CLAVULANATE SODIUM

First approved in 1984

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H8NO5.Na
Molecular Weight	221.1426
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[H][C@@]12CC(=O)N1[C@@H](C([O-])=O)\C(O2)=C\CO

InChI

InChIKey=WOGMLDNCNBLDCA-JSYANWSFSA-M

InChI=1S/C8H9NO5.Na/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);/q;+1/p-1/b4-1-;/t6-,7-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C8H8NO5
Molecular Weight	198.1528
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00766 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10082170

Clavulanic acid is produced by the fermentation of Streptomyces clavuligerus. It is a β-lactam structurally related to the penicillins and possesses the ability to inactivate a wide variety of β-lactamases by blocking the active sites of these enzymes. Clavulanic acid is particularly active against the clinically important plasmid-mediated β-lactamases frequently responsible for transferred drug resistance to penicillins and cephalosporins. Clavulanic acid is used in conjunction with amoxicillin for the treatment of bronchitis and urinary tract, skin, and soft tissue infections caused by beta-lactamase producing organisms. Clavulanic acid competitively and irreversibly inhibits a wide variety of beta-lactamases, commonly found in microorganisms resistant to penicillins and cephalosporins. Binding and irreversibly inhibiting the beta-lactamase results in a restauration of the antimicrobial activity of beta-lactam antibiotics against lactamase-secreting-resistant bacteria. By inactivating beta-lactamase (the bacterial resistance protein), the accompanying penicillin/cephalosporin drugs may be made more potent as well.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-lactamase TEM 12 Target ID: CHEMBL2065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23612724 \| https://www.ncbi.nlm.nih.gov/pubmed/7699694 \| https://www.ncbi.nlm.nih.gov/pubmed/12523623	Inhibitor 8297		0.09 µM [IC50]
Beta-lactamase 16 Target ID: CHEMBL4114 Sources: https://www.drugbank.ca/drugs/DB00766 \| https://www.ncbi.nlm.nih.gov/pubmed/23612724 \| https://www.ncbi.nlm.nih.gov/pubmed/3039137	Inhibitor 8297		80.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 51 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf	Curative	Approved 8429	Augmentin Approved Use AUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli, and Klebsiella spp. Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and Enterobacter spp. Launch Date 1996
Otitis media 41 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf	Curative	Approved 8429	Augmentin Approved Use AUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli, and Klebsiella spp. Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and Enterobacter spp. Launch Date 1996
Sinusitis 26 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf	Curative	Approved 8429	Augmentin Approved Use AUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli, and Klebsiella spp. Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and Enterobacter spp. Launch Date 1996
Urinary tract infections 205 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf	Curative	Approved 8429	Augmentin Approved Use AUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli, and Klebsiella spp. Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and Enterobacter spp. Launch Date 1996
Skin and skin structure infections 80 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf	Curative	Approved 8429	Augmentin Approved Use AUGMENTIN is indicated in the treatment of infections caused by susceptible strains of the designated organisms in the conditions listed below: Lower Respiratory Tract Infections – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Otitis Media – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Sinusitis – caused by β-lactamase–producing strains of H. influenzae and M. catarrhalis. Skin and Skin Structure Infections – caused by β-lactamase–producing strains of S. aureus, E. coli, and Klebsiella spp. Urinary Tract Infections – caused by β-lactamase–producing strains of E. coli, Klebsiella spp. and Enterobacter spp. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
2.63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/	125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
5.49 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/	125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12562705/	125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: AMOXICILLIN	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	Other AEs: Diarrhea, Rash urticarial... Other AEs: Diarrhea Rash urticarial Diaper rash Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	Other AEs: Loose stools, Nausea... Other AEs: Loose stools (9%) Nausea (3%) Rash urticarial (3%) Vomiting (1%) Vaginitis (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf

AEs

AE	Significance	Dose	Population
Diaper rash		10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Diarrhea		10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Rash urticarial		10 mg/kg 1 times / day steady, oral Recommended Dose: 10 mg/kg, 1 times / day Route: oral Route: steady Dose: 10 mg/kg, 1 times / day Co-administed with:: amoxicillin(40 to 45 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, 2 months to 12 years n = 575 Health Status: unhealthy Condition: acute otitis media Age Group: 2 months to 12 years Sex: unknown Population Size: 575 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Vaginitis	1%	125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Vomiting	1%	125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Nausea	3%	125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Rash urticarial	3%	125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf
Loose stools	9%	125 mg 1 times / day steady, oral Recommended Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Co-administed with:: amoxicillin(250 to 875 mg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: infections Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050564s053s055,050575s040s042,050597s047s049,050720s026s028,050725s028s030,050726s022s024lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:48947	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48947
ChemicalBook	CB9722501	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9722501
ZINC	ZINC000003830569	http://zinc15.docking.org/substances/ZINC000003830569

PubMed

Title	Date	PubMed
In vitro susceptibility of Mycobacterium tuberculosis, Mycobacterium fortuitum and Mycobacterium chelonei to augmentin.	1986 Aug	3093225
In vitro susceptibility of Mycobacterium tuberculosis, Mycobacterium africanum, Mycobacterium bovis, Mycobacterium avium, Mycobacterium fortuitum, and Mycobacterium chelonae to ticarcillin in combination with clavulanic acid.	1987 Jan	3105441
Immunogenicity and allergenicity studies on two beta-lactam structures, a clavam, clavulanic acid, and a carbapenem: structure-activity relationships.	1988	3338858
In vitro activity of antimicrobial agents against mycobacteria.	1988	3150951
Cholestatic hepatitis due to antibacterial combination of amoxicillin and clavulanic acid (augmentin).	1989 Oct	2791808
beta-Lactamase inhibitors and the inducibility of the beta-lactamase of Mycobacterium tuberculosis.	1992 Mar	1546847
beta-Lactamase activity in mycobacteria including Mycobacterium avium and suppression of their growth by a beta-lactamase-stable antibiotic.	1995	7752957
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis?	1995 Dec	8592990
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Suppression of the growth of six potentially-pathogenic mycobacteria by beta-lactam/beta-lactamase-inhibitors.	1997	9467917
Hypersensitivity to clavulanic acid in children.	2008 Sep-Oct	19080805
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014 Jan	24085192

Patents

Sample Use Guides

In Vivo Use Guide

Adults The usual adult dose is one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 250 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. For more severe infections and infections of the respiratory tract, the dose should be one 875 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. Adults who have difficulty swallowing may be given the 125 mg/31.25 mg per 5 mL or 250 mg/62.5 mg per 5 mL suspension in place of the 500 mg/125 mg tablet. The 200 mg/28.5 mg per 5 mL suspension or the 400 mg/57 mg per 5 mL suspension may be used in place of the 875 mg/125 mg tablet.

Route of Administration: Oral

In Vitro Use Guide

The purified beta-lactamase enzyme focused at pI 5.4 and was strongly inhibited in vitro by clavulanic acid (IC50 = 0.09 uM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:39:31 GMT 2023` Edited by `admin` on `Fri Dec 15 19:39:31 GMT 2023`
Record UNII	85A8F32FMG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLAVULANATE SODIUM

Common Name

English

4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-(2-HYDROXYETHYLIDENE)-7-OXO-, MONOSODIUM SALT, (2R,3Z,5R)-

Common Name

English

CLAVULANIC ACID SODIUM SALT

Common Name

English

4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-(2-HYDROXYETHYLIDENE)-7-OXO-, SODIUM SALT (1:1), (2R,3Z,5R)-

Common Name

English

SODIUM CLAVULANATE

Common Name

English

4-OXA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-(2-HYDROXYETHYLIDENE)-7-OXO-, MONOSODIUM SALT, (2R-(2.ALPHA.,3Z,5.ALPHA.))-

Common Name

English

Code System Code Type Description

CAS

57943-81-4