Clavulanic acid

Clavulanic acid

Basics

Clavulanic acid is an active substance used in combination with the antibiotic amoxicillin or with cephalosporins to compensate for antibiotic resistance in bacteria. By itself, the drug has only a weak antibacterial effect.

Effect

Pharmacodynamics

Bacteria produce the enzyme beta-lactamase, which is capable of deactivating the activity of beta-lactam antibiotics. Due to the structural similarity of clavulanic acid to the antibiotic, the latter is bound by the enzyme instead of the active ingredient, thus protecting the antibiotic from inactivation by the enzyme. At the same time, this extends the spectrum of activity of the antibiotic.

Pharmacokinetics

The beta-lactamase inhibitor is well absorbed into the blood by the gastrointestinal tract after oral administration and has a bioavailability of 64%. During the first six hours after ingestion, approximately half of clavulanic acid is excreted unchanged in the urine. After metabolization, the intermediates are excreted in the urine, feces, and exhaled air. The half-life, similar to amoxicillin, is 45-90 minutes.

Toxicity

Side effects

Adverse side effects include nausea, vomiting, diarrhea, and skin rashes. Tolerability improves with concomitant food intake. Serious side effects may include liver damage, anemia, and renal inflammation.

Toxicological data

Overdose may cause alterations in fluid and electrolyte balance and gastrointestinal symptoms. In rodents, low oral toxicity was observed with an LD50 greater than 2000 mg/kg. In rats, gastrointestinal disturbances and mortality occurred at doses as low as 125 mg/kg.

Chemical & physical properties

Formula C8H9NO5
Molar Mass (g·mol−1) 199,1608
Physical State solid
Melting Point (°C) 117,7-118
Boiling Point (°C) 545,8
PKS Value 2,7
CAS Number 58001-44-8
PUB Number 5280980
Drugbank ID DB00766

Editorial principles

All information used for the content comes from verified sources (recognised institutions, experts, studies by renowned universities). We attach great importance to the qualification of the authors and the scientific background of the information. Thus, we ensure that our research is based on scientific findings.
Markus Falkenstätter, BSc

Markus Falkenstätter, BSc
Author

Markus Falkenstätter is a writer on pharmaceutical topics in Medikamio's medical editorial team. He is in the last semester of his pharmacy studies at the University of Vienna and loves scientific work in the field of natural sciences.

Mag. pharm. Stefanie Lehenauer

Mag. pharm. Stefanie Lehenauer
Lector

Stefanie Lehenauer has been a freelance writer for Medikamio since 2020 and studied pharmacy at the University of Vienna. She works as a pharmacist in Vienna and her passion is herbal medicines and their effects.

The content of this page is an automated and high-quality translation from DeepL. You can find the original content in German here.

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