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Wilson and Gisvolds Textbook of Organic Medicinal and Pharmaceutical Chemistry

BPharmacy, 4th Semester, 2020 - Notes

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Wilson and Gisvolds Textbook of Organic Medicinal and Pharmaceutical Chemistry BPharmacy 4th semester 2020 Previous Year's Question Papers/Notes Download - HK Technical PGIMS

CONTENTS Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . iv Contributors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vi CHAPTER 1 Introduction . . . . . . . . . . . . . . . . . . . . . . 1 John M. Beale, Jr. and John H. Block CHAPTER 2 Drug Design Strategies . . . . . . . . . . . . . 3 John H. Block Drug Distribution. . . . . . . . . . . . . . . . . . . . . . . . . . . . 3 Acid–Base Properties . . . . . . . . . . . . . . . . . . . . . . . . 12 Computer-Aided Drug Design: Early Methods . . . 17 Computer-Aided Drug Design: Newer Methods . . 25 Selected Web Pages. . . . . . . . . . . . . . . . . . . . . . . . . 40 CHAPTER 3 Metabolic Changes of Drugs and Related Organic Compounds . . . . 43 Stephen J. Cutler and John H. Block General Pathways of Drug Metabolism . . . . . . . . . 43 Sites of Drug Biotransformation. . . . . . . . . . . . . . . 45 Role of Cytochrome P450 Monooxygenases in Oxidative Biotransformations. . . . . . . . . . . . . 45 Oxidative Reactions . . . . . . . . . . . . . . . . . . . . . . . . . 47 Reductive Reactions. . . . . . . . . . . . . . . . . . . . . . . . . 78 Hydrolytic Reactions . . . . . . . . . . . . . . . . . . . . . . . . 86 Phase II or Conjugation Reactions . . . . . . . . . . . . . 88 Factors Affecting Drug Metabolism . . . . . . . . . . . 104 CHAPTER 4 Biotechnology and Drug Discovery. . 119 John M. Beale, Jr. Biotechnology and Pharmaceutical Care . . . . . . . 119 Literature of Biotechnology . . . . . . . . . . . . . . . . . 119 Biotechnology and New Drug Development. . . . 119 The Biotechnology of Recombinant DNA . . . . . . 121 Some Types of Cloning . . . . . . . . . . . . . . . . . . . . . 126 Expression of Cloned DNA . . . . . . . . . . . . . . . . . . 127 Manipulation of DNA Sequence Information . . . 127 New Biological Targets for Drug Development. . 128 Novel Drug-Screening Strategies . . . . . . . . . . . . . 129 Processing of the Recombinant Protein . . . . . . . . 131 Pharmaceutics of Recombinant DNA-Produced Agents. . . . . . . . . . . . . . . . . . . . 131 Delivery and Pharmacokinetics of Biotechnology Products . . . . . . . . . . . . . . . . 134 Recombinant Drug Products . . . . . . . . . . . . . . . . . 134 The Interleukins . . . . . . . . . . . . . . . . . . . . . . . . . . . 141 Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 142 Vaccines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145 Preparation of Antibodies. . . . . . . . . . . . . . . . . . . 146 Genomics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150 Antisense Technology . . . . . . . . . . . . . . . . . . . . . . 152 Gene Therapy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153 Afterword. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153 CHAPTER 5 Immunobiologicals. . . . . . . . . . . . . . . 156 John M. Beale, Jr. Cells of the Immune System . . . . . . . . . . . . . . . . . 156 Immunity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 159 Acquistion of Immunity. . . . . . . . . . . . . . . . . . . . . 165 New Vaccine Technologies: Adjuvant Technology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 174 New Vaccine Technologies: Nucleic Acid Vaccines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177 CHAPTER 6 Anti-infective Agents . . . . . . . . . . . . . 179 John M. Beale, Jr. Evaluation of the Effectiveness of a Sterilant . . . 180 Alcohols and Related Compounds . . . . . . . . . . . . 181 Phenols and Their Derivatives. . . . . . . . . . . . . . . . 183 Oxidizing Agents . . . . . . . . . . . . . . . . . . . . . . . . . . 185 Halogen-Containing Compounds . . . . . . . . . . . . . 185 Cationic Surfactants. . . . . . . . . . . . . . . . . . . . . . . . 186 Dyes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 188 Mercury Compounds (Mercurials). . . . . . . . . . . . . 189 Preservatives. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 190 Antifungal Agents . . . . . . . . . . . . . . . . . . . . . . . . . 191 Synthetic Antibacterial Agents . . . . . . . . . . . . . . . 206 Antiprotozoal Agents . . . . . . . . . . . . . . . . . . . . . . 220 Anthelmintics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 224 Antiscabious and Antipedicular Agents . . . . . . . . 227 Antibacterial Sulfonamides. . . . . . . . . . . . . . . . . . 228 Dihydrofolate Reductase Inhibitors . . . . . . . . . . . 239 Sulfones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239 CHAPTER 7 Antimalarials . . . . . . . . . . . . . . . . . . . 242 John H. Block Stimulation of Antimalarial Research by War . . . 245 Cinchona Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . 245 CHAPTER 8 Antibacterial Antibiotics. . . . . . . . . . . 258 John M. Beale, Jr. Historical Background . . . . . . . . . . . . . . . . . . . . . . 258 Current Status . . . . . . . . . . . . . . . . . . . . . . . . . . . . 259 Commercial Production . . . . . . . . . . . . . . . . . . . . . 259 Spectrum of Activity . . . . . . . . . . . . . . . . . . . . . . . 259 Mechanisms of Action . . . . . . . . . . . . . . . . . . . . . . 259 Chemical Classification . . . . . . . . . . . . . . . . . . . . . 260 Microbial Resistance . . . . . . . . . . . . . . . . . . . . . . . 260 -Lactam Antibiotics . . . . . . . . . . . . . . . . . . . . . . . 260 vii 000i-000x_17865_FM.qxd 12/2/09 2:50 AM Page vii The Penicillins. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 261 -Lactamase Inhibitors. . . . . . . . . . . . . . . . . . . . . . 274 Cephalosporins. . . . . . . . . . . . . . . . . . . . . . . . . . . . 278 Monobactams. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 293 Aminoglycosides . . . . . . . . . . . . . . . . . . . . . . . . . . 294 Tetracyclines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 301 Macrolides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 308 Lincomycins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 313 Polypeptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 315 Unclassified Antibiotics . . . . . . . . . . . . . . . . . . . . . 320 Newer Antibiotics . . . . . . . . . . . . . . . . . . . . . . . . . 324 New Directions in Antibiotic Discovery . . . . . . . . 326 CHAPTER 9 Antiviral Agents . . . . . . . . . . . . . . . . . 330 John M. Beale, Jr. The Classification and Biochemistry of Viruses . . 330 Classification of Viruses . . . . . . . . . . . . . . . . . . . . . 330 Targets for the Prevention of Viral Infections—Chemoprophylaxis . . . . . . . . . . . . . 331 The Infectious Process for a Virus. . . . . . . . . . . . . 333 Nucleoside Antimetabolites: Inhibiting Viral Replication . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 339 Newer Agents for the Treatment of HIV Infection . . . . . . . . . . . . . . . . . . . . . . . . . . . 346 CHAPTER 10 Antineoplastic Agents. . . . . . . . . . . . . 355 Forrest T. Smith and C. Randall Clark Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 355 Drug Classes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 358 Antimetabolites . . . . . . . . . . . . . . . . . . . . . . . . . . . 372 Antibiotics and Natural Products . . . . . . . . . . . . . 383 Protein Kinase Inhibitors . . . . . . . . . . . . . . . . . . . . 400 Miscellaneous Compounds . . . . . . . . . . . . . . . . . . 406 CHAPTER 11 Agents for Diagnostic Imaging . . . . . 413 Jeffrey J. Christoff Radiopharmaceuticals . . . . . . . . . . . . . . . . . . . . . . 413 Contrast Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . 430 CHAPTER 12 Central Nervous System Depressants. . . . . . . . . . . . . . . . . . . . . 443 Shengquan Liu Anxiolytic, Sedative, and Hypnotic Agents . . . . . 443 Antipsychotics . . . . . . . . . . . . . . . . . . . . . . . . . . . . 457 Acknowledgment . . . . . . . . . . . . . . . . . . . . . . . . . 469 CHAPTER 13 Central Dopaminergic Signaling Agents. . . . . . . . . . . . . . . . . 471 A. Michael Crider, Marcelo J. Nieto, and Kenneth A. Witt Dopamine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 471 Parkinson Disease. . . . . . . . . . . . . . . . . . . . . . . . . . 473 Antipsychotic Drugs. . . . . . . . . . . . . . . . . . . . . . . . 478 Future Directions . . . . . . . . . . . . . . . . . . . . . . . . . . 488 CHAPTER 14 Anticonvulsants . . . . . . . . . . . . . . . . . 491 Matthias C. Lu Disease States Requiring Anticonvulsant Therapy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 491 Mechanisms of Action of Anticonvulsants. . . . . . 492 Clinically Important Anticonvulsants . . . . . . . . . . 494 Future Development of Antiepileptic Drugs . . . . 501 CHAPTER 15 Central Nervous System Stimulants . . . . . . . . . . . . . . . . . . . . . . 504 John M. Beale, Jr. Analeptics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 504 Methylxanthines . . . . . . . . . . . . . . . . . . . . . . . . . . 505 Central Sympathomimetic Agents (Psychomotor Stimulants) . . . . . . . . . . . . . . . . . 506 Antidepressants . . . . . . . . . . . . . . . . . . . . . . . . . . . 509 Miscellaneous CNS-Acting Drugs . . . . . . . . . . . . . 515 CHAPTER 16 Adrenergic Agents . . . . . . . . . . . . . . . 519 Shengquan Liu Adrenergic Neurotransmitters . . . . . . . . . . . . . . . 519 Adrenergic Receptors . . . . . . . . . . . . . . . . . . . . . . 524 Drugs Affecting Adrenergic Neurotransmission . . . . . . . . . . . . . . . . . . . . . . . 528 Sympathomimetic Agents . . . . . . . . . . . . . . . . . . . 531 Adrenergic Receptor Antagonists (Blockers) . . . . 545 Acknowledgment . . . . . . . . . . . . . . . . . . . . . . . . . 554 CHAPTER 17 Cholinergic Drugs and Related Agents . . . . . . . . . . . . . . . . . . . . . . . . . 558 Stephen J. Cutler Cholinergic Receptors . . . . . . . . . . . . . . . . . . . . . . 559 Cholinergic Neurochemistry . . . . . . . . . . . . . . . . . 563 Cholinergic Agonists . . . . . . . . . . . . . . . . . . . . . . . 564 Cholinergic Receptor Antagonists . . . . . . . . . . . . 567 Cholinergic Blocking Agents . . . . . . . . . . . . . . . . . 581 Parasympathetic Postganglionic Blocking Agents . . . . . . . . . . . . . . . . . . . . . . . . . 583 Solanaceous Alkaloids and Analogs . . . . . . . . . . . 584 Synthetic Cholinergic Blocking Agents. . . . . . . . . 588 Ganglionic Blocking Agents . . . . . . . . . . . . . . . . . 596 Neuromuscular Blocking Agents. . . . . . . . . . . . . . 599 CHAPTER 18 Drugs Acting on the Renal System . . 607 Stephen J. Cutler Renin–Angiotensin System Inhibitors. . . . . . . . . . 609 ACE-Inhibitor Prodrugs . . . . . . . . . . . . . . . . . . . . . 610 Angiotensin Antagonists. . . . . . . . . . . . . . . . . . . . 612 viii Contents 000i-000x_17865_FM.qxd 12/2/09 2:50 AM Page viii Angiotensin II Blockers . . . . . . . . . . . . . . . . . . . . . 613 Renin Inhibitors . . . . . . . . . . . . . . . . . . . . . . . . . . . 614 Aldosterone Antagonists. . . . . . . . . . . . . . . . . . . . 615 CHAPTER 19 Cardiovascular Agents . . . . . . . . . . . . 617 Stephen J. Cutler Antianginal Agents and Vasodilators. . . . . . . . . . 617 Antiarrhythmic Drugs . . . . . . . . . . . . . . . . . . . . . . 629 Antihypertensive Agents. . . . . . . . . . . . . . . . . . . . 637 Antihyperlipidemic Agents . . . . . . . . . . . . . . . . . . 647 Anticoagulants . . . . . . . . . . . . . . . . . . . . . . . . . . . . 654 Synthetic Hypoglycemic Agents . . . . . . . . . . . . . . 658 Thyroid Hormones . . . . . . . . . . . . . . . . . . . . . . . . . 663 Antithyroid Drugs . . . . . . . . . . . . . . . . . . . . . . . . . 663 CHAPTER 20 Hormone-Related Disorders: Nonsteroidal Therapies . . . . . . . . . . . 666 Ronald A. Hill Disorders of Glucose Metabolism: Diabetes and the Metabolic Syndrome . . . . . . . . . . . . . . 666 Gonadotropins, Gonadotrpoin-Releasing Hormone, and GNRH Receptor Agonists and Antagonists. . . . . . . . . . . . . . . . . . . . . . . . . 695 Concluding Remarks . . . . . . . . . . . . . . . . . . . . . . . 701 CHAPTER 21 Agents Treating Bone Disorders . . . . 705 John H. Block Diseases of Bone Tissue Utilizing Approved Drug Therapies. . . . . . . . . . . . . . . . . . . . . . . . . . 705 Drugs Used to Treat Diseases of the Bone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 706 Hormone Therapy . . . . . . . . . . . . . . . . . . . . . . . . . 708 Future Directions . . . . . . . . . . . . . . . . . . . . . . . . . . 710 CHAPTER 22 Anesthetics . . . . . . . . . . . . . . . . . . . . . 711 Carolyn J. Friel The Inhaled General Anesthetics . . . . . . . . . . . . . 711 The Injectable General Anesthetics . . . . . . . . . . . 716 The Local Anesthetics . . . . . . . . . . . . . . . . . . . . . . 718 Local Anesthetic Monographs, Individual Products Including Adverse Reactions . . . . . . . 725 CHAPTER 23 Histamine and Antihistaminic Agents . . . . . . . . . . . . . . . . . . . . . . . . . 733 Jack DeRuiter Histamine Chemistry . . . . . . . . . . . . . . . . . . . . . . . 733 Histamine as a Chemical Messenger. . . . . . . . . . . 733 Antihistamines . . . . . . . . . . . . . . . . . . . . . . . . . . . . 737 Inhibition of Histamine Release: Mast Cell Stabilizers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 757 Recent Antihistamine Developments: the “Dual-Acting” Antihistamines . . . . . . . . . . 759 Histamine H2-Antagonists . . . . . . . . . . . . . . . . . . . 760 Histamine H3- and H4-Receptor Ligands . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 773 CHAPTER 24 Analgesics . . . . . . . . . . . . . . . . . . . . . . 776 Carolyn J. Friel and Matthias C. Lu Pain and Pain Management . . . . . . . . . . . . . . . . . 776 Opioids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 777 Drug Monographs . . . . . . . . . . . . . . . . . . . . . . . . . 782 Nonsteroidal Anti-inflammatory Drugs . . . . . . . . 792 Disease-Modifying Antirheumatic Drugs . . . . . . . 806 Drugs Used in the Management of Gout and Hyperuricemia. . . . . . . . . . . . . . . . . . . . . . . 809 Triptans. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 811 CHAPTER 25 Steroid Hormones and Therapeutically Related Compounds . . . . . . . . . . . . . . . . . . . . . 819 Philip J. Proteau Steroid Nomenclature, Stereochemistry, and Numbering . . . . . . . . . . . . . . . . . . . . . . . . . 819 Steroid Biosynthesis . . . . . . . . . . . . . . . . . . . . . . . . 819 Chemical and Physical Properties of Steroids . . . 822 Changes to Modify Pharmacokinetic Properties of Steroids . . . . . . . . . . . . . . . . . . . . 822 Steroid Hormone Receptors . . . . . . . . . . . . . . . . . 823 Gonadotropin-Releasing Hormone and Gonadotropins . . . . . . . . . . . . . . . . . . . . . . 826 Sex Hormones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 827 Chemical Contraceptive Agents . . . . . . . . . . . . . . 841 Androgens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 847 Adrenal Cortex Hormones. . . . . . . . . . . . . . . . . . . 853 Neurosteroids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 864 Acknowledgment. . . . . . . . . . . . . . . . . . . . . . . . . . 864 CHAPTER 26 Prostaglandins, Leukotrienes, and Essential Fatty Acids. . . . . . . . . . 868 Thomas J. Holmes, Jr. Essential Fatty Acids. . . . . . . . . . . . . . . . . . . . . . . . 868 History of Eicosanoid Discovery . . . . . . . . . . . . . . 868 Eicosanoid Biosynthesis . . . . . . . . . . . . . . . . . . . . . 869 Drug Action Mediated by Eicosanoids . . . . . . . . . 872 COX-2 Inhibitors. . . . . . . . . . . . . . . . . . . . . . . . . . . 872 Design of Eicosanoid Drugs. . . . . . . . . . . . . . . . . . 872 Eicosanoid Receptors . . . . . . . . . . . . . . . . . . . . . . . 875 Commercially Available Essential Fatty Acid Supplements. . . . . . . . . . . . . . . . . . . . . . . . . . . . 875 Eicosanoids Approved for Human Clinical Use . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 876 Prostaglandins for Ophthalmic Use . . . . . . . . . . . 878 Veterinary Uses of Prostanoids . . . . . . . . . . . . . . . 878 Eicosanoids in Clinical Development for Human Treatment . . . . . . . . . . . . . . . . . . . . 879 Contents ix 000i-000x_17865_FM.qxd 12/2/09 2:50 AM Page ix CHAPTER 27 Proteins, Enzymes, and Peptide Hormones . . . . . . . . . . . . . . . . . . . . . . 880 Stephen J. Cutler and Horace G. Cutler Protein Hydrolysates . . . . . . . . . . . . . . . . . . . . . . . 880 Amino Acid Solutions . . . . . . . . . . . . . . . . . . . . . . 881 Proteins and Proteinlike Compounds. . . . . . . . . . 881 Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 885 Hormones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 890 Blood Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . 906 Impact of Biotechnology on the Development and Commercial Production of Proteins and Peptides as Pharmaceutical Products . . . . 907 Biotechnology-Derived Pharmaceutical Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 909 CHAPTER 28 Vitamins . . . . . . . . . . . . . . . . . . . . . . . 915 Michael J. Deimling, M. O. Faruk Khan, and Gustavo R. Ortega Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 915 Fat-Soluble Vitamins . . . . . . . . . . . . . . . . . . . . . . . 917 Water-Soluble Vitamins. . . . . . . . . . . . . . . . . . . . . 935 CHAPTER 29 An Introduction to the Medicinal Chemistry of Herbs. . . . . . . . . . . . . . . 961 John M. Beale, Jr. Historical Aspects . . . . . . . . . . . . . . . . . . . . . . . . . . 961 What Is an Herb? . . . . . . . . . . . . . . . . . . . . . . . . . . 962 Herbal Purity and Standardization. . . . . . . . . . . . 962 An Herb Is a Drug . . . . . . . . . . . . . . . . . . . . . . . . . 962 Types of Herbs . . . . . . . . . . . . . . . . . . . . . . . . . . . . 963 APPENDIX Calculated Log P, Log D, and pKa . . 976 Index . . . . . . . . . . . . . . . . . . . . . . . . . . 984



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