DIFFERENT CLASSES OF ANTIBIOTICS - AN OVERVIEW Key: COMMONLY ACT AS BACTERIOSTATIC AGENTS, RESTRICTING GROWTH & REPRODUCTION COMMONLY ACT AS BACTERICIDAL AGENTS, CAUSING BACTERIAL CELL DEATH ß-LACTAMS AMINOGLYCOSIDES chloramphenicol glycopeptides ansamycins streptogramins MOST WIDELY USED ANTIBIOTICS IN THE NHS FAMILY OF OVER 20 ANTIBIOTICS COMMONLY USED IN LOW INCOME COUNTRIES COMMON ‘DRUGS OF LAST RESORT’ CAN ALSO DEMONSTRATE ANTIVIRAL ACTIVITY TWO GROUPS OF ANTIBIOTICS THAT ACT SYNERGISTICALLY R H O O O HO O S HO HO N O HO O HO HN OH H2N O All contain a beta-lactam ring EXAMPLES Penicillins (shown) such as amoxicillin and flucloxacillin; Cephalosporins such as cefalexin. MODE OF ACTION Inhibit bacteria cell wall biosynthesis. DISCOVERY N N NH2 O OH O NH2 NH2 OH N+ OH O HO O- HO O O HO N H O OH O O NH HO All contain aminosugar substructures Distinct individual compound EXAMPLES Streptomycin (shown), neomycin, kanamycin, paromomycin. MODE OF ACTION Inhibit synthesis of proteins, preventing growth. MODE OF ACTION Inhibit the synthesis of proteins by bacteria, leading to cell death. No longer a first line drug in any developed nation due to increased resistance and worries about safety. 1940 OCH3 O OH N H H3CO O O Cl Cl NH2 1930 OH O OH O H N O N H H2N H N N H O OH HN O H3CO NH2 O OH EXAMPLES Vancomycin (shown), teicoplanin. MODE OF ACTION Inhibit bacteria cell wall biosynthesis. 1960 O O HN Consist of carbohydrate linked to a peptide formed of amino acids 1950 O O O O HO NH OH OH Cl O Cl O O N O O N All contain an aromatic ring bridged by an aliphatic chain. Combination of two structurally differing compounds, from groups denoted A & B EXAMPLES Geldanamycin (shown), rifamycin, naphthomycin. EXAMPLES Pristinamycin IIA (shown), Pristinamycin IA. MODE OF ACTION Inhibit the synthesis of RNA by bacteria, leading to cell death. MODE OF ACTION Inhibit the synthesis of proteins by bacteria, leading to cell death. 1970 1980 sulfonamides tetracyclines macrolides oxazolidinones quinolones lipopeptides FIRST COMMERCIAL ANTIBIOTICS WERE SULFONAMIDES BECOMING LESS POPULAR DUE TO DEVELOPMENT OF RESISTANCE SECOND MOST PRESCRIBED ANTIBIOTICS IN THE NHS POTENT ANTIBIOTICS COMMONLY USED AS ‘DRUGS OF LAST RESORT’ RESISTANCE EVOLVES RAPIDLY INSTANCES OF RESISTANCE RARE O H2N S O N H H All contain the sulfonamide group EXAMPLES Prontosil, sulfanilamide (shown), sulfadiazine, sulfisoxazole. MODE OF ACTION Do not kill bacteria but prevent their growth and multiplication. Cause allergic reactions in some patients. C OH O OH O OH O O NH2 HO O OH N HO OH OH C2H5 HO O O O CH3 CH3 OCH3 O O H N N O OH O N O F F N O O N HO O H2N H N C9H19 O N H O HN NH O N O NH O OH HN O O O HN NH2 O H N N H O OH O N H NH OH O NH O O HN O O OO HN OH O OH NH O O All contain 4 adjacent cyclic hydrocarbon rings All contain a 14-, 15-, or 16-membered macrolide ring All contain 2-oxazolidone somewhere in their structure All contain fused aromatic rings with a carboxylic acid group attached EXAMPLES Tetracycline (shown), doxycycline, limecycline, oxytetracycline. EXAMPLES Erythromycin (shown), clarithromycin, azithromycin. EXAMPLES Linezolid (shown), posizolid, tedizolid, cycloserine. EXAMPLES Ciprofloxacin (shown), levofloxacin, trovafloxacin. All contain a lipid bonded to a peptide MODE OF ACTION Inhibit synthesis of proteins by bacteria, preventing growth. MODE OF ACTION Inhibit protein synthesis by bacteria, occasionally leading to cell death. MODE OF ACTION Inhibit synthesis of proteins by bacteria, preventing growth. MODE OF ACTION Interfere with bacteria DNA replication and transcription. MODE OF ACTION Disrupt multiple cell membrane functions, leading to cell death. © COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | Twitter: @compoundchem | Facebook: www.facebook.com/compoundchem Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. NH2 EXAMPLES Daptomycin (shown), surfactin. BY NC ND