The Practice of Medicinal Chemistry
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1 A The Practice of Medicinal Chemistry Edited by CAMILLE G. WERMUTH Laboratoire de Pharmacochimie Moleculaire, Faculte de Pharmacie, Universite Louis Pasteur, Illkirch, France ACADEMIC PRESS Harcourt Brace and Company, Publishers London San Diego New York Boston Sydney Tokyo Toronto
2 Contents Contributors Foreword Preface ix xiii xv Part I: General Aspects of Medicinal Chemistry 1 Medicinal chemistry: Definition and objectives. Drug and disease classifications 3 2 Discovering new drugs: the legacy of the past, present approaches, and hopes for the future 11 Philippe Meyer 3 Measurement and expression of drug effects 25 Jean-Paul Kan 4 The three main phases of drug activity: the pharmaceutical, the pharmacokinetic and the pharmacodynamic phases 41 Part II: Drug Targets and Lead Compound Discovery Strategies 5 Drug targets molecular mechanisms of drug action 55 Jean-Pierre Gies 6 Strategies in the search for new lead compounds or original working hypotheses 81
3 vi Contents 7 Natural products as pharmaceuticals and sources for lead structures David G.I. Kingston 8 Combinatorial libraries and high-throughput synthesis Sheila Hobbs de Witt 9 Synthesis of peptide libraries for lead structure screening Victor J. Hruby 10 The contribution of molecular biology to drug discovery Adrian N. Hobden 11 Electronic screening: Lead finding from database mining Hans-Peter Weber Part III: Primary Exploration of Structure-Activity Relationships 12 Molecular variations in homologous series: Vinylogues and benzologues 13 Molecular variations based on isosteric replacements 14 Ring transformations 15 Identical and nonidentical twin drugs Jean-Jacques Bourguignon 16 Application strategies for primary structure activity relationship exploration Part IV: Substituents and Functions: Qualitative and Quantitative Aspects of Structure Activity Relationships 17 Specific substituent effects 18 The role of functional groups in drug receptor interactions Peter R. Andrews 19 Quantitative approaches to structure activity relationships Han van de Waterbeemd Part V: Spatial Organization, Receptor Mapping and Molecular Modelling 20 Stereochemical aspects of drug action I: Conformational restriction, steric hindrance and hydrophobic collapse Phillip A. Hart and Daniel H Rich 21 Stereochemical aspects of drug action II: Optical isomerism Miklds Simonyi and Gdbor Maksay
4 Contents vii 22 Pharmacophore identification and receptor mapping 437 Hans-Dieter Hb'ltje 23 Three-dimensional quantitative structure activity relationships: D 2 dopamine agonists as an example 459 Yvonne Connolly Martin and C. Thomas Lin 24 The use of X-ray structures of receptors and enzymes in drug discovery 485 Jean-Michel Rondeau and Herman Schreuder 25 Protein homology modelling and drug discovery 523 Marcel F. Hibert 26 The transition from agonist to antagonist activity: Symmetry and other considerations 547 David J. Triggle 27 Design of peptidomimetics 571 Hiroshi Nakanishi and Michael Kahn Part VI: Chemical Modifications Influencing the Pharmacokinetic Properties 28 The fate of xenobiotics in living organisms 593 Frans M. Belpaire and Marc G. Bogaert 29 Biotransformation reactions 615 and Bernard Testa 30 Chemical aspects of biotransformations leading to toxic metabolites 643 Andre Picot and Anne-Christine Macherey 31 Designing prodrugs and bioprecursors I: Carrier prodrugs 671, Jean-Cyr Gaignault and Christian Marchandeau 32 Designing prodrugs and bioprecursors II: Bioprecursor prodrugs Macromolecular carriers for drug targeting 717 Etienne H. Schacht, Stefan Vansteenkiste and Len Seymour Part VII: Pharmaceutical and Chemical Formulation Problems 34 Preparation of water-soluble compounds through salt formation 739 Bradley D. Anderson and Karl P. Flora 35 Preparation of water-soluble compounds by covalent attachment of solubilizing moieties Drug solubilization with organic solvents, or using micellar solutions or other colloidal dispersed systems 777 Kurt H. Bauer 37 Improvement of drug properties by cydodextrins 793 Kaneto Uekama and Fumitoshi Hirayama
5 viii Contents 38 Chemical and physicochemical solutions to formulation problems 827 Part VIII: Development of New Drugs: Legal and Economic Aspects 39 From discovery to market availability 847 Jacques A. Dangoumau 40 Drug nomenclature 863 Sabine Kopp-Kubel 41 Legal aspects of product protection - what a medicinal chemist should know about patent protection 879 Maria Souleau 42 The consumption and production of pharmaceuticals 903 Bryan G. Reuben Index 939 A colour plate section can be found between pages 446 and 447.
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