Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H9NO5 |
Molecular Weight | 199.1608 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC\C=C1/O[C@@H]2CC(=O)N2[C@H]1C(O)=O
InChI
InChIKey=HZZVJAQRINQKSD-PBFISZAISA-N
InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
Clavulanic acid is produced by the fermentation of Streptomyces clavuligerus. It is a β-lactam structurally related to the penicillins and possesses the ability to inactivate a wide variety of β-lactamases by blocking the active sites of these enzymes. Clavulanic acid is particularly active against the clinically important plasmid-mediated β-lactamases frequently responsible for transferred drug resistance to penicillins and cephalosporins. Clavulanic acid is used in conjunction with amoxicillin for the treatment of bronchitis and urinary tract, skin, and soft tissue infections caused by beta-lactamase producing organisms. Clavulanic acid competitively and irreversibly inhibits a wide variety of beta-lactamases, commonly found in microorganisms resistant to penicillins and cephalosporins. Binding and irreversibly inhibiting the beta-lactamase results in a restauration of the antimicrobial activity of beta-lactam antibiotics against lactamase-secreting-resistant bacteria. By inactivating beta-lactamase (the bacterial resistance protein), the accompanying penicillin/cephalosporin drugs may be made more potent as well.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
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In vitro susceptibility of Mycobacterium tuberculosis, Mycobacterium fortuitum and Mycobacterium chelonei to augmentin. | 1986 Aug |
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In vitro susceptibility of Mycobacterium tuberculosis, Mycobacterium africanum, Mycobacterium bovis, Mycobacterium avium, Mycobacterium fortuitum, and Mycobacterium chelonae to ticarcillin in combination with clavulanic acid. | 1987 Jan |
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Immunogenicity and allergenicity studies on two beta-lactam structures, a clavam, clavulanic acid, and a carbapenem: structure-activity relationships. | 1988 |
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In vitro activity of antimicrobial agents against mycobacteria. | 1988 |
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Cholestatic hepatitis due to antibacterial combination of amoxicillin and clavulanic acid (augmentin) | 1989 Oct |
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beta-Lactamase inhibitors and the inducibility of the beta-lactamase of Mycobacterium tuberculosis. | 1992 Mar |
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beta-Lactamase activity in mycobacteria including Mycobacterium avium and suppression of their growth by a beta-lactamase-stable antibiotic. | 1995 |
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Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis? | 1995 Dec |
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beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies. | 1996 Jul-Aug |
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Hypersensitivity to clavulanic acid in children. | 2008 Sep-Oct |
Sample Use Guides
Adults The usual adult dose is one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 250 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. For more severe infections and infections of the respiratory tract, the dose should be one 875 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. Adults who have difficulty swallowing may be given the 125 mg/31.25 mg per 5 mL or 250 mg/62.5 mg per 5 mL suspension in place of the 500 mg/125 mg tablet. The 200 mg/28.5 mg per 5 mL suspension or the 400 mg/57 mg per 5 mL suspension may be used in place of the 875 mg/125 mg tablet.
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000000202
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LIVERTOX |
215
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1 (AMO/CLA)
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NCI_THESAURUS |
C260
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WHO-ATC |
J01DH51
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NDF-RT |
N0000175930
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58001-44-8
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48203
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M3609
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DB00766
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CLAVULANIC ACID
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CHEMBL777
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58001-44-8
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261-069-2
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4948
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5280980
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SUB06642MIG
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D019818
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21216
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C61681
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)