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SyntheticantimicrobialagentsSyntheticantimicrobialagents((人工合成抗菌药人工合成抗菌药))HuifangTangtanghuifang@zju.edu.cnClassificationofSyntheticantimicrobialagents•Ⅰ.Quinolones(喹诺酮类);•Ⅱ.Sulfonamides(磺胺类);•Ⅲ.Othersyntheticantimicrobialagents:•Trimethoprim(甲氧苄啶)•Nitrofurans(硝基呋喃类),etc.Generalfeatures•Broadantimicrobialactivityandareeffectiveafteroraladministrationforthetreatmentofawidevarietyofinfectiousdisease.•Relativelyfewsideeffects.•Microbialresistancetotheiractiondoesnotdeveloprapidly.QuinolonesQuinolonesChemistry•Derivedfrombasicstructureofnalidixicacid(萘啶酸)andhavesubstituentsatN-1,C-5,C-7,position8andafluorineatomatposition6.•Fluorineatposition6enhancesgyraseinhibitionandcellpenetration.QuinolonesQuinolonesQuinolonesChemicalstructureQuinolones((诺氟沙星诺氟沙星))((环丙沙星环丙沙星))((萘啶酸萘啶酸))QuinolonesGenerationExamples1st(1962-1969)Nalidixicacid,萘啶酸2nd(1969-1979)Pipemidicacid吡哌酸Cinoxacin西诺沙星3rd(1980-1996)Norfloxacin诺氟沙星Levofloxacin左氧氟沙星Ciprofloxacin环丙沙星Ofloxacin氧氟沙星sparfloxacin司帕沙星4th(1997-)Grepafloxacin格帕沙星Clinafloxacin克林沙星Gatifloxacin加替沙星Moxifloxacin莫西沙星ClassificationQuinolonesSummaryofantimicrobialspectrumofquinolones.Typicaltherapeuticapplicationsofuoroquinolones.First-generationagents(1962-1969)First-generationagents(1962-1969)Nalidixicacid,Nalidixicacid,萘啶酸萘啶酸•ThefirstgenerationdrugofthequinoloneantibioticsThefirstgenerationdrugofthequinoloneantibiotics•Moderategram-negativeactivityandminimalsystemicdistributionModerategram-negativeactivityandminimalsystemicdistributionClinicalapplicationsClinicalapplications•UncomplicatedurinarytractinfectionsUncomplicatedurinarytractinfectionsQuinolonesQuinolonesQuinolonesSecond-generationquinolonesSecond-generationquinolones(1969-1979)(1969-1979)PipemidicacidPipemidicacid吡哌酸吡哌酸CinoxacinCinoxacin西诺沙星西诺沙星•Expandedgram-negativeactivityandatypicalpathogencoverage,butExpandedgram-negativeactivityandatypicalpathogencoverage,butlimitedgram-positiveactivity.limitedgram-positiveactivity.•Mostactiveagainstaerobicgram-negativebacilliMostactiveagainstaerobicgram-negativebacilli•CiprofloxacinremainsthequinolonemostactiveagainstPseudomonasCiprofloxacinremainsthequinolonemostactiveagainstPseudomonasaeruginosaaeruginosaQuinolonesQuinolonesQuinolonesSecond-generationquinolonesSecond-generationquinolones(1969-1979)(1969-1979)•Activeagainstgram-positiveandgram-negativebacteria,Activeagainstgram-positiveandgram-negativebacteria,mycobacteria,mycoplasmamycobacteria,mycoplasma支原体支原体andlegionellaspeciesandlegionellaspecies军团杆军团杆菌属菌属..•Longerhalf-livesduetoslowelimination,distributionintomanyLongerhalf-livesduetoslowelimination,distributionintomanytissuesandbodyfluidsandpenetrationintohumancells.tissuesandbodyfluidsandpenetrationintohumancells.QuinolonesQuinolonesQuinolonesThird-generationquinolonesThird-generationquinolones(1980-1996)(1980-1996)NorfloxacinNorfloxacin诺氟沙星诺氟沙星,,LevofloxacinLevofloxacin左氧氟沙星左氧氟沙星,,CiprofloxacinCiprofloxacin环丙沙星环丙沙星,,OfloxacinOfloxacin氧氟沙星氧氟沙星,,SparfloxacinSparfloxacin司帕沙星司帕沙星•Addedpotencyagainstgram-negativebacteria,anaerobesandAddedpotencyagainstgram-negativebacteria,anaerobesandmycobacteria.mycobacteria.•Retainexpandedgram-negativea...

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