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Antibacterial Agents: Chemistry, Mode of Action, Mechanisms of Resistance and Clinical Applications

ISBN: 978-0-470-97245-8
378 pages
July 2012
Antibacterial Agents: Chemistry, Mode of Action, Mechanisms of Resistance and Clinical Applications (0470972459) cover image
Antibacterial agents act against bacterial infection either by killing the bacterium or by arresting its growth. They do this by targeting bacterial DNA and its associated processes, attacking bacterial metabolic processes including protein synthesis, or interfering with bacterial cell wall synthesis and function.

Antibacterial Agents is an essential guide to this important class of chemotherapeutic drugs. Compounds are organised according to their target, which helps the reader understand the mechanism of action of these drugs and how resistance can arise. The book uses an integrated “lab-to-clinic” approach which covers drug discovery, source or synthesis, mode of action, mechanisms of resistance, clinical aspects (including links to current guidelines, significant drug interactions, cautions and contraindications), prodrugs and future improvements.

Agents covered include:
  • agents targeting DNA - quinolone, rifamycin, and nitroimidazole antibacterial agents
  • agents targeting metabolic processes -  sulfonamide antibacterial agents and trimethoprim
  • agents targeting protein synthesis - aminoglycoside, macrolide and tetracycline antibiotics, chloramphenicol, and oxazolidinones
  • agents targeting cell wall synthesis - β-Lactam and glycopeptide antibiotics, cycloserine, isonaizid, and daptomycin

Antibacterial Agents will find a place on the bookshelves of students of pharmacy, pharmacology, pharmaceutical sciences, drug design/discovery, and medicinal chemistry, and as a bench reference for pharmacists and pharmaceutical researchers in academia and industry.

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Preface xiii

SECTION 1 INTRODUCTION TO MICROORGANISMS AND ANTIBACTERIAL CHEMOTHERAPY 1

1.1 Microorganisms 3

Key points 3

1.1.1 Classification 3

1.1.2 Structure 4

1.1.3 Antibacterial targets 6

1.1.4 Bacterial detection and identification 17

1.1.5 Other than its mode of action, what factors determine the antibacterial activity of a drug? 25

1.1.6 Bacterial resistance 27

1.1.7 The ‘post-antibiotic age’? 29

References 31

Questions 33

SECTION 2 AGENTS TARGETING DNA 35

2.1 Quinolone antibacterial agents 37

Key points 37

2.1.1 Discovery 37

2.1.2 Synthesis 39

2.1.3 Bioavailability 41

2.1.4 Mode of action and selectivity 44

2.1.5 Bacterial resistance 45

2.1.6 Clinical applications 47

2.1.7 Adverse drug reactions 50

2.1.8 Drug interactions 55

2.1.9 Recent developments 56

References 60

2.2 Rifamycin antibacterial agents 63

Key points 63

2.2.1 Discovery 63

2.2.2 Synthesis 65

2.2.3 Bioavailability 68

2.2.4 Mode of action and selectivity 69

2.2.5 Bacterial resistance 71

2.2.6 Clinical applications 71

2.2.7 Adverse drug reactions 77

2.2.8 Drug interactions 78

2.2.9 Recent developments 81

References 81

2.3 Nitroimidazole antibacterial agents 85

Key points 85

2.3.1 Discovery 85

2.3.2 Synthesis 86

2.3.3 Bioavailability 86

2.3.4 Mode of action and selectivity 87

2.3.5 Mechanisms of resistance 89

2.3.6 Clinical applications 90

2.3.7 Adverse drug reactions 94

2.3.8 Drug interactions 95

2.3.9 Recent developments 96

References 97

Questions 101

SECTION 3 AGENTS TARGETING METABOLIC PROCESSES 103

3.1 Sulfonamide antibacterial agents 105

Key points 105

3.1.1 Discovery 105

3.1.2 Synthesis 107

3.1.3 Bioavailability 108

3.1.4 Mode of action and selectivity 111

3.1.5 Bacterial resistance 114

3.1.6 Clinical applications 115

3.1.7 Adverse drug reactions 119

3.1.8 Drug interactions 121

3.1.9 Recent developments 123

References 124

3.2 Trimethoprim 127

Key points 127

3.2.1 Discovery 127

3.2.2 Synthesis 128

3.2.3 Bioavailability 130

3.2.4 Mode of action and selectivity 130

3.2.5 Bacterial resistance 136

3.2.6 Clinical applications 136

3.2.7 Adverse drug reactions 138

3.2.8 Drug interactions 138

3.2.9 Recent developments 139

References 140

Questions 145

SECTION 4 AGENTS TARGETING PROTEIN SYNTHESIS 147

4.1 Aminoglycoside antibiotics 149

Key points 149

4.1.1 Discovery 149

4.1.2 Synthesis 152

4.1.3 Bioavailability 156

4.1.4 Mode of action and selectivity 158

4.1.5 Bacterial resistance 160

4.1.6 Clinical applications 161

4.1.7 Adverse drug reactions 165

4.1.8 Drug interactions 167

4.1.9 Recent developments 168

References 168

4.2 Macrolide antibiotics 173

Key points 173

4.2.1 Discovery 173

4.2.2 Synthesis 175

4.2.3 Bioavailability 177

4.2.4 Mode of action and selectivity 180

4.2.5 Bacterial resistance 181

4.2.6 Clinical applications 182

4.2.7 Adverse drug reactions 187

4.2.8 Drug interactions 189

4.2.9 Recent developments 191

References 193

4.3 Tetracycline antibiotics 197

Key points 197

4.3.1 Discovery 197

4.3.2 Synthesis 200

4.3.3 Bioavailability 205

4.3.4 Mode of action and selectivity 210

4.3.5 Bacterial resistance 213

4.3.6 Clinical applications 217

4.3.7 Adverse drug reactions 223

4.3.8 Drug interactions 224

4.3.9 Recent developments 224

References 225

4.4 Chloramphenicol 231

Key points 231

4.4.1 Discovery 231

4.4.2 Synthesis 231

4.4.3 Bioavailability 232

4.4.4 Mode of action and selectivity 235

4.4.5 Bacterial resistance 235

4.4.6 Clinical applications 236

4.4.7 Adverse drug reactions 239

4.4.8 Drug interactions 239

4.4.9 Recent developments 240

References 241

4.5 Oxazolidinones 243

Key points 243

4.5.1 Discovery 243

4.5.2 Synthesis 245

4.5.3 Bioavailability 247

4.5.4 Mode of action and selectivity 248

4.5.5 Bacterial resistance 249

4.5.6 Clinical applications 251

4.5.7 Adverse drug reactions 252

4.5.8 Drug interactions 253

4.5.9 Recent developments 254

References 254

Questions 259

SECTION 5 AGENTS TARGETING CELL-WALL SYNTHESIS 261

5.1 b-Lactam antibiotics 263

Key points 263

5.1.1 Discovery 263

5.1.2 Synthesis 272

5.1.3 Bioavailability 277

5.1.4 Mode of action and selectivity 284

5.1.5 Bacterial resistance 285

5.1.6 Clinical applications 290

5.1.7 Adverse drug reactions 296

5.1.8 Drug interactions 298

5.1.9 Recent developments 300

References 301

5.2 Glycopeptide antibiotics 305

Key points 305

5.2.1 Discovery 305

5.2.2 Synthesis 306

5.2.3 Bioavailability 307

5.2.4 Mode of action and selectivity 308

5.2.5 Bacterial resistance 309

5.2.6 Clinical applications 313

5.2.7 Adverse drug reactions 314

5.2.8 Drug interactions 316

5.2.9 Recent developments 316

References 317

5.3 Cycloserine 319

Key points 319

5.3.1 Discovery 319

5.3.2 Synthesis 320

5.3.3 Bioavailability 320

5.3.4 Mode of action and selectivity 321

5.3.5 Bacterial resistance 323

5.3.6 Clinical applications 323

5.3.7 Adverse drug reactions 325

5.3.8 Drug interactions 325

5.3.9 Recent developments 325

References 325

5.4 Isoniazid 327

Key points 327

5.4.1 Discovery 327

5.4.2 Synthesis 328

5.4.3 Bioavailability 329

5.4.4 Mode of action and selectivity 329

5.4.5 Bacterial resistance 330

5.4.6 Clinical applications 331

5.4.7 Adverse drug reactions 333

5.4.8 Drug interactions 334

5.4.9 Recent developments 335

References 335

5.5 Daptomycin 339

Key points 339

5.5.1 Discovery 339

5.5.2 Synthesis 340

5.5.3 Bioavailability 341

5.5.4 Mode of action and selectivity 341

5.5.5 Bacterial resistance 343

5.5.6 Clinical applications 343

5.5.7 Adverse drug reactions 344

5.5.8 Drug interactions 345

5.5.9 Recent developments 345

References 346

Questions 349

Index 351

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  • By categorizing and presenting antibacterial agents by target rather than by chemical class the book supports the thorough comprehension of the mechanism of action of these agents and also how resistance can arise.
  • Integrated “lab-to-clinic” approach covers aspects from drug discovery and mechanism of action through to clinical applications.
  • Incorporates results from the relevant Cochrane reviews.
  • Literature sources are provided for further reading
  • Diagrams are presented in full colour

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