Pharmacokinetics and metabolism in drug design:
Gespeichert in:
| Hauptverfasser: | , , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim [u.a.]
Wiley-VCH
2006
|
| Ausgabe: | 2., rev. ed. |
| Schriftenreihe: | Methods and principles in medicinal chemistry
31 |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Literaturangaben |
| Beschreibung: | XIX, 187 S. Ill., graph. Darst. |
| ISBN: | 3527313680 9783527313686 |
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Datensatz im Suchindex
| _version_ | 1804136200449032192 |
|---|---|
| adam_text | Contents
Preface IX
Abbreviations and Symbols XIII
1 Physicochemistry 1
1.1 Physicochemistry and Pharmacokinetics 1
1.2 Partition and Distribution Coefficient as Measures of Lipophilicity 2
1.3 Limitations on the Use of 1 Octanol 5
1.4 Further Understanding of Log P 6
1.4.1 Unravelling the Principal Contributions to Log P 6
1.4.2 Hydrogen Bonding 6
1.4.3 Molecular Size and Shape 8
1.5 Alternative Lipophilicity Scales 10
1.5.1 Different Solvent Systems 10
1.5.2 Chromatographic Approaches 10
1.5.3 Liposome Partitioning 10
1.6 Computational Approaches to Lipophilicity 11
1.7 Membrane Systems to Study Drug Behaviour 12
1.8 Dissolution and Solubility 13
1.8.1 Why Measure Solubility? 13
1.8.2 Calculated Solubility 14
1.9 Ionisation (pKa) 35
2 Pharmacokinetics 19
2.1 Setting the Scene 19
2.2 Intravenous Administration: Volume of Distribution 19
2.3 Intravenous Administration: Clearance 20
2.4 Intravenous Administration: Clearance and Half life 22
2.5 Intravenous Administration: Infusion 23
2.6 Oral Administration 25
2.7 Repeated Doses 26
2.8 Development of the Unbound (Free) Drug Model 28
2.9 Unbound Drug and Drug Action 28
Pharmacokinetics and Metabolism in Drug Design.
Dennis A. Smith, Han van de Waterbeemd, Don K. Walker (Eds.)
Copyright © 2006 WILEY VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 3 527 31368 0
VI I Contents
2.10 Unbound Drug Model and Barriers to Equilibrium 31
2.11 Slow Offset Compounds 33
2.12 Factors Governing Unbound Drug Concentration 35
3 Absorption 39
3.1 The Absorption Process 39
3.2 Dissolution 40
3.3 Membrane Transfer 42
3.4 Barriers to Membrane Transfer 46
3.5 Models for Absorption Estimation 49
3.6 Estimation of Absorption Potential 53
3.7 Computational Approaches 52
4 Distribution 55
4.1 Membrane Transfer Access to the Target 55
4.2 Brain Penetration 56
4.3 Volume of Distribution and Duration 59
4.4 Distribution and Tmax 64
5 Clearance 67
5.1 The Clearance Processes 67
5.2 Role of Transport Proteins in Drug Clearance 68
5.3 Interplay Between Metabolic and Renal Clearance 70
5.4 Role of Lipophilicity in Drug Clearance 71
6 Renal Clearance 83
6.1 Kidney Anatomy and Function 83
6.2 Lipophilicity and Reabsorption by the Kidney 84
6.3 Effect of Charge on Renal Clearance 85
6.4 Plasma Protein Binding and Renal Clearance 85
6.5 Balancing Renal Clearance and Absorption 87
6.6 Renal Clearance and Drug Design 88
7 Metabolic (Hepatic) Clearance 91
7.1 Function of Metabolism (Biotransformation) 91
7.2 Cytochrome P450 92
7.2.1 Catalytic Selectivity of CYP2D6 94
7.2.2 Catalytic Selectivity of CYP2C9 97
7.2.3 Catalytic Selectivity of CYP3A4 98
7.3 Other Oxidative Metabolism Processes 104
7.4 Oxidative Metabolism and Drug Design 107
7.5 Non Specific Esterases 109
7.5.1 Function of Esterases 109
7.5.2 Ester Drugs as Intravenous and Topical Agents 110
7.6 Prodrugs to Aid Membrane Transfer ill
Contents IVII
7.7 Enzymes Catalysing Drug Conjugation 112
7.7.1 Glucuronyl and Sulpho Transferases 112
7.7.2 Methyl Transferases 115
7.7.3 Glutathione S Transferases 115
7.8 Stability to Conjugation Processes 116
7.9 Pharmacodynamics and Conjugation 117
8 Toxicity 123
8.1 Toxicity Findings 121
8.1.1 Pharmacophore induced Toxicity 122
8.1.2 Structure related Toxicity 123
8.1.3 Metabolism induced Toxicity 125
8.2 Importance of Dose Size 126
8.3 Epoxides 126
8.4 Quinone Imines 128
8.5 Nitrenium Ions 133
8.6 Iminium Ions 134
8.7 Hydroxylamines 336
8.8 Thiophene Rings 237
8.9 Thioureas 139
8.10 Chloroquinolines 139
8.11 Stratification of Toxicity 240
8.12 Toxicity Prediction: Computational Toxicology 243
8.13 Toxicogenomics 342
8.14 Enzyme Induction (CYP3A4) and Drug Design 142
8.15 Enzyme Inhibition and Drug Design 346
9 Inter Species Scaling 353
9.1 Objectives of Inter Species Scaling 353
9.2 Allometric Scaling 253
9.2.1 Volume of Distribution 254
9.2.2 Clearance 356
9.3 Species Scaling: Adjusting for Maximum Life Span Potential 357
9.4 Species Scaling: Incorporating Differences in Metabolic
Clearance 258
9.5 Inter Species Scaling for Clearance by Hepatic Uptake 259
9.6 Elimination Half Life 363
9.7 Scaling to Pharmacological Effect 262
9.8 Single Animal Scaling 363
10 High(er) Throughput ADME Studies 265
10.1 The High Throughput Screening (HTS) Trend 265
10.2 Drug Metabolism and Discovery Screening Sequences 265
10.3 Physicochemistry 267
10.3.1 Solubility 368
VIII I Contents
10.3.2 Lipophilicity 168
10.4 Absorption/Permeability 369
10.5 Pharmacokinetics 369
10.6 Metabolism and Inhibition 170
10.7 The Concept of ADME Space 171
10.8 Computational Approaches in PK and Metabolism 173
10.8.1 QSPRandQSMR 173
10.8.2 PK Predictions Using QSAR and Neural Networks 173
10.8.3 Is In Silico Meeting Medicinal Chemistry Needs in ADME
Prediction? 374
10.8.4 Physiologically Based Pharmacokinetic (PBPK) Modelling 175
10.9 Outlook 175
Index 179
|
| adam_txt |
Contents
Preface IX
Abbreviations and Symbols XIII
1 Physicochemistry 1
1.1 Physicochemistry and Pharmacokinetics 1
1.2 Partition and Distribution Coefficient as Measures of Lipophilicity 2
1.3 Limitations on the Use of 1 Octanol 5
1.4 Further Understanding of Log P 6
1.4.1 Unravelling the Principal Contributions to Log P 6
1.4.2 Hydrogen Bonding 6
1.4.3 Molecular Size and Shape 8
1.5 Alternative Lipophilicity Scales 10
1.5.1 Different Solvent Systems 10
1.5.2 Chromatographic Approaches 10
1.5.3 Liposome Partitioning 10
1.6 Computational Approaches to Lipophilicity 11
1.7 Membrane Systems to Study Drug Behaviour 12
1.8 Dissolution and Solubility 13
1.8.1 Why Measure Solubility? 13
1.8.2 Calculated Solubility 14
1.9 Ionisation (pKa) 35
2 Pharmacokinetics 19
2.1 Setting the Scene 19
2.2 Intravenous Administration: Volume of Distribution 19
2.3 Intravenous Administration: Clearance 20
2.4 Intravenous Administration: Clearance and Half life 22
2.5 Intravenous Administration: Infusion 23
2.6 Oral Administration 25
2.7 Repeated Doses 26
2.8 Development of the Unbound (Free) Drug Model 28
2.9 Unbound Drug and Drug Action 28
Pharmacokinetics and Metabolism in Drug Design.
Dennis A. Smith, Han van de Waterbeemd, Don K. Walker (Eds.)
Copyright © 2006 WILEY VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 3 527 31368 0
VI I Contents
2.10 Unbound Drug Model and Barriers to Equilibrium 31
2.11 Slow Offset Compounds 33
2.12 Factors Governing Unbound Drug Concentration 35
3 Absorption 39
3.1 The Absorption Process 39
3.2 Dissolution 40
3.3 Membrane Transfer 42
3.4 Barriers to Membrane Transfer 46
3.5 Models for Absorption Estimation 49
3.6 Estimation of Absorption Potential 53
3.7 Computational Approaches 52
4 Distribution 55
4.1 Membrane Transfer Access to the Target 55
4.2 Brain Penetration 56
4.3 Volume of Distribution and Duration 59
4.4 Distribution and Tmax 64
5 Clearance 67
5.1 The Clearance Processes 67
5.2 Role of Transport Proteins in Drug Clearance 68
5.3 Interplay Between Metabolic and Renal Clearance 70
5.4 Role of Lipophilicity in Drug Clearance 71
6 Renal Clearance 83
6.1 Kidney Anatomy and Function 83
6.2 Lipophilicity and Reabsorption by the Kidney 84
6.3 Effect of Charge on Renal Clearance 85
6.4 Plasma Protein Binding and Renal Clearance 85
6.5 Balancing Renal Clearance and Absorption 87
6.6 Renal Clearance and Drug Design 88
7 Metabolic (Hepatic) Clearance 91
7.1 Function of Metabolism (Biotransformation) 91
7.2 Cytochrome P450 92
7.2.1 Catalytic Selectivity of CYP2D6 94
7.2.2 Catalytic Selectivity of CYP2C9 97
7.2.3 Catalytic Selectivity of CYP3A4 98
7.3 Other Oxidative Metabolism Processes 104
7.4 Oxidative Metabolism and Drug Design 107
7.5 Non Specific Esterases 109
7.5.1 Function of Esterases 109
7.5.2 Ester Drugs as Intravenous and Topical Agents 110
7.6 Prodrugs to Aid Membrane Transfer ill
Contents IVII
7.7 Enzymes Catalysing Drug Conjugation 112
7.7.1 Glucuronyl and Sulpho Transferases 112
7.7.2 Methyl Transferases 115
7.7.3 Glutathione S Transferases 115
7.8 Stability to Conjugation Processes 116
7.9 Pharmacodynamics and Conjugation 117
8 Toxicity 123
8.1 Toxicity Findings 121
8.1.1 Pharmacophore induced Toxicity 122
8.1.2 Structure related Toxicity 123
8.1.3 Metabolism induced Toxicity 125
8.2 Importance of Dose Size 126
8.3 Epoxides 126
8.4 Quinone Imines 128
8.5 Nitrenium Ions 133
8.6 Iminium Ions 134
8.7 Hydroxylamines 336
8.8 Thiophene Rings 237
8.9 Thioureas 139
8.10 Chloroquinolines 139
8.11 Stratification of Toxicity 240
8.12 Toxicity Prediction: Computational Toxicology 243
8.13 Toxicogenomics 342
8.14 Enzyme Induction (CYP3A4) and Drug Design 142
8.15 Enzyme Inhibition and Drug Design 346
9 Inter Species Scaling 353
9.1 Objectives of Inter Species Scaling 353
9.2 Allometric Scaling 253
9.2.1 Volume of Distribution 254
9.2.2 Clearance 356
9.3 Species Scaling: Adjusting for Maximum Life Span Potential 357
9.4 Species Scaling: Incorporating Differences in Metabolic
Clearance 258
9.5 Inter Species Scaling for Clearance by Hepatic Uptake 259
9.6 Elimination Half Life 363
9.7 Scaling to Pharmacological Effect 262
9.8 Single Animal Scaling 363
10 High(er) Throughput ADME Studies 265
10.1 The High Throughput Screening (HTS) Trend 265
10.2 Drug Metabolism and Discovery Screening Sequences 265
10.3 Physicochemistry 267
10.3.1 Solubility 368
VIII I Contents
10.3.2 Lipophilicity 168
10.4 Absorption/Permeability 369
10.5 Pharmacokinetics 369
10.6 Metabolism and Inhibition 170
10.7 The Concept of ADME Space 171
10.8 Computational Approaches in PK and Metabolism 173
10.8.1 QSPRandQSMR 173
10.8.2 PK Predictions Using QSAR and Neural Networks 173
10.8.3 Is In Silico Meeting Medicinal Chemistry Needs in ADME
Prediction? 374
10.8.4 Physiologically Based Pharmacokinetic (PBPK) Modelling 175
10.9 Outlook 175
Index 179 |
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| id | DE-604.BV022218173 |
| illustrated | Illustrated |
| index_date | 2024-07-02T16:28:11Z |
| indexdate | 2024-07-09T20:52:37Z |
| institution | BVB |
| isbn | 3527313680 9783527313686 |
| language | English |
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| physical | XIX, 187 S. Ill., graph. Darst. |
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| series | Methods and principles in medicinal chemistry |
| series2 | Methods and principles in medicinal chemistry |
| spelling | Smith, Dennis A. Verfasser aut Pharmacokinetics and metabolism in drug design Dennis A. Smith, Han van de Waterbeemd and Don K. Walker 2., rev. ed. Weinheim [u.a.] Wiley-VCH 2006 XIX, 187 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Methods and principles in medicinal chemistry 31 Literaturangaben Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Biotransformation (DE-588)4006908-4 gnd rswk-swf Arzneimitteldesign (DE-588)4278218-1 gnd rswk-swf Pharmakokinetik (DE-588)4115557-9 gnd rswk-swf Arzneimitteldesign (DE-588)4278218-1 s Pharmakokinetik (DE-588)4115557-9 s Biotransformation (DE-588)4006908-4 s DE-604 Waterbeemd, Han van de 1954- Verfasser (DE-588)11443963X aut Walker, Don K. 1960- Verfasser (DE-588)124178200 aut Methods and principles in medicinal chemistry 31 (DE-604)BV035418617 31 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015429430&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Smith, Dennis A. Waterbeemd, Han van de 1954- Walker, Don K. 1960- Pharmacokinetics and metabolism in drug design Methods and principles in medicinal chemistry Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Biotransformation (DE-588)4006908-4 gnd Arzneimitteldesign (DE-588)4278218-1 gnd Pharmakokinetik (DE-588)4115557-9 gnd |
| subject_GND | (DE-588)4006908-4 (DE-588)4278218-1 (DE-588)4115557-9 |
| title | Pharmacokinetics and metabolism in drug design |
| title_auth | Pharmacokinetics and metabolism in drug design |
| title_exact_search | Pharmacokinetics and metabolism in drug design |
| title_exact_search_txtP | Pharmacokinetics and metabolism in drug design |
| title_full | Pharmacokinetics and metabolism in drug design Dennis A. Smith, Han van de Waterbeemd and Don K. Walker |
| title_fullStr | Pharmacokinetics and metabolism in drug design Dennis A. Smith, Han van de Waterbeemd and Don K. Walker |
| title_full_unstemmed | Pharmacokinetics and metabolism in drug design Dennis A. Smith, Han van de Waterbeemd and Don K. Walker |
| title_short | Pharmacokinetics and metabolism in drug design |
| title_sort | pharmacokinetics and metabolism in drug design |
| topic | Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Biotransformation (DE-588)4006908-4 gnd Arzneimitteldesign (DE-588)4278218-1 gnd Pharmakokinetik (DE-588)4115557-9 gnd |
| topic_facet | Arzneimitteldesign - Pharmakokinetik - Biotransformation Drugs Design Drugs Metabolism Pharmacokinetics Biotransformation Arzneimitteldesign Pharmakokinetik |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015429430&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035418617 |
| work_keys_str_mv | AT smithdennisa pharmacokineticsandmetabolismindrugdesign AT waterbeemdhanvande pharmacokineticsandmetabolismindrugdesign AT walkerdonk pharmacokineticsandmetabolismindrugdesign |