Volume content, subject index and author index to volume 33

PHARMACOLOGY & THERAPEUTICS Volume 33

Executive Editors

W. C. Bowman,

A. M. Breckenridge

PERGAMON

and A. C. Sartorelli

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PHARMACOLOGY &THERAPEUTICS Chemotherapy, Toxicology and Metabolic Inhibitors Executive Editor: A. C. Sartorelli Yale University School of Medicine, Department of Pharmacology, 333 Cedar Street, New Haven, Connecticut 06510, USA

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General and Systematic Pharmacology Executive Editor: W. C. Bowman University of Strathcl)'de, Department of Physiology & Pharmacology, Royal College, 204 George Street, Glasgow G I IXW, Scotland

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Volume 33, 1987, Numbers l-3 CONTENTS

Number 1 Mechanisms of monooxygenase induction and inhibition: K. J. Netter Human drug metabolism polymorphisms: Use of recombinant DNA techniques: D. W. Nebert and A. K. Jaiswal Mechanisms of phenobarbital-type induction of cytochrome P-450 isozymes: R. Fonne and U. A. Meyer Induction and inhibition of conjugating enzymes with emphasis on UDPglucuronyltransferases: K. W. Bock, W. Lilienblum. G. Fischer, G. Schirmer and B. S. Bock-Hennig Coordinate induction of peroxisomal P-oxidation activity and cytosolic epoxide hydrolase activity: F. Oesch and L. Schladt Importance of the glutathione cycle in drug metabolism: P. Moldeus and Jiang Quanguan Formation of reactive intermediates and metabolites: Effects of macrolide antibiotics on cytochrome P-450: D. Mansuy Metabolic characterization of human liver microsomal cytochromes P-450 involved in the oxidation of debrisoquine, bufuralol and the carcinogen 2-acetylaminofluorene: h4. E. McManus Developmental aspects of enzyme induction and inhibition: W. Klinger Oxygen activation during drug metabolism: V. V. Subrahmanyam, L. G. McGirr and P. J. O’Brien Methoxyphenamine 0-demethylase and 5-hydroxylase: A GLC-ECD assay to study their activities and their inhibition by debrisoquine and sparteine: E. M. Hawes, S. D. Roy, G. McKay and K. K. Midha Stereospecificity of enzyme induction by 2-phenylpropionic acid: S. Fournel, J. Caldwell, J. Magdaiou and G. Siest Prevention of acetaminophen hepatotoxicity by disulfiram: H. E. Paulsen, L. Jorgensen and P. Thomsen Reversible inhibition and activation of hepatic GSH S-transferases by ethylene dibromide: K. M. Zvanetich and A. E. A. Thumser Induction and its influence on human cancer: H. Remmer Enzyme induction in humans, clinical aspects-An overview: A. Breckenridge In vitro studies of induction and inhibition of drug oxidation in man: A. R. Boobis, S. Murray, C. E. Seddon and D. S. Davies In vivo methods to study enzyme induction and enzyme inhibition: B. K. Park Environmental factors of enzyme induction and inhibition: 0. Pelkonen and E. A. Sotaniemi Ethanol as enzyme inducer and inhibitor: H. Hoensch HZ-receptor antagonists as inhibitors of oxidative drug metabolism in vivo: W. Kirch Drugs other than HZ-receptor antagonists as clinically important inhibitors of drug metabolism in vivo: R. Gugler and J. C. Jensen

PAGE

1 11 19

23 29 37 41

47 55 63

73 79 83 85 89 95 101 109 115 121 129 133

iv

CONTENTS

Clinical implications of hepatic microsomal enzyme induction by antiepileptic drugs: E. Perucca Aminoglutethimide as an inducer of oxidative drug metabolism in the rat: Z. Damanhouri, S. A. Herbert and P. J. Nicholls Therapeutic use of phenobarbital in intrahepatic cholestasis. Inductions in bile acid metabolism: P. Back Comparative effects of H,-receptor antagonists on drug metabolism in vitro and in vivo: U. Klotz, P. Arvela, M. Pasanen, H. Kroemer and 0. Pelkonen Influence of mexiletine on caffeine elimination: R. Joeres, H. Klinker, H. Heusler, J. Epping and E. Richter The influence of ethanol on cyclophosphamide pharmacokinetics and metabolism in tumor-bearing rats: E. A. De Brutjn, A. T. Van Oosterom and U. R. Tjaden Hydroperoxide metabolism in vitamin E-deficient hepatocytes. Studies on lowlevel chemiluminescence, lipid peroxidation, and glutathione status: F. J. Romero and E. Cadenas Aminopyrine N-demethylation in young, old and tumour bearing B6C3 Fl mice: D. A. Smith Increased cyt P-450 dependent function in healthy HB,Ag carriers: A. P. Geubel, S. Pauwels, J. P, Buchet, E. Dumont and C. Dive The urinary 6/3-hydroxycortisol excretion in man on inducers and inhibitors of the hepatic mixed function oxidase: J. P. Desager, E. Dumont and C. Harvengt Influence of the enzyme induction by rifampicin on its presystemic metabolism: U. Loos, E. Musch, J. C. Jensen, H. K. Schwabe and M. Eichelbaum Enzyme induction of renal transport mechanism by rifampicin in man? N. H. Brockmeyer, H. Heidemann and E. E. Ohnhaus Numbers

139 145 153 157 163

171

179 187 193

197 201 205

2/3

Oxytocin and vasopressin: Photoaffinity labeling of neurophysins, secretory granule hormone-binding proteins: D. M. Abercrombie and I. M. Chaiken Inhibitors of protein glycosylation and glycoprotein processing in viral systems: R. Datema, S. Olofsson and P. A. Romero Photoaffinity labelling of the adenosine nucleotide transporter of cholinergic vesicles: V. Witzemann Selenium effects on drug and foreign compound toxicity: G. F. Combs Jr und S. B. Combs Photoaffinity labeling of thyroid hormone receptors: Z. D. Horowitz and H. H. Samuels Photoaffinity labelling of N-formyl peptide receptors: R. A. Allen, A. J. Jesaitis and C. G. Cochrane Photoaffinity labelling of angiotensin receptors: Functional studies on responding tissues: G. J. Moore Clinical pharmacology of non-steroidal anti-inflammatory drugs: R. 0. Day,, G. G. Graham, K. M. Williams, G. D. Champion and J. de Jager Ethanol and minerals: J. D. Blachley and J. P. Knochel Occurrence and treatment of solvent abuse in children and adolescents: H. G. Morton

209 221 287 303 317 333 349 383 435 449

AUTHOR INDEX Abercrombie, D. M. Allen, R. A. 333 Arvela, P. 157

209

Back, P. 153 Blachley, J. D. 435 Bock. K. W. 23 Bock-Hennig, B. S. 23 Boobis, A. R. 101 Breckenridge, A. 95 Brockmeyer, N. H. 205 Buchet. J. P. 193

Cadenas, E. 179 Caldwell, J. 79 Chaiken, I. M. 209 Champion, G. D. 383 Cochrane, C. G. 333 Combs, G. F. Jr 303 Combs, S. B. 303

Damanhouri, 2. 145 Datema, R. 221 Davies, D. S. 101 Day, R. 0. 383 De Bruiin. E. A. 171 de Jager, J. 383 Desager, J. P. 197 Dive, C. 193 Dumont, E. 193, 197

Eichelbaum, Epping, J.

M. 163

Lilienblum, W. Loos, u. 201

23

Magdalou, J. 79 Mansuy, D. 41 McGirr, L. G. 63 McKay, G. 73 McManus, M. E. 47 Meyer, U. A. 19 Midha, K. K. 73 Moldeus, P. 37 Moore, G. J. 349 Morton. H. G. 449 Murray; S. 101 Musch, E. 201

Nebert, D. W. II Netter, K. J. I Nicholls, P. J. 145

O’Brien, P. J. 63 Oesch, F. 29 Ohnhaus, E. E. 205 Olofsson, S. 221

Geubel, A. P. 193 Graham, G. G. 383 Gugler, R. 133

Harvengt. C. 197 Hawes, E. M. 73 Heidemann, H. 205 Herbert, S. A. 145 Heusler, H. 163 Hoensch, H. 121 Horowitz. Z. D. 317

K. M.

Kirch, W. 129 Klinger, W. 55 Klinker, H. 163 Klotz, U. I57 Knochel, J. P. 435 Kroemer, H. 157

201

Fischer, G. 23 Fonne, R. 19 Fournel, S. 79

Ivanetich,

Jaiswal, A. K. I1 Jensen, J. C. 133,201 Jesaitis, A. J. 333 Joeres, R. 163 Jorgensen, L. 83

85

Park, B. Pasanen, Pauwels, Pelkonen, Perucca, Poulson,

Quanguan,

K. 109 M. 157 S. 193 0. 115. I57 E. 139 H. E. 83

Jiang

37

Remmer, H. 89 Richter, E. 163 Romero, F. J. 179 Romero, P. A. 221 Roy, S. D. 73

AUTHOR INDEX Samuels, H. H. 317 Schirmer, G. 23 Schladt, L. 29 Schwabe, H. K. 201 Seddon. C. E. 101 Siest, 6. 79 Smith, D. A. 187 Sotaniemi, E. A. I15 Subrahmanyam, V. V. 63

Thomsen, P. 83 Thumser, A. E. A. 85 Tjaden, U. R. 171 Van Oosterom, A. T. Williams, K. M. 383 Witzemann, V. 287

171

SUBJECT INDEX 2-Acetylaminofluorene cytochrome oxidation 47-52 metabolites 49 drug effects 50, 5 1 hydroxy derivatives 52 N-Acetyl(p)benzoquinone imine, toxicity 38, 39 Adenosine nucleotide transporter 298,299 nucleotide affinity 293 photoaffinity labeling 287-99 ADP/Fe2+-induced lipid peroxidation 183 ADP/Fe2+-promoted chemiluminescence 184 Adverse drug reactions, non-steroidal antiinflammatory drugs 402-14 Affinity labeling 349 see also photoaffin it:Y Age and antipyrene N-demethylation 187--90 Alcohol see n/so ethanol enzyme induction and inhibition 117, I I8 Aminoglutethimide 0-demethylation 149, 150 endoplasmic reticulum 149, 150 estradiol activity 148 hexobarbitone-induced hypnosis 147, 1148 liver effects I5 1 oxidative drug metabolism inducer 145-52 structure I45 GAminolevulinic acid synthetase induction 56,57 Aminopyrene N-demethylation age and tumors in mice 187-90 Angiotensin see also receptor angiotensin-mediated contraction 369 concentration-effect curves 368 microelectronic effects 374 II and III and receptor photoaffinity labeling 355-59 Antibiotics macrolide and cytochrome P-450 41-45 drug interactions 44,45 structure 42 Antiepileptic drugs, liver microsome induction 139-44 Antigens, HBsAg carriers aminopyrene breath test 194, I95 cytochrome P-450 193-95 Antiviral sugar analogs 232-37 dolichol pathway 234 Aryl hydrocarbon hydrolase induction 57, 58 ATP neuronal function 287, 288 neurotransmitter co-storage 288-91 uptake and neurotransmitter 291-93

Calcium deficiency ethanol effects 441-43 treatment 442,443 Cancer induction effects 89-93 and P-450 gene family I4 Chemicals, occupational 118, I 19 Chemiluminescence 179 and glutathione in hepatocytes I82 Cholestasis, phenobarbital 153-55 Cimetidine and metabolism 129 oxidative metabolism 130, 131 Cyclophosphamide ethanol and metabolism 171-76 metabolism I71 pharmacokinetic data 174, 175 Cytochrome P-450 HBsAg carriers 193-95 human liver microsomal 47-52 isoenzyme induction 19-21 macrolide antibiotics 41-45 TAO derivative induction 44

Debrisoquine metabolism and smoking 102 oxidation 47-52 Debrisoquine 4-hydroxylase 102, 103 Ki value 104 I-Deoxynojirimycin glucosidase inhibition 244 structure 241 Diazepam omperazole interaction 134 oral contraceptive interactions 133 Disulfiram, acetaminophen hepatotoxicity Drug conjugation tests 1I I Drug interactions, NSAIDs 414-17 Drug metabolism glutathione 37-40 oxygen activation 63-72 polymorphism II-15 Drug oxidation tests 109-I 1

83

Environmental tests co-administered drug effects 97, 98 toxic induced 98 Epoxide hydrolase, coordinate induction 29-34 Erythralosamine derivatives 43 Ethanol abuse and drug metabolism 126 acute effects 122-24 biochemical effects I21 calcium effects 441-43 chronic effects 123 cyclophosphamide interaction 171-76 drug metabolism 124-26 enzyme induction and inhibition 117, 118, 121-27

Bromoconduritol structure and glucosidase inhibition 241, 242 Bufuralol, cytochrome oxidation 47-52

Caffeine elimination and mexiletine 163-68 pharmacokinetics 165, 166

vii

viii

SUBJECT INDEX

hypophosphatemia 436, 437 magnesium effects 439,440 plasma effects 435 skeletal muscle effects 443-46 urine effects 435 7-Ethylcoumarin, dealkylation inhibition 136 Ethylene dibromide, GSH S-transferases 85-88 interactions 88 Glucosidase inhibitors 241-46 structure 241 Glutathione (GSH) drug metabolism 37-40 peroxidase-mediated oxidation 67, 68 protection 38 reactive intermediates 37 Glycoproteins, viral herpes simplex, properties 264 oligosaccharides see also oligosaccharides biosynthesis 224-32 inner cores 222 structure 221-24 types 223 processing inhihitors 240-50 sugar analogs 232-37 tunicamucin 237,238 Glycosylation inhibitor effects 250-70 inhibitor structures 239 GSH S-transferases inhibitor model 87 reversible inhibition 85-88 H2-receptor antagonists see also cimetidine, ranitidine diazepam interactions 159, 160 doses 158 enzymes inhibited 160, 161 in viva and in vitro drug metabolism 157-61 oxidative metabolism inhibition 129-31 structures 158 Hepatic mixed function oxidase, 6,8-hydroxycortisol excretion 197-99 Hormones, anticonvulsant interactions 141, 142 6B-Hydroxycortisol

and antipyrene clearance 198 excretion and mixed function oxidase Induction cancer effects 89-93 clinical aspects 95-99 conjugating enzymes 23-26 coordinate 29-34 cytochrome P-450 isoenzymes 19-21 developmental aspects 55-60 drug-drug interactions 95 drug oxidation 101-107 environmental factors 115-19 hormonal control 59, 60 in viva study 109-12 monooxygenase 1-9 old age 58, 59 stereospecificity 79-82 time-course 112 toxicity 96, 97 variability 96

197-99

cytochrome P-450 8 developmental aspects 55-60 drug oxidation 101-107 environmental aspects 115-19 in viva study 109-12 monooxygenase 6-9 protein glycosylation 221-72 reversible 85-88 Liver disease, environmentally induced

118, 119

Magnesium deficiency alcohol effects 439-41 treatment 440, 441 Mannosidase inhibitors 246-48 structure 242 Methoxyphenamine oxidative metabolism 73 metabolites 75 Methoxyphenamine O-demethylase, activity and inhibition 73-76 Met-tyr-p-azido-pheamide synthesis 211,212 Mexiletine caffeine elimination 163-68 cardiac arrhythmias 163, 164 pharmacokinetics 165, 166 Monooxygenase induction and inhibition 1-9 mechanism 3 3-methylcholanthrene 1, 2 salt effects 104 sulmazole induction 5, 6 Neurophysins amino acid composition 217 hormone binding surface 216, 217 photolabeled properties 215,216 Neurotransmitter, cholinergic and ATP 288-93 Nojirimycin glucosidase inhibition 242-44 structure 241 Non-steroidal anti-inflammatory drugs (NSAID) adverse effects 402-14 gastrointestinal 402-406 age 401,402 anaphylaxis 411,412 bleeding disorders 410, 411 chemical properties 384, 385 clinical pharmacology 383-418 CNS effects 412,413 doses 405 drug interactions 414-17 elimination half-life 393-98 hematological effects 413, 414 hepatotoxicity 409,410 liver disease effects 399,400 metabolism 398 overdose 413 pH and cellular accumulation 384 plasma protein binding 389-91 renal excretion 400, 401 renal toxicity 406-409 risk ['actors 408,409 responders 388,389 skin reactions 412 stereoselectivity 399 synovial fluid 391-93

SUBJECT Oligosaccharide biosynthesis assembly 228, 229, 231 blood group A reactive 23 1 dolichol pathway 226 inhibitors 232-40 N-linked 224-30 O-linked 230 pathways 225-27 P-Oxidation activity coordinate induction 29-34 drug effects 34 inducers 3I inducibility 33 scheme 30 temperature 32 Oxygen activation drug metabolism 63-72 thiyl radical formation 65 Oxygen uptake stimulation 66 Oxytocin, photoaffinity labeling

209-17

P-450 gene superfamily Il.- 12 and cancer 14, 15 regulation 13 P-4501 gene family 12-14 Paraquat toxicity and selenium 305 Pharmacodynamic analysis 173 Pharmacokinetic analysis ! 72, 173 Phenobarbital bile acid disappearance 154 cholestasis use 153-55 Phenobarbital induction, cytochrome P-450 19-21 2-Phenylpropionic acid enantiomers 80, 81 HPLC separation 80 three dimensional structure 79 Phenytoin, omperazole interaction 135 Phosphorus deficiency cellular injury 438 and ethanol 436,437 treatment 438,439 Photoaffinity labeling adenosine nucleotide transporter 287-99 angiotensin receptors 239-79 chemical affinity comparison 328-30 concept 349 covalent modification 215 dose-response curves 352-54 N-formyl peptide receptors 333-47 neurophysin, specificity 212-15 neurophysin structure 217, 218 oxytocin and vasopressin 209-18 spare receptors 354, 355 thyroid hormone receptors 322-30 half life 325-28 intact cells 323-25 methods 322,323 vesicle polypeptides 295-98 Photoaffinity probes coupling efficiency 330 N-formyl peptide receptor development 3134-39 prospects 346. 347 Photoaffinity reagents azido-AMP, azido-ATP 294, 295 design 209- 1 I

Ranitidine drug interactions 130, 13 I oxidative metabolism 129, 130

INDEX

ix

Receptor dualism 360-63 excited state hypothesis 370-76 application 374-76 receptor-agonist dual state (AIDS) model 363-70 bifunctional 366-70 receptor-agonist interaction kinetics 359, 360 spent 363,364 transition states 371 Receptors, angiotensin 349-79 bioactivity 355-59 bioassay 35 I desensitization 351, 352 excitation 37 I high affinity 364 isolation 376, 377 low affinity 365 model 366-70 molecular model 373 photoaffinity labeling 376, 377 photoprobe 350 Receptors, N-formyl peptide internalization 345, 346 photoaffinity labeling 333-47 photoaffinity ligands 334-39 structures 334, 335, 337 physicochemical characteristics 342-44 solubilization 339-42 structural characteristics 344, 345 Receptors, thyroid hormone chemical affinity labeling 328-30 half-life 319, j20 ohotoaffinitv labeling 322-30 properties, ciromatii 318, 319 synthetic rates 320-22 Recombinant DNA, drug metabolism polymorphisms 11-I5 Rifampicin dose 205, 206 enzyme induction 201-204 renal transport 205-207 serum levels 202

Selenium deficiency 303-306 dietary and ethane production 308 selenium-dependent glutathione peroxidase 308 supranutritional effects 309. 310 and xenobiotic toxicity 303-13 effects in mouse 313 Serum enzyme, anticonvulsant interactions Skeletal muscle, ethanol effects 443-46 Slow-acting antirheumatic drugs (SAARDs) Smokers cytochrome P-4SO monooxygenase 91 drug-metabolizing enzymes 90, 98. 102 enzyme induction and inhibition 115-17 Solvent abuse clinical featurrs 456 complications 457.458 drug abuse 46 I epidemiology 453.454 management 462-66 community 464-66 medical 462 psychological 463, 464 pharmacology 45 I psychiatric aspects 459-61 solvents 450. 45 I

307.

142. I43 384

x

SUBJECT

sudden death 459 toxicity 452, 453 Solvent abusers 454-56 classification 454 Stereospecificity, enzyme induction Sulmazole structure 5 Synaptic vesicles ATP role 299 photoaffinity labeling 295-98 polypeptide features 297,298 preparation, Torpedo 293,294 purification 294

79

Tetrachlorodibenzo(p)dioxin (TCDD) induction mechanism 4, 5 P,-450 regulation 13 Theophylline, omperazole interaction 135 Tobacco smoke, non-volatile compounds 91 Tumor aminopyrene N-demethylation 187-90 growth inhibition 92 Tunicamycin structure and viral oligosaccharides 237, 238

UDP-glucuronyl transferases induction and inhibition substrate specificity 24

23-26

INDEX Vasopressin photoaffinity labeling 209-17 structure 211 Virus glycoproteins 221-72 see also glycoproteins, oligosaccharides membrane glycoproteins 25 I multiplication, glycosylation inhibitors 250 DNA 262-70 herpes simplex 263-69 herpesvirus 269 influenza A 252-56 inhibitors 250 mouse hepatitis 259-61 retrovirus 260-62 RNA 251-62 Sindbis 258, 259 vesicular stomatitis 256-58 Vitamins, anticonvulsant interaction 139, 140 Vitamin E deficiency cytochrome P-450 185 hepatocytes and glutathione 180, I81 hydroperoxide metabolism 178-85 and selenium effects 304. 305

Xenobiotic toxicity and selenium mechanisms 310-12

303-13