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 FAMILY OF OVER 20 ANTIBIOTICS COMMONLY USED IN LOW INCOME COMMON ‘DRUGS OF LAST RESORT’ CAN ALSO DEMONSTRATE TWO GROUPS OF ANTIBIOTICS THAT IN THE NHS COUNTRIES OH ANTIVIRAL ACTIVITY ACT SYNERGISTICALLY O NH2 OCH O O 3 R O OH HO HO OH NH OH H HO O + HO O OH N H3CO OH O NH2 - HO S O O O O Cl O HO O O N O O O NH O O O 2 Cl HO OH O N Cl O O N O HO HN N OH N O O O H H H CO O O H O N N HN 3 NH2 O N N N N H H H H N NH Cl OH NH O O HN O OH 2 2 H2N O HO O Combination of two structurally differing All contain a beta-lactam ring All contain aminosugar substructures Distinct individual compound All contain an aromatic ring bridged by HO OH OH an aliphatic chain. compounds, from groups denoted A & B EXAMPLES EXAMPLES MODE OF ACTION Consist of carbohydrate linked to a EXAMPLES EXAMPLES Penicillins (shown) such as Streptomycin (shown), neomycin, Inhibit synthesis of proteins, peptide formed of amino acids Geldanamycin (shown), rifamycin, Pristinamycin IIA (shown), amoxicillin and flucloxacillin; kanamycin, paromomycin. preventing growth. EXAMPLES naphthomycin. Pristinamycin IA. Cephalosporins such as cefalexin. MODE OF ACTION Vancomycin (shown), teicoplanin. No longer a first line drug in any MODE OF ACTION MODE OF ACTION MODE OF ACTION Inhibit the synthesis of proteins by developed nation due to increased MODE OF ACTION Inhibit the synthesis of RNA by Inhibit the synthesis of proteins by Inhibit bacteria cell wall biosynthesis. bacteria, leading to cell death. resistance and worries about safety. Inhibit bacteria cell wall biosynthesis. bacteria, leading to cell death. bacteria, leading to cell death. DISCOVERY 1930 1940 1950 1960 1970 1980 sulfonamides tetracyclines macrolides oxazolidinones quinolones lipopeptides FIRST COMMERCIAL ANTIBIOTICS BECOMING LESS POPULAR DUE TO SECOND MOST PRESCRIBED POTENT ANTIBIOTICS COMMONLY RESISTANCE EVOLVES RAPIDLY INSTANCES OF RESISTANCE RARE HO O WERE SULFONAMIDES DEVELOPMENT OF RESISTANCE ANTIBIOTICS IN THE NHS USED AS ‘DRUGS OF LAST RESORT’ O O O O O N OH O OH O O H O F O NH HN OH O OH F OH H2N O H HO OH NH O NH NH OH O 2 N O H N O O H N S N HO N 2 C2H5 O O O CH3 N N N HN O HN O O NH2 O OH OH H H H OCH3 C9H19 N N HO O O HN N N HN O O N O H H O O CH O O OH O OH 3 O OH NH All contain the sulfonamide group O O NH O All contain 4 adjacent cyclic All contain a 14-, 15-, or 16-membered All contain 2-oxazolidone somewhere All contain fused aromatic rings with a hydrocarbon rings macrolide ring in their structure carboxylic acid group attached NH2 EXAMPLES All contain a lipid bonded to a peptide Prontosil, sulfanilamide (shown), EXAMPLES EXAMPLES EXAMPLES EXAMPLES sulfadiazine, sulfisoxazole. Tetracycline (shown), doxycycline, Erythromycin (shown), Linezolid (shown), posizolid, Ciprofloxacin (shown), levofloxacin, EXAMPLES limecycline, oxytetracycline. clarithromycin, azithromycin. tedizolid, cycloserine. trovafloxacin. Daptomycin (shown), surfactin. MODE OF ACTION Do not kill bacteria but prevent their MODE OF ACTION MODE OF ACTION MODE OF ACTION MODE OF ACTION MODE OF ACTION growth and multiplication. Cause Inhibit synthesis of proteins by Inhibit protein synthesis by bacteria, Inhibit synthesis of proteins by Interfere with bacteria DNA Disrupt multiple cell membrane allergic reactions in some patients. bacteria, preventing growth. occasionally leading to cell death. bacteria, preventing growth. replication and transcription. functions, leading to cell death. © COMPOUND INTEREST 2014 - WWW.COMPOUNDCHEM.COM | Twitter: @compoundchem | Facebook: www.facebook.com/compoundchem C Shared under a Creative Commons Attribution-NonCommercial-NoDerivatives licence. BY NC ND.