> Trialight public data. Index of pages: https://trialight.com/llms.txt
> Web page: https://trialight.com/data/asset/clavulanic-acid-465f3e04-3ad5-4ece-97cf-d63cae081959
> Record changed: 2026-11-04

# Clavulanic acid

Highest phase reached

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

Drug type

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

First approval year

1984

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

## Development status

**First approval year**

1984

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**Listing at source**

Listed

**Highest phase reached**

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

## Names and chemistry

**Drug type**

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**Drug name**

Clavulanic acid

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**Molecular weight**

199.16

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**Structure (SMILES)**

O=C(O)\[C@H\]1/C(=C/CO)O\[C@@H\]2CC(=O)N21

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

### Other names (36)

- 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.

## Identifiers

**CAS registry numbers**

- 58001-44-8

**ChEMBL ID**

CHEMBL777

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**InChIKey**

HZZVJAQRINQKSD-PBFISZAISA-N

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL777)

**PubChem compound IDs**

- 5280980

**FDA ingredient codes (UNII)**

- 23521W1S24

### RxNorm IDs (RxCUI) (2)

- 21216
- 48203

## Regulatory information

### United States

**Applicant**

HIKMA PHARMS

**Approval date**

25 Jan 2005

**Application number**

ANDA065191

### Other regulatory facts

**First in class**

No

**Orphan designation**

No

**Availability**

Prescription only

## Approval status

**United States (FDA)**

Approved

## Pharmacology

### Drug classification

**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

### Investigated indications (40)

- **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.

### Open Targets indications (54)

- **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.

### Reported adverse events (42)

- **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.

### Trial references (52)

- NCT00042718  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00042718)
- NCT00051753  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00051753)
- NCT00092170  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00092170)
- NCT01069900  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01069900)
- NCT02007603  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02007603)
- NCT03358576  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03358576)
- NCT05499481  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05499481)
- NCT00161330  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00161330)
- NCT03357614  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT03357614)
- NCT05584657  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT05584657)
- NCT00423176  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00423176)
- NCT01934231  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01934231)
- NCT00693056  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00693056)
- NCT00716183  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00716183)
- NCT00717561  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00717561)
- NCT02735707  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT02735707)
- NCT06229288  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT06229288)
- NCT00797108  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00797108)
- NCT00839176  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00839176)
- NCT01273376  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01273376)
- NCT01015417  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01015417)
- NCT01229046  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01229046)
- NCT01244581  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01244581)
- NCT01598402  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01598402)
- NCT01772238  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT01772238)

And 27 more, listed on the interactive page.

## Chemical properties

**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

## National Drug Codes

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

## Evidence counts

**Recorded assays**

569

**Active assays**

82

### Active assay types (2)

- Confirmatory
- Other

## Pharmacologic actions

- beta-Lactamase Inhibitors  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D065093.html)

## Biological measurements

### Observed measurements

#### 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

- F

## 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](https://trialight.com/data/condition/acute-pyelonephritis-83bd05de-bc8b-595e-ba5a-ab06709e6b77.md) Phase 3
- Anaplastic astrocytoma Phase 1
- [Asthma](https://trialight.com/data/condition/asthma-247437fb-0e60-5885-8a3a-ce40099cea88.md) Phase 2
- [Bacterial infectious disease](https://trialight.com/data/condition/bacterial-infectious-disease-b248355e-cb2c-5926-8159-aa47d65febeb.md) Phase 1
- [Bacterial pneumonia](https://trialight.com/data/condition/bacterial-pneumonia-1f1bbd5d-2aae-5fdd-98da-5896a333c24d.md) Phase 2
- Brain neoplasm Phase 1
- Bronchitis Phase 3
- Buruli ulcer disease Phase 2
- Cholecystitis Phase 3
- [Chronic bronchitis](https://trialight.com/data/condition/chronic-bronchitis-1182c6a7-3657-5c56-89e7-6c969a2220da.md) Phase 3
- Clostridium infectious disease Phase 3
- Cocaine abuse Phase 2
- Cocaine dependence Phase 2
- [COVID-19](https://trialight.com/data/condition/covid-19-13f0ebf3-c291-557d-bdef-93563d077103.md) Phase 3
- [Cystitis](https://trialight.com/data/condition/cystitis-2c4484c3-baca-5bd7-a9f2-938dbb641710.md) Phase 3
- [Diarrheal disease](https://trialight.com/data/condition/diarrheal-disease-623389f5-2a35-5350-9dae-f2dc4bc0fc34.md) Early phase 1
- [Erectile dysfunction](https://trialight.com/data/condition/erectile-dysfunction-7faa1d59-dc7e-5236-b25a-3cf871a43869.md) Phase 2
- Glioblastoma Phase 1
- [Head and neck cancer](https://trialight.com/data/condition/head-and-neck-cancer-3a2645b9-a3db-5103-b6f8-5d2ec40c5339.md) Phase 2
- [Helicobacter pylori infectious disease](https://trialight.com/data/condition/helicobacter-pylori-infectious-disease-ff5903ca-758b-5979-a633-075499e2938b.md) Phase 3

### Other linked conditions (10)

- Anal fistula
- Appendicitis
- Laryngitis
- Lymphadenitis
- Lymphangitis
- Maxillary sinusitis
- Pelvic inflammatory disease
- [Pharyngitis](https://trialight.com/data/condition/pharyngitis-81ed933e-75b3-5382-aebe-66ffd4ec6446.md)
- [Pyelonephritis](https://trialight.com/data/condition/pyelonephritis-3fc522f3-1bbe-5d31-9ffb-eacaa85f46c4.md)
- Tonsillitis

---

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