Stereochemical aspects of drug action and disposition: [with 32 tables]
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Berlin [u.a.]
Springer
2003
|
| Schriftenreihe: | Handbook of experimental pharmacology
153 |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXV, 442 S. Ill., graph. Darst. |
| ISBN: | 3540415939 |
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| 245 | 1 | 0 | |a Stereochemical aspects of drug action and disposition |b [with 32 tables] |c contributors S. K. Branch ... Ed. Michel Eichelbaum ... |
| 264 | 1 | |a Berlin [u.a.] |b Springer |c 2003 | |
| 300 | |a XXV, 442 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
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| 490 | 1 | |a Handbook of experimental pharmacology |v 153 | |
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| 650 | 4 | |a Chimie pharmaceutique | |
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| 650 | 4 | |a Médicaments - Analyse | |
| 650 | 4 | |a Médicaments - Effets physiologiques | |
| 650 | 7 | |a Stereochemie |2 gtt | |
| 650 | 4 | |a Chemistry, Pharmaceutical | |
| 650 | 4 | |a Drug Interactions | |
| 650 | 4 | |a Drugs | |
| 650 | 4 | |a Pharmaceutical Preparations |x metabolism | |
| 650 | 4 | |a Pharmaceutical chemistry | |
| 650 | 4 | |a Stereoisomerism | |
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Datensatz im Suchindex
| _version_ | 1804128941727809536 |
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| adam_text | Contents
Section I: Chemical Aspects
CHAPTER 1
Recent Developments in Asymmetric Organic Synthesis:
Principles and Examples
P. Vogel. With 26 Figures and 19 Schemes 3
A. Introduction 3
I. Definitions 3
II. The Need for Asymmetric Synthesis 6
B. Resolution of Racemates to Enantiomers 7
I. Resolution via Diastereomers 7
II. Resolution by Means of Chromatography on a
Chiral Phase 8
III. Simple Kinetic Resolutions 9
1. An Example of Chemical Kinetic Resolution 10
2. Examples of Biochemical Kinetic Resolutions 10
3. Parallel Kinetic Resolutions 12
C. The Use of Stoichiometric Chiral Auxiliaries 14
I. Chiral 1,2 amino Alcohols and Derivatives 14
II. Chiral Sulfoxides 15
III. Thermodynamic Diastereoselection 16
IV. One Chiral Auxiliary. Two Enantiomers 17
D. Asymmetric Catalysis 20
I. Biochemical Methods 20
1. Desymmetrization of Meso Difunctional
Compounds 20
2. Carbonyl Reductions 21
3. Reductive Amination of a keto Acids 22
4. Microbial Oxidations 22
5. Acyloin Condensation 23
6. The Use of Catalytic Antibodies 23
II. Chemical Methods 24
XIV Contents
1. Introduction 24
2. Hydrogenation of Alkenes 26
3. Hydrogenation of Imines 27
4. Asymmetric Reduction of Ketones 27
5. Alkene Isomerization 29
6. Alcohols from Alkenes 29
7. Carbon Nucleophile Additions to Aldehydes 30
8. Aldol Condensations 32
9. [2+2] Cycloadditions 32
10. Diels Alder and Hetero Diels Alder Additions 33
11. Other Carbon Carbon Bond Forming Reactions 34
E. Conclusion 36
References 37
CHAPTER 2
Stereoselective Separations: Recent Advances in Capillary
Electrophoresis and High Performance Liquid Chromatography
S. Rudaz and J. L. Veuthey. With 5 Figures 45
A. Introduction 45
B. Liquid Chromatography 46
I. Precolumn Formation of Diastereomers 47
II. Addition of Chiral Selectors in the Mobile Phase 47
III. Chiral Stationary Phases 48
1. Type I A (Pirkle Type) 49
2. Type I B (Ligand Exchange Chromatography) 49
3. Type II A (Cyclodextrin Bonded Phases) 52
4. Type II B (Crown Ether) 52
5. Type III A (Natural Polymers) 52
6. Type III B (Synthetic Polymers) 54
7. Type IV (Proteins Antibiotics) 54
C. Capillary Electrophoresis 56
I. Introduction 59
II. Capillary Zone Electrophoresis 59
1. Cyclodextrins 59
2. Macrocyclic Antibiotics 60
3. Crown Ethers 61
4. Proteins 61
5. Polysaccharides 62
6. Other Chiral Selectors 62
7. Dual System 62
8. Migration Order Reversal 63
9. Chiral Separation in NACE 63
10. Micellar Electrokinetic Chromatography 64
11. Capillary Electrochromatography 64
Contents XV
12. CE MS Coupling 65
13. Partial Filling Counter Current Technique 66
D. Discussion and Conclusion 67
List of Abbreviations 68
References 69
CHAPTER 3
Stereochemical Issues in Bioactive Natural Products
C. Terreaux and K. Hostettmann. With 7 Figures 77
A. Introduction 77
B. Natural Products Occurring in Opposite Enantiomeric Forms ... 78
I. Occurrence of Camphor 78
II. Organoleptic Properties of Menthol and Carvone 79
C. Stereochemistry and Pharmacological Implications 80
I. Tropane Alkaloids 80
II. Khat and Cathinone Derivatives 82
III. Kawalactones 83
IV. Gossypol 84
D. Epimerization 85
I. Stability of Pilocarpine 86
II. Lysergic Acid and Derivatives 86
E. Conclusion 88
References 88
CHAPTER 4
Drug Racemization and Its Significance in Pharmaceutical Research
M. Reist, B. Testa, and P. A. Carrupt. With 11 Figures 91
A. Introduction 91
B. Background and Concepts 92
I. Racemization, Enantiomerization, Diastereomerization
and Epimerization 92
II. Enzymatic and Nonenzymatic Inversion of
Chiral Compounds 94
III. Relevant Time Scales for the Configurational Instability
of Drugs 96
C. Methods to Assess Configurational Stability 97
I. Direct and Indirect Methods 97
II. Screening of Compounds for Configurational Stability by
H NMR 98
D. Predicting Configurational Stability 100
E. Conditions Influencing Configurational Stability 102
F The Case of Thalidomide: Interplay of Configurational Stability,
Biological Activities, Metabolism, and Stereoselectivity 104
XVI Contents
G. Conclusion 108
References 109
CHAPTER 5
Physical Properties and Crystal Structures of Chiral Drugs
C. H. Gu and D.J.W. Grant. With 10 Figures 113
A. Introduction 113
B. Nature of Racemates 113
C. Physical Properties of Chiral Drugs 116
I. Optical Activity 116
II. Thermal Properties 116
III. Solubility 118
IV. Vibrational Spectra and Nuclear Magnetic Resonance
Spectra 120
V. X ray Diffraction Patterns 122
D. Polymorphism and Pseudopolymorphism of Chiral Drugs 122
E. Influence of Impurities on the Physical Properties of
Chiral Drugs 127
F. Crystal Structures of Chiral Drugs 129
G. Comparison of the Crystal Structures of the Racemic Compound
and Enantiomer 130
I. Compactness and Symmetry 130
II. Intermolecular Interactions in the Crystal 131
H. Crystal Structural Basis of Diastereomer Separation 133
I. Concluding Remarks 135
References 135
Section II: Experimental Pharmacology
CHAPTER 6
Chiral Recognition in Biochemical Pharmacology: An Overview
B. Testa and J.M. Mayer. With 7 Figures 143
A. Introduction 143
B. Enantioselectivity at Macroscopic Biological Levels 143
I. Stereoselectivity in Drug Action and Pharmacodynamics ... 144
1. Pfeiffer s Rule and Eudismic Analysis 144
2. The Problem of Optical Purity 145
II. Stereoselectivity in Some Pharmacokinetic Responses 145
1. Oral Absorption 146
2. Distribution 146
3. Urinary Excretion 147
4. Metabolism 147
C. Mechanisms of Chiral Recognition in
Biochemical Pharmacology 149
Contents XVII
I. Physicochemical Principles 149
II. The Model of Easson and Stedman 150
III. The Four Location Model 152
IV. Binding Versus Receptor Activation 153
V. Binding Versus Enzyme Catalysis in Drug Metabolism 155
VI. Current Limitations of the Three Point and Four Location
Binding Models 156
D. Conclusion 157
References 157
CHAPTER 7
Enantioselectivity in Drug Receptor Interactions
W. Soudijn, I. van Wijngaarden, and A.P. Ijzerman.
With 4 Figures 161
A. Introduction 161
B. Receptor Ligands and Enantioselectivity 162
I. Ligands of Biogenic Amine Receptors 162
II. Ligands of Adenosine, Cannabinoid and
Melatonin Receptors 167
III. Ligands of Peptide Receptors 169
C. Receptors and Enantioselectivity 173
I. Introduction 173
II. Adrenoceptors 174
III. 5 HT1A Receptors 177
III. Melanocortin Receptors 178
D. Concluding Remarks 178
References 178
CHAPTER 8
Mechanisms of Stereoselective Binding to Functional Proteins
G. Klebe. With 9 Figures and 5 Schemes 183
A. Introduction 1^3
B. Chiral Molecules in a Crystal Environment 185
C. Recognition of Chiral Ligands at Protein Binding Sites 186
D. Recognition of Chiral Building Blocks in Stereoisomers at
the Protein Binding Site 189
E. Chemical Reactions in Protein Using Stereoisomeric
Substrates 192
F. Structural Basis for Chiral Resolution in Lipases 195
G. Conclusion 197
References 1^7
XVIII Contents
CHAPTER 9
Stereoselective Drug Channel Interactions
C. Valenzuela. With 8 Figures 199
A. Ion Channels as Drug Targets 199
B. Voltage Dependent Ion Channels 201
I. Na+ Channels 201
1. Structure 201
2. Activation 201
3. Inactivation 203
4. Ion Pore and Selectivity 204
II. Ca2+ Channels 205
1. Structure 205
2. Activation 206
3. Inactivation 206
4. Ion Pore and Selectivity 207
III. K+ Channels 207
1. Structure 209
2. Activation 209
3. Inactivation 209
4. Ion Pore and Selectivity 210
C. Stereoselective Interactions Between Local Anesthetic Like
Drugs and Na+ Channels 211
D. Stereoselective Interactions Between Calcium Channel
Antagonists and 1 Type Ca2+ Channels 215
E. Stereoselective Interactions Between Local Anesthetics
and K+ Channels 217
F. Drug Receptor Sites at Na+, Ca2+ and K+ Channels 221
G. Future Directions 221
List of Abbreviations 222
References 222
CHAPTER 10
Stereoselective Bioactivation and Bioinactivation
Toxicological Aspects
N.P.E. Vkrmeulkn. With 10 Figures 229
A. Introduction 229
B. Toxins of Natural Origins: Complex Stereochemistry 229
C. Thalidomide: A Classic Example of Stereoselectivity 231
D. Chemotherapeutic Agents and Stereoselectivity 233
E. Stereoselective Biotransformation and Bioactivation by
Cytochromes P450 235
F. Stereoselectivity and Genetic Polymorphisms in
Drug Oxidations 237
Contents XIX
G. Glucuronyl Transferases and Stereoselective Bioactivation 241
H. Sulfotransferases and Stereoselective Bioactivation 242
I. Stereoselective Bioactivation by Cysteine Conjugate /3 Lyase .... 244
J. General Conclusions 244
References 245
Section III: Drug Absorption, Distribution, Metabolism, Elimination
CHAPTER 11
Intestinal Drug Transport: Stereochemical Aspects
H. Spahn Langguth, C. Dressler, and C. Leisen. With 7 Figures .... 251
A. General Aspects Regarding Intestinal Transport of Drugs:
Mechanisms, Transporters, Techniques 251
I. The Gut Wall, Its Physiological Functions, and
Factors Affecting Drug Absorption from the
Gastrointestinal Tract 251
II. Transporters 252
III. Bioavailability Reducing Metabolic Processes in
Addition to Countertransport and Liver First Pass:
Luminal Metabolism, Metabolism At/In Enterocytes 254
IV. Stereoisomers, Mutually Competing for Binding Sites at
Receptors, Enzymes, and Transporters 257
V. Mucus Binding Prior to Interactions with the
Brush Border Membrane 257
VI. Dose Dependent Stereoselectivity in Bioavailability
Based on Active Transport and Countertransport 259
VII. Transport and Affinity Assays and Related Problems 261
1. Permeation Through Cell Monolayers 261
2. Uptake Studies, Efflux Studies 262
3. Photoaffinity Labeling 263
4. Radioligand Binding Assay 263
5. ATPase Assay 263
6. Potential of Assays to Detect Enantiomer
Differences 263
B. Chiral Drug Examples for Active Inside and Outside
Directed Transport 263
I. Active Inside Directed (Lumen To Blood) Transport 263
1. Methotrexate 264
2. Amino Acid Related Structures 264
3. Peptide Related Structures 266
4. Monocarboxylic Acid Transport 267
II. Drug Examples for Active Outside Directed
(Blood To Lumen) Transport 269
1. Fluoroquinolones Ofloxacin 269
XX Contents
2. Verapamil 270
3. /3 Adrenoceptor Blockers 270
III. The Distomer as Shoehorn or as Inhibitor for
the Eutomer? 271
IV. Model Compounds for P gp Related Processes 272
1. Talinolol 272
2. Digoxin 274
3. Fexofenadine 274
C. Drug Drug and Drug Food Interactions Based on
Transporters 274
I. General and Stereochemical Aspects 274
II. Competition (and Noncompetitive Effects at
the Transporter) 276
III. Induction 278
1. In Situ Intestinal Perfusions in Rodents 278
2. Clinical Studies 279
D. Alternative Processes and Carriers, Alternative Species, and
Variable Carrier Expression Factors That May Complicate
Data Interpretation 280
I. Studies of Intestinal Transport and p.o. Bioavailability
in the Intact Organism 280
II. Are Data Obtained with Other P gp Expressing Cell
Systems Representative of the Intestine of Animals
and Man? 280
III. P gp and Other Transporters 281
IV. Variable Carrier Expression 281
References 281
CHAPTER 12
Enantioselective Plasma and Tissue Binding
PJ. Hayball and D. Mauleon. With 2 Figures 289
A. Introduction 289
B. Enantioselective Plasma Protein Binding 292
I. Binding to Albumin 292
II. Specific Albumin Binding Regions 292
III. Binding to arAcid Glycoprotein 293
IV. Binding to Other Plasma Proteins 294
V. Species Differences in Plasma Protein Binding 294
VI. Enantiomer Interactions at Plasma Protein Binding Sites . . . 294
C. Methods for Determining Plasma Protein Binding of
Enantiomers 295
I. Classical Methods: Isolation of Unbound Drug 295
II. Quantification Using Radiolabeled Ligands 296
III. Binding Studies Using Immobilized Plasma Protein 296
Contents XXI
D. Enantioselective Tissue Binding and Partitioning 297
I. Blood Brain Barrier Passage of Drugs:
Impact of Chirality 298
II. Partitioning of Chiral Drugs into Red Blood Cells 301
III. Uptake into Adipose Tissue 301
IV. Sequestration into Synovial Fluid and Articular Tissue 302
E. Pharmacological Ramifications of Enantioselective Plasma and
Tissue Binding 303
I. Enantioselective Plasma Protein Binding: Implications
for Interpretation of Pharmacokinetics of Chiral Drugs .... 303
II. Pharmacokinetic Implications of Enantioselective Plasma
Protein Binding: Case Studies of Chiral NSAIDs 304
III. Enantioselective Tissue Binding: Implications for
Interpretation of Pharmacokinetics of Chiral Drugs 305
F. Conclusions 306
References 306
CHAPTER 13
Stereoselective Drug Metabolism and Drug Interactions
A.S. Gross, A. Somogyi, and M. Eichelbaum. With 6 Figures 313
A. Introduction 313
B. Stereoselective Metabolism 314
I. Substrate and Product Stereoselectivity 314
1. Different Rates and Routes of Metabolism 316
2. Achiral Chiral 318
3. Chiral Chiral 318
4. Chiral Diastereoisomer 318
5. Chiral Achiral 318
II. Chiral Inversion 319
III. Species Differences 319
C. Stereoisomerism and Metabolic Drug Interactions 319
I. Inhibition 320
II. Induction 322
III. Enantiomer Enantiomer Interaction 323
D. Additional Consequences of Stereoselective Metabolism 325
I. In Vivo and In Vitro Pharmacological Potency 325
II. Active Chiral Metabolites 325
III. First Pass Metabolism 326
1. Intestinal and Hepatic Metabolism 326
2. Bioequivalence 327
IV. Impact of Disease 328
V. Genetics 329
1. Genetic Polymorphisms in Drug Metabolism 329
XXII Contents
2. Inter Ethnic Differences 331
VI. Influence of Age 332
VII. Influence of Sex 333
E. Conclusion 333
References 333
CHAPTER 14
Metabolic Chiral Inversion of 2 Arylpropionic Acids
I. Tegeder, K. Williams, and G. Geisslinger. With 2 Figures 341
A. Introduction 341
I. 2 Arylpropionic Acids 341
II. Inversion in Man 342
III. Inversion in Animals: Models of Inflammation 342
IV. In Vitro Models Used to Study Inversion 344
V. The In Vivo Site of Inversion 345
B. Mechanism of Inversion 345
I. Formation of Coenzyme A Thioesters 345
II. Racemization (Epimerization) of the Coenzyme A
Thioesters 347
III. Hydrolysis of Coenzyme A Thioesters 347
C. Consequences of Chiral Inversion 348
I. Factors That May Modulate Inversion 350
D. Conclusions 350
References 350
CHAPTER 15
Stereoselective Renal Elimination
CM. Brett, R.J. Ott, and K.M. Giacomini. With 1 Figure 355
A. Introduction 355
B. Overview of Renal Handling: Filtration, Secretion,
Reabsorption 355
C. Transporters Involved in Active Secretion and Reabsorption .... 358
I. P Glycoprotein or MDR1 359
1. Tissue Distribution 359
2. Molecular Characteristics 360
II. Multidrug Resistance Associated Proteins
(MRP1 and MRP2) 360
1. Tissue Distribution 360
2. Molecular Characteristics 361
III. Organic Cation Transporters 361
1. Tissue Distribution 361
2. Molecular Characteristics 361
IV. Organic Anion Transporters 361
Contents XXIII
1. Tissue Distribution 362
2. Molecular Characteristics 362
V. Nucleoside Transporters 362
1. Tissue Distribution 363
2. Molecular Characteristics 363
VI. Oligopeptide Transporters 363
1. Tissue Distribution 364
2. Molecular Characteristics 364
D. Stereoselective Interactions of Drugs with Transporters
in the Kidney 364
I. Stereoselective Interactions with Organic Cation
Transporters 364
1. Pindolol 365
2. Quinine and Quinidine 365
3. Other Organic Cation Drugs 366
a) NS 49 366
b) Fluorinated Quinolone Derivatives
(e.g., Ciprofloxacin, Levofloxacin) 366
c) Carnitine 367
II. Stereoselective Interactions with Oligopeptide
Transporters 367
III. Stereoselective Interactions with Nucleoside
Transporters 367
IV. Stereoselective Interactions with Organic Anion
Transporters 368
1. DBCA 368
2. Ofloxacin 369
3. Ibuprofen 369
E. Clinical Examples 369
I. Carbenicillin 369
II. Pindolol 370
III. Quinine and Quinidine 370
IV. Metabolite of Verapamil 371
V. Carprofen Glucuronides 371
References 372
Section IV: Implications for Drug Development and Therapy
CHAPTER 16
Regulatory Requirements for the Development of
Chirally Active Drugs
R.R. Shah and S.K. Branch 379
A. Introduction 3?9
I. Historical Background 379
XXIV Contents
II. Regional Evolution of Regulatory Requirements 380
III. Scope of Regulatory Control on Chiral Drugs 381
IV. Justifying the Risk/Benefit 382
B. Pharmaceutical Requirements 383
I. Synthesis of the Active Substance 384
II. Chemical Development 385
III. Quality of the Active Substance and Finished Product 385
IV. Status of Distomer as an Impurity 386
C. Preclinical and Clinical Requirements 387
I. Development of a Single Enantiomer as a New
Active Substance 388
II. Development of a Racemate as a New Active Substance . . . 389
HI. Development of a Single Enantiomer from an
Approved Racemate 391
IV. Development of a Racemate from an Approved
Single Enantiomer 393
V. Development of a Nonracemic Mixture from an
Approved Racemate or Single Enantiomer 393
VI. Generic Applications of Chiral Medicinal Products 394
D. Status of Approved Racemic Drugs 395
E. The Effect of Regulatory Guidelines 395
F. Conclusions 397
References 398
CHAPTER 17
Improving Clinical Risk/Benefit Through Stereochemistry
R.R. Shah. With 14 Figures 401
A. Introduction 401
I. Stereochemistry and Pharmacogenetics 401
II. Stereochemistry and Metabolites 402
B. Stereochemistry and Regulatory Control of Drugs 403
I. Thalidomide 403
II. Ethambutol 405
C. Clinical Aspects of Stereochemistry 405
I. Flecainide and Encainide 407
D. Improving Risk/Benefit Through Stereochemistry 407
I. Levofloxacin 408
II. Nebivolol 409
III. Indacrinone 410
IV. Sotalol 411
V. Carvedilol 412
VI. Timolol 413
VII. Fluoxetine 414
E. Stereogenic Origin of Clinical Safety Concerns 415
Contents XXV
I. Disopyramide 416
II. Propafenone 416
III. Salbutamol 418
IV. Oxybutynin 419
V. Citalopram 420
VI. Halofantrine 420
F. Stereoselectivity and Drug Withdrawals 421
I. Bufenadrine 421
II. Dilevalol 422
III. Prenylamine 423
IV. Terodiline 424
V. Levacetylmethadol 425
G. Conclusions 426
References 427
Index 433
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV014078512 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T18:57:15Z |
| institution | BVB |
| isbn | 3540415939 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009642304 |
| oclc_num | 52515592 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-12 DE-188 DE-578 |
| owner_facet | DE-355 DE-BY-UBR DE-19 DE-BY-UBM DE-12 DE-188 DE-578 |
| physical | XXV, 442 S. Ill., graph. Darst. |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| publisher | Springer |
| record_format | marc |
| series | Handbook of experimental pharmacology |
| series2 | Handbook of experimental pharmacology |
| spelling | Stereochemical aspects of drug action and disposition [with 32 tables] contributors S. K. Branch ... Ed. Michel Eichelbaum ... Berlin [u.a.] Springer 2003 XXV, 442 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Handbook of experimental pharmacology 153 Drugs cabt Neurotransmitters cabt Chimie pharmaceutique Geneesmiddelen gtt Médicaments - Analyse Médicaments - Effets physiologiques Stereochemie gtt Chemistry, Pharmaceutical Drug Interactions Drugs Pharmaceutical Preparations metabolism Pharmaceutical chemistry Stereoisomerism Arzneimittel (DE-588)4003115-9 gnd rswk-swf Chiralität Chemie (DE-588)4147732-7 gnd rswk-swf Stereochemie (DE-588)4129569-9 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Arzneimittel (DE-588)4003115-9 s Stereochemie (DE-588)4129569-9 s DE-604 Chiralität Chemie (DE-588)4147732-7 s Eichelbaum, Michel 1941- Sonstige (DE-588)106352261 oth Branch, S. K. Sonstige oth Handbook of experimental pharmacology 153 (DE-604)BV002390716 153 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009642304&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Stereochemical aspects of drug action and disposition [with 32 tables] Handbook of experimental pharmacology Drugs cabt Neurotransmitters cabt Chimie pharmaceutique Geneesmiddelen gtt Médicaments - Analyse Médicaments - Effets physiologiques Stereochemie gtt Chemistry, Pharmaceutical Drug Interactions Drugs Pharmaceutical Preparations metabolism Pharmaceutical chemistry Stereoisomerism Arzneimittel (DE-588)4003115-9 gnd Chiralität Chemie (DE-588)4147732-7 gnd Stereochemie (DE-588)4129569-9 gnd |
| subject_GND | (DE-588)4003115-9 (DE-588)4147732-7 (DE-588)4129569-9 (DE-588)4143413-4 |
| title | Stereochemical aspects of drug action and disposition [with 32 tables] |
| title_auth | Stereochemical aspects of drug action and disposition [with 32 tables] |
| title_exact_search | Stereochemical aspects of drug action and disposition [with 32 tables] |
| title_full | Stereochemical aspects of drug action and disposition [with 32 tables] contributors S. K. Branch ... Ed. Michel Eichelbaum ... |
| title_fullStr | Stereochemical aspects of drug action and disposition [with 32 tables] contributors S. K. Branch ... Ed. Michel Eichelbaum ... |
| title_full_unstemmed | Stereochemical aspects of drug action and disposition [with 32 tables] contributors S. K. Branch ... Ed. Michel Eichelbaum ... |
| title_short | Stereochemical aspects of drug action and disposition |
| title_sort | stereochemical aspects of drug action and disposition with 32 tables |
| title_sub | [with 32 tables] |
| topic | Drugs cabt Neurotransmitters cabt Chimie pharmaceutique Geneesmiddelen gtt Médicaments - Analyse Médicaments - Effets physiologiques Stereochemie gtt Chemistry, Pharmaceutical Drug Interactions Drugs Pharmaceutical Preparations metabolism Pharmaceutical chemistry Stereoisomerism Arzneimittel (DE-588)4003115-9 gnd Chiralität Chemie (DE-588)4147732-7 gnd Stereochemie (DE-588)4129569-9 gnd |
| topic_facet | Drugs Neurotransmitters Chimie pharmaceutique Geneesmiddelen Médicaments - Analyse Médicaments - Effets physiologiques Stereochemie Chemistry, Pharmaceutical Drug Interactions Pharmaceutical Preparations metabolism Pharmaceutical chemistry Stereoisomerism Arzneimittel Chiralität Chemie Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009642304&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV002390716 |
| work_keys_str_mv | AT eichelbaummichel stereochemicalaspectsofdrugactionanddispositionwith32tables AT branchsk stereochemicalaspectsofdrugactionanddispositionwith32tables |