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KUCERS’ THE USE OF ANTIBIOTICS A CLINICAL REVIEW OF ANTIBACTERIAL, ANTIFUNGAL, ANTIPARASITIC AND ANTIVIRAL DRUGS This page intentionally left blank KUCERS’ THE USE OF ANTIBIOTICS A CLINICAL REVIEW OF ANTIBACTERIAL, ANTIFUNGAL, ANTIPARASITIC AND ANTIVIRAL DRUGS VOLUME 1 6TH EDITION M Lindsay Grayson MB BS MD MSC FRACP FRCP FAFPHM Professor of Medicine and Director, Infectious Disease and Microbiology Departments, Austin Health Department of Epidemiology and Preventive Medicine, Monash University Department of Medicine, University of Melbourne, Melbourne, Australia Suzanne M Crowe MBBS FRACP MD Head, Centre for Virology, Burnet Institute for Medical Research and Public Health Consultant Physician in Infectious Diseases and General Medicine, The Alfred Hospital Professor of Medicine, Monash University, Victoria, Australia James S McCarthy MD FRACP Queensland Institute for Medical Research, University of Queensland Department of Infectious Diseases, Royal Brisbane and Womens Hospital Brisbane, Australia John Mills MD FACP FRACP Professor of Medicine, Microbiology & Epidemiology, Monash University and Consultant Physician in Infectious Diseases, The Alfred Hospital, Melbourne, Australia Johan W Mouton MD PhD Department of Medical Microbiology and Infectious Diseases, Canisius Wilhelmina Hospital, Nijmegen; Department of Medical Microbiology, Radboud University Nijmegen Medical Center, The Netherlands S Ragnar Norrby MD PhD FRCP Professor Emeritus, Swedish Institute for Infectious Disease Control, Solna, Sweden David L Paterson MBBS PhD FRACP FRCPA Professor of Medicine, University of Queensland Centre for Clinical Research, Consultant Physician, Infectious Diseases Unit, Royal Brisbane and Women’s Hospital, Consultant Clinical Microbiologist, Pathology, Queensland, Brisbane, Queensland, Australia Michael A Pfaller MD Professor Emeritus, Departments of Pathology and Epidemiology, University of Iowa College of Medicine and College of Public Health, Iowa, USA FirstpublishedinGreatBritainin1972byButterworth-Heinemann Secondedition1975 Reprinted1977 Thirdedition1979 Reprinted1982 Fourthedition1987 Reprinted1988,1989 Fifthedition1997 Thissixtheditionpublishedin2010by HodderArnold,animprintofHodderEducation,anHachetteUKCompany, 338EustonRoad,LondonNW13BH http://www.hoddereducation.com r2010EdwardArnold(Publishers)Ltd Allrightsreserved.ApartfromanyusepermittedunderUKcopyrightlaw,thispublicationmayonlybe reproduced,storedortransmitted,inanyform,orbyanymeanswithpriorpermissioninwritingofthepublishers orinthecaseofreprographicproductioninaccordancewiththetermsoflicencesissuedbytheCopyright LicensingAgency.IntheUnitedKingdomsuchlicencesareissuedbytheCopyrightLicensingAgency: SaffronHouse,6-10KirbyStreet,LondonECIN8TS Whilsttheadviceandinformationinthisbookarebelievedtobetrueandaccurateatthedateofgoingtopress, neithertheauthor[s]northepublishercanacceptanylegalresponsibilityorliabilityforanyerrorsoromissionsthat maybemade.Inparticular(butwithoutlimitingthegeneralityoftheprecedingdisclaimer)everyefforthasbeen madetocheckdrugdosages;howeveritisstillpossiblethaterrorshavebeenmissed.Furthermore,dosage schedulesareconstantlybeingrevisedandnewside-effectsrecognized.Forthesereasonsthereaderisstrongly urgedtoconsultthedrugcompanies’printedinstructionsbeforeadministeringanyofthedrugsrecommendedin thisbook. BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary LibraryofCongressCataloging-in-PublicationData AcatalogrecordforthisbookisavailablefromtheLibraryofCongress ISBN 9780340927670 12345678910 CommissioningEditor: CarolineMakepeace ProductionEditor: SarahPenny ProductionController: KateHarris CoverDesigner: HelenTownsonandLyndaKing Typesetin8.5ptGoudybyMacmillanPublishingSolutions,Bangalore-25 PrintedandboundinIndiabyReplikaPressPvtLtd Whatdoyouthinkaboutthisbook?OranyotherHodderArnoldtitle? Pleasevisitourwebsite:www.hodderarnold.com This eBook does not include access to the VitalBook edition that was packaged with the printed version of the book. Contents Contributors ix Cefotaxime 319 Foreword xix Ceftriaxone 351 Obituary xxi Ceftizoxime, Cefdinir, Cefditoren, Cefpodoxime, Preface xxiii Ceftibuten, Cefsulodin, and Cefpiramide 390 Abbreviations xxv Cefixime 398 Ceftazidime 405 Volume I Cefpirome 422 Cefepime 427 Section I - ANTIBIOTICS Ceftaroline 442 Ceftobiprole 448 Part - 1 Penicillins and Related Drugs Aztreonam 458 Benzylpenicillin (Penicillin G) 5 Part - 3 Carbapenems Phenoxypenicillins 59 Ampicillin, Amoxicillin and Other Ampicillin-Like Imipenem 471 Penicillins 65 Meropenem 500 Methicillin 93 Doripenem 514 Isoxazolyl Penicillins: Oxacillin, Cloxacillin, Dicloxacillin Ertapenem 526 and Flucloxacillin 100 Biapenem 542 Nafcillin 115 Faropenem 547 Carbenicillin, Carindacillin, Carfecillin and Panipenem 553 Ticarcillin 123 Ritipenem 558 Mezlocillin, Azlocillin, Apalcillin and Piperacillin 135 Sulopenem 562 Mecillinam (Amdinocillin) and Pivmecillinam 152 Temocillin 160 Part - 4 Glycopeptides and Lipopeptides Vancomycin 569 Beta-Lactamase Inhibitors and Combinations Teicoplanin 601 Daptomycin 621 Clavulanic Acid 167 Oritavancin 638 Sulbactam 175 Dalbavancin 645 Tazobactam and Brobactam 180 Telavancin 654 Amoxicillin–Clavulanic Acid (Co-Amoxiclav) 187 Ramoplanin 661 Ampicillin–Sulbactam 204 Ticarcillin–Clavulanic Acid 221 Part - 5 Aminoglycosides Piperacillin–Tazobactam 238 Kanamycin 667 Part - 2 Cephalosporins and Related Drugs Gentamicin 674 Tobramycin 699 Cephalothin and Cefazolin 257 Amikacin 712 Cephalexin 268 Sisomicin and Netilmicin 727 Cephadroxil, Cephaloridine, Cephacetrile, Cephapirin, Isepamicin 736 Cephradine, and Other Rarely Used First-Generation Neomycin 742 Cephalosporins 275 Cefaclor, Cefprozil, and Loracarbef 280 Part - 6 Macrolides and Ketolides Cefuroxime 286 Cefotiam, Cefuzonam, Cefamandole, Cefonicid and Erythromycin 751 Ceforanide 295 Roxithromycin 770 Cefoxitin, Cefotetan and Other Cephamycins Clarithromycin 779 (Cefmetazole and Flomoxef) 301 Azithromycin 801 Cefoperazone and Cefoperazone–Sulbactam 311 Josamycin and Rosaramicin 819 vi Contents Telithromycin 825 Gemifloxacin 1466 Cethromycin 834 Sitafloxacin 1475 Enoxacin 1482 Part - 7 Tetracyclines and Related Drugs Pefloxacin 1490 Sparfloxacin 1501 Lomefloxacin 1509 Tetracycline 843 Rufloxacin 1517 Doxycycline 851 Tosufloxacin 1521 Minocycline 870 Fleroxacin 1526 Tigecycline 881 Newer, Discontinued Fluoroquinolones: Temafloxacin, Trovafloxacin, Grepafloxacin, and Clinafloxacin 1538 Part - 8 Other Antibiotics Part - 12 Anti-Tuberculous Drugs Linezolid 895 Quinupristin–Dalfopristin 920 Pristinamycin 930 Isoniazid 1549 Fosfomycin 935 Ethambutol 1570 Fusidic Acid (Fusidate Sodium) 945 Pyrazinamide 1581 Polymyxins 955 Rifampicin (Rifampin) 1587 Novobiocin 971 Rifabutin 1627 Bacitracin and Gramicidin 975 Rifaximin 1637 Mupirocin 980 Rifapentine 1645 Lincomycin and Clindamycin 987 Streptomycin 1650 Chloramphenicol and Thiamphenicol 1008 Para-Aminosalicylic Acid (PAS) 1662 Spectinomycin 1030 Ethionamide and Prothionamide 1666 Thiacetazone 1672 Capreomycin 1677 Part - 9 Anti-Folate Agents and Other Cycloserine 1681 Synthetic Antibacterials Viomycin 1687 Sulfonamides 1037 Trimethoprim, Co-Trimoxazole (Co-T) and Related Volume 2 Agents 1076 Pyrimethamine 1150 Section II - ANTI-FUNGAL DRUGS Dapsone 1164 Trimetrexate 1182 Part - 1 Polyenes Iclaprim 1187 Nitrofurans: Nitrofurazone, Furazolidone and Amphotericin B (AMP): Deoxycholate and Lipid Nitrofurantoin 1195 Formulations 1693 Methenamine Mandelate and Methenamine Nystatin 1728 Hippurate 1205 Natamycin (Pimaricin) 1733 Part - 10 Nitroimidazoles Part - 2 Echinocandins, Allylamines and Benzylamine Derivatives Metronidazole 1211 Tinidazole 1238 Echinocandins – Caspofungin, Anidulafungin and Micafungin 1739 Part - 11 Quinolones and Fluoroquinolones Terbinafine 1763 Butenafine 1772 Nalidixic Acid and Other Older Quinolones 1249 Naftifine 1776 Ciprofloxacin 1265 Norfloxacin 1347 Ofloxacin 1362 Part - 3 Systemic Azoles Levofloxacin 1396 Moxifloxacin 1412 Ketoconazole 1781 Gatifloxacin 1429 Fluconazole 1806 Garenoxacin 1452 Itraconazole 1824 Contents vii Miconazole 1844 Mefloquine 2024 Voriconazole 1852 Halofantrine 2036 Posaconazole 1862 Lumefantrine 2042 Ravuconazole 1871 Primaquine 2049 Albaconazole 1877 Piperaquine 2059 Isavuconazole 1882 Tafenoquine 2068 Atovaquone 2073 Proguanil and Chloroproguanil 2082 Part - 4 Topical Azoles Artemisinins 2090 Bifonazole 1889 Butoconazole 1893 Part - 2 Agents Active Against Intestinal and Clotrimazole 1896 Intra-Abdominal Protozoa Croconazole 1903 Eberconazole 1905 Iodoquinol and Quinacrine 2107 Econazole 1907 Fumagillin 2110 Enilconazole 1911 Furazolidone (Furazolidine) 2114 Fenticonazole 1912 Diloxanide Furoate 2121 Flutrimazole 1915 Spiramycin 2125 Isoconazole 1917 Nitazoxanide 2132 Lanoconazole 1919 Paromomycin 2140 Neticonazole 1921 Oxiconazole 1923 Part - 3 Agents Active Against American Sertaconazole 1926 Trypanosomiasis Sulconazole 1930 Terconazole 1933 Benznidazole 2151 Tioconazole 1936 Nifurtimox 2155 KP-103 1939 Part - 4 Agents Active Against African Part - 5 Topical Agents - Thiocarbamates, Trypanosomiasis Hydroxypridones and Morpholine Suramin 2167 Tolnaftate 1943 Melarsoprol 2177 Amorolfine 1945 Eflornithine 2189 Ciclopirox 1949 Rilopirox 1953 Part - 5 Agents Active Against Leishmania and Other Pathogens Part - 6 Other Antifungal Agents and New Agents in Development Pentamidine 2203 Antimonial Agents 2208 Flucytosine (5-Fluorocytosine; 5-FC) 1957 Miltefosine 2214 Griseofulvin 1964 Haloprogin 1970 Part - 6 Agents Active Against Helminths New Agents in Development – Nikkomycin Z, CAY-1, Sodarins,Butenolides,Enfungumab,InositolPhosphocer- Albendazole 2227 amide Synthase Inhibitors 1972 Mebendazole 2240 Thiabendazole 2246 Triclabendazole 2250 Section III Anti - Parasitic Drugs Ivermectin 2254 Diethylcarbamazine (DEC) 2263 Part - 1 Anti-Malarial Agents Pyrantel Pamoate 2272 Praziquantel 2276 Chloroquine 1989 Oxamniquine 2285 Amodiaquine 2003 Metrifonate 2289 Quinine and Quinidine 2011 Niclosamide 2293 viii Contents Part - 7 Agents Active Against Ectoparasites Delavirdine 2702 Etravirine 2711 Permethrin 2299 Rilpivirine 2723 Piperonyl Butoxide 2306 Lindane 2310 Inhibitors of HIV Protease Malathion 2318 Crotamiton 2325 Saquinavir 2731 Ritonavir 2759 Section IV ANTI-VIRAL DRUGS Indinavir 2776 Nelfinavir 2788 Part - 1 Agents Active Against Herpesviruses Lopinavir 2797 Amprenavir and Fosamprenavir 2809 Aciclovir 2333 Darunavir 2824 Valaciclovir 2361 Atazanavir 2830 Famciclovir and Penciclovir 2370 Tipranavir 2842 Ganciclovir and Valganciclovir 2378 Cidofovir 2403 Other Anti-HIV Agents Vidarabine 2429 Foscarnet 2433 Enfuvirtide 2861 Maribavir 2456 Maraviroc 2869 Trifluridine (Trifluorothymidine) 2461 Raltegravir and Other HIV Integrase Inhibitors 2877 Idoxuridine 2465 Fomivirsen 2470 Part - 3 Agents Active Against Hepatitis Viruses Part - 2 Agents Active Against the Human Immunodeficiency Virus Entecavir 2891 Adefovir Dipivoxil 2899 Inhibitors of Reserve Transcriptase Telbivudine 2908 Torcitabine and Valtorcitabine 2915 Zidovudine 2479 Clevudine 2918 Didanosine 2512 Ribavirin and Viramidine 2923 Zalcitabine 2533 Pegylated Interferon Alfa 2959 Lamivudine 2545 Protease and Polymerase Inhibitors for the Treatment of Stavudine (d4T) 2563 Hepatitis C Virus Infection 2976 Abacavir 2575 Emtricitabine 2595 Part - 4 Agents Active Against Respiratory Tenofovir 2613 Viruses Amdoxovir 2627 Apricitabine 2636 Amantadine and Rimantadine 2993 Zanamivir and Polymeric Zanamivir Conjugates 3013 Non-Nucleoside Reverse Transcriptase Inhibitors Oseltamivir 3029 (NNRTIs) Peramivir 3043 Nevirapine 2645 Index 3051 Efavirenz 2675 Contributors RahulAnandMBBSMD MarkA Boyd BABMBSMDFRACPMHIDDCTM&H Division ofInfectious Diseases,ThomasJefferson University TherapeuticandVaccine ResearchProgram Philadelphia, PA, USA NationalCentre inHIVEpidemiologyandClinical Research UniversityofNew SouthWales DavidAndes MD Darlinghurst, NSW,Australia Departmentof Medicine andMedical Microbiologyand Immunology, Sectionof InfectiousDiseases SumuduBritton MBBSBSc Universityof Wisconsin MaterAdult Hospital Madison,WI,USA Queensland,Australia Graciela Andrei PhD KirstyBuisingMBBSMDMPHFRACP Laboratory ofVirology andChemotherapy StVincent Hospital,Melbourne andVictorian Infectious Departmentof MicrobiologyandImmunology DiseasesService, RoyalMelbourneHospital, Parkville RegaInstitute forMedical Research Victoria,Australia Leuven, Belgium PaulUCameronMBBSPhDFRACPFRCPA Fred YAoki MD InfectiousDiseases Unit,Alfred Hospital; Departmentsof Medical Microbiology, andPharmacology and DepartmentofMedicine, MonashUniversity, Therapeutics, Universityof Manitoba Melbourne,Australia Winnipeg,Canada DeonV Canyon PScFPhDMPH Jennifer AudsleyBAppSciPhD AntonBreinlCentre forPublic HealthandTropicalMedicine InfectiousDiseases Unit, TheAlfredHospital andtheBurnet JamesCookUniversity Institute, Townsville,Australia Melbourne,Australia HisashiBaba MDPhD ChristinaCChang MBBSFRACP InfectiousDisease Unit,Alfred Hospital,andtheBurnet Departmentof InfectiousDiseases Institute,Melbourne,Australia NagoyaUniversity Hospital Nagoya,Japan PatrickGPCharles MBBSPhDFRACP InfectiousDiseases Department, AustinHealth Bridget EBarber MBBSDTM&H Heidelberg,Victoria, Australia Victorian InfectiousDiseases Service, RoyalMelbourneHospital Victoria,Australia SharonCAChenPhDMBBSFRACPFRCPA Brenda LBartlettMD CentreforInfectious DiseasesandMicrobiology andthe Center forClinical Studies UniversityofSydney, Westmead Hospital Houston,Texas,USA Westmead,NSW,Australia Paul BBartley BMedScMBBSFRACPFRCPAPhD AllenC Cheng MBBSFRACPMPHPhD GriffithUniversity Schoolof Medicine;University ofQueensland InfectiousDiseases Unit,Alfred Hospital School ofMedicine; DepartmentofEpidemiology andPreventive Medicine, WesleyPrivate Hospital MonashUniveristy Auchenflower,Queensland, Australia Melbourne,Australia MilesH BeamanMBBSFRACPFRCPAFACTM CatherineLCherryMBBSPhDFRACPGradDip(ClinEpi) Universityof NotreDame, WesternDiagnosticPathology InfectiousDisease Unit,Alfred Hospital,andTheBurnet Myaree, WesternAustralia, Australia Institute,Melbourne,Australia FrancescoBlasiMD RuthChin MBBSPhD Institute ofRespiratory Diseases,University ofMilan, IRCCS DepartmentofMedicine, AustinHealth OspedaleMaggioreMilano TheUniversityofMelbourne Milan, Italy Heidelberg,Victoria, Australia

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Frontmatter -- Color Plates -- Human Immunodeficiency Virus. Discovery and Development of Atazanavir / Awny Farajallah, R Todd Bunch, Nicholas A Meanwell -- Discovery and Development of PL-100, A Novel HIV-1 Protease Inhibitor / Jinzi J Wu, Joseph Musto -- Darunavir (Prezista, TMC114): From Bench to
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Frontmatter -- Color Plates -- Human Immunodeficiency Virus. Discovery and Development of Atazanavir / Awny Farajallah, R Todd Bunch, Nicholas A Meanwell -- Discovery and Development of PL-100, A Novel HIV-1 Protease Inhibitor / Jinzi J Wu, Joseph Musto -- Darunavir (Prezista, TMC114): From Bench to

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