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Table of Contents
Front Cover
Remington
Copyright Page
Publication history
Dedication
Contents
List of contributors
Foreword-Remington 23rd edition
Preface to the first edition
Preface to the 23rd edition
Acknowledgments
1 Introduction
1. History of pharmacy
1.1 The drug-taking animal
1.2 Prehistoric pharmacy
1.3 Antiquity
1.4 The Middle Ages
1.5 The Renaissance and Early Modern Europe
1.6 American pharmacy
1.7 Antebellum America: Pharmacy finds its niche
1.8 The search for professionalism
1.9 Legislation
1.10 Transition to a modern profession
1.11 The era of Count and Pour
1.12 The emergence of clinical pharmacy
1.13 The conflicting paradigms of pharmaceutical care and managed care
1.14 The promise of a new century
1.15 The future
1.16 History as a discipline
1.17 Bibliographic notes
1.18 A chronology of pharmacy
2. Integrated approach to drug nomenclature
2.1 Introduction
2.2 The changing face of drug nomenclature
2.3 Principles of drug nomenclature
2.4 Types of drug nomenclature
2.5 Global cooperation on harmonization of drug nomenclature
2.5.1 Role of World Health Organization-International Nonproprietary Names
2.5.1.1 International Nonproprietary Names assignment process
2.5.2 Role of Food Drug and Administration
2.5.3 Role of United States Pharmacopeia
2.5.4 Role of United State Adopted Name Council
2.5.5 The British Approved Names
2.5.6 The Australian Approved Names
2.6 The challenges of selecting INN for biologics
2.6.1 International Nonproprietary Names for therapeutic proteins
2.6.2 International Nonproprietary Names for monoclonal antibodies
2.6.3 International Nonproprietary Names for vaccines
2.6.4 International Nonproprietary Names for gene therapy products
2.7 Integrated approach to drug nomenclature.
2.8 Conclusion
Acknowledgment
References
2 Natural Products
3. Botanical dietary products
3.1 Botanical dietary supplements
3.1.1 Introduction
3.1.2 Use of botanical dietary supplements in the United States
3.2 Botanicals standardization and quality evaluation
3.2.1 Preliminary remarks
3.2.1.1 Preclinical standardization
3.2.1.2 Clinical standardization
3.3 Quality control and quality assurance of botanicals
3.4 Potential toxicity of botanical dietary supplements
3.5 Kratom (Mitragyna speciosa), a controversial psychoactive plant
3.6 Concluding remarks
References
4. Natural products and derivatives as human drugs
4.1 Introduction
4.2 Agents against pain
4.2.1 Modification of the alkaloids from Papaver somniferum
4.2.2 Opiates with a smaller number of condensed rings
4.2.3 Cone-snail toxins and other treatments
4.2.4 Cyclooxygenase inhibitors
4.3 Antiinfectives (antibacterial, antiparasitic, and antiviral)
4.3.1 Introduction
4.3.2 Natural product-based antibacterial agents from 2009 to 2018
4.3.3 Synthetic modifications to overcome resistance to vancomycin
4.3.4 Antifungal agents (Fig. 4.3)
4.3.5 Antifungal natural product compounds in the preclinical pipeline
4.3.6 Antiparasitic agents (Fig. 4.4)
4.3.7 Antiviral agents (nucleoside based) (Fig. 4.5)
4.3.8 Antiviral agents based upon arabinose and derivatives (Fig. 4.5)
4.4 Anticancer agents (Fig. 4.6)
4.4.1 Kinase inhibitors
4.4.2 Use of natural products and derivatives as antibody-drug conjugate warheads
4.5 Conclusion
References
5. Medicinal Cannabis: an overview for health-care providers
5.1 History of Cannabis use
5.1.1 Nomenclature and vernacular of Cannabis
5.2 Clinical indications
5.3 Cannabis subjective effects
5.4 "Stimulation versus couch lock?"
5.5 Formulations.
5.6 Routes of ingestion
5.6.1 Inhalational routes
5.6.2 Oral ingestion
5.6.3 Sublingual ingestion
5.6.4 Transdermal ingestion
5.6.5 Topical use
5.6.6 Rectal ingestion
5.7 Product labeling
5.8 The endocannabinoid system
5.8.1 Endocannabinoids
5.8.2 Endocannabinoid receptors
5.9 Pharmacology of phytocannabinoids
5.9.1 Pharmacokinetics
5.9.2 Absorption
5.9.3 Distribution
5.9.4 Metabolism
5.9.5 Excretion
5.10 Mechanisms of action
5.11 (−)-trans-Δ9-Tetrahydrocannabinol
5.12 Cannabidiol
5.13 Cannabinol
5.14 (−)-trans-Δ8-Tetrahydrocannabinol
5.14.1 Cannabigerol
5.15 Propyl, butyl, and heptyl phytocannabinoid homologs
5.16 Phytocannabinoid acids
5.17 Terpenes
5.18 Additional small molecule components in Cannabis
5.19 The entourage effect
5.20 Adverse effects
5.21 Pharmaceutical cannabinoid products
5.21.1 Dronabinol (Marinol, Syndros, (−)-trans-Δ9-tetrahydrocannabinol)
5.21.2 Nabilone (e.g., Cesamet)
5.21.3 Sativex (nabiximols)
5.21.4 Epidiolex (cannabidiol)
5.21.5 Additional cannabinoid-based agents in clinical development
5.22 Conclusion
References
3 Pharmaceutical Chemistry
6. Pharmaceutical chemistry
6.1 Introduction
6.2 Functional groups
6.2.1 Prodrugs
6.2.2 Isomers
6.2.3 Structural isomers
6.2.4 Tautomerism
6.2.5 Stereoisomers
6.2.6 Optical isomers
6.2.7 Geometric isomerism
6.2.8 Conformational isomerism
6.2.9 Biological activities of isomers
6.3 Acids and bases
6.3.1 Ionization of acids and bases
6.3.2 Ionization of water
6.3.3 Relationship of Ka and Kb
6.3.4 Electronegativity and dissociation constants
6.3.5 Ionic strength and dissociation constants
6.3.6 Microdissociation constants
6.3.7 Species concentration
6.3.8 Proton-balanced equation
6.3.9 Drug stability.
6.3.10 Drug activity
6.3.11 Drug absorption
6.4 Salts
6.4.1 Polymorphism
6.4.2 Cocrystals
6.5 Structural determinants of drug action
6.5.1 Partition coefficient (P)
6.5.2 Thermodynamic activity
6.5.3 Structurally specific drugs and receptors
6.5.4 Binding
6.6 Intermolecular forces of attraction
6.6.1 Ionic interactions
6.6.2 Dipole-dipole and ion-dipole interactions
6.6.3 Hydrogen bonding interactions
6.6.4 Charge-transfer complexes
6.6.5 van der Waals or London dispersion forces
6.6.6 Hydrophobic interactions
6.6.7 Binding site studies
6.7 Quantitative structure-activity relationship studies
6.7.1 Hansch linear free-energy model
6.7.2 Free-Wilson method
6.7.3 Topliss scheme
6.7.4 Bioisosterism
6.7.5 Polar surface area and topological polar surface area
6.8 Inorganic pharmaceutical chemistry
6.9 Drugs
6.10 Excipients
References and further reading
7. Structure-activity relationships and drug design
7.1 Introduction
7.2 Analog approach
7.2.1 Ligand-based design
7.2.2 Homologs
7.2.3 Fragment-based approaches
7.3 Chemical space
7.3.1 Functional groups
7.3.2 Isosteric replacement
7.3.3 Ionization state
7.3.4 Combinatorial organic synthesis
7.3.4.1 Configurational space
7.3.5 Structural isomers
7.3.6 Cis/trans isomers
7.3.7 Enantiomers
7.3.8 Diastereoisomers
7.3.9 Conformers
7.3.9.1 Absorption-distribution-metabolism-excretion-toxicity
7.3.10 Absorption
7.3.11 Distribution
7.3.12 Metabolism
7.3.13 Excretion
7.3.14 Toxicity
7.4 Quantitative structure-activity relationships
7.4.1 Descriptors
7.4.2 Models
7.4.3 Applications
7.5 Molecular docking for virtual screening
7.6 In silico prediction of protein-ligand binding affinities by free energy methods
7.7 Machine-learning approaches.
7.7.1 Neural networks
7.7.2 Support vector machines
References
8. Pharmaceutical profiling
8.1 Introduction
8.2 Pharmaceutical profiling in drug discovery
8.3 Profiling of active pharmaceutical ingredients and drug products' degradants
8.4 Pharmaceutical profiling in drug development
8.4.1 Drug-likeness
8.4.2 Drug formulation screening
8.5 Pharmaceutical profiling in pharmacokinetics and pharmacodynamics
8.6 Pharmaceutical profiling in toxicology and adverse drug reactions
8.7 Methods in pharmaceutical profiling
8.7.1 Methods in drug discovery: synthesis, screening, and reprofiling
8.7.2 Methods in drug-likeness prediction
8.7.3 Methods in profiling active pharmaceutical ingredient degradants
8.8 Absorption, distribution, metabolism, and excretion prediction models and methodologies
8.9 Methods in toxicity prediction
8.10 Automation in pharmaceutical profiling
8.11 Concluding remarks
References
9. Prodrugs
9.1 Introduction
9.2 Prodrug approaches based on drug delivery
9.3 Prodrug approaches based on functional groups
9.4 Prodrug approaches for anticancer drugs
9.5 Summary
References
10. Fundamentals of medical radionuclides
10.1 Applications of radionuclides in medicine and pharmacy
10.2 Radioactivity and radiation
10.2.1 Radiation from radioactive nuclei
10.2.2 Extranuclear radiation
10.3 The atom
10.3.1 Atomic structure
10.3.2 Nuclides and isotopes
10.3.3 Nuclear notation
10.3.4 Nuclear equations
10.4 Radioactive decay
10.4.1 Statistics
10.4.2 Kinetics of decay
10.4.3 Units of radioactivity
10.4.4 Modes of radioactive decay
10.5 Production of radionuclides
10.5.1 Fission by-products
10.5.2 Neutron reactions
10.5.3 Cyclotron-produced radionuclides
10.5.4 Radionuclide generators.
10.6 Radiolabeling of compounds to prepare radiotracers and radiopharmaceuticals.
Remington
Copyright Page
Publication history
Dedication
Contents
List of contributors
Foreword-Remington 23rd edition
Preface to the first edition
Preface to the 23rd edition
Acknowledgments
1 Introduction
1. History of pharmacy
1.1 The drug-taking animal
1.2 Prehistoric pharmacy
1.3 Antiquity
1.4 The Middle Ages
1.5 The Renaissance and Early Modern Europe
1.6 American pharmacy
1.7 Antebellum America: Pharmacy finds its niche
1.8 The search for professionalism
1.9 Legislation
1.10 Transition to a modern profession
1.11 The era of Count and Pour
1.12 The emergence of clinical pharmacy
1.13 The conflicting paradigms of pharmaceutical care and managed care
1.14 The promise of a new century
1.15 The future
1.16 History as a discipline
1.17 Bibliographic notes
1.18 A chronology of pharmacy
2. Integrated approach to drug nomenclature
2.1 Introduction
2.2 The changing face of drug nomenclature
2.3 Principles of drug nomenclature
2.4 Types of drug nomenclature
2.5 Global cooperation on harmonization of drug nomenclature
2.5.1 Role of World Health Organization-International Nonproprietary Names
2.5.1.1 International Nonproprietary Names assignment process
2.5.2 Role of Food Drug and Administration
2.5.3 Role of United States Pharmacopeia
2.5.4 Role of United State Adopted Name Council
2.5.5 The British Approved Names
2.5.6 The Australian Approved Names
2.6 The challenges of selecting INN for biologics
2.6.1 International Nonproprietary Names for therapeutic proteins
2.6.2 International Nonproprietary Names for monoclonal antibodies
2.6.3 International Nonproprietary Names for vaccines
2.6.4 International Nonproprietary Names for gene therapy products
2.7 Integrated approach to drug nomenclature.
2.8 Conclusion
Acknowledgment
References
2 Natural Products
3. Botanical dietary products
3.1 Botanical dietary supplements
3.1.1 Introduction
3.1.2 Use of botanical dietary supplements in the United States
3.2 Botanicals standardization and quality evaluation
3.2.1 Preliminary remarks
3.2.1.1 Preclinical standardization
3.2.1.2 Clinical standardization
3.3 Quality control and quality assurance of botanicals
3.4 Potential toxicity of botanical dietary supplements
3.5 Kratom (Mitragyna speciosa), a controversial psychoactive plant
3.6 Concluding remarks
References
4. Natural products and derivatives as human drugs
4.1 Introduction
4.2 Agents against pain
4.2.1 Modification of the alkaloids from Papaver somniferum
4.2.2 Opiates with a smaller number of condensed rings
4.2.3 Cone-snail toxins and other treatments
4.2.4 Cyclooxygenase inhibitors
4.3 Antiinfectives (antibacterial, antiparasitic, and antiviral)
4.3.1 Introduction
4.3.2 Natural product-based antibacterial agents from 2009 to 2018
4.3.3 Synthetic modifications to overcome resistance to vancomycin
4.3.4 Antifungal agents (Fig. 4.3)
4.3.5 Antifungal natural product compounds in the preclinical pipeline
4.3.6 Antiparasitic agents (Fig. 4.4)
4.3.7 Antiviral agents (nucleoside based) (Fig. 4.5)
4.3.8 Antiviral agents based upon arabinose and derivatives (Fig. 4.5)
4.4 Anticancer agents (Fig. 4.6)
4.4.1 Kinase inhibitors
4.4.2 Use of natural products and derivatives as antibody-drug conjugate warheads
4.5 Conclusion
References
5. Medicinal Cannabis: an overview for health-care providers
5.1 History of Cannabis use
5.1.1 Nomenclature and vernacular of Cannabis
5.2 Clinical indications
5.3 Cannabis subjective effects
5.4 "Stimulation versus couch lock?"
5.5 Formulations.
5.6 Routes of ingestion
5.6.1 Inhalational routes
5.6.2 Oral ingestion
5.6.3 Sublingual ingestion
5.6.4 Transdermal ingestion
5.6.5 Topical use
5.6.6 Rectal ingestion
5.7 Product labeling
5.8 The endocannabinoid system
5.8.1 Endocannabinoids
5.8.2 Endocannabinoid receptors
5.9 Pharmacology of phytocannabinoids
5.9.1 Pharmacokinetics
5.9.2 Absorption
5.9.3 Distribution
5.9.4 Metabolism
5.9.5 Excretion
5.10 Mechanisms of action
5.11 (−)-trans-Δ9-Tetrahydrocannabinol
5.12 Cannabidiol
5.13 Cannabinol
5.14 (−)-trans-Δ8-Tetrahydrocannabinol
5.14.1 Cannabigerol
5.15 Propyl, butyl, and heptyl phytocannabinoid homologs
5.16 Phytocannabinoid acids
5.17 Terpenes
5.18 Additional small molecule components in Cannabis
5.19 The entourage effect
5.20 Adverse effects
5.21 Pharmaceutical cannabinoid products
5.21.1 Dronabinol (Marinol, Syndros, (−)-trans-Δ9-tetrahydrocannabinol)
5.21.2 Nabilone (e.g., Cesamet)
5.21.3 Sativex (nabiximols)
5.21.4 Epidiolex (cannabidiol)
5.21.5 Additional cannabinoid-based agents in clinical development
5.22 Conclusion
References
3 Pharmaceutical Chemistry
6. Pharmaceutical chemistry
6.1 Introduction
6.2 Functional groups
6.2.1 Prodrugs
6.2.2 Isomers
6.2.3 Structural isomers
6.2.4 Tautomerism
6.2.5 Stereoisomers
6.2.6 Optical isomers
6.2.7 Geometric isomerism
6.2.8 Conformational isomerism
6.2.9 Biological activities of isomers
6.3 Acids and bases
6.3.1 Ionization of acids and bases
6.3.2 Ionization of water
6.3.3 Relationship of Ka and Kb
6.3.4 Electronegativity and dissociation constants
6.3.5 Ionic strength and dissociation constants
6.3.6 Microdissociation constants
6.3.7 Species concentration
6.3.8 Proton-balanced equation
6.3.9 Drug stability.
6.3.10 Drug activity
6.3.11 Drug absorption
6.4 Salts
6.4.1 Polymorphism
6.4.2 Cocrystals
6.5 Structural determinants of drug action
6.5.1 Partition coefficient (P)
6.5.2 Thermodynamic activity
6.5.3 Structurally specific drugs and receptors
6.5.4 Binding
6.6 Intermolecular forces of attraction
6.6.1 Ionic interactions
6.6.2 Dipole-dipole and ion-dipole interactions
6.6.3 Hydrogen bonding interactions
6.6.4 Charge-transfer complexes
6.6.5 van der Waals or London dispersion forces
6.6.6 Hydrophobic interactions
6.6.7 Binding site studies
6.7 Quantitative structure-activity relationship studies
6.7.1 Hansch linear free-energy model
6.7.2 Free-Wilson method
6.7.3 Topliss scheme
6.7.4 Bioisosterism
6.7.5 Polar surface area and topological polar surface area
6.8 Inorganic pharmaceutical chemistry
6.9 Drugs
6.10 Excipients
References and further reading
7. Structure-activity relationships and drug design
7.1 Introduction
7.2 Analog approach
7.2.1 Ligand-based design
7.2.2 Homologs
7.2.3 Fragment-based approaches
7.3 Chemical space
7.3.1 Functional groups
7.3.2 Isosteric replacement
7.3.3 Ionization state
7.3.4 Combinatorial organic synthesis
7.3.4.1 Configurational space
7.3.5 Structural isomers
7.3.6 Cis/trans isomers
7.3.7 Enantiomers
7.3.8 Diastereoisomers
7.3.9 Conformers
7.3.9.1 Absorption-distribution-metabolism-excretion-toxicity
7.3.10 Absorption
7.3.11 Distribution
7.3.12 Metabolism
7.3.13 Excretion
7.3.14 Toxicity
7.4 Quantitative structure-activity relationships
7.4.1 Descriptors
7.4.2 Models
7.4.3 Applications
7.5 Molecular docking for virtual screening
7.6 In silico prediction of protein-ligand binding affinities by free energy methods
7.7 Machine-learning approaches.
7.7.1 Neural networks
7.7.2 Support vector machines
References
8. Pharmaceutical profiling
8.1 Introduction
8.2 Pharmaceutical profiling in drug discovery
8.3 Profiling of active pharmaceutical ingredients and drug products' degradants
8.4 Pharmaceutical profiling in drug development
8.4.1 Drug-likeness
8.4.2 Drug formulation screening
8.5 Pharmaceutical profiling in pharmacokinetics and pharmacodynamics
8.6 Pharmaceutical profiling in toxicology and adverse drug reactions
8.7 Methods in pharmaceutical profiling
8.7.1 Methods in drug discovery: synthesis, screening, and reprofiling
8.7.2 Methods in drug-likeness prediction
8.7.3 Methods in profiling active pharmaceutical ingredient degradants
8.8 Absorption, distribution, metabolism, and excretion prediction models and methodologies
8.9 Methods in toxicity prediction
8.10 Automation in pharmaceutical profiling
8.11 Concluding remarks
References
9. Prodrugs
9.1 Introduction
9.2 Prodrug approaches based on drug delivery
9.3 Prodrug approaches based on functional groups
9.4 Prodrug approaches for anticancer drugs
9.5 Summary
References
10. Fundamentals of medical radionuclides
10.1 Applications of radionuclides in medicine and pharmacy
10.2 Radioactivity and radiation
10.2.1 Radiation from radioactive nuclei
10.2.2 Extranuclear radiation
10.3 The atom
10.3.1 Atomic structure
10.3.2 Nuclides and isotopes
10.3.3 Nuclear notation
10.3.4 Nuclear equations
10.4 Radioactive decay
10.4.1 Statistics
10.4.2 Kinetics of decay
10.4.3 Units of radioactivity
10.4.4 Modes of radioactive decay
10.5 Production of radionuclides
10.5.1 Fission by-products
10.5.2 Neutron reactions
10.5.3 Cyclotron-produced radionuclides
10.5.4 Radionuclide generators.
10.6 Radiolabeling of compounds to prepare radiotracers and radiopharmaceuticals.