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clavulanate

Trade name: Augmentin

Small moleculeapproved

Approved

Aug 6, 1984

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. — NCATS

Clinical trial activity

215 trials · 268 clinical orgs · 16 marketing orgs

Phase 1
24
Phase 2
64
Phase 3
47
Phase 4
76

Earliest trial started Jan 1, 1998 (NCT01559753)

Timeline

1980s

  1. Aug 6, 1984

    Earliest FDA Approval

  2. Aug 6, 1984

    Neopharma — NDA Secondary Org

  3. Aug 6, 1984

    US Antibiotics — NDA Secondary Org

  4. Apr 1, 1985

    GlaxoSmithKline — NDA Secondary Org

  5. Dec 19, 1986

    GlaxoSmithKline — Marketing Organization

1990s

  1. Jan 1, 1999

    Earliest Phase 3 Sponsor(trial)

2000s

  1. Jan 1, 2002

    Teva — Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2002

    Earliest Phase 2 Sponsor(trial)

  3. Mar 14, 2002

    Novartis — Marketing Organization

  4. Apr 18, 2002

    Chartwell Pharmaceuticals — Marketing Organization

  5. Sep 17, 2002

    Sun Pharmaceuticals — Marketing Organization

  6. Oct 30, 2002

    Teva — Marketing Organization

  7. Nov 21, 2002

    Sandoz — Marketing Organization

  8. Jan 25, 2005

    Hikma — Marketing Organization

  9. Oct 20, 2008

    Apotex — Marketing Organization

  10. Nov 25, 2008

    Wockhardt — Marketing Organization

  11. Nov 25, 2008

    Cipla — Marketing Organization

2010s

  1. Dec 20, 2011

    Aurobindo Pharma — Marketing Organization

  2. Dec 30, 2016

    Micro Labs Ltd India — Marketing Organization

2020s

  1. Sep 13, 2023

    Deva Holding A.S. — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • augmentin '500'

    with amoxicillin

    Also known as augmentin '125', augmentin '200', augmentin '250', augmentin '400', augmentin '875', augmentin es, augmentin xr

  • timentin

    with ticarcillin

Approval history

  • approvedPriority reviewAug 6, 1984

Chemistry & pharmacology

Loading structure…

SMILES

O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21
Mol. weight
199.16 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • acide clavulanique
  • acide clavulanique
  • ácido clavulánico
  • ácido clavulánico
  • acidum clavulanicum
  • acidum clavulanicum
  • amoxicillin potassium clavulanate
  • antibiotic mm 14151
  • antibiotic mm 14151
  • augmentin
  • augmentin
  • augmentin
  • brl-14151
  • brl-14151
  • brl-14151k
  • brl-14151k
  • clavulanate
  • clavulanate
  • clavulanate
  • clavulanate
  • clavulanate
  • clavulanate
  • clavulanate
  • clavulanate acid
  • clavulanate acid
  • clavulanate potassium
  • clavulanate potassium
  • clavulanate potassium
  • clavulanate potassium
  • clavulanate potassium salt
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulanic acid
  • clavulansäure
  • clavulansäure
  • clavulante potasium
  • combination of fosfomycin, metronidazole and rhgm-csf (administered together intraperitoneally) and three days of antibiotics p.o.
  • mm 14151
  • mm 14151
  • rx-10100
  • rx-10100
  • (z)-(2r,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • (z)-(2r,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07015736Phase 4Jun 10, 2025Eskisehir Osmangazi University
NCT06895135N/AMay 31, 2025University of Health Sciences Lahore
NCT07202052Phase 2/Phase 3 (Phase 3)May 6, 2025Monash University
NCT07202091Phase 2/Phase 3 (Phase 3)May 6, 2025Monash University
NCT06850714N/AFeb 23, 2025Liaquat University of Medical & Health Sciences, University of Insubria
NCT06502288N/AJan 1, 2025Chittagong Medical College
NCT06494072Phase 4Aug 22, 2024Medical College of Wisconsin
NCT05867654Phase 4Jul 31, 2024University of Louisville
NCT06437964N/AMay 25, 2024Zhejiang University
NCT06229288Phase 3Apr 25, 2024Roche, University of Nantes, University of Western Brittany
NCT06250413N/AFeb 29, 2024University of Helsinki
NCT06277609Phase 1Feb 27, 2024Lundbeck
NCT06076304Phase 4Dec 31, 2023Georgetown University, Patient-Centered Outcomes Research Institute, Pennsylvania State University, University of California, Los Angeles, University of Washington, University of Wisconsin, Virginia Commonwealth University
NCT05753735Phase 2Dec 20, 2023Case Western Reserve University
NCT06261736N/AOct 24, 2023Atlantic Health System
NCT05846399Phase 4Sep 7, 2023University of Missouri
NCT06020716Phase 4Aug 16, 2023Helse Møre og Romsdal HF, Northern Norway Regional Health Authority, Norwegian University of Science and Technology, Oslo Metropolitan University, University of Bergen, University of Oslo, University of Stavanger
NCT05977868Phase 4Aug 4, 2023West Virginia University
NCT05925179Phase 4Aug 1, 2023Biruni University
NCT05830162Phase 4Mar 21, 2023Region Hovedstadens Apotek, University of Copenhagen
Showing 20 of 215 trials
Page 1 / 11

Organizations

Research & Development (268)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
GlaxoSmithKlineFor profit11641998
BayerFor profit6622006
University of PittsburghAcademic/Hospital6642003
Johnson and JohnsonFor profit5512001
PfizerFor profit5532002
Monash UniversityAcademic/Hospital4422012
National Institute of Allergy and Infectious Diseases (NIAID)Government4132006
RanbaxyFor profit4412002
Seoul National UniversityAcademic/Hospital4432008
Temple UniversityAcademic/Hospital4422016
TevaFor profit4412002
University of ParisAcademic/Hospital4332003
Cairo UniversityAcademic/Hospital3332017
Georgetown UniversityAcademic/Hospital3322019
Harvard UniversityAcademic/Hospital3232012
Iterum TherapeuticsFor profit3312018
MerckFor profit3322002
Rexahn Pharmaceuticals, Inc.For profit3312008
University of BarcelonaAcademic/Hospital3122007
University of ChicagoAcademic/Hospital3322005
268 organizations
Page 1 / 14

Marketing (21)

OrganizationOrg typeRelationshipDate
ApotexFor profitMKTGOct 20, 2008
Aurobindo PharmaFor profitMKTGDec 20, 2011
Aurobindo PharmaFor profitSYNApr 19, 2019
BeechamFor profitNDA—
Chartwell PharmaceuticalsFor profitMKTGApr 18, 2002
CiplaFor profitMKTGNov 25, 2008
Deva Holding A.S.For profitMKTGSep 13, 2023
GlaxoSmithKlineFor profitNDA2Apr 1, 1985
GlaxoSmithKlineFor profitMKTGDec 19, 1986
HikmaFor profitMKTGJan 25, 2005
Micro Labs Ltd IndiaFor profitMKTGDec 30, 2016
Micro Labs Ltd IndiaFor profitSYNDec 8, 2023
NeopharmaFor profitNDA2Aug 6, 1984
NovartisFor profitMKTGMar 14, 2002
SandozFor profitMKTGNov 21, 2002
SandozFor profitSYNMar 14, 2002
Sun PharmaceuticalsFor profitMKTGSep 17, 2002
TevaFor profitMKTGOct 30, 2002
TevaFor profitSYNOct 29, 2002
US AntibioticsFor profitNDA2Aug 6, 1984
WockhardtFor profitMKTGNov 25, 2008