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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H9NO5
Molecular Weight 199.1611
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLAVULANIC ACID

SMILES

C(\[H])(=C/1\[C@]([H])(C(=O)O)N2C(=O)C[C@@]2([H])O1)/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

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
3732
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
63
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
7998
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

832118400000
Curative
Approved
7998
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

832118400000
Curative
Approved
7998
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

832118400000
Curative
Approved
7998
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

832118400000
Curative
Approved
7998
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

832118400000
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
experiment_type: steady
dose_type: Recommended
co-adm with
    data_source:
    https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
    unhealthy, 2 months to 12 years
    population: unhealthy
    age: 2 months to 12 years
    sex: unknown
    food_status:
    n:
    data_source:
    https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
    Other AEs: Diarrhea, Rash urticarial...
    Other AEs:
    Diarrhea (1 times / day)
    Rash urticarial (1 times / day)
    Diaper rash (1 times / day)

    data_source:
    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
    experiment_type: steady
    dose_type: Recommended
    co-adm with
      data_source:
      https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
      unhealthy, adult
      population: unhealthy
      age: adult
      sex: unknown
      food_status:
      n:
      data_source:
      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 (1 times / day)
      Nausea (1 times / day)
      Rash urticarial (1 times / day)
      Vomiting (1 times / day)
      Vaginitis (1 times / day)

      data_source:
      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
      experiment_type: steady
      dose_type: Recommended
      co-adm with
        data_source:
        https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
        unhealthy, 2 months to 12 years
        population:
        age:
        sex:
        food_status:
        n:
        data_source:
        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
        experiment_type: steady
        dose_type: Recommended
        co-adm with
          data_source:
          https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
          unhealthy, 2 months to 12 years
          population:
          age:
          sex:
          food_status:
          n:
          data_source:
          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
          experiment_type: steady
          dose_type: Recommended
          co-adm with
            data_source:
            https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
            unhealthy, 2 months to 12 years
            population:
            age:
            sex:
            food_status:
            n:
            data_source:
            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
            experiment_type: steady
            dose_type: Recommended
            co-adm with
              data_source:
              https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
              unhealthy, adult
              population:
              age:
              sex:
              food_status:
              n:
              data_source:
              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
              experiment_type: steady
              dose_type: Recommended
              co-adm with
                data_source:
                https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
                unhealthy, adult
                population:
                age:
                sex:
                food_status:
                n:
                data_source:
                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
                experiment_type: steady
                dose_type: Recommended
                co-adm with
                  data_source:
                  https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
                  unhealthy, adult
                  population:
                  age:
                  sex:
                  food_status:
                  n:
                  data_source:
                  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
                  experiment_type: steady
                  dose_type: Recommended
                  co-adm with
                    data_source:
                    https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
                    unhealthy, adult
                    population:
                    age:
                    sex:
                    food_status:
                    n:
                    data_source:
                    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
                    experiment_type: steady
                    dose_type: Recommended
                    co-adm with
                      data_source:
                      https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
                      unhealthy, adult
                      population:
                      age:
                      sex:
                      food_status:
                      n:
                      data_source:
                      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
                      ZINC
                      ZINC000003830569
                      http://zinc15.docking.org/substances/ZINC000003830569
                      PubMed

                      PubMed

                      TitleDatePubMed
                      In vitro activity of antimicrobial agents against mycobacteria.
                      1988
                      beta-Lactamase inhibitors and the inducibility of the beta-lactamase of Mycobacterium tuberculosis.
                      1992 Mar
                      beta-Lactamase activity in mycobacteria including Mycobacterium avium and suppression of their growth by a beta-lactamase-stable antibiotic.
                      1995
                      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
                      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
                      3
                      05827537
                      4
                      JP2002541113A
                      43
                      JP2004509136A
                      3
                      JP4854084B2
                      11
                      JPH02167286A
                      3
                      JPS5677283A
                      3

                      Sample Use Guides

                      In Vivo Use Guide
                      Adults
                      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
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		LIVERTOX 215
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		WHO-ESSENTIAL MEDICINES LIST 6.2.1 (AMO/CLA)
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		NCI_THESAURUS C260
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		WHO-ATC J01DH51
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		NDF-RT N0000175930
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      Code System Code Type Description
                      EPA CompTox
                      		58001-44-8
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      RXCUI
                      		48203
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		ALTERNATIVE
                      MERCK INDEX
                      		M3609
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY Merck Index
                      DRUG BANK
                      		DB00766
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      WIKIPEDIA
                      		CLAVULANIC ACID
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      ChEMBL
                      		CHEMBL777
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      LACTMED
                      		Ticarcillin and Clavulanic Acid
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      CAS
                      		58001-44-8
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      ECHA (EC/EINECS)
                      		261-069-2
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      INN
                      		4948
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      PUBCHEM
                      		5280980
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      EVMPD
                      		SUB06642MIG
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      MESH
                      		D019818
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      FDA UNII
                      		23521W1S24
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      RXCUI
                      		21216
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      DRUG CENTRAL
                      		669
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      NCI_THESAURUS
                      		C61681
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      LACTMED
                      		Amoxicillin and Clavulanic Acid
                      Created by admin on Sat Jun 26 11:25:15 UTC 2021 , Edited by admin on Sat Jun 26 11:25:15 UTC 2021
                      		PRIMARY
                      ACTIVE MOIETY
                      Structure of CLAVULANIC ACID
                      SALT/SOLVATE (PARENT)
                      Structure of CLAVULANATE POTASSIUM
                      SALT/SOLVATE (PARENT)
                      Structure of CLAVULANATE SODIUM
                      NIH
                      NCATS
                      PRIVACY ACT
                      ACCESSIBILITY
                      DISCLAIMER
                      For language access assistance, contact the NCATS Public Information Officer
                      National Center for Advancing Translational Sciences (NCATS),
                      6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966