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Chapter 28 : Codrugs
Author:
A. Bryskier
Content Type: Reference
Publication Year:
2005
Category: Bacterial Pathogenesis
Book DOI:
10.1128/9781555815929
Chapter DOI:
10.1128/9781555815929.ch28
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Codrugs, Page 1 of 2
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Abstract:
The majority of codrugs studied possess either a cephalosporin, a penem, or a carbapenem. Studies of the mechanisms of action of codrugs have been conducted principally with Ro-23-9424, Ro-24-4384 (carbamate), and Ro-24-8138 (tertiary amine). The activity of the fluoroquinolones is evaluated in vitro in terms of the inhibition of DNA gyrase activity and in vivo in the bacterium in terms of its action on the nucleoid (topoisomerase IV) using 4’,6’-diamidino-2-phenylindole. Studies have been conducted on E. coli TE-18, which is a strain derived from E. coli K-12. The selection of fleroxacin-resistant mutants from this strain is greater than that observed with fleroxacin alone or from another strain, such as E. coli JF 568. The 3’-esters are much less chemically stable than the other derivatives. The first molecule in which a cephalosporin and a quinolone were combined was Ro-23-5068. The most widely studied molecule has been Ro-23-9424, but Ro-24-6392 has also been widely studied in vitro and in terms of the mechanism of action. Ro-25-0534 is a combination of a catechol-type cephalosporin and ciprofloxacin, linked by a tertiary amine bond. This molecule is active against strains of Enterobacteriaceae which are cefotaxime resistant as a result of cephalosporinase production. Combinations of penems and fluoroquinolones have been synthesized with the various bonds described for the cephalosporins. The chapter also talks about carbapenems-fluoroquinolones, penicillins-Quinolones, monocyclic β-lactams/quinolones, and oxazolidinones-quinolones.
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
Figures
Codrugs
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Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig1
Figure 1
Release of the compound at C-3’ of the cephem nucleus
10.1128/9781555815929/f0798-01_thmb.gif
10.1128/9781555815929/f0798-01.gif
Figure 1
Release of the compound at C-3’ of the cephem nucleus
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig2
Figure 2
Cephem: C-3’-omidine derivative mercaptopyridine-N-oxide (MCO)
10.1128/9781555815929/f0799-01_thmb.gif
10.1128/9781555815929/f0799-01.gif
Figure 2
Cephem: C-3’-omidine derivative mercaptopyridine-N-oxide (MCO)
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig3
Figure 3
Haloalanyl cephalosporin
10.1128/9781555815929/f0799-02_thmb.gif
10.1128/9781555815929/f0799-02.gif
Figure 3
Haloalanyl cephalosporin
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig4
Figure 4
Classification of combined molecules
10.1128/9781555815929/f0800-01_thmb.gif
10.1128/9781555815929/f0800-01.gif
Figure 4
Classification of combined molecules
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig5
Figure 5
β-Lactam–fluoroquinolone bond
10.1128/9781555815929/f0800-02_thmb.gif
10.1128/9781555815929/f0800-02.gif
Figure 5
β-Lactam–fluoroquinolone bond
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig6
Figure 6
Structures of cefotaxime, Ro-23-9424, desacetylcefotaxime, and fleroxacin
10.1128/9781555815929/f0801-01_thmb.gif
10.1128/9781555815929/f0801-01.gif
Figure 6
Structures of cefotaxime, Ro-23-9424, desacetylcefotaxime, and fleroxacin
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig7
Figure 7
CQ-414 and CQ-397
10.1128/9781555815929/f0801-02_thmb.gif
10.1128/9781555815929/f0801-02.gif
Figure 7
CQ-414 and CQ-397
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig8
Figure 8
Mechanism of action of β-lactams–fluoroquinolones (adapted from Dax et al., 1993)
10.1128/9781555815929/f0802-01_thmb.gif
10.1128/9781555815929/f0802-01.gif
Figure 8
Mechanism of action of β-lactams–fluoroquinolones (adapted from Dax et al., 1993)
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig9
Figure 9
Carbamate derivatives
10.1128/9781555815929/f0803-01_thmb.gif
10.1128/9781555815929/f0803-01.gif
Figure 9
Carbamate derivatives
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig10
Figure 10
Ro-23-5068
10.1128/9781555815929/f0804-01_thmb.gif
10.1128/9781555815929/f0804-01.gif
Figure 10
Ro-23-5068
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig11
Figure 11
Ro-24-6392
10.1128/9781555815929/f0807-01_thmb.gif
10.1128/9781555815929/f0807-01.gif
Figure 11
Ro-24-6392
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig12
Figure 12
Oral codrugs
10.1128/9781555815929/f0807-02_thmb.gif
10.1128/9781555815929/f0807-02.gif
Figure 12
Oral codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig13
Figure 13
PD-147767 and PD-152915
10.1128/9781555815929/f0808-01_thmb.gif
10.1128/9781555815929/f0808-01.gif
Figure 13
PD-147767 and PD-152915
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig14
Figure 14
Quinolonylcephem secondary amines
10.1128/9781555815929/f0808-02_thmb.gif
10.1128/9781555815929/f0808-02.gif
Figure 14
Quinolonylcephem secondary amines
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig15
Figure 15
Ro-25-0534
10.1128/9781555815929/f0809-01_thmb.gif
10.1128/9781555815929/f0809-01.gif
Figure 15
Ro-25-0534
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig16
Figure 16
Thioester derivative of Ro-23-9424
10.1128/9781555815929/f0809-02_thmb.gif
10.1128/9781555815929/f0809-02.gif
Figure 16
Thioester derivative of Ro-23-9424
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig17
Figure 17
Quaternary ammonium codrugs
10.1128/9781555815929/f0809-03_thmb.gif
10.1128/9781555815929/f0809-03.gif
Figure 17
Quaternary ammonium codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig18
Figure 18
PGE-8335534
10.1128/9781555815929/f0810-01_thmb.gif
10.1128/9781555815929/f0810-01.gif
Figure 18
PGE-8335534
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig19
Figure 19
Penem-quinolone codrugs
10.1128/9781555815929/f0811-01_thmb.gif
10.1128/9781555815929/f0811-01.gif
Figure 19
Penem-quinolone codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig20
Figure 20
Ro-25-0695
10.1128/9781555815929/f0811-02_thmb.gif
10.1128/9781555815929/f0811-02.gif
Figure 20
Ro-25-0695
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig21
Figure 21
Procter & Gamble molecules (1993)
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10.1128/9781555815929/f0812-01.gif
Figure 21
Procter & Gamble molecules (1993)
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig22
Figure 22
Carbapenems synthesized by Hoffmann-La Roche
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10.1128/9781555815929/f0813-01.gif
Figure 22
Carbapenems synthesized by Hoffmann-La Roche
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig23
Figure 23
Penicillin-norfloxacin codrugs
10.1128/9781555815929/f0813-02_thmb.gif
10.1128/9781555815929/f0813-02.gif
Figure 23
Penicillin-norfloxacin codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig24
Figure 24
Monobactam-quinolone
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10.1128/9781555815929/f0813-03.gif
Figure 24
Monobactam-quinolone
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28fig25
Figure 25
MCB 116, MCB 2038, and MCB 1033
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10.1128/9781555815929/f0814-01.gif
Figure 25
MCB 116, MCB 2038, and MCB 1033
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
References
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Tables
Codrugs
[com.pub2web.rdf.cci.facet.ContentItem[id=http://asm.metastore.ingenta.com/content/author/10.1128/9781555815929.ch28-1,webId=/content/author/10.1128/9781555815929.ch28-1,properties={foaf_givenname=A., foaf_name=A. Bryskier, foaf_surname=Bryskier}]]
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab1
Table 1
In vitro activity of mercaptopyridine-N-oxide
Table 1
In vitro activity of mercaptopyridine-N-oxide
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab2
Table 2
Activity of the omidine nucleus against β-lactamase-producing strains
Table 2
Activity of the omidine nucleus against β-lactamase-producing strains
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab3
Table 3
Affinities of β-lactams for S. aureus ATCC 25923 PBP
Table 3
Affinities of β-lactams for S. aureus ATCC 25923 PBP
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab4
Table 4
Activities of codrugs against DNA
Table 4
Activities of codrugs against DNA
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab5
Table 5
Degradation half-lives of Ro-23-9424 according to the biological medium
Table 5
Degradation half-lives of Ro-23-9424 according to the biological medium
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab6
Table 6
Degradation half-lives of codrugs
Table 6
Degradation half-lives of codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab7
Table 7
Activity of Ro-23-9424 against gram-negative bacilli
Table 7
Activity of Ro-23-9424 against gram-negative bacilli
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab8
Table 8
In vitro activity of Ro-23-9424 against cephalosporinase-producing Enterobacteriaceae
Table 8
In vitro activity of Ro-23-9424 against cephalosporinase-producing Enterobacteriaceae
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab9
Table 9
In vitro activity of Ro-23-9424 against S. pneumoniae
Table 9
In vitro activity of Ro-23-9424 against S. pneumoniae
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab10
Table 10
In vitro activity of Ro-23-9424 against gram positive bacteria
Table 10
In vitro activity of Ro-23-9424 against gram positive bacteria
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab11
Table 11
Selection of mutants of Ro-23-9424
Table 11
Selection of mutants of Ro-23-9424
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab12
Table 12
Plasma pharmacokinetics of Ro-23-9424 (20 mg/kg intravenously) in animals
Table 12
Plasma pharmacokinetics of Ro-23-9424 (20 mg/kg intravenously) in animals
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab13
Table 13
Plasma pharmacokinetics of Ro-23-9424 in humans
Table 13
Plasma pharmacokinetics of Ro-23-9424 in humans
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab14
Table 14
In vivo activity of Ro-24-4383
Table 14
In vivo activity of Ro-24-4383
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab15
Table 15
Plasma pharmacokinetics kinetics of PD-152915 and PD-147767 orally (50 mg/kg) in the rat
Table 15
Plasma pharmacokinetics kinetics of PD-152915 and PD-147767 orally (50 mg/kg) in the rat
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab16
Table 16
In vitro activities of CQ-397 and CQ-414
Table 16
In vitro activities of CQ-397 and CQ-414
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab17
Table 17
In vitro activities of penem-quinolone codrugs
Table 17
In vitro activities of penem-quinolone codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab18
Table 18
Affinities of penem-quinolone prodrugs for S. aureus ATCC 29213 PBP
Table 18
Affinities of penem-quinolone prodrugs for S. aureus ATCC 29213 PBP
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab19
Table 19
Plasma pharmacokinetics (20 mg/kg intravenously) of PGE-4924490
Table 19
Plasma pharmacokinetics (20 mg/kg intravenously) of PGE-4924490
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab20
Table 20
In vitro activities of carbapenem-quinolone codrugs
Table 20
In vitro activities of carbapenem-quinolone codrugs
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28
/content/10.1128/9781555815929.ch28.ch28tab21
Table 21
Antibacterial activities of oxazolidinones-quinolones
Table 21
Antibacterial activities of oxazolidinones-quinolones
Citation:
Bryskier A.
2005.
Codrugs,
p 798-815.
In
Bryskier, M.D. A (ed),
Antimicrobial Agents.
ASM Press, Washington, DC.
doi: 10.1128/9781555815929.ch28