Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H8NO5.Li |
| Molecular Weight | 205.094 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Li+].[H][C@@]12CC(=O)N1[C@@]([H])(C([O-])=O)\C(O2)=C\CO
InChI
InChIKey=JMRXTGCDVQLAFM-JSYANWSFSA-M
InChI=1S/C8H9NO5.Li/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);/q;+1/p-1/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
Curator's Comment: Clavulanic acid is a CNS-modulating compound with exceptional blood-brain barrier permeability and safety profile. Clavulanic acid has been proposed to have anti-depressant activity and was in Phase IIb clinical trials for the treatment of Major Depressive Disorder (MDD). Studies have also shown that clavulanic acid suppresses anxiety and enhances sexual functions in rodent and primate models by a mechanism involving central nervous system (CNS) modulation.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.09 µM [IC50] | |||
| 80.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Augmentin Approved UseAUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the
designated organisms in the conditions listed below:
Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and
M. catarrhalis.
Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli,
and Klebsiella spp.
Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and
Enterobacter spp. Launch Date1996 |
|||
| Curative | Augmentin Approved UseAUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the
designated organisms in the conditions listed below:
Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and
M. catarrhalis.
Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli,
and Klebsiella spp.
Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and
Enterobacter spp. Launch Date1996 |
|||
| Curative | Augmentin Approved UseAUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the
designated organisms in the conditions listed below:
Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and
M. catarrhalis.
Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli,
and Klebsiella spp.
Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and
Enterobacter spp. Launch Date1996 |
|||
| Curative | Augmentin Approved UseAUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the
designated organisms in the conditions listed below:
Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and
M. catarrhalis.
Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli,
and Klebsiella spp.
Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and
Enterobacter spp. Launch Date1996 |
|||
| Curative | Augmentin Approved UseAUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the
designated organisms in the conditions listed below:
Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and
M. catarrhalis.
Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis.
Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli,
and Klebsiella spp.
Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and
Enterobacter spp. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN |
CLAVULANIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.49 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN |
CLAVULANIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/ |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN |
CLAVULANIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: |
unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: |
Other AEs: Diarrhea, Rash urticarial... Other AEs: Diarrhea Sources: Rash urticarial Diaper rash |
125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
Other AEs: Loose stools, Nausea... Other AEs: Loose stools (9%) Sources: Nausea (3%) Rash urticarial (3%) Vomiting (1%) Vaginitis (1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diaper rash | 10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: |
unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: |
|
| Diarrhea | 10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: |
unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: |
|
| Rash urticarial | 10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: |
unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: |
|
| Vaginitis | 1% | 125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
| Vomiting | 1% | 125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
| Nausea | 3% | 125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
| Rash urticarial | 3% | 125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
| Loose stools | 9% | 125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: |
unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro susceptibility of Mycobacterium tuberculosis, Mycobacterium fortuitum and Mycobacterium chelonei to augmentin. | 1986 Aug |
|
| Cholestatic hepatitis due to antibacterial combination of amoxicillin and clavulanic acid (augmentin). | 1989 Oct |
|
| Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis? | 1995 Dec |
|
| beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies. | 1996 Jul-Aug |
|
| Suppression of the growth of six potentially-pathogenic mycobacteria by beta-lactam/beta-lactamase-inhibitors. | 1997 |
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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ACTIVE MOIETY
SUBSTANCE RECORD
