The practice of medicinal chemistry:
Saved in:
| Other Authors: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Amsterdam [u.a.]
Academic Press
2015
|
| Edition: | 4. ed. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis Klappentext |
| Item Description: | Literaturangaben |
| Physical Description: | XXII, 880 S. Ill., graph. Darst. 28 cm |
| ISBN: | 9780124172050 |
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Record in the Search Index
| _version_ | 1804175257304563712 |
|---|---|
| adam_text | Contents
List of Contributors xi
Foreword xiii
Preface to the Fourth Edition XV
Preface to the Third Edition xvii
Preface to the Second Edition xix
Preface to the First Edition xxi
_____________________i____________________
GENERAL ASPECTS OF
MEDICINAL CHEMISTRY
1. Medicinal Chemistry: Definitions and Objectives,
Drug Activity Phases, Drug Classification Systems
PETER IMM1NG
I. Definitions and Objectives 3
II. Drug Activity Phases 7
III. Drug Classification Systems 8
References 12
2. Evaluation of the Biological Activity
of Compounds: Techniques and Mechanism
of Action Studies
IAIN G. DOUGALL AND JOHN UNITT
I. Introduction 15
II. Drug Discovery Approaches and Screening Cascades 16
III. In Vitro Assays 17
IV. Ex Vivo Assays 38
V. In Vivo Assays 39
Acknowledgements 42
References 42
3. Drug Targets, Target Identification, Validation,
and Screening
WALTER M.M. VAN DEN BROECK
I. Introduction 45
II. What is a Drug Target? 46
III. The Purpose of Target Identification 47
IV. Target Options and Treatment Options 51
V. Target Deconvolution and Target Discovery 53
VI. Methods for Target Identification and Validation 54
VII. Target Validation 68
VIII. Conclusion 68
References 68
____________II____________
LEAD COMPOUND DISCOVERY
STRATEGIES
4. Strategies in the Search for New Lead Compounds
or Original Working Hypotheses
CAMILLE G. WERMUTH, BRUNO VILLOUTREIX, SERGE GRISONI,
ANNE OLIVIER AND JEAN-PHILIPPE ROCHER
I. introduction 73
II. First Strategy: Analog Design 74
III. Second Strategy: Systematic Screening 78
IV. Third Strategy: Exploitation of Biological Information 84
V. Fourth Strategy: Planned Research and Rational
Approaches 90
VI. Fifth Strategy: Applying Biophysical Technologies
and Computational Methods 93
VII. Conclusion 96
References 96
5. Natural Products as Pharmaceuticals and
Sources for Lead Structures
DAVID J. NEWMAN, GORDON M. CRAGG AND DAVID G.I. KINGSTON
I. Introduction 102
II. The Importance of Natural Products in Drug Discovery
and Development 102
III. The Design of an Effective Natural-Products-Based
Approach to Drug Discovery 106
IV. Examples of Natural Products or Analogues as Drugs 116
V. Future Directions in Natural Products as Drugs
and Drug Design Templates 128
VI, Summary 130
References 131
6. In Silico Screening: Hit Linding from
Database Mining
T1AGO RODRIGUES AND GISBERT SCHNEIDER
I. Introduction 141
II. in Silico Screening 143
III. De Novo Design 150
v
VI
CONTENTS
IV. Conclusions and Future Directions
Glossary
References
7. Fragment-Based Drug Discovery
VENKATA VELVADAPU, BENNETT T. FARMER AND ALLEN B. REITZ
I. Ligand—Protein Interactions: First Principles
II. What is Fragment-Based Drug Discovery?
III. Creation and Analysis of FBDD Libraries
IV. Fragment Screening Methods
V. Other Biochemical and Biophysical Methods
VI. Fragment Merging/Linking/Growing
VII. Fragment Hit Follow-Up, and Pitfalls to Avoid
VIII. Zelboraf®, First Approved Drug from FBDD
IX. Limitations of FBDD
X. Trends for the Future
References
8. Molecular Variations Based on Isosteric
Replacements
PAOLA CIAPETTI AND BRUNO GIETHLEN
I. Introduction
II. History: Development of the Isosterism Concept
III. Currently Encountered Isosteric and Bioisosteric
Modifications
IV. Scaffold Hopping
V. Analysis of the Modifications Resulting from Isosterism
VI. Minor Metalloids-Toxic Isosteres
References
9. Ring Transformations
CHRISTOPHE MORICE AND CAMILLE G. WERMUTH
I. Introduction
II. Analogical Approaches
III. Disjunctive Approaches
IV. Conjunctive Approaches
V. Conclusion
References
10. Macrocycles: Under-Explored and Poorly
Exploited Drug Class Despite the Proven
Therapeutic Potential
PIERRE RABOISSON
I. Nature as a Source of Macrocycles
II. Identification of Macrocyclic Drugs Using Either
Phenotypic Screen or Target-Based Approach
III. Macrocycles: The Drugs in the Middle Space
IV. Effect of the Macrocyclization on Drug-Like Properties
V. Interaction of Macrocycles with their Targets
VI. Synthesis of Macrocycles Library Enrichment
VII. Conclusion
References
_________________m_____________
PRIMARY EXPLORATION OF
STRUCTURE-ACTIVITY
RELATIONSHIPS
11. Conformational Restriction and Steric
Hindrance in Medicinal Chemistry
PETER WIPF, ERIN M. SKODA AND ANDRÉ MANN
I. Introduction 279
II. Case Studies 285
III. Summary and Outlook 297
References 297
12. Application Strategies for the Primary
Structure—Activity Relationship Exploration
CAMILLE G. WERMUTH, SERGE GRISONI, BRUNO VILLOUTREIX
AND JEAN-PHILIPPE ROCHER
I. Introduction 302
II. Preliminary Considerations 302
III. Hit Optimization Strategies 303
IV. Application Rules 312
References 317
13. Substituent Groups
PATRICK BAZZINI AND CAMILLE G. WERMUTH
I. Introduction 319
II. Methyl Groups 320
III. Effects of Unsaturated Groups 331
IV. Effects of Halogénation 338
V. Effects of Hydroxylation 345
VI. Effects of Thiols and Other Sulfur-Containing
Groups 346
VII. Acidic Functions 349
VIII. Basic Groups 351
IX. Attachment of Additional Binding Sites 352
References 354
14- The Role of Functional Groups in
Drug-Receptor Interactions
LAURENT SCHAEFFER
I. Introduction 359
II. General Principles 360
III. The Importance of the Electrostatic and Steric
Match Between Drug and Receptor 360
IV. The Strengths of Functional Group Contributions
to Drug-Receptor Interactions 370
V. Cooperative Binding 376
References 377
154
156
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166
167
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172
174
175
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177
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186
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224
229
233
243
244
258
260
263
263
267
268
270
270
271
274
274
274
CONTENTS
Vil
15. Compound Properties and their Influence
on Drug Quality
HONGMING CHEN, OLA ENGKVIST AND THIERRY KOOEJ
I. Introduction
II. Compound Drug-Likeness Analysis
III. Compound Promiscuity
IV. Compound ADMET Properties
V. Ligand Binding Efficiency Metrics
VI. Conclusions and Future Outlook
References
16. Pharmacological Space
ANDREW L. HOPKINS
I. What is Pharmacological Space?
II. Chemical Space
III. Target Space
IV Conclusions
Acknowledgments
References
17. Systems Biology: A New Paradigm for Drug
Discovery
HIBA ABI HUSSEIN, ALEXANDRE BORREL, LESLIE REGAD,
DELPHINE RATTERS, ANNE BADEL, COLETTE GENEIX,
MICHEL PETITJEAN, ANN E-CLAUDE CAMPROUX AND
OLIVIER TABOUREAU
I. Introduction
II. Drug-Target Space (off-target)
III. Systems Biology Space
IV. Phenotype Space
V. Examples
VI. Conclusion
References
_______________________IV______________________
SUBSTITUENTS AND FUNCTIONS
QUALITATIVE ASPECTS OF
STRUCTURE-ACTIVITY
RELATIONSHIPS
18. Optical Isomerism in Drugs
CAMILLE G. WERMUTH
I. Introduction
II. Experimental Facts and their Interpretation
III. Optical Isomerism and Pharmacodynamic Aspects
IV. Optical Isomerism and Pharmacokinetic Aspects
V. Practical Considerations
References
19. Multitarget Drugs: Strategies and Challenges
for Medicinal Chemists
RICHARD MORPHY AND ZORAN RANKOVIC
I. Introduction 449
II. Strategies for Lead Generation 451
III. Main Areas of Focus in Discovery 453
IV. Optimization of the Activity Profile and Wider
Selectivity 465
V. The Physicochemical Challenge 467
VI. Summary 469
References 470
20. Selective Optimization of Side Activities
(SOSA) in Drug Discovery
TIM JONCKERS
I. Introduction 473
II. Ritonavir: Rejuvenating a Suboptimal Drug 474
III. Sildenafil, Side Effects are Not Always Bad 477
IV. Nucleotide Prodrugs: Chemical Trojan Horses 478
V. Miltefosine 481
VI. Aztreonam 483
VII. Conclusions 485
References 485
__________________V___________________
SPATIAL ORGANIZATION, RECEPTOR
MAPPING AND MOLECULAR
MODELING
21. Pharmacophore Identification and
Pseudo-Receptor Modeling
GERHARD WOIBER AND WOLFGANG SIPPL
I. Introduction 489
II. Methodology 493
III. Advanced Approaches 497
IV. Application Study: Novel Histamine H3-Receptor
Antagonists 501
V. Recent Developments and Outlook 505
VI. Conclusions 507
References 507
22. Protein Crystallography and Drug Discovery
JEAN-MICHEL RONDEAU AND HERMAN SCHREUDER
I. Introduction 511
II. Historical Background 512
III. Basic Principles and Methods of Protein Crystallography 514
IV Applications 527
V. Two Selected Examples 531
VI. Outlook 532
References 533
379
380
382
384
386
390
391
393
395
399
405
407
407
409
413
415
418
418
421
421
!:
429
430
435
437
439
444
Vlll
CONTENTS
23. Physiological Aspects Determining the
Pharmacokinetic Properties of Drugs
KOEN BOUSSERY, FRANS M. BELPAIRE AND JOHAN VAN DE VOORDE
I. Introduction 539
II. Passage of Drugs Through Biological Barriers 541
III. Drug Absorption 542
IV. Drug Distribution 547
V. Drug Elimination 548
VI. Some Pharmacokinetic Parameters and Terminology 552
VII. Variability in Pharmacokinetics 557
Further Reading 559
24. Biotransformation Reactions and their Enzymes
BERNARD TESTA AND BERND CLEMENT
I. Introduction 561
II. Functionalization Reactions 563
III. Conjugation Reactions 571
IV. Biological Factors Influencing Drug Metabolism 579
V. What is the Relative Significance of These Many
Types of Metabolic Reactions? 580
VI. Concluding Remarks 581
References 582
25. Biotransformations Leading to Toxic
Metabolites: Chemical Aspects
ANNE-CHRISTINE MACHEREY AND PATRICK M. DANSETTE
I. Historical Background 585
II. Introduction 586
III. Reactions Involved in Bioactivation Processes 587
IV. Examples of Metabolic Conversions Leading to Toxic
Metabolites 599
V. Conclusion 608
Acknowledgments 611
References 611
26. Drug Transport Mechanisms and their Impact
on the Disposition and Effects of Drugs
JEAN-MICHEL SCHERRMANN
I. Introduction 615
II. Biology and Function of Transporters 616
III. Transporters in Drug Disposition 620
IV. Roles of Transporters in Drug Pharmacokinetics,
Pharmacodynamics and Toxicology 624
V. Conclusion 628
Acknowledgments 628
References 528
27. Strategies for Enhancing Oral Bioavailability
and Brain Penetration
GERHARD GROSS
I. Introduction 631
II. Enhancing Oral Bioavailability 632
III. Enhancing Brain Penetration 645
References 653
28. Designing Prodrugs and Bioprecursors
YONG MI CHOI-SLEDESKI AND CAMILLE G. WERMUTH
I. Introduction 657
II. The Different Kinds of Prodrugs 658
III. Practical Applications of Carrier Prodrugs 661
IV. Unique Approaches to Carrier Prodrug Design 668
V. Bioprecursor Prodrug Examples 686
VI. Discussion 690
VII. Difficulties and Limitations 690
VIII. Conclusion 691
References 692
_________________V1_________________
CHEMICAL MODIFICATIONS
INFLUENCING THE
PHARMACOKINETIC PROPERTIES
29. Drug Delivery with Organic Solvents
or Colloidal Dispersed Systems
BERND U. RIEBESEHL
I. Introduction 699
II. Physicochemical Drug Properties 700
III. Oral Drug Delivery 700
IV Parenteral Drug Delivery 704
References 720
30. Preparation of Water-Soluble Compounds by
Covalent Attachment of Solubilizing Moieties
CAMILLE G. WERMUTH AND DOMINIQUE LESUISSE
I. Introduction 723
II. Solubilization Strategies 724
III. Acidic Solubilizing Chains 726
IV. Basic Solubilizing Chains 734
V. Nonionizable Side Chains 739
VI. Concluding Remarks 741
References 742
31. Improving the Water-Solubility of Compounds by
Molecular Modification to Disrupt Crystal Packing
MINORU ISH1KAWA AND YUICHI HASHIMOTO
I. Introduction 747
II. Rationale for Disruption of Crystal Packing as an
Alternative Method to Improve Solubility 748
III. Improvement of Solubility by Disrupting
Intermolecular Hydrogen Bonds
749
CONTENTS
IX
IV. Improvement of Solubility by Disrupting Molecular
Planarity 751
V. Improvement of Solubility by Bending the Molecular
Structure 760
VI. Advantages of Improving Solubility by Molecular
Modification to Weaken Intermolecular Interaction 762
VII. Conclusion 763
References 764
32. Chemical and Physicochemical Approaches to
Solve Formulation Problems
HARVEY LIEBERMAN AND N. MURTIVEMURI
I. Introduction 767
II. Stability 767
III. Bioavailability 774
IV. Modifying the Duration of Action 781
V. Manufacturing Issues 782
VI. Adapting to Patient’s Needs 783
References 788
33. Discover a Drug Substance, Formulate, and
Develop It to a Product
PIERRE deMONTIGNY, DAVID HARRIS, CHRIS HO, FRANZ WEIBERTH,
BRUNO GAILI AND BERNARD FALLER
I. Introduction 793
II. The Discovery Phase 794
III. Defining Experimental Formulations, the Creative Phase 796
IV. Preparation for a New Drug-Product Launch 800
V. Conclusion: Drug Discovery and Development
in Industry 801
Reference 802
_________________VII__________________
PHARMACEUTICAL AND CHEMICAL
MEANS TO SOLUBILITY AND
FORMULATION PROBLEMS
34. Drug Nomenclature
RAFFAEIXA.G. BALOCCO MATTAVELU, Jl-CUi DONG, SOPHIE LASSEUR,
A. ROMEO AND SABINE KOPP
III. Drug Nomenclature 808
IV. Use and Protection of Nonproprietary Names 819
V. Summary 819
References 820
Annex 820
35. Web Alert: Using the Internet for Medicinal
Chemistry
DAVID CAVALLA
I. Introduction 825
II. Blogs 826
III. Wikis 826
IV. Compound Information 827
V. Biological Properties of Compounds 829
VI. Drug Information 831
VII. Physical Chemical Information 832
VIII. Prediction and Calculation of Molecular Properties 832
IX. Chemical Suppliers 834
X. Chemical Synthesis 835
XI. Chemoinformatics Software Programs 836
XII. Chemical Analysis 836
XIII. Chemical Publications 837
XIV. Patent Information 838
XV. Toxicology 839
XVI. Meta-Sites and Technology Service Provider
Databases 841
XVII. Conclusion 842
36. Protection of Inventions in Medicinal
Chemistry
RICHARD LUTHI AND CHRISTOPHER BRICE
I. Patents and the Medicinal Chemist 843
II. What Kinds of Medical Inventions can be Patented? 845
III. The Basics of Patent Law 846
IV. The Role of the Medicinal Chemist in the Patent
Arena 858
V. Patents as a Source of Scientific Information 860
VI. Other Forms of Protection 861
VII. Conclusion 862
Index 863
I. Introduction
II. Trade Names and Nonproprietary Names
807
807
|
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| building | Verbundindex |
| bvnumber | BV042944995 |
| classification_rvk | VS 5000 YV 3300 |
| ctrlnum | (OCoLC)915351804 (DE-599)OBVAC12254823 |
| dewey-full | 615.19 |
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| dewey-ones | 615 - Pharmacology and therapeutics |
| dewey-raw | 615.19 |
| dewey-search | 615.19 |
| dewey-sort | 3615.19 |
| dewey-tens | 610 - Medicine and health |
| discipline | Chemie / Pharmazie Medizin |
| edition | 4. ed. |
| format | Book |
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| oclc_num | 915351804 |
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| owner | DE-20 DE-11 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-83 |
| owner_facet | DE-20 DE-11 DE-19 DE-BY-UBM DE-355 DE-BY-UBR DE-83 |
| physical | XXII, 880 S. Ill., graph. Darst. 28 cm |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Academic Press |
| record_format | marc |
| spelling | The practice of medicinal chemistry ed. by Camille Georges Wermuth ... 4. ed. Amsterdam [u.a.] Academic Press 2015 XXII, 880 S. Ill., graph. Darst. 28 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Pharmaceutical chemistry Drugs Design Klinische Chemie (DE-588)4135255-5 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf (DE-588)4151278-9 Einführung gnd-content Pharmazeutische Chemie (DE-588)4132158-3 s DE-604 Klinische Chemie (DE-588)4135255-5 s 1\p DE-604 Wermuth, Camille Georges edt Digitalisierung UB Regensburg - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028371349&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028371349&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | The practice of medicinal chemistry Pharmaceutical chemistry Drugs Design Klinische Chemie (DE-588)4135255-5 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| subject_GND | (DE-588)4135255-5 (DE-588)4132158-3 (DE-588)4151278-9 |
| title | The practice of medicinal chemistry |
| title_auth | The practice of medicinal chemistry |
| title_exact_search | The practice of medicinal chemistry |
| title_full | The practice of medicinal chemistry ed. by Camille Georges Wermuth ... |
| title_fullStr | The practice of medicinal chemistry ed. by Camille Georges Wermuth ... |
| title_full_unstemmed | The practice of medicinal chemistry ed. by Camille Georges Wermuth ... |
| title_short | The practice of medicinal chemistry |
| title_sort | the practice of medicinal chemistry |
| topic | Pharmaceutical chemistry Drugs Design Klinische Chemie (DE-588)4135255-5 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| topic_facet | Pharmaceutical chemistry Drugs Design Klinische Chemie Pharmazeutische Chemie Einführung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028371349&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028371349&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wermuthcamillegeorges thepracticeofmedicinalchemistry |