Clavulanic acid
Identification
- Summary
Clavulanic acid is a beta lactamase inhibitor used to enhance the effectiveness of beta lactam antibiotics.
- Brand Names
- Augmentin, Clavulin
- Generic Name
- Clavulanic acid
- DrugBank Accession Number
- DB00766
- Background
Clavulanic acid is a beta-lactamase inhibitor that is frequently combined with Amoxicillin or Ticarcillin to fight antibiotic resistance by preventing their degradation by beta-lactamase enzymes, broadening their spectrum of susceptible bacterial infections.8 Clavulanic acid is derived from the organism Streptomyces clavuligerus.1When it is combined with amoxicillin, clavulanic acid is frequently known as Augmentin, Co-Amoxiclav, or Clavulin.10,13,15
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
- Weight
- Average: 199.1608
Monoisotopic: 199.048072403 - Chemical Formula
- C8H9NO5
- Synonyms
- (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
- Acide clavulanique
- ácido clavulánico
- Acidum clavulanicum
- Clavulanate
- Clavulanic acid
- Clavulansäure
- External IDs
- Antibiotic MM 14151
- BRL 14151
- MM 14151
- RX-10100
Pharmacology
- 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.10,13
The following conditions, when they produced beta-lactamases, have been treated with a combination of amoxicillin and clavulanic acid or ticarcillin and clavulanic acid10,13:
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.10 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.13
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Acute Cystitis
- Acute Uncomplicated Pyelonephritis
- Bacterial Infections
- Bacterial Pneumonia
- Bacterial infection due to streptococcus, group A
- Bone and Joint Infections
- Bronchitis
- Cysto-Urethritis
- Gynecological Infection
- Haemophilus Influenzae
- Infection Due to Escherichia Coli
- Intraabdominal Infections
- Lower Respiratory Infection
- Lower Respiratory Tract Infection (LRTI)
- Moraxella catarrhalis
- Neisseria Gonorrhoeae Infection
- Otitis Media (OM)
- Pharyngitis
- Proteus mirabilis
- Septicemia
- Sinusitis
- Skin and skin structure infections
- Streptococcus Pneumoniae
- Tonsillitis
- Upper Respiratory Tract Infection
- Urinary Tract Infection
- Susceptible Bacterial Infections
- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- 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.10,11,13
- 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.1,2
Target Actions Organism ABacterial beta-lactamase enzymes inhibitor- Absorption
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%.6 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.5 Tmax is reported to be 40-120 minutes according to another pharmacokinetic study.4
- Volume of distribution
A study in 4 healthy volunteers administered a radiolabeled dose of clavulanic acid determined a volume of distribution of 12L.6Clavulanic acid is distributed to various tissues and interstitial fluid. Clinically significant concentrations have been measured in the gallbladder, abdomen, skin, fat, and muscle tissues. Bile, pus, synovial and peritoneal fluids are also found to have therapeutic concentrations of clavulanic acid.11 Studies of animals have demonstrated that clavulanic crosses the placenta.11
- Protein binding
The plasma protein binding of amoxicillin is about 25%.11
- Metabolism
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.6,11 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.6
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- Route of elimination
About 40 to 65% of the clavulanic acid is excreted as unchanged drug in urine during the first 6 hours following ingestion. The metabolites of clavulanic acid are found to be excreted in the urine and feces and as carbon dioxide in expired air. Clavulanate is cleared by both renal and non-renal processes.11 About 17% of radiolabeled dose of clavulanic acid was found to be exhaled in expired air and 8% of a dose was found to be excreted in the feces.6
- Half-life
The half-life of clavulanic acid is reported to be similar to amoxicillin, and last 45-90 minutes.4 A study of radiolabeled clavulanic acid administered to 4 healthy volunteers determined a half-life of 0.8 h.6
- Clearance
The clearance of clavulanic acid in a pharmacokinetic study of 4 healthy volunteers administered a radiolabeled dose of clavulanic acid was 0.21 l/min.6 Another resource indicates the average clearance of clavulanic acid is 12.20 liters/h/70 kg.7 Dose adjustments may be required in patients with renal failure.10
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
LD50 information
Clavulanic acid has demonstrated low oral acute toxicity in adult rodents, having an LD50 of more than 2000 mg/kg. The toxicity of clavulanic acid on pre-weaning rats was also studied. Gastrointestinal disturbance and mortality occurred, even at lower clavulanic acid doses of 125 mg/kg.12
Overdose information
Overdose information has been obtained for the combination of amoxicillin and clavulanic acid, as these drugs are frequently administered together in a single product.10,11 Changes in fluid and electrolyte balances and gastrointestinal symptoms may occur in the case of an overdose. Offer symptomatic treatment or gastrointestinal disturbances, while considering the importance of fluid and electrolyte balance. This drug may be removed by a session of hemodialysis. When coadministered with amoxicillin, crystalluria causing renal failure has been observed.11 Seizures may also occur in a case of overdose, or in a patient with renal failure.13
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Clavulanic acid is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Clavulanic acid. Benzocaine The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Capsaicin. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take with food. Take at the beginning of a meal to reduce gastric irritation.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Clavulanate potassium Q42OMW3AT8 61177-45-5 ABVRVIZBZKUTMK-JSYANWSFSA-M - Product Images
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACIX® Clavulanic acid (0.858 g) + Amoxicillin (12 g) Powder, for suspension Oral SYNTOFARMA S.A. 2019-03-06 Not applicable Colombia Ag-amoxi Clav Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (250 mg) Tablet Oral Angita Pharma Inc. Not applicable Not applicable Canada Ag-amoxi Clav Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (500 mg) Tablet Oral Angita Pharma Inc. 2022-08-18 Not applicable Canada Ag-amoxi Clav Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (875 mg) Tablet Oral Angita Pharma Inc. 2021-12-31 Not applicable Canada ALVOCLAV POWDER FOR SOLUTION FOR INJECTION 1.2G/VIAL Clavulanate potassium (200 mg) + Amoxicillin sodium (1000 mg) Injection, powder, for solution Intravenous PAN-MALAYAN PHARMACEUTICALS PTE LTD 2016-04-07 Not applicable Singapore AMK INJECTION 1.2 G Clavulanate potassium (200 MG/1VIAL) + Amoxicillin sodium (1 G/1VIAL) Powder บริษัท อาร์เอ็กซ์ จำกัด 2009-03-06 Not applicable Thailand AMOCLA TABLETS 625 mg Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (500 mg) Tablet, film coated Oral PHARMAFORTE SINGAPORE PTE LTD 1999-09-11 Not applicable Singapore Amoclanhexal 1 g (875 mg/125 mg) - Filmtabletten Clavulanate potassium (125 mg) + Amoxicillin (875 mg) Tablet, film coated Oral Hexal Pharma Gmb H 2003-07-22 Not applicable Austria AMOCLAV 500 PLUS Clavulanic acid (125 mg) + Amoxicillin (500 mg) Tablet, film coated Oral 2014-01-01 Not applicable Germany AMOCLAV 500 PLUS Clavulanic acid (125 mg) + Amoxicillin (500 mg) Tablet, film coated Oral 2014-01-01 2021-12-15 Germany - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image KLAVUNAT 625 MG FİLM KAPLI, 10 TABLET Clavulanic acid (125 mg) + Amoxicillin (500 mg) Tablet Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 1000 MG FİLM KAPLI TABLET, 10 ADET Clavulanic acid (125 mg) + Amoxicillin (875 mg) Tablet Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 1000 MG FİLM KAPLI TABLET, 14 ADET Clavulanic acid (125 mg) + Amoxicillin (875 mg) Tablet Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 200/28 MG 100 ML ORAL SUSPANSIYON Clavulanic acid (28 mg) + Amoxicillin (200 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 200/28 MG 70 ML ORAL SUSPANSIYON Clavulanic acid (28 mg) + Amoxicillin (200 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 400/57 MG 100 ML ORAL SUSPANSIYON Clavulanic acid (57 mg) + Amoxicillin (400 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT BID 400/57 MG 70 ML ORAL SUSPANSIYON Clavulanic acid (57 mg) + Amoxicillin (400 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT ES 600/42,9 MG ORAL SUSPANSIYON ICIN KURU TOZ 100 ML Clavulanic acid (42.9 mg) + Amoxicillin (600 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey KLAVUNAT ES 600/42,9 MG ORAL SUSPANSIYON ICIN KURU TOZ 150 ML Clavulanic acid (42.9 mg) + Amoxicillin (600 mg) Suspension Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Clavams / 1,4-oxazepines / Tertiary carboxylic acid amides / Oxazolidines / Azetidines / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Primary alcohols show 5 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid / Clavam show 15 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- oxapenam (CHEBI:48947) / Clavams (C06662)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 23521W1S24
- CAS number
- 58001-44-8
- InChI Key
- HZZVJAQRINQKSD-PBFISZAISA-N
- 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
- IUPAC Name
- (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO
References
- Synthesis Reference
Dennis Edward Clark, Shaukat Hussain Malik, Paul Gerard Butterly, Clive Elton Badman, Jeffrey David Haseler, "Process for preparing potassium clavulanate in rossette form." U.S. Patent US5750685, issued April, 1978.
US5750685- General References
- Saudagar PS, Survase SA, Singhal RS: Clavulanic acid: a review. Biotechnol Adv. 2008 Jul-Aug;26(4):335-51. doi: 10.1016/j.biotechadv.2008.03.002. Epub 2008 Mar 26. [Article]
- Geddes AM, Klugman KP, Rolinson GN: Introduction: historical perspective and development of amoxicillin/clavulanate. Int J Antimicrob Agents. 2007 Dec;30 Suppl 2:S109-12. doi: 10.1016/j.ijantimicag.2007.07.015. Epub 2007 Sep 27. [Article]
- Adam D, de Visser I, Koeppe P: Pharmacokinetics of amoxicillin and clavulanic acid administered alone and in combination. Antimicrob Agents Chemother. 1982 Sep;22(3):353-7. doi: 10.1128/aac.22.3.353. [Article]
- Weber DJ, Tolkoff-Rubin NE, Rubin RH: Amoxicillin and potassium clavulanate: an antibiotic combination. Mechanism of action, pharmacokinetics, antimicrobial spectrum, clinical efficacy and adverse effects. Pharmacotherapy. 1984 May-Jun;4(3):122-36. [Article]
- Ferslew KE, Daigneault EA, Aten EM, Roseman JM: Pharmacokinetics and urinary excretion of clavulanic acid after oral administration of amoxicillin and potassium clavulanate. J Clin Pharmacol. 1984 Oct;24(10):452-6. [Article]
- Bolton GC, Allen GD, Davies BE, Filer CW, Jeffery DJ: The disposition of clavulanic acid in man. Xenobiotica. 1986 Sep;16(9):853-63. doi: 10.3109/00498258609038967. [Article]
- De Cock PA, Standing JF, Barker CI, de Jaeger A, Dhont E, Carlier M, Verstraete AG, Delanghe JR, Robays H, De Paepe P: Augmented renal clearance implies a need for increased amoxicillin-clavulanic acid dosing in critically ill children. Antimicrob Agents Chemother. 2015 Nov;59(11):7027-35. doi: 10.1128/AAC.01368-15. Epub 2015 Sep 8. [Article]
- Justin Evans; Micah Wittler (2019). Amoxicillin Clavulanate. Stat Pearls.
- Augmentin drug summary [Link]
- FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
- Public assessment report: CO-AMOXCOO [Link]
- EMA, Clavulanic acid summary report [Link]
- Augmentin IV, Medicines UK [Link]
- Timentin FDA label [Link]
- Product monograph: Clavulin (amoxicillin and clavulanate potassium) oral tablets and suspension [Link]
- External Links
- Human Metabolome Database
- HMDB0014904
- KEGG Compound
- C06662
- PubChem Compound
- 5280980
- PubChem Substance
- 46508845
- ChemSpider
- 4444466
- BindingDB
- 50021959
- 21216
- ChEBI
- 48947
- ChEMBL
- CHEMBL777
- ZINC
- ZINC000003830569
- Therapeutic Targets Database
- DAP000948
- PharmGKB
- PA164742987
- PDBe Ligand
- J01
- Wikipedia
- Clavulanic_acid
- PDB Entries
- 2jap / 2xf3 / 2xfs / 2xh9 / 6nvu / 6pq8
- MSDS
- Download (57.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Pneumonia 1 4 Completed Basic Science Antibiotic Associated Diarrhoea 1 4 Completed Other Acute Otitis Media (AOM) 1 4 Completed Prevention Antibiotic Associated Diarrhoea 1 4 Completed Prevention Complications / Infection / Prostate Cancer 1 4 Completed Prevention Fever / Pneumonia 1 4 Completed Prevention Infectious Diseases 1 4 Completed Treatment Acute Bacterial Sinusitis (ABS) 1 4 Completed Treatment Acute Diverticulitis 1 4 Completed Treatment Acute Otitis Media (AOM) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Aidarex Pharmacuticals LLC
- Amerisource Health Services Corp.
- Apotex Inc.
- Apotheca Inc.
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Bryant Ranch Prepack
- Cardinal Health
- Casa De Amigos Pharmacy
- Comprehensive Consultant Services Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- GlaxoSmithKline Inc.
- H.J. Harkins Co. Inc.
- Hikma Pharmaceuticals
- Innoviant Pharmacy Inc.
- Keltman Pharmaceuticals Inc.
- Lek Pharmaceuticals Inc.
- Liberty Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Neuman Distributors Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prescription Dispensing Service Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Resource Optimization and Innovation LLC
- Sandoz
- Southwood Pharmaceuticals
- Stat Scripts LLC
- Teva Pharmaceutical Industries Ltd.
- Tya Pharmaceuticals
- UDL Laboratories
- West-Ward Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Tablet, orally disintegrating Oral Powder, for suspension Oral Suspension Oral Tablet, chewable Oral Tablet, film coated Oral Tablet, multilayer, extended release Oral Powder, for solution Intravenous Injection, powder, for solution Parenteral Injection, powder, for solution Intravenous; Parenteral Tablet, coated Oral Tablet, film coated Oral 500 mg Tablet Oral Tablet, soluble Oral For suspension Oral Powder, for suspension Oral 200 mg/5ml Injection, powder, for solution Intravenous 500 mg Tablet, multilayer, extended release Oral 1000 mg Tablet, film coated, extended release Oral Tablet, coated Injection, powder, for solution Injection Intravenous Powder Oral Granule, for suspension Oral Granule, for solution Oral Granule, for suspension Oral 200 mg/5ml Granule, for suspension Oral 125 mg/5ml Solution / drops Cutaneous; Oral Syrup Oral Powder, for solution Oral Powder Intravenous Tablet, effervescent Oral Suspension, extended release Oral Powder, for suspension Oral 400 mg/5ml Tablet, film coated Oral 250 mg Powder, for suspension Oral 125 mg/5ml Powder, for suspension Oral 250 mg/5ml Granule Oral Injection, powder, for solution Intravenous Injection, solution Intravenous Powder Tablet, extended release - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6878386 No 2005-04-12 2020-04-04 US US7217430 No 2007-05-15 2020-04-04 US US7250176 No 2007-07-31 2020-04-04 US US6783773 No 2004-08-31 2020-04-04 US US6746692 No 2004-06-08 2020-04-04 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 117.5-118 http://clav-acid.weebly.com/physical-characteristics.html boiling point (°C) 545.8 http://clav-acid.weebly.com/physical-characteristics.html logP -2.3 https://www.speronline.com/japer/Articlefile/202.pdf logS 0.23 http://www.hmdb.ca/metabolites/HMDB0014904 pKa 2.7 http://wildpro.twycrosszoo.org/S/00Chem/ChComplex/Clavulanic_acid.htm - Predicted Properties
Property Value Source Water Solubility 337.0 mg/mL ALOGPS logP -1.2 ALOGPS logP -1.5 Chemaxon logS 0.23 ALOGPS pKa (Strongest Acidic) 3.32 Chemaxon pKa (Strongest Basic) -2.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 87.07 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 44.25 m3·mol-1 Chemaxon Polarizability 18.13 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.745 Blood Brain Barrier - 0.6848 Caco-2 permeable - 0.6054 P-glycoprotein substrate Non-substrate 0.7667 P-glycoprotein inhibitor I Non-inhibitor 0.9483 P-glycoprotein inhibitor II Non-inhibitor 0.9902 Renal organic cation transporter Non-inhibitor 0.8446 CYP450 2C9 substrate Non-substrate 0.8719 CYP450 2D6 substrate Non-substrate 0.8279 CYP450 3A4 substrate Non-substrate 0.5362 CYP450 1A2 substrate Non-inhibitor 0.8694 CYP450 2C9 inhibitor Non-inhibitor 0.8957 CYP450 2D6 inhibitor Non-inhibitor 0.9295 CYP450 2C19 inhibitor Non-inhibitor 0.8915 CYP450 3A4 inhibitor Non-inhibitor 0.9798 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9926 Ames test Non AMES toxic 0.7146 Carcinogenicity Non-carcinogens 0.8718 Biodegradation Ready biodegradable 0.8501 Rat acute toxicity 1.4312 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9875 hERG inhibition (predictor II) Non-inhibitor 0.9753
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

References
- Saudagar PS, Survase SA, Singhal RS: Clavulanic acid: a review. Biotechnol Adv. 2008 Jul-Aug;26(4):335-51. doi: 10.1016/j.biotechadv.2008.03.002. Epub 2008 Mar 26. [Article]
- Weber DJ, Tolkoff-Rubin NE, Rubin RH: Amoxicillin and potassium clavulanate: an antibiotic combination. Mechanism of action, pharmacokinetics, antimicrobial spectrum, clinical efficacy and adverse effects. Pharmacotherapy. 1984 May-Jun;4(3):122-36. [Article]
- Justin Evans; Micah Wittler (2019). Amoxicillin Clavulanate. Stat Pearls.
- FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
- Augmentin IV, Medicines UK [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Glucose:sodium symporter activity
- Specific Function
- Actively transports glucose into cells by Na(+) cotransport with a Na(+) to glucose coupling ratio of 2:1. Efficient substrate transport in mammalian kidney is provided by the concerted action of a...
- Gene Name
- SLC5A1
- Uniprot ID
- P13866
- Uniprot Name
- Sodium/glucose cotransporter 1
- Molecular Weight
- 73497.275 Da
References
- Kim J, John J, Langford D, Walker E, Ward S, Rawls SM: Clavulanic acid enhances glutamate transporter subtype I (GLT-1) expression and decreases reinforcing efficacy of cocaine in mice. Amino Acids. 2016 Mar;48(3):689-696. doi: 10.1007/s00726-015-2117-8. Epub 2015 Nov 5. [Article]
- Hakami AY, Sari Y: beta-Lactamase inhibitor, clavulanic acid, attenuates ethanol intake and increases glial glutamate transporters expression in alcohol preferring rats. Neurosci Lett. 2017 Sep 14;657:140-145. doi: 10.1016/j.neulet.2017.08.013. Epub 2017 Aug 5. [Article]
- Goodwani S, Rao PS, Bell RL, Sari Y: Amoxicillin and amoxicillin/clavulanate reduce ethanol intake and increase GLT-1 expression as well as AKT phosphorylation in mesocorticolimbic regions. Brain Res. 2015 Oct 5;1622:397-408. doi: 10.1016/j.brainres.2015.07.008. Epub 2015 Jul 10. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:39