{"Abbreviation":["RX-10100"],"Absorption, Distribution and Excretion":"Clavulanic acid, when taken orally, is well absorbed in the gastrointestinal tract.  After administration of radiolabeled clavulanic acid to four human subjects, a minimum of 73% absorption and the average absolute bioavailability was calculated at 64%. The mean Cmax in a group of 8 healthy research volunteers was  2.098 ± 0.441 micrograms/ml in a pharmacokinetic study. The same study reported a mean Tmax of 1.042 ± 0.80 hours. Tmax is reported to be 40-120 minutes according to another pharmacokinetic study.","Adverse Effects":"Clavulanic acid, when administered with amoxicillin, can cause some mild gastrointestinal adverse effects. These include vomiting, nausea, loose stools, and discomfort. Antibiotic-associated diarrhea due to amoxicillin-clavulanic acid treatment is the most common adverse effect. There is a higher incidence of diarrhea when clavulanic acid is added to amoxicillin compared to amoxicillin alone. Diarrhea is more common in those taking a high dose of the extended-release form of clavulanic acid and amoxicillin. Drug-induced pancreatitis from clavulanic acid and amoxicillin has occurred in a few cases.","Aliases":["Clavulanic Acid","Acido clavulanico","Acide clavulanique","Antibiotic MM 14151","acidum clavulanicum","Clavulansaeure","MM 14151","BRL-14151","Serdaxin","BRL 14151","rx-10100","(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","Chebi:48947","BRL14151","(2R,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","Clavulanate, Sodium","4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R-(2α,3Z,5α))","Dtxcid702830","MM14151","261-069-2","Sodium Clavulanate","(2r,5r,z)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","CHEMBL777","Clavulinic Acid","Acidum clavulanicum","Clavulox","Einecs 261-069-2","3008-B","Brn 0787059","Clavulanateacid","clavulonic acid","(Z)-(2R,5R)-3-(2-Hydroxyethyliden)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptan-2-carbonsaeure","Epitope ID:117130","Schembl6093","BSPBio_002430","orb1705935","orb2901544","GTPL11128","HY-A0256","Bdbm50021959","EBC-26183","EX-A10878","Mfcd00867004","Akos016009164","DB00766","FC29986","Ncgc00188985-01","4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R-(2-α,3Z,5-α))-","DA-62377","MS-23077","SY130865","Sbi-0206779.p001","CS-0017600","NS00068017","C06662","D07711","T19860","En300-7431555","Brd-k94250879-001-01-9","Brd-k94250879-235-03-9","1365254-41-6","4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2r-(2α,3z,5α))-"],"Biological Half-Life":"The half-life of clavulanic acid is reported to be similar to amoxicillin, and last 45-90 minutes. A study of radiolabeled clavulanic acid administered to 4 healthy volunteers determined a half-life of 0.8 h.","CAS":"58001-44-8","ChemicalClasses":["amine"],"Chirality":"absolute","Classes":["Antibiotic"],"DTXSID":"2022830","Drug Indication":"Clavulanic acid combined with other antibiotics is indicated to prevent the development of drug-resistant strains of bacteria and promotes their therapeutic antibacterial effects.  The following conditions, when they produced beta-lactamases, have been treated with a combination of amoxicillin and clavulanic acid or ticarcillin and clavulanic acid:  Acute otitis media caused by  H. influenzae and M. catarrhalis  Sinusitis due to H. influenzae and M. catarrhalis  Lower respiratory tract infections due to Haemophilus influenzae, S.aureus, Klebsiella species, and Moraxella catarrhalis   Skin and skin structure infections caused by Staphylococcus aureus, Escherichia coli, and Klebsiella species  Urinary Tract Infections due to E. coli, Klebsiella species of bacteria, and Enterobacter species of bacteria, S.marcescens, or S.aureus  Gynecologic infections due to a variety of bacteria, including P.melaninogenicus, Enterobacter species, E.Coli species, Klebsiella species, S. aureus, S.epidermidis  Septicemia due to a variety of bacteria, including Klebsiella species, E.Coli species, S.aureus, or Pseudomonas species  Bone and joint infections due to S.aureus  Intraabdominal infections due to E.Coli, K.pnemoniae, or B.fragilis group  **A note on susceptibility**  It should be noted that it is only to be administered in infections that are confirmed or highly likely to be caused by susceptible bacteria. Culture and susceptibility tests should be performed if possible and used in selecting whether this antibiotic is prescribed. When beta-lactamase enzyme production is not detected during microbiological testing, clavulanic acid should not be used. When these tests are not available patterns of local infection and susceptibility may be used to determine the appropriateness of using clavulanic acid. Ticarcillin with clavulanate has shown particular efficacy in mixed infections in addition to empiric therapy before determining the susceptibility of causative organisms. The ticarcillin-clavulanic acid combination may prove to be an effective single-agent antibiotic therapy to treat infections where a regimen of several drugs may normally be used.","DurationOfAction":"","EliminationHalfLife":"0.8 – 1.2 hours","Esters":[],"European Community (EC) Number":"261-069-2","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":22,"Value":{"StringWithMarkup":[{"String":"23521W1S24"}]}},{"Name":"Active Moiety","ReferenceNumber":22,"Value":{"StringWithMarkup":[{"String":"CLAVULANIC ACID"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":22,"Value":{"StringWithMarkup":[{"String":"Established Pharmacologic Class [EPC] - beta Lactamase Inhibitor"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":22,"Value":{"StringWithMarkup":[{"String":"Mechanisms of Action [MoA] - beta Lactamase Inhibitors"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":22,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5280980","Length":15,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Clavulanic%20acid"},{"Extra":"CID-5280980","Length":15,"Start":74,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/clavulanic%20acid"}],"String":"Clavulanic acid is a beta Lactamase Inhibitor. The mechanism of action of clavulanic acid is as a beta Lactamase Inhibitor."}]}}],"Formating":[],"HMDB ID":"HMDB0014904","HeavyAtomCount":14,"Human Drugs":"Pharmaceuticals","IUPACName":"(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","InChI":"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","InChIKey":"HZZVJAQRINQKSD-PBFISZAISA-N","MeSH Headers":[{"Id":"M0029416","Link":"https://id.nlm.nih.gov/mesh/M0029416.html","Name":"Clavulanic Acid","Ref":55},{"Id":"M0577449","Link":"https://id.nlm.nih.gov/mesh/M0577449.html","Name":"RX-10100","Ref":56},{"Id":"M0372715","Link":"https://id.nlm.nih.gov/mesh/M0372715.html","Name":"BRL-14151","Ref":58},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":59},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":78},{"Id":"M0587245","Link":"https://id.nlm.nih.gov/mesh/M0587245.html","Name":"beta-Lactamase Inhibitors","Ref":79}],"MeSH Pharmacological Classification":[{"Id":"M0587245","Link":"https://id.nlm.nih.gov/mesh/M0587245.html","Name":"beta-Lactamase Inhibitor","Ref":79}],"Mechanism of Action":"Clavulanic acid contains a beta-lactam ring in its structure that binds in an irreversible fashion to beta-lactamases, preventing them from inactivating certain beta-lactam antibiotics, with efficacy in treating susceptible gram-positive and gram-negative infections.","Melting Point":"117.5-118","Metabolism/Metabolites":"Clavulanic acid is heavily metabolized to form the metabolites 2,5-dihydro-4-(2- hydroxyethyl)-5-oxo-1H-pyrrole-3-carboxylic acid and 1-amino-4-hydroxy-butan-2-one. The first metabolite was found to account for 15.6% of the dose while the second metabolite was reported to account for 8.8% of the dose in one pharmacokinetic study.","MolecularFormula":"C\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e9\u003c/sub\u003eNO\u003csub\u003e5\u003c/sub\u003e","MolecularWeight":"199.16 g/mol","Opticalactivity":"UNSPECIFIED","Pharmacodynamics":"Clavulanic acid inactivates some beta-lactamase enzymes that are produced by bacteria, therefore preventing enzymatic destruction of amoxicillin. This helps to treat a variety of bacterial infections which would otherwise be resistant to antibiotics without the addition of clavulanic acid.","Physical Description":"Solid","PubChemId":5280980,"PubChemTitle":"Clavulanic Acid","Record Description":["LiverTox|Antimicrobial|Antibacterial|Enzyme inhibitor, beta lactamase"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"5695","RefCount":2,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Clavulanic_acid","Name":"Clavulanic acid","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q415709","Name":"Clavulanic acid","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00766","Name":"Clavulanic acid","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5280980","Name":"Clavulanic acid","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=58001-44-8","Name":"Clavulanic acid","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014904","Name":"Clavulanic acid","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C06662","Name":"Clavulanic acid","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/23521W1S24","Name":"Clavulanic acid","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2022830","Name":"Clavulanic acid","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5280980, Clavulanic acid. Accessed October 16, 2026. \u003ca href='https://pubchem.ncbi.nlm.nih.gov/compound/5280980'\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5280980\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Clavulanic acid. UNII: 23521W1S24. Global Substance Registration System. Accessed October 16, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/23521W1S24\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/23521W1S24\u003c/a\u003e"],"SMILES":"C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"Schedule 4 substance"}],"Solubility":"3.37e+02 g/L","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 97.687 57.793\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h98v58H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M13.649 8.805h15.24\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M29.289 8.805h-.8l-1.462 11.14h3.724z\" class=\"bond\"/\u003e\u003cpath d=\"M25.396 24.045H13.649M13.649 8.805v15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m15.373 24.045-8.727 8.727M13.649 22.321l-8.727 8.727\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m6.646 32.772 4.363-4.363M4.922 31.048l4.363-4.364\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m32.302 25.167 11.116 3.653M43.418 28.82l8.941-12.395\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m67.599 16.395-15.24.03M66.186 13.96l-12.587.024\"/\u003e\u003c/g\u003e\u003cpath d=\"m67.599 16.395 7.594-13.213M75.193 3.182 86.52 3.16M52.359 16.425l-6.487-8.919M28.889 8.805l10.693-3.439\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m43.798 28.697-.761.247M44.743 30.679l-1.305.424M45.688 32.661l-1.848.601M46.632 34.644l-2.391.777M47.577 36.626l-2.935.954M48.521 38.608l-3.478 1.13M49.466 40.59l-4.022 1.307M50.41 42.573l-4.565 1.483\"/\u003e\u003c/g\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m48.128 43.314 11.029 2.345M48.998 45.992l9.652 2.052\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m59.157 45.659-5.515-1.173M58.65 48.044l-4.826-1.026\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m48.128 43.314-7.435 8.258\" class=\"bond\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M26.996 21.545h.911l2.214 4.185v-4.185h.661v5.001h-.911l-2.22-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M2.876 32.777q-.738 0-1.173.553-.429.548-.429 1.495 0 .946.429 1.494.435.547 1.173.547t1.167-.547q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.053 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.626.702-1.679.702-1.054 0-1.685-.702-.631-.703-.631-1.887t.631-1.888q.631-.708 1.685-.708\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M90.436 1.108q-.738 0-1.173.553-.429.548-.429 1.495 0 .946.429 1.494.435.547 1.173.547t1.167-.547q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.054 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.625.702-1.679.702t-1.685-.702q-.631-.703-.631-1.887t.631-1.888Q89.382.56 90.436.56M93.317.649h.679v2.048h2.458V.649h.673V5.65h-.673V3.269h-2.458V5.65h-.679z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M43.421 2.087q-.738 0-1.173.553-.429.548-.429 1.495 0 .946.429 1.494.435.548 1.173.548t1.167-.548q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.054 0 1.679.709.631.702.631 1.887 0 1.178-.631 1.887-.625.702-1.679.702t-1.685-.702q-.631-.703-.631-1.887t.631-1.887q.631-.709 1.685-.709M62.784 45.63q-.738 0-1.173.554-.428.548-.428 1.494 0 .947.428 1.495.435.547 1.173.547t1.167-.547q.429-.548.429-1.495 0-.946-.429-1.494-.429-.554-1.167-.554m0-.547q1.054 0 1.679.708.631.703.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.685-.708\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M37.933 52.595q-.738 0-1.172.554-.429.548-.429 1.494 0 .947.429 1.494.434.548 1.172.548t1.167-.548q.429-.547.429-1.494 0-.946-.429-1.494-.429-.554-1.167-.554m0-.547q1.054 0 1.679.708.631.703.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703-1.053 0-1.684-.703-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.684-.708M31.236 52.137h.679v2.048h2.458v-2.048h.673v5.001h-.673v-2.382h-2.458v2.382h-.679z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"M25.396 24.045h-5.873M32.302 25.167l5.558 1.827\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m86.52 3.16-5.664.011M86.52 3.16l-5.664.011M45.872 7.506l3.243 4.46M39.582 5.366l-5.346 1.719M40.693 51.572l3.717-4.129\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Title":"Clavulanic acid","UNII":"23521W1S24","Wikidata":"Q415709","Wikipedia":"Clavulanic_acid","XLogP":-1.2}