Volume 1 About the Editors xxxiii Preface xxxvii List of Contributors of Volumes 1 and 2 xxxix Abbreviations and Acronyms xli A personal and historical perspective on drug metabolism 1 Gerald T. Miwa and Arthur K. Cho Fundamentals of organic chemistry as applicable to the biotransformation of foreign compounds 27 Antonia F. Stepan and Amit S. Kalgutkar Functional group biotransformations 61 R. Scott Obach Drugs as victims and perpetrators and the pharmacokinetic concept of maximum exposure 103 Brian W. Ogilvie and Andrew Parkinson Drug-metabolizing enzymes: a group of promiscuous catalysts 125 Qiang Ma and Anthony Y.H.

Lu Unusual metabolic reactions and pathways 147 F. Peter Guengerich and Emre M. Isin Role of biotransformation in drug discovery 199 Ronald E. White Role of metabolism in drug development 215 Role of biotransformation in pesticide discovery and development 233 Michael E. Krolski and Stephen C. Dacus Role of cytochrome P450 enzymes in biotransformation 249 Paul R. Ortiz de Montellano Major human conjugative drug-metabolizing enzymes 267 Daniel R. Albaugh and Michael B.

Fisher Metabolic activation and associated drug toxicity 303 Thomas A. Baillie In vitro experimental models for studying drug biotransformation 321 Tonika Bohnert and Lawrence L. Gan In vivo experimental models for studying drug biotransformation 383 W. Griffith Humphreys Volume 2 About the Editors xxxiii Preface xxxvii List of Contributors of Volumes 1 and 2 xxxix Abbreviations and Acronyms xli Theory and instrumentation of mass spectrometry and its application to drug metabolism 393 Stacy L. Gelhaus and Ian A. Blair Mass spectral interpretation 419 Li-Kang Zhang and Birendra N. Pramanik Computational approaches in drug biotransformation studies: metabolite prediction 457 Nigel J. Waters and Michelle K.

Dennehy High-throughput metabolite detection and quantitative-qualitative bioanalysis 481 Donghui Cui and Sean Yu Metabolic stability screen in drug discovery 499 Chuang Lu Application of triple-quadrupole and its hybrid mass spectrometers for the identification of drug metabolites 523 Zhi-Yi Zhang, Chandra Prakash, and Lin Xu Role of ion trap LC-MS techniques for the identification of drug metabolites 553 Robert D. Pelletier and W. George Lai Drug metabolite identification with high-resolution mass spectrometry 567 Haiying Zhang and Mingshe Zhu Strategies for the identification of unusual and novel metabolites using derivatization, hydrogen-deuterium exchange (HDX), and liquid chromatography-nuclear magnetic resonance (LC-NMR) spectroscopy techniques 591 Amin Kamel, Shawn Harriman, and Chandra Prakash The use of nanoelectrospray mass spectrometry for the quantitation of metabolites in the absence of synthetic standards 619 Jing-Tao Wu Quantitation of drug metabolites by radioactivity detection including accelerator mass spectrometry (AMS) 633 Angus N.R. Nedderman and Mark E. Savage Application of quantitative NMR in drug metabolism studies 661 Abdul E. Mutlib Early assessment of exposure of drug metabolites in humans using mass spectrometry 693 Natalia A. Penner, Joanna Zgoda-Pols, and Chandra Prakash Profiling and characterization of bioactive substances of herbal medicine and their metabolites using mass spectrometry 723 Xiaoyan Chen Application of in silico metabolism and environmental degradation data to support chemical PBT assessment 787 Sabcho Dimitrov, Gilman Veith, and Ovanes Mekenyan Volume 3 About the Editors xxxiii Preface xxxvii List of Data Compilers of Volumes 3-5 xxxix Abbreviations and Acronyms xli Abacavir 809 Acebutolol 813 Acequinocyl 815 Acetaminophen 821 Acibenzolar- S -methyl 825 Acyclovir 829 Adapalene 832 Adonifoline 834 Albuterol 837 Alendronate 840 Alfentanil 842 Aliskiren 847 Alloxan 849 Almotriptan 851 Alprazolam 856 Amantadine 859 Ambroxol 861 Amiodarone 864 Amisulbrom 867 Amitriptyline 875 Amlodipine 878 Amoxicillin 884 Amphetamine 887 Anastrozole 889 trans -Anethole 892 Aniracetam 895 Antipyrine 898 Apixaban 902 Apremilast 905 Aprepitant 909 Aranidipine 913 Arbidol 915 Aripiprazole 918 Asenapine 921 Aspirin 924 Atazanavir 927 Atenolol 931 Atomoxetine 933 Atorvastatin 937 Azelastine 942 Barnidipine 945 Benazepril 949 Bendamustine 952 Benfuresate 956 Benidipine 959 Benthiavalicarb isopropyl 964 Benzophenone 969 Benzoyl peroxide 972 Berberine 974 Betaxolol 979 Bexarotene 981 Bicalutamide 986 Bicifadine 990 Bimatoprost 994 Bisoprolol 996 BMS-214778 999 Boceprevir 1002 Bortezomib 1006 Bosentan 1009 Brimonidine 1012 Brivaracetam 1015 Bromhexine 1018 Brompheniramine 1024 Budesonide 1027 Buprenorphine 1030 Bupropion 1033 Buspirone 1036 Butalbital 1041 3- n -Butylphthalide 1043 Caffeine 1047 Calcipotriene 1051 Candesartan 1054 Capecitabine 1057 Capravirine 1061 Captopril 1067 Carazolol 1070 Carfilzomib 1072 Carvedilol 1076 Casopitant 1081 Cefdinir 1085 Cefepime 1088 Celecoxib 1090 Cetirizine 1094 Chlorpheniramine 1098 Chlorpromazine 1102 Cholecalciferol 1106 Cibenzoline 1110 Ciclesonide 1113 Cidofovir 1118 Cinacalcet 1121 Ciprofloxacin 1125 Cisapride 1128 Cladribine 1136 Clebopride 1139 Clenbuterol 1142 Clindamycin 1145 Clobazam 1147 Clofarabine 1151 Clofibrate 1154 Clopidogrel 1156 Coumarin 1159 Cyclamate 1163 Cyclobenzaprine 1165 Dabigatran 1170 Darifenacin 1174 Darunavir 1177 Dauricine 1181 Degarelix 1186 Desloratadine 1190 Dexamethasone 1193 Dexfenfluramine 1196 Dexmethylphenidate 1198 Dextroamphetamine 1201 Diazepam 1204 Diazoxide 1208 Dichlobenil 1210 Dichlorprop 1212 Diclofenac 1214 Diclosulam 1218 Difloxacin 1220 Digoxin 1223 Diltiazem 1227 Diniconazole-M 1230 Dinotefuran 1232 Diphenhydramine 1237 Dipyridamole 1241 Divalproex 1244 Domperidone 1249 Donepezil 1253 Dopamine 1257 Doripenem 1260 Dorzolamide 1263 Doxazosin 1266 Doxorubicin 1269 Dronabinol 1274 Drospirenone 1278 Duloxetine 1281 Dutasteride 1283 Edoxaban 1286 Efavirenz 1291 Eletriptan 1297 Eltrombopag 1299 Elzasonan 1302 Emtricitabine 1305 Enalapril 1308 Enfuvirtide 1311 Enoxaparin 1315 Eplerenone 1318 Erdosteine 1322 Erlotinib 1324 Ertugliflozin 1327 Escitalopram 1331 Esomeprazole 1335 Estazolam 1338 Estrogens 1341 Ethinylestradiol 1347 Ethionamide 1350 Ethiprole 1354 Ethoxysulfuron 1360 Etonogestrel 1362 Etoricoxib 1365 Etridiazole 1368 Exemestane 1370 Ezetimibe 1373 Ezlopitant 1377 Chemical Name Index I CAS Number Index IX Volume 4 About the Editors xxxiii Preface xxxvii List of Data Compilers of Volumes 3-5 xxxix Abbreviations and Acronyms xli Famciclovir 1381 Famitinib 1385 Famotidine 1391 FDDNP 1393 Febuxostat 1395 Felodipine 1399 Fenazaquin 1404 Fenofibrate 1406 Fenpropimorph 1411 Fenproporex 1416 Fenpyroximate 1419 Fentanyl 1422 Fexofenadine 1425 Finasteride 1427 Fingolimod 1431 Flonicamid 1435 Fluazinam 1439 Fluconazole 1444 Flumioxazin 1446 Flunarizine 1450 Flunitrazepam 1455 Fluopicolide 1458 Fluoxastrobin 1462 Flupyrsulfuron methyl 1467 Fluroxypyr 1469 Flutamide 1471 Fluticasone furoate 1475 Fluticasone propionate 1478 Fluvastatin 1480 Fluvoxamine 1483 Forchlorfenuron 1487 Fosinopril 1489 Furametpyr 1492 Gabapentin 1495 Galantamine 1497 Gambogic acid 1502 Ganoderic acid D 1506 Garenoxacin 1509 Gefitinib 1511 Gemfibrozil 1516 Gemopatrilat 1522 Genipin 1525 Glafenine 1527 Glatiramer acetate 1531 Gliclazide 1533 Glipizide 1536 Granisetron 1538 Harmaline 1541 Hexaconazole 1543 Hydrochlorothiazide 1546 Hydrocodone (oxycodone) 1548 Hydroxychavicol 1551 Ibandronate 1553 Ibuprofen 1555 Ilaprazole 1559 Iloperidone 1562 Imatinib 1567 Imazamethabenz-methyl 1571 Imazamox 1573 Imazosulfuron 1577 Imidafenacin 1579 Imiprothrin 1582 Imiquimod 1584 Imrecoxib 1587 Indacaterol 1590 Indapamide 1593 Indinavir.