PHENYLPROPANOLAMINE A REVIEW
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1 0 PHENYLPROPANOLAMINE A REVIEW LOUIS LASAGNA Sackler School of Graduate Biomedical Sciences Tufts University Boston, Massachusetts WILEY AWILEY-INTERSCIENCE PUBLICATION JOHN WILEY & SONS NEW YORK / CHICHESTER / BRISBANE / TORONTO / SINGAPORE
2 CHAPTER 1. HISTORY 1 EARLY STUDIES OF PHENYLPROPANOLAMINE: SYNTHESIS AND PATENTING 2 EARLY BASIC PHARMACOLOGY STUDIES 4 THERAPEUTIC USES 7 STREET DRUG ABUSE: AMPHETAMINE LOOK-ALIKES, PSEUDOSPEED, AND COUNTERFEIT CONTROLLED SUBSTANCES 12 CHAPTER 2. CHEMISTRY 21 STEREOCHEMISTRY OF PHENYLPROPANOLAMINE 22 SYNTHESIS OF PHENYLPROPANOLAMINE 29 PHARMACEUTICAL PREPARATIONS CONTAINING PHENYLPROPANOLAMINE 31 Sustained-Release Preparations 32 Formulations of Cough-Cold Preparations 37 ix
3 X Formulations of Appetite Suppressants 40 CHEMICAL ANALYSIS OF PHENYLPROPANOLAMINE 40 ANALYSIS OF PHENYLPROPANOLAMINE IN PHARMACEUTICAL PREPARATIONS 40 Spectrophotometric Methods. 40 UV Absorption of Phenylpropanolamine Itself 41 UV Absorption of Benzaldehyde Derived from Phenylpropanolamine 41 Colorimetrlc Determination of Phenylpropanolamine after Derivatizatlon 44 Colorimetric Determination of Phenylpropanolamine as an Ion Pair 44 Fluorometric Determination of Phenylpropanolamine 44 Gas Chromatography 45 High-Performance Liquid Chromatography 51 Miscellaneous Analytical Methods 60 Room Temperature Phosphorescence 60 Nuclear Magnetic Resonance 61 Raman Spectroscopy 62 ANALYSIS OF PHENYLPROPANOLAMINE IN BIOLOGICAL FLUIDS 62 Spectrophotometric Determination 62 Thin-Layer Chromatography 63 Gas Chromatography 64 High-Performance Liquid Chromatography 71 Radiochemical Method 73 Drug Screening Procedures x 73 CHAPTER 3. BASIC PHARMACOLOGY 84 PHARMACOKINETICS 85 Absorption 85 Distribution 86 Metabolism 87 Elimination 87 Disappearance from Blood 89 Protein Binding 91
4 Xi Bioavailability: Comparison of Immediate- and Sustained-Release Formulations 91 PHARMACODYNAMICS 93 Pharmacology of /3-Phenylethylamines 93 Direct, Indirect, and Mixed Activity of Phenylpropanolamine at Sympathetic Sites 95 Effects of Phenylpropanolamine on Adrenergic Neurons 100 Release of Norepinephrine 100 Inhibition of Norepinephrine Uptake 100 Effects of Phenylpropanolamine on Storage of Norepinephrine in Nerve Terminals 102 False Transmitter 103 Effects of Phenylpropanolamine on Smooth Muscle 103 Effects on Smooth Muscle in the Vas Deferens 104 Effects on Gastrointestinal Smooth Muscle 104 Effects on Vascular Smooth Muscle 107 Effects on the Urinary Tract 107 Effects on the Estrogen-Primed Uterus 108 Effects on the Pupil 108 Effects on the Nictitating Membrane of the Cat 109 Effects on Bronchial Smooth Muscle 109 Summary of Effects of Phenylpropanolamine on Smooth Muscle 111 Receptor Binding Studies 111 a-adrenergic Receptors 112 Effects of Phenylpropanolamine on 0-Adrenergic Receptors 114 Mechanism of Action 115 Effects of Phenylpropanolamine on the Cardiovascular System 116 Phenylpropanolamine: Direct- or Indirect-Acting Amine? 124 Miscellaneous Sympathomimetic Effects 129 Nasopharyngeal and Pulmonary Effects 130 Anorectic Activity 132 Mechanisms of Regulation of Food Intake 132 Effects of Phenylpropanolamine on Body Weight 134 Effects of Phenylpropanolamine on Food Intake 135 Tolerance to Effects of Phenylpropanolamine on Food Intake or Body Weight 136
5 Xii Mechanism of Anorectic Effects of Phenylpropanolamine: CNS Theories 136 Mechanism of Anorectic Effects of Phenylpropanolamine: Peripheral Mechanisms 139 Comparison of Phenylpropanolamine and Other Anorectic Drugs 142 Other CNS Effects 146 Effects on Locomotor Activity 147 Drug Discrimination Studies 149 Operant Conditioning 150 Biochemical Studies 152 Miscellaneous CNS Effects 155 Metabolic Effects 156 Structure-Activity Relationships 157 Overall Structure-Activity Relationships of Phenethylamines Related to Phenylpropanolamine 159 Structure-Activity Relationships for Effects of Phenylpropanolamine on Adrenergic Neurons 160 Structure-Activity Relationships for Effects on Smooth Muscle Activity 162 Miscellaneous Structure-Activity Relationship Studies 163 Comparison of the Isomers of Norephedrine 166 Drug Interactions 167 Potentiation of Phenylpropanolamine by Monoamine Oxidase Inhibitors 170 Potentiation of Phenylpropanolamine by Antihypertenslve Drugs 171 Potentiation of Effects of Tyramine by Phenylpropanolamine 172 Interactions with Antihistamines 173 Interactions with Anticholinergic Drugs 173 Interactions between Phenylpropanolamine and Caffeine 175 Interaction between Phenylpropanolamine and Nonsteroidal Antiinflammatory Drugs 176 Interactions between Phenylpropanolamine and Adrenergic Blocking Drugs 177 Interaction with Other Sympathomimetic Amines 178 Miscellaneous Interactions 178 Potential Drug Interactions 178 Abuse Liability 179
6 Xiii CHAPTER 4. SAFETY 191 ANIMAL TOXICOLOGY STUDIES 193 Acute Toxicity 193 Comparative Toxicity 197 Drug Combinations 200 HUMAN SAFETY STUDIES 204 Safety of Phenylpropanolamine Alone 205 Cardiovascular Studies 205 Effects of Phenylpropanolamine on Subjective Rating of Drug Effect and Affective State 223 High-Dose Studies 224 Safety of Phenylpropanolamine in Combination with Caffeine 225 Safety of Phenylpropanolamine Combined with Belladonna Alkaloids 226 Miscellaneous Studies 228 Teratology 231 Drug Abuse Liability 233 ADVERSE EFFECTS 235 Adverse Drug Reactions: Decongestant Preparations Containing Phenylpropanolamine 238 Preparations Containing Phenylpropanolamine Alone 238 Combination Decongestant Products 238 Adverse Drug Reactions: Appetite Suppressants 251 Appetite Suppressants Containing Phenylpropanolamine Alone 251 Appetite Suppressants: Trimolets 253 Appetite Suppressants Containing Phenylpropanolamine and Caffeine 256 Street Drugs Containing Phenylpropanolamine 257 Adverse Drug Reactions: Other Reported Effects 258 Rhabdomyolosis 258 Raynaud's Phenomenon 260 Adverse Drug Reactions: Summary 260 OVERDOSE CASES 262 Overdose Cases: Decongestant Preparations Containing Phenylpropanolamine 263 Overdose Cases: Appetite Suppressants 272 Appetite Suppressants Containing Phenylpropanolamine Without Caffeine 272
7 XlV Appetite Suppressants Containing Phenylpropanolamine and Caffeine 273 Overdose Cases: Illicit Drugs Containing Phenylpropanolamine 275 ADVERSE DRUG INTERACTIONS 280 Monoamine Oxidase Inhibitors 280 Beta Blockers 282 Nonsteroidal Antiinflammatory Drugs 283 Imipramine 284 Thioridazine 285 Amphetamine 286 Theophylline 287 Miscellaneous Drug Interactions 288 OVERVIEW OF PHENYLPROPANOLAMINE SAFETY 289 Cardiovascular Toxicity 289 CNS Toxicity 291 CHAPTER 5. CLINICAL EFFICACY STUDIES 301 EFFICACY OF PHENYLPROPANOLAMINE AS A DECONGESTANT IN COUGH-COLD PREPARATIONS 302 Pathophysiology of Rhinitis 302 Methods Used to Investigate Clinical Pharmacology of Decongestants 304 Evaluation of Phenylpropanolamine Alone or in Combination Products 307 Studies Investigating the Efficacy of Phenylpropanolamine Alone as a Decongestant 307 Laboratory Studies 307 Clinical Studies of the Efficacy of Phenylpropanolamine Alone in Rhinitis 316 Studies Investigating the Efficacy of Phenylpropanolamine as a Component Of Combination Products 319 Combination of Phenylpropanolamine with an Antihistamine 320 Combination of Phenylpropanolamine with an Antihistamine and Belladonna Alkaloids 323 Miscellaneous Combinations 324 Studies Investigating the Efficacy of Phenylpropanolamine- Containing Combination Products: Decongestant Efficacy 326
8 XV Combinations of Phenylpropanolamine and Antihistamines 326 Combinations of Phenylpropanolamine, Antihistamines, and Anticholinergics 332 Multiple Component Combinations 333 Special Studies 336 Studies in Pediatric Patients 336 Antitussive Efficacy 344 Efficacy of a Phenylpropanolamine-Containing Combination Product in Asthma 346 Side Effects of Phenylpropanolamine-Containing Decongestant Products 347 EFFICACY OF PHENYLPROPANOLAMINE AS AN ANORECTIC DRUG IN THE TREATMENT OF OBESITY 354 Early Studies 356 Controlled Clinical Trials 359 Effects of Phenylpropanolamine on Food Intake in Humans 359 Effects of Phenylpropanolamine on Body Weight 363 Side Effects of Phenylpropanolamine-Containing Anorectic Products 373 EFFICACY OF PHENYLPROPANOLAMINE IN TREATMENT OF URINARY INCONTINENCE 376 Pathophysiology of Urinary Incontinence 376 Efficacy of Phenylpropanolamine-Containing Products in Stress Incontinence 381 Efficacy of Phenylpropanolamine Alone in Stress Incontinence 382 Efficacy of Phenylpropanolamine-Containing Combination Products in Stress Incontinence 386 Efficacy of Phenylpropanolamine-Containing Products in Other Types of Urinary Incontinence 387 Combined Treatment with Norephedrine and Estrogens in Urinary Incontinence 393 Side Effects of Phenylpropanolamine-Containing Products in Treatment of Urinary Incontinence 394 USE OF PHENYLPROPANOLAMINE FOR CORRECTION OF RETROGRADE EJACULATION 395 OVERVIEW OF CLINICAL SAFETY STUDIES 397 AUTHOR INDEX 405 SUBJECT INDEX 419
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