NMR Spectroscopy in Pharmaceutical Analysis
For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as a valuable tool in drug analysis. In all disciplines, such as drug identification, impurity profiling and assay, qNMR can be utilized. Separation techniques such as high performance liquid chromatography, gas chromatog...
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Oxford
Elsevier
2008
Elsevier Science & Technology Elsevier Science |
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| Abstract | For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as a valuable tool in drug analysis. In all disciplines, such as drug identification, impurity profiling and assay, qNMR can be utilized. Separation techniques such as high performance liquid chromatography, gas chromatography, super fluid chromatography and capillary electrophoresis techniques, govern the purity evaluation of drugs. However, these techniques are not always able to solve the analytical problems often resulting from insufficient methods. Nevertheless, such methods find their way into international pharmacopoeias. Thus, the aim of this book is to describe the possibilities of qNMR in pharmaceutical analysis. Besides the introduction to the physical fundamentals and techniques, the principles of the application in drug analysis are described: Quality evaluation of drugs, Polymer characterization, Natural products and corresponding reference compounds, Metabolism, and Solid phase NMR spectroscopy for the characterization drug substances, e.g. the water content, polymorphism, and drug formulations, e.g. tablets, powders. This part is accompanied by more special chapters dealing with representative examples that give more detailed information by means of concrete examples. |
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| AbstractList | For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as valuable tool in drug analysis. In all disciplines, i. e. drug identification, impurity profiling and assay, qNMR can be utilized. Separation techniques such as high performance liquid chromatography, gas chromatography, super fluid chromatography and capillary electrophoresis techniques, govern the purity evaluation of drugs. However, these techniques are not always able to solve the analytical problems often resulting in insufficient methods. Nevertheless such methods find their way into international pharmacopoeias. Thus, the aim of the book is to describe the possibilities of qNMR in pharmaceutical analysis. Beside the introduction to the physical fundamentals and techniques the principles of the application in drug analysis are described: quality evaluation of drugs, polymer characterization, natural products and corresponding reference compounds, metabolism, and solid phase NMR spectroscopy for the characterization drug substances, e.g. the water content, polymorphism, and drug formulations, e.g. tablets, powders. This part is accompanied by more special chapters dealing with representative examples. They give more detailed information by means of concrete examples.
. combines theory, techniques, and concrete applications-all of which closely resemble the laboratory experience . considers international pharmacopoeias, addressing the concern for licensing . features the work of academics and researchers, appealing to a broad readership For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as a valuable tool in drug analysis. In all disciplines, such as drug identification, impurity profiling and assay, qNMR can be utilized. Separation techniques such as high performance liquid chromatography, gas chromatography, super fluid chromatography and capillary electrophoresis techniques, govern the purity evaluation of drugs. However, these techniques are not always able to solve the analytical problems often resulting from insufficient methods. Nevertheless, such methods find their way into international pharmacopoeias. Thus, the aim of this book is to describe the possibilities of qNMR in pharmaceutical analysis. Besides the introduction to the physical fundamentals and techniques, the principles of the application in drug analysis are described: Quality evaluation of drugs, Polymer characterization, Natural products and corresponding reference compounds, Metabolism, and Solid phase NMR spectroscopy for the characterization drug substances, e.g. the water content, polymorphism, and drug formulations, e.g. tablets, powders. This part is accompanied by more special chapters dealing with representative examples that give more detailed information by means of concrete examples. For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as valuable tool in drug analysis. In all disciplines, i. e. drug identification, impurity profiling and assay, qNMR can be utilized. Separation techniques such as high performance liquid chromatography, gas chromatography, super fluid chromatography and capillary electrophoresis techniques, govern the purity evaluation of drugs. However, these techniques are not always able to solve the analytical problems often resulting in insufficient methods. Nevertheless such methods find their way into international pharmacopoeias. Thus, the aim of the book is to describe the possibilities of qNMR in pharmaceutical analysis. Beside the introduction to the physical fundamentals and techniques the principles of the application in drug analysis are described: quality evaluation of drugs, polymer characterization, natural products and corresponding reference compounds, metabolism, and solid phase NMR spectroscopy for the characterization drug substances, e.g. the water content, polymorphism, and drug formulations, e.g. tablets, powders. This part is accompanied by more special chapters dealing with representative examples. They give more detailed information by means of concrete examples. |
| Author | Holzgrabe Ulrike Wawer Iwona Diehl Bernd |
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| Discipline | Pharmacy, Therapeutics, & Pharmacology Medicine |
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| Notes | Includes bibliographical references and index |
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| Snippet | For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as a valuable tool in drug analysis. In all disciplines, such as drug... For almost a decade, quantitative NMR spectroscopy (qNMR) has been established as valuable tool in drug analysis. In all disciplines, i. e. drug... |
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| SubjectTerms | Drugs Drugs -- Analysis Nuclear magnetic resonance spectroscopy Pharmaceuticals Pharmaceuticals, Cosmetics & Toiletries |
| TableOfContents | Front Matter
Preface
Table of Contents
Part I. Fundamentals and Techniques
1. Principles in NMR Spectroscopy
2. Quantitative NMR in the Solution State NMR
3. qNMR in Solid State
4. Microcoil Nuclear Magnetic Resonance Spectroscopy
5. qNMR Spectroscopy in Drug Analysis - A General View
Part II. General Applications
6. Investigation of Multi-Component Drugs by NMR Spectroscopy
7. NMR Application for Polymer Characterisation
8. NMR Spectroscopy of Natural Substances
9. Solid-State Measurements of Drugs and Drug Formulation
10. Metabolic Profiling
11. DOSY NMR for Drug Analysis
12. The Use of qNMR for the Analysis of Agrochemicals
Part III. Special Applications
13. NMR-Based Mixture Analysis on the Example of Fruit Juice Quality Control Using Statistics and Quantification
14. NMR Assays for Carbohydrate-Based Vaccines
15. Fluorine-19 or Phosphorus-31 NMR Spectroscopy: A Powerful Technique for Biofluid Metabolic Studies and Pharmaceutical Formulation Analysis of Fluorinated or Phosphorylated Drugs
16. Quantitative 2D NMR Analysis of Glycosaminoglycans
17. The Use of Proton NMR as an Alternative for the Amino Acid Analysis as Identity Test for Peptides
18. Assessment of the Inhibitory Potency of Antibiotics by MRI
19. Hypernation and Concatenation: Multiple On-Line Spectroscopic Analysis for Drug and Natural Product Characterisation
20. Quantitative High-Resolution Online NMR Spectroscopy in Pharmaceutical Reaction and Process Monitoring
Index 3 Development of Small Coils for High-Resolution NMR -- 3.1 Saddle/Helmholtz coils -- 3.2 Solenoidal coils -- 3.3 Planar RF coils -- 3.4 Novel microcoil designs -- 3.5 High-temperature superconducting microprobes -- 4 Sensitivity Comparisons -- 5 Nanoliter Volume Applications of RF Microcoils - Hyphenated cITP-NMR -- 6 Microliter Volume Applications of RF Microcoils -- 6.1 Helmholtz/saddle coils -- 6.2 Solenoidal coils -- 6.3 Superconducting microcoils -- 7 Hyphenation of Microseparation Techniques with Microliter NMR Detection -- 8 Multiple Coil Probeheads -- 9 Solid-State Applications of Small Coils -- 10 Conclusion -- Chapter 5 qNMR Spectroscopy in Drug Analysis - A General View -- 1 Introduction -- 2 NMR Spectroscopy in International Pharmacopoeias -- 2.1 Identification of drugs -- 2.2 Tests -- 2.3 Assay -- 3 Validation -- 4 Conclusions -- Part II GENERAL APPLICATIONS -- Chapter 1 Investigation of Multi-Component Drugs by NMR Spectroscopy -- 1 Introduction -- 1.1 Solvent -- 1.2 pH value -- 1.3 Temperature -- 1.4 Auxiliary reagents -- 1.5 Limitations -- 2 Codergocrine Mesylate -- 2.1 1H NMR spectroscopy -- 2.2 13C NMR spectroscopy -- 2.3 High-performance liquid chromatography -- 2.4 HPLC versus NMR spectroscopy -- Chapter 2 NMR Applications for Polymer Characterisation -- 1 Introduction -- 2 Polydimethyl Siloxane -- 3 Polysaccharides -- 4 Polyether Formulation Aids -- 5 Formaldehyde -- 6 Polyester -- 7 Poly- and Oligopeptides -- 8 Polyvinyl Compounds -- 9 Experimental Data -- Chapter 3 NMR Spectroscopy of Natural Substances -- 1 Introduction -- 2 Characterisation of Natural Substances as a Finger Print Analysis -- 3 Characterisation of Natural Substances According to Single Target Molecules -- 4 Characterisation and Definition of Primary Reference Standards -- 5 Multi-Component Analysis of Complex Natural Substance Mixtures and Phytopharmaceutics Front Cover -- NMR Spectroscopy in Pharmaceutical Analysis -- Copyright Page -- Table of Contents -- Preface -- List of Contributors -- List of Editors -- Part I FUNDAMENTALS AND TECHNIQUES -- Chapter 1 Principles in NMR Spectroscopy -- 1 Short History -- 2 The NMR Experiment -- 2.1 Excitation, relaxation and sensitivity -- 2.2 Relaxation -- 3 Chemical Shift -- 3.1 Electronic density -- 3.2 Anisotropy -- 3.3 Mesomerism -- 3.4 Steric effects -- 4 Calibration and Relative Scale ppm -- 5 Spin-Spin Coupling -- 5.1 The coupling constant -- 5.2 Multiplicity -- 5.3 Roof effect -- 5.4 Angular dependence of the coupling constant -- 5.5 Heteronuclear coupling -- 5.6 13C NMR satellites in 1H NMR spectra -- 6 Heteronuclear Spectra -- 6.1 Decoupling -- 6.2 Quantitative heteronuclear NMR -- 7 Molecular Dynamics -- 7.1 Deuterium exchange and solvent effects -- 8 Chemical Derivatisation -- 9 Stereochemistry -- 9.1 Diastereomerism -- 9.2 Atrop or axial chirality -- 9.3 Enantiomeric excess -- 9.4 Diastereotopy -- 10 Two-dimensional Methods for Structure Elucidation -- 11 Experimental Data -- Chapter 2 Quantitative NMR in the Solution State NMR -- 1 Introduction -- 2 Basics -- 3 Quantitative NMR Spectroscopy -- 3.1 Relative method -- 3.2 Absolute method -- 4 Validation -- 4.1 Linearity -- 4.2 Robustness -- 4.3 Specificity and selectivity -- 4.4 Accuracy -- 4.5 Precision -- 4.6 Measurement uncertainty -- 4.7 Round robin tests -- 5 Sensitivity -- 6 Conclusion -- Chapter 3 qNMR in Solid State -- 1 Introduction to Solid-state NMR -- 2 Quantitative Aspects of Solid-state NMR, Protocol for Quantitation -- 3 An Example: Quantitation of Pseudoephedrine in Dosage Form -- 4 Quantitation of Polymorphs and Formulated Drugs -- Chapter 4 Microcoil Nuclear Magnetic Resonance Spectroscopy -- 1 Introduction -- 2 Intrinsic NMR Sensitivity 4.3 Selection of integral regions -- 4.4 Peak alignment -- 4.5 Normalization -- 4.6 Centering, scaling, and transformation -- 5 Illustration -- 6 Conclusions and Future Perspectives -- Chapter 6 DOSY NMR for Drug Analysis -- 1 Introduction -- 2 Theory -- 2.1 DOSY -- 2.2 TOSY -- 3 Applications to the Analysis of Drug Formulations -- 3.1 DOSY 1H NMR analysis of ciprofloxacin formulations -- 3.2 DOSY 1H NMR analysis of oral formulations of fluoxetine -- 3.3 DOSY 1H NMR analysis of formulations of genuine Cialis® and a Chinese imitation -- 3.4 DOSY 1H NMR analysis of an herbal Chinese formulation -- 3.5 TOSY NMR analysis of ibuprofen -- 4 Advantages and Drawbacks of the Methods -- 5 Conclusion -- Chapter 7 The Use of qNMR for the Analysis of Agrochemicals -- 1 Introduction -- 2 Limitations of Present Methods for Analysis of Technical Grade Materials -- 2.1 Purity and supply of standard reference materials -- 2.2 Limitations of chromatographic methods -- 2.3 Shortcomings of some official agrochemical analytical methods -- 3 Analysis of the Active Ingredient in Agrochemicals by qNMR -- 3.1 General considerations -- 3.2 qNMR using the subtraction method -- 3.3 qNMR using a standard of known purity -- 3.4 The concept of universal standard reference material -- 3.5 Practical analysis of technical grade agrochemicals by qNMR -- 4 qNMR Analysis of Proscribed Impurities in Agrochemicals -- 5 qNMR Analysis of Manufacturing Impurities in Agrochemicals -- 6 Conclusion -- Part III SPECIAL APPLICATIONS -- Chapter 1 NMR-Based Mixture Analysis on the Example of Fruit Juice Quality Control Using Statistics and Quantification -- 1 Introduction -- 2 Instrumental Aspects of Fruit Juice Quality Control -- 3 Identification of Compounds in the Mixture -- 4 Quantification of Compounds in Fruit Juice Spectra -- 5 Ridge-Regression in Fruit Juice Quality Control 5.1 Extracts from medical plants -- 5.2 Lipids -- 5.3 Lecithin -- 5.4 Fats and oils -- 6 Experimental Data -- Chapter 4 Solid-State Measurements of Drugs and Drug Formulations -- 1 Solid-state NMR in Pharmacy -- 2 Solid-state NMR Measurements of Drugs -- 2.1 Amphetamine and ephedrine hydrochlorides and related compounds -- 2.2 Erythromycin A - formation of a hemiketal -- 2.3 Paracetamol - characterization of polymorphic forms -- 2.4 Procaine and procainamide derivatives -- 2.5 Rifampicin - molecular structure of polymorphs -- 2.6 Ketoconazole - amorphous form required -- 2.7 Paclitaxel (Taxol) - molecular structure and interactions -- 2.8 Troglitazone - hydration of diastereomers -- 2.9 Delavirdine mesylate tablets - hydration and solubility -- 2.10 MAS NMR of steroids: finasteride, estradiol, testosterone -- 2.11 Nifedipine and amlodipine -- 2.12 Ibuprofen preparations -- 2.13 Sildenafil citrate (Viagra) - structure and hydrogen bonding -- 2.14 Oxybuprocaine hydrochloride - NMR crystallography -- 2.15 Bupivacaine in protein matrix -- 2.16 Warfarin - cyclic hemiketal -- 3 Medicinal Plants Extracts -- 3.1 Mixture of α-amyrin and β-amyrin -- 3.2 Euphol from Euphorbia -- 3.3 Oxindole alkaloids from Uncaria tomentosa -- 3.4 Lanatoside C -- 3.5 Curcumin -- 4 13C CPMAS NMR of Excipients -- 5 Drugs in Membranes -- Chapter 5 Metabolic Profiling -- 1 Introduction -- 1.1 Definition of metabolic profiling -- 1.2 Goals of metabolic profiling experiments -- 1.3 Dynamic range of NMR measurements -- 1.4 Scope of chapter -- 2 Sample Preparation -- 2.1 General considerations -- 2.2 Sample specific considerations -- 2.3 Tissues -- 3 Data Acquisition -- 3.1 Requirements for quantitative NMR measurements -- 3.2 Water suppression -- 3.3 Experiments utilizing nuclei other than 1H -- 4 Spectral Processing -- 4.1 Apodization -- 4.2 Phasing and baseline correction 6 Statistical Analysis on Fruit Juices Other than Ridge Regression -- 7 Information on the Statistical Methods Applied -- 8 Conclusion -- Chapter 2 NMR Assays for Carbohydrate-Based Vaccines -- 1 Vaccines Based on the Cell Surface Carbohydrates of Microbial Pathogens -- 1.1 Cell surface carbohydrates -- 1.2 Carbohydrate-based vaccines -- 1.3 The structures of bacterial polysaccharides -- 2 NMR Tests for the Identity and Purity of Polysaccharides Used in Vaccine Manufacture -- 2.1 Traditional chemical approaches -- 2.2 Polysaccharide identity determination by NMR spectroscopy -- 2.3 NMR analysis of blends and CPSs in the presence of excipients -- 2.4 Quantitation of the O-acetyl contents of CPSs -- 2.5 Quantitation of contaminants and process-related impurities -- 2.6 Polysaccharide quantification -- 3 Identification of End Groups as Markers of Polysaccharide Degradation -- 4 Characterisation of Activated Intermediates in Vaccine Manufacture -- 4.1 Combined activation and depolymerisation using periodate oxidation or acid hydrolysis -- 4.2 Random activation without depolymerisation -- 5 NMR Analysis of Glycoconjugate Vaccines -- 5.1 Identity and integrity of the saccharide component of glycoconjugate vaccines -- 5.2 Determination of polysaccharide-protein ratio in glycoconjugate vaccines -- 6 Conclusions -- Chapter 3 Fluorine-19 or Phosphorus-31 NMR Spectroscopy: A Powerful Technique for Biofluid Metabolic Studies and Pharmaceutical Formulation Analysis of -- 1 Introduction -- 2 Advantages and Limitations of 19F and 31P NMR for in vitro Studies -- 3 19F NMR Studies of Fluorinated Drugs -- 3.1 Anti-bacterials -- 3.2 Neuroleptics -- 3.3 Analgesics -- 3.4 Anti-inflammatory drugs -- 3.5 Anaesthetics -- 3.6 Anti-cancer drugs -- 3.7 Anti-fungals -- 3.8 Miscellaneous drugs -- 4 31P NMR Studies of Phosphorylated Drugs -- 4.1 Amifostine 4.2 Cyclophosphamide and ifosfamide |
| Title | NMR Spectroscopy in Pharmaceutical Analysis |
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