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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Clavulanic acid (DB00766)

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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 acid^10,13:

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

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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

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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.^1,2

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

Hover over products below to view reaction partners

• Clavulanic acid
  • 1-amino-4-hydroxybutan-2-one + 2,5-dihydro-4-(2- hydroxyethyl)-5-oxo-1H-pyrrole-3-carboxylic acid

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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acenocoumarol	The risk or severity of bleeding can be increased when Clavulanic acid is combined with Acenocoumarol.
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.
Chloroprocaine	The risk or severity of methemoglobinemia can be increased when Clavulanic acid is combined with Chloroprocaine.

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Food Interactions

• Take with food. Take at the beginning of a meal to reduce gastric irritation.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Clavulanate potassium	Q42OMW3AT8	61177-45-5	ABVRVIZBZKUTMK-JSYANWSFSA-M

Product Images

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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
Ag-amoxi Clav	Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (250 mg)	Tablet	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Ag-amoxi Clav	Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (500 mg)	Tablet	Oral	Angita Pharma Inc.	2022-08-18	Not applicable
Ag-amoxi Clav	Clavulanate potassium (125 mg) + Amoxicillin Trihydrate (875 mg)	Tablet	Oral	Angita Pharma Inc.	2021-12-31	Not applicable
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
AMK INJECTION 1.2 G	Clavulanate potassium (200 MG/1VIAL) + Amoxicillin sodium (1 G/1VIAL)	Powder		บริษัท อาร์เอ็กซ์ จำกัด	2009-03-06	Not applicable
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
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
AMOCLAV 500 PLUS	Clavulanic acid (125 mg) + Amoxicillin (500 mg)	Tablet, film coated	Oral		2014-01-01	Not applicable
AMOCLAV 500 PLUS	Clavulanic acid (125 mg) + Amoxicillin (500 mg)	Tablet, film coated	Oral		2014-01-01	2021-12-15

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
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
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
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
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
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
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
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
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

Categories

Drug Categories

• Anti-Bacterial Agents
• Anti-Infective Agents
• beta-Lactamase Inhibitors
• beta-Lactams
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• Lactams

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 / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

show 5 more

Substituents

Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid / Clavam / Hydrocarbon derivative / Lactam / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Oxazolidine / Para-oxazepine / Primary alcohol / Tertiary carboxylic acid amide

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]

External Links

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

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
US7217430	No	2007-05-15	2020-04-04
US7250176	No	2007-07-31	2020-04-04
US6783773	No	2004-08-31	2020-04-04
US6746692	No	2004-06-08	2020-04-04

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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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]

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Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:39