Molecules and Medicine

E. J. Corey has been a Professor at Harvard University since 1959. He was educated at The Massachusetts Institute of Technology (1945-1950) and served as a faculty member at the University of Illinois from1951 to 1959. He is the 1990 Nobel Laureate in Chemistry, and the recipient of over seventy international awards and honorary degrees, including the U.S. National Medal of Science, the Japan Prize in Science, and the Priestley Medal of the American Chemical Society. He is amember of the U.S. National Academy of Sciences and the U.S. National Institute of Medicine. Professor Corey is the author of more than 1,000 publications and is one of the most cited authors in science. Barbara Czakó completed undergraduate studies at the University of Debrecen, Hungary, where she worked with Dr. Sándor Berényi. She obtained a Master of Science degree at the University of Missouri-Columbia with Professor Shon R. Pulley. Dr. Czakó received her Ph.D. degree (2006) in synthetic organic chemistry under the guidance of Professor Gary A. Molander at the University of Pennsylvania. Currently she is a postdoctoral fellow with Professor E.J. Corey at Harvard University. In 2005 she published with László Kürti the textbook Strategic Applications of Named Reactions in Organic Synthesis. László Kürti was born and raised in Hungary. He received his diploma from the University of Debrecen, Hungary, where he conducted research in the laboratory of Professor Sándor Antus. Subsequently he received his Master of Science degree at the University of Missouri-Columbia working with Professor Michael Harmata, and his Ph.D. degree (2006) in synthetic organic chemistry under the supervision of Professor Amos B. Smith III (the University of Pennsylvania). Currently he is a Damon Runyon Cancer Fellow in the group of Professor E.J. Corey at Harvard University. In 2005 he published with Barbara Czakó the textbook Strategic Applications of Named Reactions in Organic Synthesis.

Part I.

Introduction 2

Understanding Structural Diagrams of Organic Molecules 4

Some Common Molecules 23

Proteins and Three-Dimensional Protein Structure 26

Some of the Protein Structures That Appear in This Book 32

Part II. Inflammatory, Cardiovascular and Metabolic Diseases

Anti-Inflammatory Agents

Acetylsalicylic acid (AspirinTM) 38

Naproxen (AleveTM) 39

How Do Anti-Inflammatory Drugs Work? 40

Other Eicosanoids in Inflammation 41

An Overview of Inflammation 42

Celecoxib (CelebrexTM) 43

Prednisone (DeltasoneTM) 44

Methotrexate (TrexallTM) 46

Allopurinol (ZyloprimTM) 47

Antiasthmatic and Antiallergic Agents

Salmeterol (SereventTM) 50

Fluticasone Propionate (FloventTM) 51

Montelukast Sodium (SingulairTM) 52

Tiotropium Bromide (SpirivaTM) 53

Loratadine (ClaritinTM) 54

Type 2 Diabetes

An Overview of Metabolic Syndrome 56

Antidiabetic and Cholesterol-Lowering Agents

Metformin (GlucophageTM) 60

Glipizide (GlucotrolTM) 61

Pioglitazone (ActosTM) 62

Sitagliptin (JanuviaTM) 63

Atorvastatin (LipitorTM) 64

Ezetimibe (ZetiaTM) 65

Cardiovascular Agents

Atenolol (TenorminTM) 68

Enalapril (VasotecTM) 69

Candesartan Cilexetil (AtacandTM) 70

Aliskiren (TekturnaTM) 71

Amlodipine (NorvascTM) 72

Nitroglycerin 73

Clopidogrel Bisulfate (PlavixTM) 74

Digoxin (LanoxinTM) 75

Receptors and Signaling

Information Flow into the Cell by Chemical Signaling 78

References for Part II 80

Part III. Reproductive Medicine

Oral Contraceptives 90

Testosterone 91

Mifepristone (MifeprexTM) 92

Oxytocin (OxytocinTM) 93

Sildenafil (ViagraTM) 94

Osteoporosis

Some Aspects of Osteoporosis 96

Alendronate (FosamaxTM) 97

Calcitriol (RocaltrolTM) 98

Raloxifene (EvistaTM) 99

Teriparatide (ForteoTM) 100

Glaucoma and Antiulcer Agents

Latanoprost (XalatanTM) 102

Ranitidine (ZantacTM) 103

Omeprazole (PrilosecTM) 104

References for Part III 105

Part IV.  Autoimmune Disease and Organ Transplant

A Brief Survey of the Immune System 112

Immunosuppressive Agents

Azathioprine (ImuranTM) 122

Mycophenolate Mofetil (CeIlCeptTM) 123

Cyclosporin (NeoralTM) 124

Tacrolimus (PrografTM) 125

FTY720 (Fingolimod) 126

Infectious Diseases

Antibiotics

Amoxicillin (AmoxilTM) 130

Cefaclor (CeclorTM) 132

Doxycycline (VibramycinTM) 133

Azithromycin (ZithromaxTM) 134

Ciprofloxacin (CiproTM) 135

Trimethoprim (TriprimTM) 136

Amikacin (AmikinTM) 137

Vancomycin (VancocinTM) 138

Linezolid (ZyvoxTM) 139

Isoniazid (LaniazidTM) 140

Ancillary Antibiotics 142

Drug Resistance 143

Antiviral Agents

On Viruses and Viral Diseases 146

Acyclovir (ZoviraxTM) 148

Ribavirin (VirazoleTM) 149

Oseltamivir (TamifluTM) 150

Zidovudine (Retrovir, AZTTM) 151

Zalcitabine (HividTM) 152

Nevirapine (ViramuneTM) 153

Efavirenz (SustivaTM) 154

Lopinavir + Ritonavir (KaletraTM) 155

UK427857 (Maraviroc) 156

Antifungal Agents

Amphotericin (FungizoneTM) 160

Fluconazole (DiflucanTM) 161

Caspofungin (CancidasTM) 162

Terbinafine (LamisilTM) 163

Antimalarial and Antiparasitic Agents

Parasitic Diseases: A Focus on Malaria 166

Chloroquine (ArdenTM) 167

Artemether + Lumefantrine (CoArtemTM) 168

Atovaquone + Proguanil (MalaroneTM) 169

Miltefosine (I mpavidoTM) 170

Nitazoxanide (AliniaTM) 171

Ivermectin (StromectolTM) 172

References for Part IV 173

Part V. Malignant Disease

An Overview of Cancer 184

Capecitabine (XelodaTM) 187

Carboplatin (ParaplatinTM) 188

Vinblastine (VelbanTM) 189

Paclitaxel (TaxolTM) 190

Cyclophosphamide (CytoxanTM) 191

Tamoxifen (NolvadexTM) 192

Irinotecan (CamptosarTM) 193

Bleomycin (BlenoxaneTM) 194

Imatinib (GleevecTM) 195

Sunitinib (SutentTM) 196

Bortezomib (VelcadeTM) 197

Ancillary Anticancer Agents 198

References for Part V 200

Part VI. Drugs Acting on the Nervous System

Pain and Analgesia

Lidocaine (XylocaineTM) 208

Morphine (AvinzaTM) 209

Acetaminophen (Tylenol TM) 210

Fentanyl (DuragesicTM) 211

Sodium Thiopental (Sodium PentothalTM) 212

Gabapentin (NeurontinTM) 213

Diazepam (ValiumTM) 214

Sumatriptan (ImitrexTM) 215

Hypnotics (Insomnia) and Antismoking

Zolpidem (AmbienTM) 218

Ramelteon (RozeremTM) 219

Varenicline (ChantixTM) 220

The Brain, Neurotransmission and Molecular Neurotransmitters 221

Neurodegenerative and Psychiatric Diseases

Levodopa (LarodopaTM) 224

Donepezil (AriceptTM) 225

Antiepileptic Agents 226

Antianxiety Agents 228

Antidepressants 229

Antipsychotics 232

References for Part VI 233

Glossary 237

Index 249