-unsaturated ketone, J Org Chem, 53, 23402345.
8. Barry AL,, Brown SD,, Fuchs PC, 1997, Antipneumococcal activity of a ketolide (HMR 3647) and seven related drugs in vitro, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-107, p 164.
9. Beebe X,, Yang F,, Bui MH,, Mitten MJ,, Ma Z,, Nilius AM,, Djuric SW, 2004, Synthesis and antibacterial activity of 6-O-arylpropargyl-9-oxime-11,12-carbamate ketolides, Bioorg Med Chem Lett, 14, 24172421.
10. Bermudez LE,, Inderlied CB,, Kolonoski P,, Aralat P,, Petrosky M,, Wu M,, Wang G,, Niu D,, Young LS, 2004, In vitro and in vivo activity of 6-11 bridged-bicyclic ketolides (including EP 013420) against Mycobacterium avium complex (MAC), 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1408.
11. Blackman J,, Hicklin MD,, Chandler F, 1978, Legionnaires’ diseases, pathological and historical aspect of a new disease, Arch Pathol Lab Med, 102, 337343.
12. Bonnefoy A,, Denis A,, Bretin F,, Fromentin C, 1999, In vivo antibacterial activity of two ketolides, HMR 3562 and HMR 3787, highly active against respiratory pathogens, 39th Intersci Conf Antimicrob Agents Chemother, abstract 2156, p 352.
13. Bonnefoy A,, Girard AM,, Agouridas C,, Chantot JF, 1997, Ketolides lack inducibility properties of MLS(B) resistance pheno-type, J Antimicrob Chemother, 40, 8590.
14. Bryskier A, 1992, Newer macrolides and their potential target organisms, Curr Opin Infect Dis, 5, 764772.
15. Bryskier A, 1997, Novelties in the field of macrolides, Exp Opin Investig Drugs, 6, 16971709.
16. Bryskier A,, Agouridas C,, Chantot JF, 1993a, Acid stability of new macrolides, J Chemother, 5, suppl 1, 158159.
17. Bryskier A,, Agouridas C,, Chantot JF, 1995, New insights into the structure-activity relationship of macrolides and azalides, p 330, in Neu HC,, Young LS,, Zinner SH,, Acar JF, ed, New Macrolides, Azalides and Streptogramins in Clinical Practice, Marcel Dekker, New York.
18. Bryskier A,, Agouridas C,, Chantot JF, 1997, Ketolides, new semi-synthetic 14-membered-ring macrolides, p 39–50, in Zinner SH,, Young LS,, Acar JF,, Neu HC, ed, Expanding Indications for the New Macrolides, Azalides and Streptogramins, Marcel Dekker, New York.
19. Bryskier A,, Agouridas C,, Gasc JC, 1993b, Classification of macrolide antibiotics, p 5–66, in Bryskier AJ,, Butzler JP,, Neu HC,, Tulkens PM, ed, Macrolides: Chemistry, Pharmacology and Clinical Use, Arnette-Blackwell, Paris.
20. Bryskier A,, Labro MT, 1994, Macrolides, nouvelles perspectives thérapeutiques, Presse Med, 223, 17621766.
21. Cantalloube C,, Scaglione F,, Pukander J,, Van Dyk K,, Pascual MH,, Montay G,, Leroy B, 2004, Telithromycin concentration in middle-ear fluid in children with acute otitis media or otitis media with effusion, 44th Intersci Conf Antimicrob Agents Chemother, abstract A7.
22. Cantalloube C,, Vargayava V,, Sultan E,, Vacheron F,, Batista I,, Montay G, 2003, Pharmacokinetics of the ketolide telithromycin after single and repeated dose in patients with hepatic impairement, Int J Antimicrob Agents, 22, 112121.
23. Cocuzza CE,, Tomasini A,, Reuzetti D, et al, 1998. Ketolide (HMR 3647) in vitro activity on 4000 strains of S. pyogenes isolated in northern Italy, 4th Int Conf Macrolides, Azalides, Streptogramins, Ketolides, abstract 1.06, p 21.
24. Collette P,, Douthwaite S,, Monkin A,, Mauvais P, 1998, Similarities and differences in ketolides and macrolide interaction within two distinct domains of 23 ribosomal RNA, 4th Int Conf Macrolides, Azalides, Streptogramins, Ketolides, abstract 1.2, p 25.
25. Corbaz R,, Ettlinger L,, Gaumann E, et al, 1955, Stoffwechselprodukte von Actinomyceten, Helv Chim Acta, 38, 935942.
26. Denis A,, Agouridas C,, Bonnefoy A,, Bretin F,, Fromentin C,, Bonnet A, 1999, Synthesis and antibacterial activity of 2-halogeno, 2-methyl, and 2,3 enol-ether ketolides using β-keto-ester chemistry, 39th Intersci Conf Antimicrob Agents Chemother, abstract 2152, p 351.
27. Denis A,, Pejac JM,, Bretin F,, Bonnefoy A, 2003, Synthesis of 9-oxime-11,12 carbamate ketolides through a novel diamineation reaction of 11,12-hydrazinocarbamate ketolide, Bioorg Med Chem, 11, 23892394.
28. Ednie LM,, Jacobs MR,, Appelbaum PC, 1997, Comparative anti-anaerobic activities of the ketolides HMR 3647 (RU 66647) and HMR 3004 (RU 64004), Antimicrob Agents Chemother, 41, 20192022.
29. Elliott RL,, Pireh D,, Griesgraber G, et al, 1997a, Synthesis and in vitro activity of novel 2,3-anhydro 6-O-methyl-11,12-carbamate erythromycin analogues, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-265, p 191.
30. Elliott RL,, Pireh D,, Griesgraber G, et al, 1998, Anhydrolide macrolides. I. Synthesis and antibacterial activity of 2,3 anhydro-6-O-methyl 11,12 carbamate erythromycin analogues, J Med Chem, 41, 16511652.
31. Elliott RL,, Pireh D,, Nilius AM, et al, 1997b, Novel 3-deoxy-3-descladinosyl-6-O-methyl erythromycin A analogues. Synthesis and in vitro activity, Bioorg Med Chem Lett, 7, 641647.
32. Engler KH,, Warner M,, George RC, 1997, In vitro susceptibility of Corynebacterium diphtheriae to a new macrolide, HMR 3647, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-124, p 167.
33. Felmingham D, 1996, HMR data in file.
34. Felmingham D, 1997, HMR data in file.
35. Felmingham D,, Robbins MJ,, Clark S,, Mathias I,, Bryskier A, 1998, The comparative in vitro activity of HMR 3647 against speciated coagulase-negative Staphylococcus spp., 4th Int Conf Macrolides, Azalides, Streptogramins, Ketolides, abstract 1.07, p 21.
36. Felmingham D,, Robbins MJ,, Leakey A, et al, 1997, The comparative in vitro activity of HMR 3647, a ketolide antimicrobial, against clinical bacterial isolates, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-116, p 166.
37. Felmingham D,, Robbins MJ,, Mathias I,, Bryskier A, 1999, In vitro activity of two ketolides, HMR 3562 and HMR 3787, against clinical bacterial isolates, 39th Intersci Conf Antimicrob Agents Chemother, abstract 2154, p 351.
38. Fernandes PB,, Baker WR,, Freiberg LA,, Hardy DJ,, McDonald EJ, 1989, New macrolides active against Streptococcus pyogenes with inducible or constitutive type of macrolide-lincosamide-streptogramin B resistance, Antimicrob Agents Chemother, 33, 7881.
39. Fiese EP,, Steffen SH, 1990, Comparison of the acid stability of azithromycin and erythromycin A, J Antimicrob Chemother, 25, suppl A, 3947.
40. Goldstein E, 1997, HMR data on file.
41. Graystone JT,, Wang SP,, Kuo CC,, Campbell LA, 1989, Current knowledge on C. pneumoniae strain TWAR, an important cause of pneumonia and other acute respiratory diseases, Eur J Clin Microbiol, 8, 191202.
42. Griesgraber G,, Elliott RL,, Kramer MJ, et al, 1997, Synthesis and in vitro activity of novel 2,3-anhydro-11-hydrazo-6-O-methyl-11,12-carbamate erythromycin derivative, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-267, p 191.
43. Griesgraber G,, Kramer MJ,, Elliott RL, et al, 1998, Anhydrolide macrolides. 2. Synthesis and antibacterial activity of 2,3-anhydro-6-O-methyl-11,12-carbazate erythromycin A analogues, J Med Chem, 41, 16601670.
44. Griesgraber G,, Or YS,, Chu DTW,, Nilius AM,, Johnson PM,, Flamm RK,, Henry RE,, Plattner JJ, 1996, 3-Keto-11,12-carbazate derivative of 6-O-methyl erythromycin A. Synthesis and in vitro activity, J Antibiot, 49, 465477.
45. Gupta S,, Leatham E,, Carrington D,, Mendall M,, Kaski JC,, Camm J, 1997, Elevated Chlamydia pneumoniae antibodies, cardiovascular events, and azithromycin in male survivors of myocardiac infarctus, Circulation, 96, 404407.
46. Gurfinkel E, 1998, Is there a role for macrolides in atherosclerosis? 4th Int Conf Macrolides, Azalides, Streptogramins, Ketolides, abstract 8, p 19.
47. Gurfinkel E,, Bozovich G,, Daroca A,, Beek E,, Mautuer B, 1997, Randomised trial of roxithromycin in non-Q-wave coronary syndromes, ROXIS pilot study, Lancet, 350, 404407.
48. Henninger TC,, Xu X,, Abbanat D,, Baum EZ,, Foleno BD,, Hilliard JJ,, Burh K,, Hlaska DJ,, Macielag MJ, 2004, Synthesis and antibacterial activity of C-6 carbamate ketolides, a novel series of orally active ketolide antibiotics, Bioorg Med Chem Lett, 14, 44954499.
49. Hoban D,, Karlowsky J,, Weshnoweski B,, Kabani A,, Zhanel G, 1997, In vitro activity of a new ketolide, HMR 3647, against geographically diverse Canadian isolates of Enterococcus spp., 37th Intersci Conf Antimicrob Agents Chemother, abstract F-119, p 166.
50. Hoppe JE,, Bryskier A, 1998, In vitro susceptibility of B. pertussis and B. parapertussis to the ketolides HMR 3004 and HMR 3647, to the macrolides azithromycin, clarithromycin, erythromycin A and roxithromycin and to the ansamycins, rifampicin and rifapentine, 4th Int Conf Macrolides, Azalides, Streptogramins, Ketolides, abstract 1.13, p 23.
51. Hunziker D,, Wyss PC,, Angehrn P,, Mueller A,, Marty HP,, Holm R,, Kellenberger L,, Bitsch V,, Biringer G,, Wolf A,, Stämpfi A,, Schmitt-Hofmann A,, Cousot D, 2004, Novel ketolide antibiotics with a fused five-membered lactone ring. Synthesis, physicochemical and antimicrobial properties, Bioorg Med Chem, 12, 35033519.
52. Iannelli F,, Santagi M,, Doquier JD,, Cassone M,, Oggioni MR,, Rossolini G,, Stefani S,, Pozzi G, 2004, Type M resistance to macrolides in streptococci is not due to the mef(A) gene but to mat(A) encoding an ATP-dependent efflux pump, 44th Intersci Conf Antimicrob Agents Chemother, abstract C1-1188.
53. Kingsley E,, Gray P,, Tolman KC,, Tweedale R, 1983, The toxicity of metabolites of sodium valproate in culture hepatocytes, J Clin Pharmacol, 23, 178185.
54. Kitzis MD,, Goldstein FW,, Bismuth R,, Meigi M,, Acar JF, 1997, Comparative in vitro activity of HMR 3647, a new ketolide antibiotic, against S. aureus (SA) and coagulase negative staphylococci (CNS), 37th Intersci Conf Antimicrob Agents Chemother, abstract F-111, p 165.
55. Ma Z,, Li L,, Rupp M,, Zhang S,, Zhang X, 2002, Regio selective synthesis of bifunctional macrolides, for probing ribosomal binding, Org Lett, 4, 987990.
56. Macielag M,, Abbanat D,, Ashley G,, Foleno B,, Fu H,, Li Y,, Wira E,, Bush K, 2003, Structure-activity studies of 15-methyl ketolides, optimization of the heterocyclic substituent, 43rd Intersci Conf Antimicrob Agents Chemother, abstract F-1662.
57. Maglio D,, Sun HK,, Patel T,, Banevicius MA,, Nightingale CH,, Nicolau DP,, Araya A,, Wang G,, Chen Z,, Phan LT, 2004, Pharmacodynamics of a new bridged bicyclic ketolide EP 013420 in a murine Streptococcus pneumoniae pneumonia model, 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1407.
58. Namour F,, Wessels DH,, Pascual MH,, Reynolds D,, Sultan E,, Lenfant B, 2001, Pharmacokinetics of the new ketolide telithromycin (HMR 3647) administered in ascending single and multiple doses, Antimicrob Agents Chemother, 45, 170175.
59. Nilius AM,, Mitten M,, Bui MH,, Hensey-Rudloff D,, Clark R,, Ma Z,, Meulbroek J,, Flam RK, 2001, In vitro and in vivo activities of A-217213, a new ketolide antibiotic against respiratory pathogens, 41st Intersci Conf Antimicrob Agents Chemother, abstract F-1172.
60. Pankuch G,, Jacobs MR,, Appelbaum PC, 2004, In vitro activity of GW 773546 and GW 708408, telithromycin, erythromycin, azithromycin and clarithromycin against 223 Haemophilus influenzae by MIC, 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1398.
61. Perret C,, Lenfant B,, Weinling E,, Wessels DH,, Scholtz HE,, Montay G,, Sultan E, 2002, Pharmacokinetics and absolute bioavailability of an 800-mg oral dose of telithromycin in healthy young and elderly volunteers, Chemotherapy, 48, 217223.
62. Phan LT,, Or YS,, Chen Y,, Chu DTW,, Ewing P,, Nilius AM,, Bui MH,, Raney PM,, Hensey-Rudloff D,, Mitten M,, Henry RF,, Plattner JJ, 1998, 2-Substituted tricyclic ketolides, new antibacterial macrolides. Synthesis and biological activity, 38th Intersci Conf Antimicrob Agents Chemother, abstract F-127, p 264.
63. Sugiyama H,, Suzuki K,, Oyauchi R,, Yamasaki Y,, Nanaumi K,, Kaneda Y,, Kawauchi H,, Akashi T,, Manaka A,, Asaka T,, Nakaike S, 2004, FMA 0713, α-methoxyimino acylide, antibacterial activity against Streptococcus pneumoniae, Streptococcus pyogenes, and Staphylococcus aureus, 44th Intersci Conf Antimicrob Agents Chemother, abstract F-1397.
64. Torres C,, Zarazaga M,, Tenorio C,, Saenz Y,, Portillo A,, Baquero F, 1997, Susceptibility of Lactobacillus, Leuconostoc and Pediococcus to ketolide HMR 3647 and other antibiotics, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-247, p 188.
65. Vesga O,, Andes D,, Craig WA, 1997, Comparative in vivo activity of HMR 3647, azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) against S. pneumoniae (SP) and S. aureus (SA), 37th Intersci Conf Antimicrob Agents Chemother, abstract F-258, p 189.
66. Vesga O,, Craig WA, 1997, Impact of macrolide resistance on the in vivo activity of a new ketolide, HMR 3647, against S. pneumoniae (SP) and S. aureus (SA), 37th Intersci Conf Antimicrob Agents Chemother, abstract F-259, p 189.
67. Vesga O,, Craig WA,, Bonnat C, 1997, In vivo pharmacodynamic activity of HMR 3647, a new ketolide, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-255, p 189.
68. Visalli MA,, Jacobs MR,, Appelbaum PC, 1997, Antipneumococcal activity of HMR 3647 (RU 6647), a new ketolide, compared to other drugs, by time-kill, 37th Intersci Conf Antimicrob Agents Chemother, abstract F-109, p 164.
69. Wang G,, Niu D,, Qiu YL,, Phan LT,, Chen Z,, Polemeropoulos A,, Or YS, 2004, Synthesis of novel 6,11-O-bridged bicyclic ketolides via palladium-catalyzed bis-allylation, Org Lett, 6, 44554458.

Tables

Generic image for table
Table 1

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 2

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 3

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 4

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 5

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 6

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 7

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 8

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 9

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 10

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 11

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 12

μg/ml)

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 13

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 14

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 15

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 16

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 17

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 18

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 19

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 20

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 21

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 22

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 23

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 24

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 25

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 26

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 27

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 28

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 29

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 30

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 31

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 32

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 33

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 34

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 35

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 36

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 37

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 38

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 39

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 40

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 41

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 42

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 43

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 44

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 45

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 46

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 47

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 48

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 49

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 50

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 51

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 52

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 53

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19
Generic image for table
Table 54

Citation: Bryskier A. 2005. Ketolides, p 527-569. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch19

This is a required field
Please enter a valid email address
Please check the format of the address you have entered.
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error