U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CLAVULANIC ACID

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO

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

HIDE SMILES / InChI

Description

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

CNS Active
3913
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.

Originator

Approval Year

1984
98
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.09 µM [IC50]
Inhibitor
8297
 80.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Augmentin

Approved Use

AUGMENTIN 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 Date

1996
Curative
Approved
8429
Augmentin

Approved Use

AUGMENTIN 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 Date

1996
Curative
Approved
8429
Augmentin

Approved Use

AUGMENTIN 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 Date

1996
Curative
Approved
8429
Augmentin

Approved Use

AUGMENTIN 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 Date

1996
Curative
Approved
8429
Augmentin

Approved Use

AUGMENTIN 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
AMOXICILLIN
 CLAVULANIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
AMOXICILLIN
 CLAVULANIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
AMOXICILLIN
 CLAVULANIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse 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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Other AEs: Diarrhea, Rash urticarial...
Other AEs:
Diarrhea
Rash urticarial
Diaper rash
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Other AEs: Loose stools, Nausea...
Other AEs:
Loose stools (9%)
Nausea (3%)
Rash urticarial (3%)
Vomiting (1%)
Vaginitis (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
AEs

AEs

AESignificanceDosePopulation
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: infections
Age Group: adult
Sex: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:48947
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48947
ChemicalBook
CB9722501
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9722501
ZINC
ZINC000003830569
http://zinc15.docking.org/substances/ZINC000003830569
PubMed

PubMed

TitleDatePubMed
In vitro activity of antimicrobial agents against mycobacteria.
1988
Cholestatic hepatitis due to antibacterial combination of amoxicillin and clavulanic acid (augmentin).
1989 Oct
beta-Lactamase inhibitors and the inducibility of the beta-lactamase of Mycobacterium tuberculosis.
1992 Mar
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis?
1995 Dec
Hypersensitivity to clavulanic acid in children.
2008 Sep-Oct
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Patents

Patents

04415584
4
05827537
6
JP2002541113A
46
JP2004509136A
4
JP4854084B2
12
JPH02167286A
4
JPS5677283A
4

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
The purified beta-lactamase enzyme focused at pI 5.4 and was strongly inhibited in vitro by clavulanic acid (IC50 = 0.09 uM).
Name Type Language
CLAVULANIC ACID
INN   MART.   MI   WHO-DD  
INN  
Official Name English
Clavulanic acid [WHO-DD]
Common Name English
CLAVULANATE [VANDF]
Common Name English
BRL 14151
Code English
clavulanic acid [INN]
Common Name English
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
BRL-14151
Code English
CLAVULANIC ACID [MART.]
Common Name English
CLAVULANATE
VANDF  
Common Name English
SERDAXIN
Brand Name English
4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-(2-HYDROXYETHYLIDENE)-7-OXO-, (2R-(2.ALPHA.,3Z,5.ALPHA.))-
Common Name English
(Z)-(2R,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
RX-10100
Code English
CLAVULANIC ACID [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000202
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LIVERTOX NBK548183
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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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Code System Code Type Description
EPA CompTox
DTXSID2022830
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PRIMARY
RXCUI
48203
Created by admin on Fri Dec 15 15:03:19 GMT 2023 , Edited by admin on Fri Dec 15 15:03:19 GMT 2023
ALTERNATIVE
MERCK INDEX
m3609
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PRIMARY Merck Index
DRUG BANK
DB00766
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PRIMARY
WIKIPEDIA
CLAVULANIC ACID
Created by admin on Fri Dec 15 15:03:19 GMT 2023 , Edited by admin on Fri Dec 15 15:03:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL777
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PRIMARY
LACTMED
Ticarcillin and Clavulanic Acid
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PRIMARY
DAILYMED
23521W1S24
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PRIMARY
CAS
58001-44-8
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PRIMARY
ECHA (EC/EINECS)
261-069-2
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PRIMARY
INN
4948
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PRIMARY
PUBCHEM
5280980
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PRIMARY
EVMPD
SUB06642MIG
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PRIMARY
SMS_ID
100000089842
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PRIMARY
MESH
D019818
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PRIMARY
FDA UNII
23521W1S24
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PRIMARY
CHEBI
48947
Created by admin on Fri Dec 15 15:03:19 GMT 2023 , Edited by admin on Fri Dec 15 15:03:19 GMT 2023
PRIMARY
RXCUI
21216
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PRIMARY
DRUG CENTRAL
669
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PRIMARY
CHEBI
487869
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PRIMARY
NCI_THESAURUS
C61681
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PRIMARY
LACTMED
Amoxicillin and Clavulanic Acid
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PRIMARY
ACTIVE MOIETY
Structure of CLAVULANIC ACID
SALT/SOLVATE (PARENT)
Structure of CLAVULANATE POTASSIUM
SALT/SOLVATE (PARENT)
Structure of CLAVULANATE LITHIUM
SALT/SOLVATE (PARENT)
Structure of CLAVULANATE SODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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