If you're working on or studying the effects of drug metabolisms, then this reference is for you!
Handbook of Metabolic Pathways of Xenobiotics is an essential new reference which presents the metabolic fate of xenobiotics in animals and plants, and shows the metabolic pathways in the environment.
Presenting a comprehensive guide to understanding the metabolisms of xenobiotics, the Handbook of Metabolic Pathways of Xenobiotics spans five volumes: Volumes 1-2 are Review Articles and Volumes 3-5 are Compound Articles. Review Articles present detailed reviews on the techniques and methods used to establish in vitro and in vivo metabolic pathways. Compound Articles are carefully selected lists of key chemicals representing agrochemicals, pharmaceuticals, animal health products and industrial chemicals.
An essential addition to every library, this introduction, guide and catalogue presents:
Current topics in the metabolism of xenobiotics Topics of both scientific and regulatory importance are covered, including in vitro high throughput metabolism screens, computer-aided metabolism predictions, and advances in bioanalytical techniques.
Techniques and methods used in metabolic pathways 29 chapters provide an introduction to the understanding of drug metabolism and detail how to establish in vitro and in vivo metabolic pathways.
Biotransformation pathways Presented as a catalogue of short articles covering major pharmaceuticals, agrochemicals, animal health products and industrial chemicals. Each article summarizes the chemical properties and uses, and presents a detailed review of the chemical and metabolic pathways in soil, plants and animals.
Over 450 examples of xenobiotics and their fate in animals and plants Each compound includes systematic information about the metabolic pathway of drugs for human and veterinary medicine, agrochemicals and major industrial chemicals.
Chemical and biological fate data The Handbook summarises data from scientific literature, patent literature, industrial resources and regulatory agencies, such as the EPA, FDA, EU, WHO and FAO, in a single reference for the first time.
An essential reference for everyone working and studying pharmacokinetics and drug metabolism Coverage of the chemical and biological reactivity of molecules and primary sub-structures makes this an ideal reference for students and research scientists. The broad and diverse coverage of chemical and biological fate under different exposure and biological compartments make this a useful resource for regulatory and developmental scientists.
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 1597 Ipconazole 1601 Ipratropium 1603 Irbesartan 1606 Irinotecan 1609 Irofulven 1614 Isoeugenol 1617 Isoxaflutole 1619 Isoxicam 1621 Ivermectin 1624 Ixabepilone 1628 Lamivudine 1632 Lamotrigine 1634 Lansoprazole 1638 Lapatinib 1640 Laropiprant 1643 Lasofoxifene 1647 Latanoprost 1651 Lefucoxib 1655 Lersivirine 1657 Letosteine 1660 Letrozole 1662 Levalbuterol 1665 Levocetirizine 1668 Levofloxacin 1671 Levonorgestrel 1673 Levothyroxine 1677 Lidocaine 1679 Linagliptin 1682 Lindane 1685 Linezolid 1687 Lithocholic acid 1690 Lithospermic acid 1693 Lopinavir 1696 Loratadine 1701 Lorazepam 1706 Losartan 1710 Lovastatin 1715 Lufenuron 1719 Lumiracoxib 1723 Lurasidone 1726 Mandipropamid 1732 Mebeverine 1738 Medroxyprogesterone acetate 1741 Meisoindigo 1745 Meloxicam 1747 Memantine 1752 Menadione 1754 Mesalamine 1758 Mesosulfuron-methyl 1761 Mesotrione 1764 Metaxalone 1767 Metformin 1769 Methadone 1771 Methoxyfenozide 1775 Methyldopa 1780 Methylphenidate 1783 Metoclopramide 1786 Metofluthrin 1790 Metoprolol 1792 Metoxuron 1795 Metronidazole 1797 Mexiletine 1800 Mianserin 1803 Mifepristone 1808 Milnacipran 1812 Minocycline 1814 Mirabegron 1816 Misoprostol 1819 Modafinil 1821 Mometasone furoate 1824 Montelukast 1827 Moricizine 1830 Morinidazole 1833 Moxifloxacin 1836 Moxonidine 1838 Mycophenolate mofetil 1841 Nabumetone 1845 Naloxone 1847 Nateglinide 1850 Nevirapine 1853 Niacin 1858 Nicardipine 1861 Nicotine 1865 Nifedipine 1870 Nilotinib 1874 Nilutamide 1878 Nimodipine 1881 Nizatidine 1885 Norelgestromin 1888 Norfloxacin 1891 Norgestimate 1893 Nortriptyline 1897 Novaluron 1900 Chemical Name Index I CAS Number Index IX Volume 5 About the Editors xxxiii Preface xxxvii List of Data Compilers of Volumes 3–5 xxxix Abbreviations and Acronyms xli Olanzapine 1905 Olmesartan medoxomil 1909 Olopatadine 1912 Omeprazole 1915 Ondansetron 1918 Ornidazole 1921 Orphenadrine 1923 Oxadiargyl 1925 Oxcarbazepine 1930 Oxybenzone 1933 Oxycodone 1936 Paclitaxel 1940 Paclobutrazol 1945 Paeonol 1949 Paliperidone 1951 Pantoprazole 1953 Paroxetine 1957 Pefloxacin 1960 Peliglitazar 1962 Penthiopyrad 1965 Pentoxazone 1970 Perphenazine 1972 Phenolphthalein 1976 Picolinafen 1978 Pindolol 1981 Pioglitazone 1984 Piperacillin 1988 Piroxicam 1991 Pirprofen 1993 Pitavastatin 1998 Pramipexole 2004 Pravastatin 2006 Prazosin 2012 Pregabalin 2016 Prochloraz 2018 Propafenone 2020 Prosulfuron 2024 Prothioconazole 2027 20(S )-Protopanaxadiol 2030 Proxyphylline 2033 Pseudoephedrine 2035 (2S )-Pterosin A 2037 Pyraflufen-ethyl 2039 Pyrasulfotole 2042 Pyrazosulfuron methyl 2045 Pyribenzoxim 2047 Pyridalyl 2050 Pyrimethanil 2055 Quetiapine 2058 Rabeprazole 2061 Raloxifene 2065 Ramelteon 2069 Ranitidine 2072 Repaglinide 2075 Rifapentine 2079 Risedronate 2082 Risperidone 2084 Ritonavir 2087 Rivaroxaban 2092 Rizatriptan 2096 Rofecoxib 2100 Roflumilast 2105 Ropinirole 2107 Rosiglitazone 2110 Rosuvastatin 2115 Rotigotine 2119 Ruboxistaurin 2122 Rufinamide 2125 Ruxolitinib 2127 Salmeterol 2130 Sameridine 2133 Saxagliptin 2136 Selegiline 2139 Seliciclib 2142 Sertraline 2145 Silafluofen 2149 Sildenafil 2151 Simvastatin 2155 Sitagliptin 2160 Sorafenib 2164 Sudoxicam 2166 Sulcotrione 2169 Sulindac 2172 Sumatriptan 2175 Sunepitron 2178 Tacrolimus 2183 Tadalafil 2187 Tafluprost 2190 Tamoxifen 2193 Tamsulosin 2197 Telmisartan 2200 Temozolomide 2202 Tenofovir 2205 Tepraloxydim 2208 Terazosin 2212 Terbinafine 2215 Tetraconazole 2219 Thalidomide 2222 Theophylline 2226 Thiamethoxam 2231 Ticagrelor 2236 Ticlopidine 2239 Timolol 2242 Tinidazole 2245 Tiotropium 2247 Tipranavir 2250 Tirapazamine 2253 Tobramycin 2255 Tolbutamide 2257 Tolcapone 2261 Tolfenpyrad 2265 Tolterodine 2267 Tolvaptan 2270 Topiramate 2274 Torcetrapib 2277 Tramadol 2281 Trandolapril 2284 Traxoprodil 2286 Triamcinolone 2289 Triamcinolone acetonide 2291 Triasulfuron 2294 Triclosan 2296 Trimebutine 2298 Tropisetron 2302 Vabicaserin 2305 Valacyclovir 2310 Valdecoxib 2313 Valsartan 2317 Vardenafil 2319 Varenicline 2322 Vemurafenib 2325 Venlafaxine 2328 Verapamil 2332 Veratridine 2336 Vilanterol 2339 Vildagliptin 2343 Vinorelbine 2348 Vismodegib 2353 Warfarin 2357 Ximelagatran 2361 Zafirlukast 2363 Zearalenone 2366 Zibotentan 2369 Zidovudine 2372 Ziprasidone 2375 Zofenopril 2382 Zolmitriptan 2385 Zolpidem 2387 Chemical Name Index I CAS Number Index IX
Dr Philip W. Lee, School of Pharmacy, East China University of Science and Technology, Shanghai, Peoples' Republic of China.Dr. Philip W. Lee has more than 35 years of industrial experience in the field of agrochemical research and development. He is currently Professor at School of Pharmacy, East China University of Science and Technology. He has published more than 40 scientific articles in pesticides and drug metabolism and environmental chemistry. Dr. Lee is a contributing editor for the Volume 1 and 2 of the Metabolic Pathways of Agrochemicals, published by Royal Society of Chemistry (RSC) in 1998 and 1999, and is the Editor-in-Chief of a 2-volume Handbook of Residue Analytical Methods for Agrochemicals, published by Wiley in 2003. He is the editor of Pesticide Chemistry: Crop Protection, Public Health and Environmental Safety, conference proceeding book of the 2006 IUPAC International Pesticide Congress, Kobe, Japan, published by Wiley-VCH, 2007. Hiroyasu Aizawa, Hiro Research Consultancy Inc. (HRCI), Toyko, Japan. Lawrence L. Gan, Biogen Idec, Inc., Cambridge, MA, USA. Chandra C. Prakash, Biogen Idec, Inc., Cambridge, MA, USA. Dafang D. Zhong, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, Peoples' Republic of China. Dr. Hiro Aizawa has been active for more than 20 years in the study of animal drug metabolism. Dr Lawrence Gan and Dr. Chandrah Prakash are active with a long experience in the development of human drugs and the study of human drug metabolism.
