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
Thumb
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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

TargetActionsOrganism
UBacterial 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
Adverseeffects
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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.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Clavulanic acid is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Clavulanic acid.
DicoumarolThe risk or severity of bleeding can be increased when Clavulanic acid is combined with Dicoumarol.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Clavulanic acid.
FluindioneThe risk or severity of bleeding can be increased when Clavulanic acid is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Clavulanic acid.
MethotrexateMethotrexate may increase the hepatotoxic activities of Clavulanic acid.
PhenindioneThe risk or severity of bleeding can be increased when Clavulanic acid is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Clavulanic acid is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Clavulanic acid.
Interactions
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Food Interactions
  • Take with food. Take at the beginning of a meal to reduce gastric irritation.

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Clavulanate potassiumQ42OMW3AT861177-45-5ABVRVIZBZKUTMK-JSYANWSFSA-M
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACIX®Clavulanic acid (0.858 g) + Amoxicillin (12 g)Powder, for suspensionOralSYNTOFARMA S.A.2019-03-06Not applicableColombia flag
Ag-amoxi ClavClavulanate potassium (125 mg) + Amoxicillin (250 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-amoxi ClavClavulanate potassium (125 mg) + Amoxicillin (875 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-amoxi ClavClavulanate potassium (125 mg) + Amoxicillin (500 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
AMK INJECTION 1.2 GClavulanate potassium (200 MG/1VIAL) + Amoxicillin sodium (1 G/1VIAL)Powderบริษัท อาร์เอ็กซ์ จำกัด2009-03-06Not applicableThailand flag
AMOKLAVİN 1,2 G I.V. ENJEKSİYONLUK/İNFÜZYONLUK ÇÖZELTİ HAZIRLAMAK İÇİN TOZ VE ÇÖZÜCÜ, 1 ADETClavulanic acid (200 mg) + Amoxicillin (1000 mg)InjectionIntravenousDeva Holding A.S.2020-08-14Not applicableTurkey flag
AMOKLAVIN 400 MG/57 MG ORAL SÜSPANSIYON HAZIRLAMAK IÇIN KURU TOZ IÇEREN SAŞE ,20 SAŞEClavulanic acid (57 mg) + Amoxicillin Trihydrate (400 mg)Powder, for suspensionOralDeva Holding A.S.2020-08-142018-11-06Turkey flag
AMOKLAVIN BID 1000 MG FILM TABLET, 10 ADETClavulanate potassium (125 mg) + Amoxicillin Trihydrate (875 mg)Tablet, film coatedOralDeva Holding A.S.2020-08-14Not applicableTurkey flag
AMOKLAVIN BID 1000 MG FILM TABLET, 14 ADETClavulanate potassium (125 mg) + Amoxicillin Trihydrate (875 mg)Tablet, film coatedOralDeva Holding A.S.2020-08-14Not applicableTurkey flag
AMOKLAVIN BID 1000 MG FILM TABLET, 20 ADETClavulanate potassium (125 mg) + Amoxicillin Trihydrate (875 mg)Tablet, film coatedOralDeva Holding A.S.2020-08-14Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
KLAVUNAT 625 MG 10 TABLETClavulanic acid (125 mg) + Amoxicillin (500 mg)TabletOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 1GR 10 TABLETClavulanic acid (125 mg) + Amoxicillin (875 mg)TabletOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 1GR TABLET, 14 ADETClavulanic acid (125 mg) + Amoxicillin (875 mg)TabletOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 200/28 MG 100 ML ORAL SUSPANSIYONClavulanic acid (28 mg) + Amoxicillin (200 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 200/28 MG 70 ML ORAL SUSPANSIYONClavulanic acid (28 mg) + Amoxicillin (200 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 400/57 MG 100 ML ORAL SUSPANSIYONClavulanic acid (57 mg) + Amoxicillin (400 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT BID 400/57 MG 70 ML ORAL SUSPANSIYONClavulanic acid (57 mg) + Amoxicillin (400 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT ES 600/42,9 MG ORAL SUSPANSIYON ICIN KURU TOZ 100 MLClavulanic acid (42.9 mg) + Amoxicillin (600 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
KLAVUNAT ES 600/42,9 MG ORAL SUSPANSIYON ICIN KURU TOZ 150 MLClavulanic acid (42.9 mg) + Amoxicillin (600 mg)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. Justin Evans; Micah Wittler (2019). Amoxicillin Clavulanate. Stat Pearls.
  9. Augmentin drug summary [Link]
  10. FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
  11. Public assessment report: CO-AMOXCOO [Link]
  12. EMA, Clavulanic acid summary report [Link]
  13. Augmentin IV, Medicines UK [Link]
  14. Timentin FDA label [Link]
  15. Product monograph: Clavulin (amoxicillin and clavulanate potassium) oral tablets and suspension [Link]
Human Metabolome Database
HMDB0014904
KEGG Compound
C06662
PubChem Compound
5280980
PubChem Substance
46508845
ChemSpider
4444466
BindingDB
50021959
RxNav
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
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentPneumonia1
4CompletedPreventionAntibiotic Associated Diarrhoea1
4CompletedPreventionFever / Pneumonia1
4CompletedTreatmentAcute Bacterial Sinusitis (ABS)1
4CompletedTreatmentAcute Diverticulitis1
4CompletedTreatmentAcute Otitis Media (AOM)1
4CompletedTreatmentAmoxicillin / Post-Op Complications / Tooth Extractions1
4CompletedTreatmentAmputation, Wound / Wound Infections1
4CompletedTreatmentAppendicitis Acute / Lower Abdominal Pain / Right Iliac Fossa Pain1
4CompletedTreatmentChildren / Chronic Sinusitis1

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
FormRouteStrength
Tablet, orally disintegratingOral
Powder, for suspensionOral
SuspensionOral
Tablet, chewableOral
Tablet, film coatedOral
Tablet, multilayer, extended releaseOral
Injection, powder, for solutionParenteral
Injection, powder, for solutionIntravenous; Parenteral
Tablet, coatedOral
TabletOral
Tablet, solubleOral
Tablet, film coated, extended releaseOral
Tablet, coated
SyrupOral
Injection, powder, for solution
InjectionIntravenous
PowderOral
Granule, for solutionOral
Granule, for suspensionOral
Solution / dropsCutaneous; Oral
Powder, for solutionIntravenous
PowderIntravenous
Powder, for solutionOral
Tablet, effervescentOral
Suspension, extended releaseOral
GranuleOral
Injection, powder, for solutionIntravenous
Injection, solutionIntravenous
Powder
Tablet, extended release
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6878386No2005-04-122020-04-04US flag
US7217430No2007-05-152020-04-04US flag
US7250176No2007-07-312020-04-04US flag
US6783773No2004-08-312020-04-04US flag
US6746692No2004-06-082020-04-04US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)117.5-118 http://clav-acid.weebly.com/physical-characteristics.html
boiling point (°C) 545.8http://clav-acid.weebly.com/physical-characteristics.html
logP-2.3https://www.speronline.com/japer/Articlefile/202.pdf
logS0.23http://www.hmdb.ca/metabolites/HMDB0014904
pKa2.7http://wildpro.twycrosszoo.org/S/00Chem/ChComplex/Clavulanic_acid.htm
Predicted Properties
PropertyValueSource
Water Solubility337.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.25 m3·mol-1ChemAxon
Polarizability18.13 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.745
Blood Brain Barrier-0.6848
Caco-2 permeable-0.6054
P-glycoprotein substrateNon-substrate0.7667
P-glycoprotein inhibitor INon-inhibitor0.9483
P-glycoprotein inhibitor IINon-inhibitor0.9902
Renal organic cation transporterNon-inhibitor0.8446
CYP450 2C9 substrateNon-substrate0.8719
CYP450 2D6 substrateNon-substrate0.8279
CYP450 3A4 substrateNon-substrate0.5362
CYP450 1A2 substrateNon-inhibitor0.8694
CYP450 2C9 inhibitorNon-inhibitor0.8957
CYP450 2D6 inhibitorNon-inhibitor0.9295
CYP450 2C19 inhibitorNon-inhibitor0.8915
CYP450 3A4 inhibitorNon-inhibitor0.9798
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9926
Ames testNon AMES toxic0.7146
CarcinogenicityNon-carcinogens0.8718
BiodegradationReady biodegradable0.8501
Rat acute toxicity1.4312 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9875
hERG inhibition (predictor II)Non-inhibitor0.9753
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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insights and accelerate drug research.
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1. Bacterial beta-lactamase enzymes
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Clavulanic acid, when combined with other antibiotics, targets the beta-lactamase enzymes produced by Pseudomonas species, Haemophilus Influenzae, Bacteroides fragilis, Moraxella catarrhalis, Citrobacter species, and other bacteria deemed susceptible to this antibiotic.
A group comprised of beta-lactamase enzymes produced by various bacteria.
References
  1. 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]
  2. 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]
  3. Justin Evans; Micah Wittler (2019). Amoxicillin Clavulanate. Stat Pearls.
  4. FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
  5. Augmentin IV, Medicines UK [Link]

Enzymes

1. Bacterial beta-lactamase enzymes
Kind
Group
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Clavulanic acid, when combined with other antibiotics, targets the beta-lactamase enzymes produced by Pseudomonas species, Haemophilus Influenzae, Bacteroides fragilis, Moraxella catarrhalis, Citrobacter species, and other bacteria deemed susceptible to this antibiotic.
A group comprised of beta-lactamase enzymes produced by various bacteria.
References
  1. 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]
  2. 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]
  3. Justin Evans; Micah Wittler (2019). Amoxicillin Clavulanate. Stat Pearls.
  4. FDA Approved Drug Products: Augmentin Amoxicillin and Clavulanate Oral Tablets and Suspension [Link]
  5. 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
  1. 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]
  2. 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]
  3. 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 on June 13, 2005 13:24 / Updated on May 07, 2021 21:41