Amoxicillin-clavulanic acid

    Research output: Chapter in Book/Report/Conference proceedingChapter

    Abstract

    Amoxicillin-clavulanic acid is a combination product consisting of the semisynthetic antibiotic amoxicillin with the beta-lactamase-inhibitor clavulanic acid as a potassium salt. Clavulanic acid is a naturally occurring beta-lactamase inhibitor isolated from Streptomyces clavuligerus (Brown et al., 1976; Reading and Cole, 1977; see Chapter 13, Beta- Lactamase inhibitors). It contains a beta-lactam ring, and the sulfur of the penicillin thiazolidine ring is replaced with oxygen to form an oxazolidine ring (see Figure 14.1). Clavulanic acid has weak intrinsic beta-lactam activity, but its clinical utility relates to its potent inhibition of many beta-lactamases (Reading et al., 1983) and its ability to protect substrate drugs from hydrolysis (Bush, 1988). The molecular formula of clavulanic acid is C8H8KNO5. Chemically, clavulanate potassium is potassium -(2R,5R)-3-(2-hydroxyethylidine)-7-oxo-4-oxa- 1-azabicyclo[3.2.0]-heptane-2-carboxylate and has a molecular weight of 237.25.

    Original languageEnglish
    Title of host publicationKucers' the Use of Antibiotics
    Subtitle of host publicationA Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs, Seventh Edition
    EditorsM. Lindsay Grayson, Sara E. Cosgrove, Suzanne Crowe, William Hope, James S. McCarthy, John Mills, Johan W. Mouton, David L. Paterson
    Place of PublicationBoca Raton, FL
    PublisherCRC Press
    Chapter14
    Pages254-279
    Number of pages26
    Volume1
    Edition7th
    ISBN (Electronic)9781498747967, 9781351648158, 9781315152110
    ISBN (Print)9781498747950
    DOIs
    Publication statusPublished - 2017

    Keywords

    • Amoxicillin–clavulanic acid
    • antibiotic
    • beta-lactamase-inhibitor
    • potassium salt
    • Streptomyces clavuligerus

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  • Cite this

    Gordon, D. (2017). Amoxicillin-clavulanic acid. In M. L. Grayson, S. E. Cosgrove, S. Crowe, W. Hope, J. S. McCarthy, J. Mills, J. W. Mouton, & D. L. Paterson (Eds.), Kucers' the Use of Antibiotics: A Clinical Review of Antibacterial, Antifungal, Antiparasitic, and Antiviral Drugs, Seventh Edition (7th ed., Vol. 1, pp. 254-279). CRC Press. https://doi.org/10.1201/9781498747967