Clavulanic acid

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

1984

www.ebi.ac.uk

First approval year: 1984
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Clavulanic acid
www.ebi.ac.uk

Molecular weight: 199.16
www.ebi.ac.uk

Structure (SMILES): O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21
www.ebi.ac.uk

4 oxa 1 azabicyclo 3 2 0 heptane 2 carboxylic acid 3 2 hydroxyethylidene 7 oxo 2r 2 alpha 3z 5 alpha
4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-(2-HYDROXYETHYLIDENE)-7-OXO-, (2R-(2.ALPHA.,3Z,5.ALPHA.))-
acide clavulanique
Acide clavulanique
acido clavulanico
Acido clavulanico
amoxicilline acide clavulanique
brl 14151
BRL 14151
BRL-14151
clavulanate
Clavulanate
CLAVULANATE [VANDF]
clavulanate vandf
clavulanic acid
Clavulanic acid
clavulanic acid [INN]
CLAVULANIC ACID [MART.]
CLAVULANIC ACID [MI]
Clavulanic acid [WHO-DD]
clavulanic acid 1200 mg or cefuroksim 1500mg
clavulanic acid 1200 mg or Cefuroksim 1500mg
clavulanic acid inn
clavulanic acid mart
clavulanic acid mi

And 11 more, listed on the interactive page.

CAS registry numbers

58001-44-8

ChEMBL ID: CHEMBL777
www.ebi.ac.uk

InChIKey: HZZVJAQRINQKSD-PBFISZAISA-N
www.ebi.ac.uk

PubChem compound IDs

5280980

FDA ingredient codes (UNII)

23521W1S24

21216
48203

Applicant: HIKMA PHARMS
Approval date: 25 Jan 2005
Application number: ANDA065191

First in class: No
Orphan designation: No
Availability: Prescription only

United States (FDA): Approved

Pharmacology name: clavulanic acid
Type: Natural product
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral
Parenteral

Open Targets mechanisms

Mechanism
Bacterial beta-lactamase TEM inhibitor
Action type
Inhibitor
Target
Beta-lactamase TEM

DrugCentral mechanisms

Action type
Inhibitor
Gene symbol
bla; blaT-3; blaT-4;
Protein identifier
P62593
Organism
Escherichia coli

Condition
Glioblastoma
Highest recorded phase
1
Condition identifier
EFO:0000519
Subject identifier
D005909
Condition
Infections
Highest recorded phase
3
Condition identifier
EFO:0000544
Subject identifier
D007239
Condition
Bacterial Infections
Highest recorded phase
1
Condition identifier
EFO:0000771
Subject identifier
D001424
Condition
Obesity
Highest recorded phase
1
Condition identifier
EFO:0001073
Subject identifier
D009765
Condition
Astrocytoma
Highest recorded phase
1
Condition identifier
EFO:0002499
Subject identifier
D001254
Condition
Cocaine-Related Disorders
Highest recorded phase
2
Condition identifier
EFO:0002610
Subject identifier
D019970
Condition
Osteomyelitis
Highest recorded phase
0.5
Condition identifier
EFO:0003102
Subject identifier
D010019
Condition
Urinary Tract Infections
Highest recorded phase
3
Condition identifier
EFO:0003103
Subject identifier
D014552
Condition
Pneumonia
Highest recorded phase
3
Condition identifier
EFO:0003106
Subject identifier
D011014
Condition
Tobacco Use Disorder
Highest recorded phase
2
Condition identifier
EFO:0003768
Subject identifier
D014029
Condition
Brain Neoplasms
Highest recorded phase
1
Condition identifier
EFO:0003833
Subject identifier
D001932
Condition
Erectile Dysfunction
Highest recorded phase
2
Condition identifier
EFO:0004234
Subject identifier
D007172
Condition
Otitis Media
Highest recorded phase
3
Condition identifier
EFO:0004992
Subject identifier
D010033
Condition
Bronchitis, Chronic
Highest recorded phase
3
Condition identifier
EFO:0006505
Subject identifier
D029481
Condition
Head and Neck Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0006859
Subject identifier
D006258
Condition
Influenza, Human
Highest recorded phase
3
Condition identifier
EFO:0007328
Subject identifier
D007251
Condition
Sinusitis
Highest recorded phase
3
Condition identifier
EFO:0007486
Subject identifier
D012852
Condition
Otitis Media, Suppurative
Highest recorded phase
3
Condition identifier
EFO:0007503
Subject identifier
D010035
Condition
Bronchitis
Highest recorded phase
3
Condition identifier
EFO:0009661
Subject identifier
D001991
Condition
Cystitis, Hemorrhagic
Highest recorded phase
3
Condition identifier
EFO:1000025
Subject identifier
D000096722
Condition
Tuberculosis, Pulmonary
Highest recorded phase
2
Condition identifier
EFO:1000049
Subject identifier
D014397
Condition
Clostridium Infections
Highest recorded phase
3
Condition identifier
EFO:1000874
Subject identifier
D003015
Condition
Helicobacter Infections
Highest recorded phase
3
Condition identifier
EFO:1000961
Subject identifier
D016481
Condition
Mastitis
Highest recorded phase
2
Condition identifier
EFO:1001034
Subject identifier
D008413
Condition
Pneumonia, Bacterial
Highest recorded phase
2
Condition identifier
EFO:1001272
Subject identifier
D018410

And 15 more, listed on the interactive page.

Condition identifier
EFO_0000544
Condition identifier
EFO_0000544
Highest recorded phase
3
Condition identifier
EFO_0000771
Condition identifier
EFO_0001073
Condition identifier
EFO_0002610
Highest recorded phase
2
Condition identifier
EFO_0003102
Condition identifier
EFO_0003103
Highest recorded phase
3
Condition identifier
EFO_0003106
Highest recorded phase
3
Condition identifier
EFO_0003768
Highest recorded phase
2
Condition identifier
EFO_0004234
Highest recorded phase
2
Condition identifier
EFO_0004318
Highest recorded phase
2
Condition identifier
EFO_0004992
Highest recorded phase
3
Condition identifier
EFO_0005741
Condition identifier
EFO_0006859
Condition identifier
EFO_0007149
Condition identifier
EFO_0007486
Highest recorded phase
3
Condition identifier
EFO_0010445
Highest recorded phase
2
Condition identifier
EFO_1000025
Highest recorded phase
3
Condition identifier
EFO_1000049
Highest recorded phase
2
Condition identifier
EFO_1000874
Highest recorded phase
3
Condition identifier
EFO_1001034
Condition identifier
EFO_1001313
Highest recorded phase
3
Condition identifier
EFO_1001391
Condition identifier
HP_0001082
Highest recorded phase
3
Condition identifier
HP_0002014

And 29 more, listed on the interactive page.

Event
acute generalised exanthematous pustulosis
Reports
60
Reporting signal score
139.993
Event
acute kidney injury
Reports
85
Reporting signal score
39.2137
Event
anaphylactic reaction
Reports
106
Reporting signal score
137.244
Event
anaphylactic shock
Reports
49
Reporting signal score
69.0142
Event
angioedema
Reports
53
Reporting signal score
38.6448
Event
aspartate aminotransferase increased
Reports
57
Reporting signal score
38.2279
Event
cholestasis
Reports
64
Reporting signal score
105.531
Event
cholestatic liver injury
Reports
18
Reporting signal score
49.7111
Event
clostridium difficile colitis
Reports
33
Reporting signal score
59.4546
Event
clostridium difficile infection
Reports
41
Reporting signal score
65.9223
Event
drug hypersensitivity
Reports
121
Reporting signal score
45.4578
Event
drug rash with eosinophilia and systemic symptoms
Reports
14
Reporting signal score
31.506
Event
drug reaction with eosinophilia and systemic symptoms
Reports
119
Reporting signal score
234.794
Event
drug-induced liver injury
Reports
89
Reporting signal score
157.099
Event
eosinophilia
Reports
34
Reporting signal score
41.1747
Event
erythema
Reports
120
Reporting signal score
94.9459
Event
erythema multiforme
Reports
30
Reporting signal score
45.8265
Event
hepatitis
Reports
37
Reporting signal score
37.2351
Event
hepatitis cholestatic
Reports
44
Reporting signal score
106.494
Event
hepatocellular injury
Reports
63
Reporting signal score
98.6494
Event
hepatotoxicity
Reports
41
Reporting signal score
54.7928
Event
hyperbilirubinaemia
Reports
32
Reporting signal score
53.9834
Event
jaundice
Reports
71
Reporting signal score
106.084
Event
jaundice cholestatic
Reports
21
Reporting signal score
47.9153
Event
klebsiella infection
Reports
18
Reporting signal score
37.5464

And 17 more, listed on the interactive page.

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And 27 more, listed on the interactive page.

Hydrogen bond acceptors: 4
Hydrogen bond donors: 2
Polar surface area: 87.07
Calculated partition coefficient (ALogP): -1.1
Calculated partition coefficient (XLogP): -1.2
Prodrug: No
Chirality: Single enantiomer
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 2
Heavy atoms: 14
Molecular formula: C8H9NO5
Monoisotopic mass: 199.04807239
Natural product: Yes

0143-9981
0143-9982
63187-826
50090-0928
68071-1619
68788-4179

Recorded assays: 569
Active assays: 82

Confirmatory
Other

beta-Lactamase Inhibitors
id.nlm.nih.gov

Oral bioavailability

Median: 75
Mean: 75
Minimum: 75
Maximum: 75
Unit: %
Assays: 1
Standard deviation: 0
Summary method: median
Censored results excluded: 0
Other units excluded: 0
Unknown units excluded: 0

Measurement types

Related records

Trials (160)

2-day Prophylactic Antibiotic is Effective in Transoral Endoscopic Thyroidectomy
A Clinical Study to Explore Biomarkers for Drug-induced Liver Injury (DILI)
A Multicentre, Randomised, Open-Label Study To Compare The Efficacy And Safety Of Azithromycin For 5 Days With Those Of Amoxicillin-Clavulanic Acid In Patients With Chronic Bronchitis
A Multicentre, Randomized as a Double Blind Study, Triple Placebo, Comparative of the Efficacy and Safety of an Association Secnidazol-Ciprofloxacin Compared With Amoxicillin-Clavulanic Acid for the Treatment of Uncomplicated Episode of Diverticular Sigmoïditis Among Adults
A Pharmacokinetic Study of LP-001 in Children With a Bacterial Infection
A Pharmacokinetics and Safety Study of Augmentin ES-600 in Children With CAP and ABRS
A Study Comparing Continuous Infusion Antibiotics to Standard Treatment for Lung Infections in Cystic Fibrosis
A Study Of Intravenous Sulopenem And Oral PF-03709270 In Community Acquired Pneumonia That Requires Hospitalization
A Study of the Effectiveness and Safety of High Dose, Short-course Levofloxacin in the Treatment of Acute Bacterial Exacerbation (Worsening) of Chronic Bronchitis.
A Study to Assess the Efficacy and Safety of IV/PO Moxifloxacin in Subjects With Community-acquired Pneumonia
A Study to Assess the Safety, Tolerability and Efficacy of OP0201 as an Adjunct Treatment for Acute Otitis Media in Infants and Children Aged 6 to 24 Months
A Study to Compare Different Antibiotics and Different Modes of Fluid Treatment for Children With Severe Pneumonia
A Trial Investigating Lu AF28996 in Healthy Adult Participants
Acute Otitis Media (AOM) Therapy Trial in Young Children
Adjunctive Therapy of Andrographolid Sulfonatein Community Acquired Pneumonia
Amoxicillin Alone Versus Amoxicillin/Clavulanate for Community-acquired Pneumonia in Patients Aged 65 Years or Older, and Hospitalized in a Non-intensive Care Unit Ward
Amoxicillin Clavulanate in Treatment of Acute Otitis Media
Amoxicillin-clavulanate Alone or in Combination With Ciprofloxacin in Low-Risk Febrile Neutropenic Adult Patients: A Prospective, Double-blind, Randomized, Non-Inferiority Multicenter, Phase III Clinical Trial.
Amoxicillin-clavulanate in Treating Acute Otitis Media Evaluated by Daily Tympanometry
Amoxicillin-clavulanate Versus Amoxicillin Versus Placebo in Acute Otitis Media in Children

In development for (38)

Acute pyelonephritis Phase 3
Anaplastic astrocytoma Phase 1
Asthma Phase 2
Bacterial infectious disease Phase 1
Bacterial pneumonia Phase 2
Brain neoplasm Phase 1
Bronchitis Phase 3
Buruli ulcer disease Phase 2
Cholecystitis Phase 3
Chronic bronchitis Phase 3
Clostridium infectious disease Phase 3
Cocaine abuse Phase 2
Cocaine dependence Phase 2
COVID-19 Phase 3
Cystitis Phase 3
Diarrheal disease Early phase 1
Erectile dysfunction Phase 2
Glioblastoma Phase 1
Head and neck cancer Phase 2
Helicobacter pylori infectious disease Phase 3

Clavulanic acid

Development status

Names and chemistry

Other names (36)

Identifiers

RxNorm IDs (RxCUI) (2)

Regulatory information

United States

Other regulatory facts

Approval status

Pharmacology

Drug classification

Administration routes

Open Targets mechanisms

DrugCentral mechanisms

Investigated indications (40)

Open Targets indications (54)

Reported adverse events (42)

Trial references (52)

Chemical properties

National Drug Codes

Evidence counts

Active assay types (2)

Pharmacologic actions

Biological measurements

Observed measurements

Oral bioavailability

Measurement types

Related records

Trials (160)

In development for (38)

Other linked conditions (10)