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Ertapenem: a Group 1 carbapenem with distinct antibacterial and pharmacological properties Hammond MLJ Antimicrob Chemother 2004[Jun]; 53 Suppl 2 (ä): ii7-9Ertapenem, a Group 1 carbapenem, is the most recent beta-lactam antibiotic to enter clinical practice in the USA and Europe. While structurally a carbapenem, the overall molecular structure of ertapenem has been modified to focus its antibacterial spectrum on important community-acquired aerobic and anaerobic pathogens, and to increase its plasma half-life, permitting once-a-day dosing for this parenteral antibiotic. A number of chemical features are responsible for the unique properties of ertapenem. The inclusion of a trans-1-hydroxyethyl group in the structure of ertapenem enables the drug to maintain antibacterial efficacy against the vast majority of beta-lactamase-producing organisms. A critical 1beta-methyl substituent shields the beta-lactam carbonyl group and serves to reduce dehydropeptidase (DHP)-1 catalysed hydrolysis of the beta-lactam, enabling ertapenem to be administered without a DHP-1 inhibitor. A meta-substituted benzoic acid substituent increases the molecular weight and lipophilicity of the molecule, and the carboxylic acid moiety, ionized at physiological pH, results in ertapenem having a net negative charge. As a result, ertapenem is highly protein bound and has an extended half-life, permitting a once-a-day treatment regimen.|Anti-Bacterial Agents/administration & dosage/*chemistry/pharmacology[MESH]|Bacteria, Aerobic/*drug effects[MESH]|Bacteria, Anaerobic/*drug effects[MESH]|Bacterial Infections/drug therapy/microbiology[MESH]|Carbapenems/classification[MESH]|Community-Acquired Infections/*drug therapy/microbiology[MESH]|Ertapenem[MESH]|Humans[MESH]|Lactams/administration & dosage/*chemistry/pharmacology[MESH]|beta-Lactams[MESH] |
