Fundamentals of medicinal chemistry:
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Chichester [u.a.]
Wiley
2003
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XV, 285 S. Ill., graph. Darst. |
| ISBN: | 0470843063 0470843071 |
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| adam_text | - 050 FUNDAMENTALS OF MEDICINAL CHEMISTRY GARETH THOMAS UNIVERSITY OF
PORTSMOUTH, UK WILEY CONTENTS PREFACE XI ACKNOWLEDGEMENTS XII
ABBREVIATIONS/ACRONYMS XIII 1 BIOLOGICAL MOLECULES 1 1.1 INTRODUCTION 1
1.2 AMINO ACIDS 1 1.2.1 INTRODUCTION 1 1.2.2 STRUCTURE 3 1.2.3
NOMENCLATURE 3 1.3 PEPTIDES AND PROTEINS 4 1.3.1 STRUCTURE 6 1.4
CARBOHYDRATES 10 1.4.1 THE STRUCTURE OF MONOSACCHARIDES 11 1.4.2 THE
NOMENCLATURE OF MONOSACCHARIDES 14 1.4.3 GLYCOSIDES 15 1.4.4
POLYSACCHARIDES 17 1.4.5 THE NOMENCLATURE OF POLYSACCHARIDES 18 1.4.6
NATURALLY OCCURRING POLYSACCHARIDES 18 1.5 LIPIDS 20 1.5.1 INTRODUCTION
20 1.5.2 FATTY ACIDS 20 1.5.3 ACYLGLYCEROLS (GLYCERIDES) 21 1.5.4
STEROIDS 21 1.5.5 TERPENES 22 1.5.6 PHOSPHOLIPIDS 23 1.5.7 GLYCOLIPIDS
25 1.6 NUCLEIC ACIDS 26 1.6.1 INTRODUCTION 26 1.6.2 DNA, STRUCTURE AND
REPLICATION 28 1.6.3 GENES AND THE HUMAN GENOME PROJECT 30 1.6.4 RNA,
STRUCTURE AND TRANSCRIPTION 31 1.6.5 CLASSIFICATION AND FUNCTION OF RNA
33 1.7 QUESTIONS 34 2 AN INTRODUCTION TO DRUGS AND THEIR ACTION 37 2.1
INTRODUCTION 37 2.2 WHAT ARE DRUGS AND WHY DO WE NEED NEW ONES? 37 2.3
DRUG DISCOVERY AND DESIGN, A HISTORICAL OUTLINE 39 2.4 SOURCES OF DRUGS
AND LEAD COMPOUNDS 43 VI CONTENTS 2.4.1 NATURAL SOURCES 43 2.4.2 DRUG
SYNTHESIS 45 2.4.3 MARKET FORCES AND ME-TOO DRUGS 45 2.5
CLASSIFICATION OF DRUGS 45 2.6 ROUTES OF ADMINISTRATION, THE
PHARMACEUTICAL PHASE 46 2.7 INTRODUCTION TO DRUG ACTION 49 2.7.1 THE
PHARMACOKINETIC PHASE 49 ABSORPTION 49 DISTRIBUTION 50 METABOLISM 51
ELIMININATION 51 2.7.2 BIOAVAILABILITY OF A DRUG 53 2.7.3 THE
PHARMACODYNAMIC PHASE 53 2.8 QUESTIONS 55 3 AN INTRODUCTION TO DRUG
DISCOVERY 57 3.1 INTRODUCTION 57 3.2 STEREOCHEMISTRY AND DRUG DESIGN 59
3.2.1 STRUCTURALLY RIGID GROUPS 59 3.2.2 CONFORMATION 60 3.2.3
CONFIGURATION 60 3.3 SOLUBILITY AND DRUG DESIGN 61 3.3.1 THE IMPORTANCE
OF WATER SOLUBILITY 62 3.4 SOLUBILITY AND DRUG STRUCTURE 63 3.5 SALT
FORMATION 64 3.6 THE INCORPORATION OF WATER SOLUBILIZING GROUPS IN A
STRUCTURE 65 3.6.1 THE TYPE OF GROUP 66 3.6.2 REVERSIBLY AND
IRREVERSIBLY ATTACHED GROUPS 66 3.6.3 THE POSITION OF THE WATER
SOLUBILIZING GROUP 67 3.6.4 METHODS OF INTRODUCTION 67 3.7 QUESTIONS 70
4 THE SAR AND QSAR APPROACHES TO DRUG DESIGN 71 4.1 STRUCTURE-ACTIVITY
RELATIONSHIPS (SARS) 71 4.2 CHANGING SIZE AND SHAPE 73 4.3 INTRODUCTION
OF NEW SUBSTITUENTS ^ 4.3.1 THE INTRODUCTION OF A GROUP IN AN
UNSUBSTITUTED POSITION 4.3.2 THE INTRODUCTION OF A GROUP BY REPLACING AN
EXISTING GROUP 4.4 QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSARS)
4.4.1 LIPOPHILICITY 79 PARTITION COEFFICIENTS (P) 79 LIPOPHILIC
SUBSTITUTION CONSTANTS (TT) 4.4.2 ELECTRONIC EFFECTS 82 THE HAMMETT
CONSTANT (O-) 4.4.3 STERIC EFFECTS ^ THE TAFT STERIC PARAMETER (E S )
* MOLAR REFRACTIVITY (MR) J ~ OTHER PARAMETERS CONTENTS VII 4.4.4 HANSCH
ANALYSIS CRAIG PLOTS 4.5 THE TOPLISS DECISION TREE 4.6 QUESTIONS
COMPUTER AIDED DRUG DESIGN 5.1 INTRODUCTION 5.1.1 MOLECULAR MODELLING
METHODS 5.1.2 COMPUTER GRAPHICS 5.2 MOLECULAR MECHANICS 5.2.1 CREATING A
MOLECULAR MODEL USING MOLECULAR MECHANICS 5.3 MOLECULAR DYNAMICS 5.3.1
CONFORMATIONAL ANALYSIS 5.4 QUANTUM MECHANICS 5.5 DOCKING 5.6 QUESTIONS
COMBINATORIAL CHEMISTRY 6.1 INTRODUCTION 6.1.1 THE DESIGN OF
COMBINATORIAL SYNTHESES 6.1.2 THE GENERAL TECHNIQUES USED IN
COMBINATORIAL SYNTHESIS 6.2 THE SOLID SUPPORT METHOD 6.2.1 PARALLEL
SYNTHESIS 6.2.2 FURKA S MIX AND SPLIT TECHNIQUE 6.3 ENCODING METHODS
6.3.1 SEQUENTIAL CHEMICAL TAGGING METHODS 6.3.2 STILL S BINARY CODE TAG
SYSTEM 6.3.3 COMPUTERIZED TAGGING 6.4 COMBINATORIAL SYNTHESIS IN
SOLUTION 6.5 SCREENING AND DECONVOLUTION 6.6 QUESTIONS SELECTED EXAMPLES
OF DRUG ACTION AT SOME COMMON TARGET AREAS 7.1 INTRODUCTION 7.2 EXAMPLES
OF DRUGS THAT DISRUPT CELL MEMBRANES AND WALLS 7.2.1 ANTIFUNGAL AGENTS
AZOLES ALLYLAMINES PHENOLS 7.2.2 ANTIBACTERIAL APENTS IONOPHORIC
ANTIBIOTIC ACTION CELL WALL SYNTHESIS INHIBITION 7.3 DRUGS THAT TARGET
ENZYMES 7.3.1 REVERSIBLE INHIBIHORS 7.3.2 IRREVERSIBLE INHIBITION 7.3.3
TRANSITION STATE INHIBITORS 7.4 DRUGS THAT TARGET RECEPTORS 7.4.1
AGONISTS 7.4.2 ANTAGONISTS 7.4.3 PARTIAL AGONISTS 85 88 89 92 95 95 96
98 98 102 104 105 105 109 110 113 113 115 116 117 118 12! 123 123 124
126 127 128 130 131 131 131 132 133 134 135 135 135 136 138 139 140 142
144 144 145 147 CONTENTS 7.5 DRUGS THAT TARGET NUCLEIC ACIDS 147 7.5.1
ANTIMETABOLITES 47 7.5.2 ENZYME INHIBITORS 1^0 7.5.3 INTERCALATION
AGENTS 15 7.5.4 ALKYLATING AGENTS 152 7.5.5 ANTISENSE DRUGS 7.5.6
CHAIN CLEAVING AGENTS 54 7.6 ANTIVIRAL DRUGS 155 7.6.1 NUCLEIC ACID
SYNTHESIS INHIBITORS 55 7.6.2 HOST CELL PENETRATION INHIBITORS 56
7.6.3 INHIBITORS OF VIRAL PROTEIN SYNTHESIS 57 7.7 QUESTIONS 157
PHARMACOKINETICS 159 8.1 INTRODUCTION TO PHARMACOKINETICS 159 8.1.1
GENERAL CLASSIFICATION OF PHARMACOKINETIC PROPERTIES 60 8.2
PHARMACOKINETICS AND DRUG DESIGN 160 8.3 PHARMACOKINETIC MODELS 161 8.4
INTRAVASCULAR ADMINISTRATION 162 8.4.1 INTRAVENOUS INJECTION (IV BOLUS)
63 8.4.2 CLEARANCE AND ITS SIGNIFICANCE 66 8.4.3 INTRAVENOUS INFUSION
6 8.5 EXTRAVASCULAR ADMINISTRATION 171 8.5.1 SINGLE ORAL DOSE 174
8.5.2 THE CALCULATION OF ( MAX AND C MAX 176 8.5.3 REPEATED ORAL DOSES
176 8.6 THE USE OF PHARMACOKINETICS IN DRUG DESIGN 177 8.7 QUESTIONS I
78 DRUG METABOLISM 181 9.1 INTRODUCTION 1 8 1 9.1.1 THE STEREOCHEMISTRY
OF DRUG METABOLISM 9.1.2 BIOLOGICAL FACTORS AFFECTING METABOLISM
9.1.3 ENVIRONMENTAL FACTORS AFFECTING METABOLISM 84 9.1.4 SPECIES AND
METABOLISM 184 9.2 SECONDARY PHARMACOLOGICAL IMPLICATIONS OF METABOLISM
I* 9.3 SITES OF ACTION I 84 9.4 PHASE I METABOLIC REACTIONS 1 9.4.1
OXIDATION 186 9.4.2 REDUCTION 186 9.4.3 HYDROLYSIS 189 9.4.4 HYDRATION
189 1 RQ 9.4.5 OTHER PHASE I REACTIONS 10 9.5 PHASE II METABOLIC ROUTES
I 90 9.6 PHARMACOKINETICS OF METABOLITES 1 9.7 DRUG METABOLISM AND DRUG
DESIGN 1^ 9.8 PRODRUGS L95 9.8.1 BIOPRECURSOR PRODRUGS 9.8.2 CARRIER
PRODRUGS CONTENTS IX 9.8.3 THE DESIGN OF PRODRUG SYSTEMS FOR SPECIFIC
PURPOSES 197 IMPROVING ABSORPTION AND TRANSPORT THROUGH MEMBRANES 197
IMPROVING PATIENT ACCEPTANCE 198 SLOW RELEASE 198 SITE SPECIFICITY 198
MINIMIZING SIDE EFFECTS 200 9.9 QUESTIONS 200 10 AN INTRODUCTION TO LEAD
AND ANALOGUE SYNTHESES 203 10.1 INTRODUCTION 203 10.2 ASYMMETRY IN
SYNTHESES 205 10.2.1 THE USE OF NON-STEREOSELECTIVE REACTIONS TO PRODUCE
STEREOSPECIFIC CENTRES 206 10.2.2 THE USE OF STEREOSELECTIVE REACTIONS
TO PRODUCE STEREOSPECIFIC CENTRES 207 10.2.3 GENERAL METHODS OF
ASYMMETRIC SYNTHESIS 208 METHODS THAT USE CATALYSTS TO OBTAIN
STEREOSELECTIVITY 210 METHODS THAT DO NOT USE CATALYSTS TO OBTAIN
STEREOSELECTIVITY 211 10.3 DESIGNING ORGANIC SYNTHESES 214 10.3.1 AN
INTRODUCTION TO THE DISCONNECTION APPROACH 214 10.4 QUESTIONS 220 11
DRUG DEVELOPMENT AND PRODUCTION 223 11.1 INTRODUCTION 223 11.2 CHEMICAL
DEVELOPMENT 224 11.2.1 CHEMICAL ENGINEERING ISSUES 225 11.2.2 CHEMICAL
PLANT, HEALTH AND SAFETY CONSIDERATIONS 226 11.2.3 SYNTHESIS QUALITY
CONTROL 227 11.2.4 A CASE STUDY 228 11.3 PHARMACOLOGICAL AND
TOXICOLOGICAL TESTING 231 11.4 DRUG METABOLISM AND PHARMACOKINETICS 234
11.5 FORMULATION DEVELOPMENT 235 11.6 PRODUCTION AND QUALITY CONTROL 235
11.7 PATENT PROTECTION 236 11.8 REGULATION 237 11.9 QUESTIONS 238
APPENDIX 239 A.I SICKLE-CELL ANAEMIA 239 A.2 BACTERIA 240 A.3 CELL
MEMBRANES 244 A.4 RECEPTORS 246 A.5 TRANSFER THROUGH MEMBRANES 249 A.6
REGRESSION ANALYSIS 250 A.7 ENZYMES 252 X CONTENTS A.8 PROSTAGLANDINS
255 A.9 CANCER 256 A. 10 VIRUSES 257 A. 11 BLOOD-BRAIN BARRIER 259 A. 12
ENZYME STRUCTURE AND SPECIES 260 ANSWERS TO QUESTIONS 261 SELECTED
FURTHER READING 273 INDEX 275
|
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| spelling | Thomas, Gareth Verfasser aut Fundamentals of medicinal chemistry Gareth Thomas Chichester [u.a.] Wiley 2003 XV, 285 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Chimie pharmaceutique Química médica larpcal Drug Design Pharmaceutical Preparations chemistry Pharmaceutical Preparations metabolism Pharmaceutical chemistry Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010427330&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Thomas, Gareth Fundamentals of medicinal chemistry Chimie pharmaceutique Química médica larpcal Drug Design Pharmaceutical Preparations chemistry Pharmaceutical Preparations metabolism Pharmaceutical chemistry Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| subject_GND | (DE-588)4132158-3 |
| title | Fundamentals of medicinal chemistry |
| title_auth | Fundamentals of medicinal chemistry |
| title_exact_search | Fundamentals of medicinal chemistry |
| title_full | Fundamentals of medicinal chemistry Gareth Thomas |
| title_fullStr | Fundamentals of medicinal chemistry Gareth Thomas |
| title_full_unstemmed | Fundamentals of medicinal chemistry Gareth Thomas |
| title_short | Fundamentals of medicinal chemistry |
| title_sort | fundamentals of medicinal chemistry |
| topic | Chimie pharmaceutique Química médica larpcal Drug Design Pharmaceutical Preparations chemistry Pharmaceutical Preparations metabolism Pharmaceutical chemistry Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| topic_facet | Chimie pharmaceutique Química médica Drug Design Pharmaceutical Preparations chemistry Pharmaceutical Preparations metabolism Pharmaceutical chemistry Pharmazeutische Chemie |
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