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Journal of Antimicrobial Chemotherapy (2004) 53, ii7-ii9
© 2004 The British Society for Antimicrobial Chemotherapy

Supplement

Ertapenem: a Group 1 carbapenem with distinct antibacterial and pharmacological properties

Milton L. Hammond*

Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, NJ 07065, USA

Abstract

Ertapenem, a Group 1 carbapenem, is the most recent ß-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 ß-lactamase-producing organisms. A critical 1ß-methyl substituent shields the ß-lactam carbonyl group and serves to reduce dehydropeptidase (DHP)-1 catalysed hydrolysis of the ß-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.

Keywords: pharmacology, ß-lactams, antimicrobial agents, molecular structure, once-daily dosing

Footnotes

* Tel: +1-732-594-4254; Fax: +1-732-594-9490; E-mail: milton_hammond{at}merck.com


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