Clavulanic Acid
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Also known as Acide clavulaniqueAcido clavulanicoBRL 14151BRL-14151ClavulanateRX-10100SerdaxinClavulanicacidCLAVULANATE POTASSIUM
Summary
Clavulanic Acid (CHEMBL777) is an approved small-molecule EC 3.5.2.6 (β-lactamase) inhibitor; indicated across 40 conditions including urinary tract infection and pneumonia.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Indications: 40 conditions
- Clinical trials: 72
- Chemistry: 199.16 Da · C8H9NO5
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL777 |
| Name | Clavulanic Acid |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 5280980 |
| ChEBI | CHEBI:48947 |
| Molecular formula | C8H9NO5 |
| Molecular weight | 199.16 |
| InChIKey | HZZVJAQRINQKSD-PBFISZAISA-N |
SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
IUPAC name: (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
ChEBI definition: Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial β-lactamase enzymes.
Pharmacological roles (ChEBI): EC 3.5.2.6 (β-lactamase) inhibitor, antibacterial drug, anxiolytic drug.
Other ChEBI roles (chemical / environmental): bacterial metabolite.
Also known as: Acide clavulanique, Acido clavulanico, BRL 14151, BRL-14151, Clavulanate, Clavulanic acid, RX-10100, Serdaxin, clavulanic acid, Clavulanic Acid, clavulanate, Clavulanicacid
Parent form; salt/anhydrous children: CHEMBL8290, CHEMBL9306, CHEMBL1003
Patent coverage: 10,735 distinct patent families (36,884 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 11 (assay-derived). Sample: Beta-lactamase SHV-5, Beta-lactamase, Beta-lactamase TEM, Beta-lactamase TEM, Beta-lactamase, Beta-lactamase, Beta-lactamase OXA-1, Beta-lactamase, Beta-lactamase SHV-1, Beta-lactamase SHV-1.
Bioactivity
ChEMBL activities: 16 potent at pChembl ≥ 5 of 22 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P00811 | 7.82 | IC50 | 15 | nM | CHEMBL_ACT_756441 |
| P00811 | 7.82 | IC50 | 15 | nM | CHEMBL_ACT_756442 |
| P0AD63 | 7.55 | IC50 | 28 | nM | CHEMBL_ACT_1917369 |
| P62593 | 7.53 | IC50 | 29.5 | nM | CHEMBL_ACT_17702872 |
| P0AD63 | 7.52 | IC50 | 30.3 | nM | CHEMBL_ACT_17702871 |
| P62593 | 7.52 | IC50 | 30 | nM | CHEMBL_ACT_1917354 |
| P62593 | 7.4 | IC50 | 40 | nM | CHEMBL_ACT_561763 |
| P62593 | 7.22 | IC50 | 60 | nM | CHEMBL_ACT_962069 |
| P62593 | 7.1 | IC50 | 80 | nM | CHEMBL_ACT_2635598 |
| P00807 | 7.1 | IC50 | 80 | nM | CHEMBL_ACT_913754 |
| P62593 | 6.77 | IC50 | 170 | nM | CHEMBL_ACT_2125193 |
| P0AD64 | 6.77 | IC50 | 170 | nM | CHEMBL_ACT_3475752 |
| P0AD64 | 6.77 | IC50 | 170 | nM | CHEMBL_ACT_3476065 |
| P62593 | 6.1 | Ki | 800 | nM | CHEMBL_ACT_1175930 |
| P24735 | 6.1 | IC50 | 800 | nM | CHEMBL_ACT_756440 |
| P13661 | 5.5 | IC50 | 3200 | nM | CHEMBL_ACT_913752 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
40 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| urinary tract infection | 3 | MONDO:0100338 | EFO:0003103 |
| pneumonia | 3 | MONDO:0005249 | EFO:0003106 |
| otitis media | 3 | MONDO:0005441 | EFO:0004992 |
| chronic bronchitis | 3 | MONDO:0005607 | EFO:0006505 |
| sinusitis | 3 | MONDO:0005961 | EFO:0007486 |
| suppurative otitis media | 3 | MONDO:0005975 | EFO:0007503 |
| Helicobacter pylori infectious disease | 3 | MONDO:0006781 | EFO:1000961 |
| cholecystitis | 3 | MONDO:0002155 | HP:0001082 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | MONDO:0100096 |
| influenza | 3 | MONDO:0005812 | EFO:0007328 |
| cystitis | 3 | MONDO:0006032 | EFO:1000025 |
| bronchitis | 3 | MONDO:0003781 | EFO:0009661 |
| Clostridium infectious disease | 3 | MONDO:0024388 | EFO:1000874 |
| cocaine dependence | 2 | MONDO:0005186 | EFO:0002610 |
| head and neck cancer | 2 | MONDO:0005627 | EFO:0006859 |
| pulmonary tuberculosis | 2 | MONDO:0006052 | EFO:1000049 |
| bacterial pneumonia | 2 | MONDO:0004652 | EFO:1001272 |
| periapical periodontitis | 2 | MONDO:0004508 | EFO:1001391 |
| nicotine dependence | 2 | MONDO:0008575 | EFO:0003768 |
| erectile dysfunction | 2 | MONDO:0005362 | EFO:0004234 |
| major depressive disorder | 2 | MONDO:0002009 | MONDO:0002009 |
| mastitis | 2 | MONDO:0006849 | EFO:1001034 |
| Buruli ulcer disease | 2 | MONDO:0000327 | MONDO:0000327 |
| asthma | 2 | MONDO:0004979 | MONDO:0004979 |
| tuberculosis | 2 | MONDO:0018076 | MONDO:0018076 |
| obesity disorder | 1 | MONDO:0011122 | EFO:0001073 |
| glioblastoma | 1 | MONDO:0018177 | EFO:0000519 |
| anaplastic astrocytoma | 1 | MONDO:0016684 | EFO:0002499 |
| respiratory tract infectious disorder | 1 | MONDO:0024355 | MONDO:0024355 |
| brain neoplasm | 1 | MONDO:0021211 | EFO:0003833 |
| bacterial infectious disease | 1 | MONDO:0005113 | EFO:0000771 |
| osteomyelitis | 0 | MONDO:0005246 | EFO:0003102 |
| diarrheal disease | 0 | MONDO:0001673 | HP:0002014 |
7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 72.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 23 |
| PHASE3 | 17 |
| Not specified | 14 |
| PHASE2 | 9 |
| PHASE1 | 4 |
| PHASE2/PHASE3 | 3 |
| PHASE1/PHASE2 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT05846399 | PHASE4 | RECRUITING | CAT BITE Antibiotic Prophylaxis for the Hand/Forearm (CATBITE) |
| NCT06076304 | PHASE4 | RECRUITING | Nasal Steroids, Irrigation, Oral Antibiotics, and Subgroup Targeting for Effective Management of Acute Sinusitis |
| NCT00147914 | PHASE4 | COMPLETED | Comparison Study Between Cefdinir & Amoxicilline/Clavulanate in Acute Sinusitis and Assessment of Quality of Life |
| NCT00343135 | PHASE4 | COMPLETED | AUGMENTIN 1gm In Skin And Soft Tissue Infection |
| NCT00367120 | PHASE4 | COMPLETED | Zmax Compared to Augmentin in Sinusitis |
| NCT00456339 | PHASE4 | TERMINATED | Systemic Steroids Plus Antibiotics in Sleep Apnea Syndrome in Children |
| NCT00493038 | PHASE4 | TERMINATED | Study to Evaluate the Efficacy and Safety of Moxifloxacin Versus Amoxicillin/Clavulanate in the Treatment of Acute Bacterial Rhinosinusitis |
| NCT00495586 | PHASE4 | COMPLETED | Effectiveness of Antibiotic Therapy for Exacerbations of Chronic Obstructive Pulmonary Disease |
| NCT00665873 | PHASE4 | COMPLETED | Antibiotic Therapy is Not Necessary to Implant Totally Implantable Venous Access Devices: Randomized Prospective Study |
| NCT01089218 | PHASE4 | COMPLETED | The Impact of Antibiotic Prophylaxis on Incidence of Post-bronchoscopy Fever and Change of Serum Cytokines |
| NCT01096927 | PHASE4 | COMPLETED | Non Operative Treatment for Acute Appendicitis |
| NCT01166932 | PHASE4 | COMPLETED | Comparison Between Amoxycillin/Clavulanic Acid and Oxacillin/Ceftriaxone for Community Acquired-pneumonia |
| NCT01919411 | PHASE4 | COMPLETED | Prophylactic Antibiotics After Functional Endoscopic Sinus Surgery: a Randomized, Double-blind Placebo Controlled Trial |
| NCT02141217 | PHASE4 | COMPLETED | AUGMENTIN™ in Dental Infections |
| NCT02340000 | PHASE4 | COMPLETED | Clinical Trial of the Treatment of Acute Sinusitis With Standard-dose Versus High-dose Amoxicillin/Clavulanate |
| NCT02783404 | PHASE4 | TERMINATED | An Oral Amoxicillin-Clavulanate Regimen to Prevent Bacteremia Following Dental Procedures |
| NCT02935374 | PHASE4 | COMPLETED | Effect of Antimicrobial Treatment of Acute Otitis Media on the Intestinal Microbiome in Children |
| NCT03247920 | PHASE4 | COMPLETED | Reduction of Intravenous Antibiotics In Neonates |
| NCT03369717 | PHASE4 | TERMINATED | Use of Perioperative Antibiotics in Endoscopic Sinus Surgery |
| NCT03574090 | PHASE4 | COMPLETED | Study the Efficacy of Topical Antibiotherapy in the Prophylaxis of Incisional Surgical Infection in Colorectal Surgery |
| NCT03795194 | PHASE4 | TERMINATED | Antibiotic Duration in Post-appendectomy Abscess |
| NCT04082598 | PHASE4 | COMPLETED | Antibiotic Therapy in Erupted Tooth Extractions |
| NCT05393505 | PHASE4 | UNKNOWN | Fast-track Blood Test for Suspected Fever by Deficiency of a Kind of White Blood Cells As Main Defense Against Infection |
| NCT05224401 | PHASE3 | RECRUITING | Pivmecillinam With Amoxicillin/Clavulanic Acid for Step Down Oral Therapy in ESBL UTIs |
| NCT06229288 | PHASE3 | RECRUITING | 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 |
| NCT07202091 | PHASE2/PHASE3 | RECRUITING | Role of Antibiotic Therapy or Immunoglobulin On iNfections in hAematoLogy Immunoglobulin Stopping or Extension (Stop Ig) |
| NCT07556991 | PHASE2/PHASE3 | RECRUITING | Prospective Clinical Investigation on Infection as a Cause of Chronic Subdural Hematoma. |
| NCT07587450 | PHASE3 | NOT_YET_RECRUITING | Efficacy of Non Operative Treatment With Amoxicillin/Clavulanic Acid Versus Surgical Treatment in Acute Uncomplicated Appendicitis in Children |
| NCT00042718 | PHASE3 | COMPLETED | A Study of the Effectiveness and Safety of High Dose, Short-course Levofloxacin in the Treatment of Acute Bacterial Exacerbation (Worsening) of Chronic Bronchitis. |
| NCT00051753 | PHASE3 | COMPLETED | Levofloxacin In The Treatment Of Children With Recurrent And/or Persistent Acute Otitis Media |
| NCT00161330 | PHASE3 | TERMINATED | Oral vs Initial Intravenous Antibiotic Treatment of Urinary Tract Infections in Children: a RCT |
| NCT00402727 | PHASE3 | COMPLETED | Comparison of Sequential IV/PO Moxifloxacin With IV Piperacillin/Tazobactam Followed by PO Amoxicillin/Clavulanic Acid in Patients With a Complicated Skin and Skin Structure Infection |
| NCT01069900 | PHASE3 | COMPLETED | Moxifloxacin in Pediatric Subjects With Complicated Intra-abdominal Infection |
| NCT01110382 | PHASE3 | TERMINATED | A Safety and Tolerability Study of Doripenem Compared With Meropenem in Children Hospitalized With Complicated Intra-abdominal Infections |
| NCT01110408 | PHASE3 | TERMINATED | A Safety and Tolerability Study of Doripenem Compared With Cefepime in Children Hospitalized With Complicated Urinary Tract Infections |
| NCT01110421 | PHASE3 | TERMINATED | A Safety and Tolerability Study of Doripenem Compared With Cefepime in Hospitalized Children With Bacterial Pneumonia |
| NCT01530763 | PHASE2/PHASE3 | COMPLETED | Safety and Efficacy Study of Ceftaroline Versus a Comparator in Pediatric Subjects With Community Acquired Bacterial Pneumonia (CABP) |
| NCT02007603 | PHASE3 | COMPLETED | Concentration of Ampicillin / Sulbactam and Amoxicillin / Clavulanic Acid in the Blood During Renal Replacement Therapy in Longterm Renal Replacement Therapy Patients |
| NCT03003273 | PHASE3 | TERMINATED | Early Stoppage Versus Continuation of Antimicrobial Therapy in Low Risk Pediatric Cancer Patients With Febrile Neutropenia, Before Recovery of Counts: -DALFEN Study |
| NCT04041791 | PHASE3 | COMPLETED | A Study to Compare Different Antibiotics and Different Modes of Fluid Treatment for Children With Severe Pneumonia |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 25 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).