Quinolone antibacterials: [with 103 tables]
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Berlin [u.a.]
Springer
1998
|
| Series: | Handbook of experimental pharmacology
127 |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XVIII, 491 S. Ill., graph. Darst. |
| ISBN: | 3540625127 |
Staff View
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Record in the Search Index
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| adam_text | Contents
CHAPTER 1
History and Introduction
J.T. Smith and H. J. Zeiler. With 1 Figure 1
A. Chemistry 1
B. Antibacterial Activity 4
C. Oxygen and 4 Quinolones 6
D. 4 Quinolone Kinetics and Distribution in Humans 6
E. Outlook 8
References 9
CHAPTER 2
The Chemistry of the Quinolones: Methods of Synthesizing
the Quinolone Ring System
K. Grohe. With 42 Figures 13
A. Introduction 13
B. Methods of Synthesizing the Quinolone Ring System 16
I. Gould Jacobs Reaction 16
II. Dieckmann Cyclization of Diesthers 21
III. Cycloaracylation Procedure 25
IV. Biere and Seelen Approach 35
V. Isatoic Anhydride Procedure 35
VI. Camps Quinolone Synthesis 39
VII. Meth Cohn Quinolone Synthesis 41
VIII. Synthesis of Quinolone Analogues 42
IX. Synthesis of 4 Cinnolone 3 carboxylic Acids 45
X. Synthesis of 4 Pyridone 3 carboxylic Acids 49
References 52
CHAPTER 3
The Chemistry of the Quinolones:
Chemistry in the Periphery of the Quinolones
U. Petersen and T. Schenke. With 35 Figures 63
XII Contents
A. Introduction 63
B. 1 Position 63
C. 2 Position 65
D. 3 Position 65
E. 4 Position 71
F. 5 Position 71
G. 6 Position 76
H. 7 Position 78
I. Synthesis of Specific Amines 78
1. Bicyclic Piperazine Derivatives 78
2. Aminopyrrolidine and Aminomethylpyrrolidine
Derivatives 79
3. 3,4 Bridged Pyrrolidine Derivatives 83
4. Mixed Derivatives 88
II. C N Linkage 89
III. C S Linkage 94
IV. C O Linkage 95
V. C C Linkage 95
I. 8 Position 99
References 101
CHAPTER 4
Mode of Action
A. Maxwell and S.E. Critchlow. With 12 Figures 119
A. Introduction 119
B. Effects on Bacteria 124
C. Effects on DNA Gyrase 130
I. Reactions of Gyrase 130
II. Mechanistic Steps 131
1. DNA Binding 131
2. DNA Cleavage 133
3. ATPase 136
III. Illegitimate Recombination 137
IV. Summary 137
D. Mode of Binding 137
I. Binding of Quinolones to DNA 138
II. Effect of DNA Gyrase on Quinolone Binding 139
III. Cooperative Quinolone DNA Binding Model 140
IV. DNA Cleavage is not an Absolute Requirement for
Quinolone Binding to a Gyrase DNA Complex 141
V. A Role for Magnesium Ions in the Binding of
Quinolones to DNA 142
VI. Binding of Quinobenzoxazines to DNA 144
Contents XIII
VII. Quinolone Binding to Quinolone Resistant Mutants of
DNA Gyrase 145
VIII. Mode of Binding of Topoisomerase II Targeting Drugs ... 146
IX. Problems with Current Models 149
X. Conclusions 150
E. Mechanism of Cell Killing 150
I. Paradoxical Effects of Quinolones 150
II. Poison Hypothesis 153
III. Polymerase Blocking 153
F. Conclusions and Future Prospects 156
References 158
CHAPTER 5
The In Vitro Antibacterial Activity of Quinolones: A Review
C. Thornsberry 167
A. Introduction 167
B. In Vitro Activity 169
C. The Future 174
References 177
CHAPTER 6
Pharmacokinetics of Fluoroquinolones in Experimental Animals
A. Dalhoff and T. Bergan. With 8 Figures 179
A. Introduction 179
B. Norfloxacin 180
C. Pefloxacin 181
D. Enoxacin 184
E. Ofloxacin 186
F. Ciprofloxacin 188
G. Temafloxacin 189
H. Tosufloxacin 191
I. Fleroxacin 191
J. Lomefloxacin 193
K. Sparfloxacin 195
L. Penetration of Quinolones at Sites of Infection 195
References 202
CHAPTER 7
Pharmacodynamics of Fluoroquinolones in Experimental Animals
W.A. Craig and A. Dalhoff. With 5 Figures 207
XIV Contents
A. Introduction 207
B. Bacterial Killing In Vivo 208
C. In Vivo Postantibiotic Effects 208
D. Pharmacodynamic Parameters Determining Efficacy 208
E. Emergence of Resistance to Fluoroquinolones 217
I. P. aeruginosa Experimental Infections 220
II. Staphylococcal Infections in Experimental Animals 222
III. Miscellaneous Infection Models 223
IV. Factors Contributing to the Emergence of Resistance
In Vivo 223
References 226
CHAPTER 8
Interaction of Quinolones with Host Parasite Relationship
A. Dalhoff. With 3 Figures 233
A. Introduction 233
B. Effect on Adherence 235
C. Effect Against Slowly Growing Bacteria 241
D. Effect on Exoenzyme Production 245
I. E.coli 245
II. P. aeruginosa 245
E. Quinolone Induced Endotoxin Release 248
F. Summary 252
References 253
CHAPTER 9
Mechanisms of Resistance to Fluoroquinolones
M.J. Everett and L.J. V. Piddock. With 5 Figures 259
A. Introduction 259
B. Target Site Modification 260
I. Mutations in gyrA 260
II. Mutations in gyrB 267
III. Mutations in Other Topoisomerase Genes 268
C. Reduced Intracellular Accumulation 270
I. Decreased Uptake 273
II. Increased Efflux 275
III. The mar Operon 277
D. Reduced Killing 278
E. Prevalence of Fluoroquinolone Resistance 281
I. Community Acquired Pathogens 281
II. Nosocomial Pathogens 282
Contents XV
III. Impact of Fluoroquinolone Use in Agriculture 284
F. Distribution of Resistance Mechanisms 285
G. Summary 286
References 286
CHAPTER 10
Toxicology and Safety Pharmacology of Quinolones
E. von Keutz and W. Christ. With 1 Figure 297
A. Introduction 297
B. Arthropathy 297
C. Achilles Tendinitis and Rupture 302
D. Nephropathy 304
E. Effects on Central Nervous System 306
F. Ocular Toxicity 313
G. Impairment of Spermatogenesis 315
H. Cardiovascular Effects 316
I. Possible Mutagenic and Carcinogenic Effects 317
J. Phototoxicity 322
K. Photocarcinogenicity and Photomutagenicity 327
L. Drug Interactions 329
M. Metabolic and Nutritional Effects 330
N. Conclusion 330
References 331
CHAPTER 11
Clinical Pharmacology
J. Kuhlmann, H. G. Schaefer, and D. Beermann 339
A. Introduction 339
B. Pharmacokinetics of Fluoroquinolone Antibiotics 340
I. Healthy Subjects 341
1. Absorption 343
2. Intravenous Administration 346
3. Bioavailability 347
4. Distribution 347
5. Disposition 349
II. The Elderly 350
III. Patients with Various Degrees of Renal Failure 353
1. Ciprofloxacin 353
2. Norfloxacin 354
3. Ofloxacin 354
4. Enoxacin 354
XVI Contents
5. Fleroxacin 354
6. Pefloxacin 354
7. Lomefloxacin 355
8. Summary 355
IV. Patients with Hepatic Failure 355
V. Fluoroquinolones in Pediatric Patients 356
C. Interactions of Fluoroquinolone Antibiotics with Other Drugs ... 357
I. Interactions During the Absorption Process 357
1. Food and Dairy Products 358
2. AP+ , Ca2+ and Mg2+ Containing Antacids 359
3. Sucralfate 361
4. Didanosine 362
5. Other Metal Cations 362
6. Chemotherapy Treatment 363
7. Activated Charcoal 364
II. Interactions of Fluoroquinolones Due to Alterations
in Metabolism 365
1. Theophylline, Caffeine and Structurally Closely
Related Substances 365
2. Antipyrine 370
3. Phenytoin 370
4. H2 Receptor Antagonists 371
5. K+/Na+ ATPase Inhibitors 372
6. Warfarin 372
7. Cyclosporine 372
8. Rifampin 373
9. Oral Contraceptive Steroids 374
10. Benzodiazepines (Diazepam, Temazepam) 374
III. Alterations in Renal Excretion 375
1. Probenecid 375
2. /3 Lactam Antibiotics 375
IV. Pharmacodynamic Interactions 376
1. Nonsteroidal Anti inflammatory Drugs 376
2. Metronidazole 377
V. Conclusions 377
D. Adverse Reactions of Fluoroquinolones 378
I. Gastrointestinal Tract 379
II. Central Nervous System 379
III. Skin and Allergic Reactions 381
1. Photosensitivity 381
2. Photoallergy 384
IV. Nephropathy and Crystalluria 384
V. Arthropathy and Musculoskeletal Disorders 385
VI. Body Systems 385
VII. Others 386
References 386
Contents XVII
CHAPTER 12
Concentration Effect Relationship of the Fluoroquinolones
R. Stahlmann and H. Lode. With 3 Figures 407
A. Introduction 407
B. Pharmacodynamic Data of Antimicrobials as a Basis for
Clinical Use 408
I. /J Lactams: Concentration Independent Killing Rate 408
II. Aminoglycosides: Concentration Dependent
Killing Rate 409
III. Fluoroquinolones 410
1. In Vitro Models 411
2. Animal Models 411
3. Clinical Data 414
4. Overall Evaluation of Pharmacodynamics 416
C. Pharmacokinetic Aspects 416
I. Protein Binding 417
II. Tissue Concentrations and Volume of Distribution 417
D. Summary and Conclusion 419
References 419
CHAPTER 13
Clinical Use of Quinolones
P. SCHACHT 421
A. Introduction 421
B. Urinary Tract Infections and Prostatitis 421
I. Acute Uncomplicated Urinary Tract Infection 422
II. Complicated Urinary Tract Infection 422
III. Prostatitis 422
C. Gastrointestinal Infections and Traveller s Diarrhea 425
I. Salmonella typhi Enteric Fever 425
II. Salmonella typhi Carriers 426
III. Salmonella Gastroenteritis Outbreaks 427
IV. Shigellosis 427
V. Cholera 428
VI. Traveller s Diarrhea Prevention 429
VII. Traveller s Diarrhea Therapy 429
D. Respiratory Tract Infections 429
I. Acute Exacerbation of Chronic Bronchitis 430
II. Pneumonia 432
III. Recurrent Respiratory Tract Infections in Patients with
Cystic Fibrosis 435
IV. Sinusitis 435
V. Bacterial Otitis (Chronic Suppurative Otitis Media) 436
VI. Malignant External Otitis 436
XVIII Contents
E. Osteomyelitis 437
F. Skin and Skin Structure Infection 438
G. Sexually Transmitted Diseases 439
I. Gonorrhea 439
II. Chancroid 440
III. Nongonococcal Urethritis 440
H. Intra abdominal Infections 440
I. Anaerobic Intra abdominal Infections 440
II. Cholangitis 441
III. Peritonitis in Chronic Ambulatory Dialysis Patients 441
IV. Gynecological Infections 441
I. Bacteremia and Sepsis 442
J. Surgical Prophylaxis 443
I. Transurethral Prostatic Surgery 443
II. Endoscopic Retrograde Cholangiopancreatography 443
III. Abdominal Surgery 443
K. Infections in Neutropenic Patients 444
I. Empirical Treatment of Febrile Neutropenic Patients 444
II. Prophylaxis in Neutropenic Cancer Patients 444
L. Use of Quinolones in Pediatrics 445
M. Remarks 445
References 445
CHAPTER 14
Future Aspects
S. Segev and E. Rubinstein 455
A. Introduction 455
B. Molecular Structure and Mechanism of Action 455
C. Antimicrobial Activity 458
I. Gram Positive Bacteria 459
1. Staphylococci 459
2. Streptococci 460
3. Enterococci 462
II. Anaerobic Bacteria 463
III. Mycobacterium tuberculosis 464
D. Bacterial Resistance 465
E. Future Use of Quinolones in Pediatrics 466
F. Antitumor Potential 467
G. New Attitudes 468
H. Directions of Future Research on the Quinolones 469
References 469
Subject Index 477
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| oclc_num | 36225972 |
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| owner | DE-355 DE-BY-UBR DE-12 DE-19 DE-BY-UBM DE-20 DE-188 DE-578 |
| owner_facet | DE-355 DE-BY-UBR DE-12 DE-19 DE-BY-UBM DE-20 DE-188 DE-578 |
| physical | XVIII, 491 S. Ill., graph. Darst. |
| publishDate | 1998 |
| publishDateSearch | 1998 |
| publishDateSort | 1998 |
| publisher | Springer |
| record_format | marc |
| series | Handbook of experimental pharmacology |
| series2 | Handbook of experimental pharmacology |
| spelling | Quinolone antibacterials [with 103 tables] contributors D. Beermann ... Ed. J. Kuhlmann ... Berlin [u.a.] Springer 1998 XVIII, 491 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Handbook of experimental pharmacology 127 Quinolone cabt Therapeutic Indications cabt Antiinfective Agents cabt Antibacteriële middelen gtt Chinolonen gtt Anti-Infective Agents therapeutic use Quinolone antibacterial agents Quinolones pharmacology Quinolones therapeutic use Gyrasehemmer (DE-588)4217839-3 gnd rswk-swf Antibiotikum (DE-588)4002257-2 gnd rswk-swf Infektionskrankheit (DE-588)4026879-2 gnd rswk-swf Pharmakologie (DE-588)4045687-0 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Gyrasehemmer (DE-588)4217839-3 s Antibiotikum (DE-588)4002257-2 s DE-604 Infektionskrankheit (DE-588)4026879-2 s Pharmakologie (DE-588)4045687-0 s Kuhlmann, Jochen Sonstige oth Beermann, Dieter Sonstige oth Handbook of experimental pharmacology 127 (DE-604)BV002390716 127 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007645057&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Quinolone antibacterials [with 103 tables] Handbook of experimental pharmacology Quinolone cabt Therapeutic Indications cabt Antiinfective Agents cabt Antibacteriële middelen gtt Chinolonen gtt Anti-Infective Agents therapeutic use Quinolone antibacterial agents Quinolones pharmacology Quinolones therapeutic use Gyrasehemmer (DE-588)4217839-3 gnd Antibiotikum (DE-588)4002257-2 gnd Infektionskrankheit (DE-588)4026879-2 gnd Pharmakologie (DE-588)4045687-0 gnd |
| subject_GND | (DE-588)4217839-3 (DE-588)4002257-2 (DE-588)4026879-2 (DE-588)4045687-0 (DE-588)4143413-4 |
| title | Quinolone antibacterials [with 103 tables] |
| title_auth | Quinolone antibacterials [with 103 tables] |
| title_exact_search | Quinolone antibacterials [with 103 tables] |
| title_full | Quinolone antibacterials [with 103 tables] contributors D. Beermann ... Ed. J. Kuhlmann ... |
| title_fullStr | Quinolone antibacterials [with 103 tables] contributors D. Beermann ... Ed. J. Kuhlmann ... |
| title_full_unstemmed | Quinolone antibacterials [with 103 tables] contributors D. Beermann ... Ed. J. Kuhlmann ... |
| title_short | Quinolone antibacterials |
| title_sort | quinolone antibacterials with 103 tables |
| title_sub | [with 103 tables] |
| topic | Quinolone cabt Therapeutic Indications cabt Antiinfective Agents cabt Antibacteriële middelen gtt Chinolonen gtt Anti-Infective Agents therapeutic use Quinolone antibacterial agents Quinolones pharmacology Quinolones therapeutic use Gyrasehemmer (DE-588)4217839-3 gnd Antibiotikum (DE-588)4002257-2 gnd Infektionskrankheit (DE-588)4026879-2 gnd Pharmakologie (DE-588)4045687-0 gnd |
| topic_facet | Quinolone Therapeutic Indications Antiinfective Agents Antibacteriële middelen Chinolonen Anti-Infective Agents therapeutic use Quinolone antibacterial agents Quinolones pharmacology Quinolones therapeutic use Gyrasehemmer Antibiotikum Infektionskrankheit Pharmakologie Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007645057&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV002390716 |
| work_keys_str_mv | AT kuhlmannjochen quinoloneantibacterialswith103tables AT beermanndieter quinoloneantibacterialswith103tables |