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.
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.
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.
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.
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.
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.
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 |
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