Page last updated: 2024-11-13

clavulanate potassium

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Description

potassium clavulanate : A potassium salt having clavulanate as the counterion. It acts as a suicide inhibitor of bacterial beta-lactamase enzymes and has only weak anitbiotic activity when administered alone. However it can be used in combination with amoxicillin trihydrate (under the trade name Augmentin) for treatment of a variety of bacterial infections, where it prevents antibiotic inactivation by microbial lactamases. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID23665591
CHEMBL ID1003
CHEBI ID85264
SCHEMBL ID203411
MeSH IDM0329136

Synonyms (75)

Synonym
AC-13551
clavulanate potassium
potassium (2r-(2alpha,3z,5alpha))-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylate
potassium (z)-(2r,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylate
amonate
4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, monopotassium salt, (2r-(2alpha,3z,5alpha))-
potassium clavulanate
brl 14151k
einecs 262-640-9
clavulanate potassium (jp17/usp)
D02370
61177-45-5
chebi:85264 ,
CHEMBL1003
brl-14151k
potassium (2r,3z,5r)-3-(2-oxidanylethylidene)-7-oxidanylidene-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
A833076
potassium (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
potassium, clavulanate
clavulanate, potassium
AKOS015961326
q42omw3at8 ,
unii-q42omw3at8
clavulansaeure kaliumsalz
clavulanate potassium [usan:usp:jan]
potassium clavulanate [mart.]
clavulanate potassium component of timentin
augmentin component clavulanate potassium
timentin component clavulanate potassium
clavulanate potassium [orange book]
clavulanate potassium [green book]
clavulanate potassium component of clavulox
clavulanic acid (as clavulanate potassium)
clavulanate potassium [usan]
potassium clavulanate [ep monograph]
potassium clavulanate [jan]
clavulanate potassium [vandf]
potassium (z)-(2r,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
clavulanate potassium [usp monograph]
clavulox component clavulanate potassium
4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, monopotassium salt, (2r-(2.alpha.,3z,5.alpha.))-
clavulanate potassium [who-dd]
clavulanate potassium component of augmentin
clavulanic acid potassium salt
BP-30181
CCG-221126
SCHEMBL203411
clavulanate potassium salt, antibiotic for culture media use only
C-6660
ABVRVIZBZKUTMK-JSYANWSFSA-M
W-105420
DTXSID60210067 ,
clavulanic acid potassium
potassium clavulanate; potassium (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
HMS3715B13
potassium clavulanate (50%) : microcrystalline cellulose
potassium (2r,5r,z)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
potassium clavulanate cellulose(1:1)
potassium clavlanate
potassium (2r,5r,z)- 3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
Q27158444
HY-A0256A
clavulanate (potassium)
clavulanic acid potassium 100 microg/ml in water
BCP13548
CS-0019771
D84066
potassium clavulanate - 1:1 mixture with cellulose
potassium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
potassium(2r,5r,z)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate
clavulanate potassium (usp monograph)
potassium clavulanate (ep monograph)
dtxcid60132558
clavulanate potassium (usan:usp:jan)
potassium clavulanate (mart.)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
EC 3.5.2.6 (beta-lactamase) inhibitorAn EC 3.5.2.* (non-peptide cyclic amide C-N hydrolase) inhibitor that interferes with the action of beta-lactamase (EC 3.5.2.6).
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
potassium saltAny alkali metal salt having potassium(1+) as the cation.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)566.50000.11007.190310.0000AID1449628; AID1473738
Chymotrypsinogen ABos taurus (cattle)IC50 (µMol)434.50000.98004.05607.2000AID1510602; AID1510604
Beta-lactamaseEnterobacter cloacaeIC50 (µMol)434.50000.10001.87457.7000AID1510602; AID1510604
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
digestionChymotrypsinogen ABos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
protein bindingChymotrypsinogen ABos taurus (cattle)
serpin family protein bindingChymotrypsinogen ABos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
extracellular regionChymotrypsinogen ABos taurus (cattle)
serine protease inhibitor complexChymotrypsinogen ABos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1189020Inhibition of beta-lactamase TEM1 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1189025Inhibition of beta-lactamase OXA-10 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1510602Inhibition of Enterobacter cloacae beta-lactamase incubated for 10 mins followed by nitrocefin substrate challenge and measured for 5 mins by spectrophotometric analysis2019ACS medicinal chemistry letters, Jun-13, Volume: 10, Issue:6
DMSO-Perturbing Assay for Identifying Promiscuous Enzyme Inhibitors.
AID1808092Drug metabolism in human gut microbes assessed as metabolite formation by LC-MS/MS analysis2021Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23
Searching for New Microbiome-Targeted Therapeutics through a Drug Repurposing Approach.
AID1808093Stability of compound in mini gut model at 24 hrs by LC-MS analysis2021Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23
Searching for New Microbiome-Targeted Therapeutics through a Drug Repurposing Approach.
AID1473739Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID1113476Inhibition of beta lactamase assessed as time for decolorization of iodine (Rvb = 79.5 secs)2013Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, , Volume: 22, Issue:4
Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID1510604Inhibition of Enterobacter cloacae beta-lactamase incubated for 10 mins followed by nitrocefin substrate challenge and measured for 5 mins in presence of Triton X-100 by spectrophotometric analysis2019ACS medicinal chemistry letters, Jun-13, Volume: 10, Issue:6
DMSO-Perturbing Assay for Identifying Promiscuous Enzyme Inhibitors.
AID1510616Inhibition of Bacillus cereus 569/H9 beta-lactamase treated with enzyme for 10 mins following enzyme incubation with 0.7 to 2.1 M DMSO for 5 mins followed by nitrocefin substrate challenge and measured for 5 mins by DMSO-perturbation assay2019ACS medicinal chemistry letters, Jun-13, Volume: 10, Issue:6
DMSO-Perturbing Assay for Identifying Promiscuous Enzyme Inhibitors.
AID1189024Inhibition of Pseudomonas aeruginosa PAO1 beta-lactamase AmpC using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1189027Inhibition of beta-lactamase OXA48 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1473740Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 10 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID1189022Inhibition of beta-lactamase KPC-2 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1473741Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID1113475Inhibition of beta lactamase assessed as increase in time taken for iodine decolorization relative to control2013Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, , Volume: 22, Issue:4
Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-
AID1189023Inhibition of Enterobacter cloacae ARC3525 beta-lactamase P99 using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1808091Drug metabolism in mini gut model assessed as metabolite formation by LC-MS/MS analysis2021Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23
Searching for New Microbiome-Targeted Therapeutics through a Drug Repurposing Approach.
AID1473738Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-taurocholate in presence of ATP measured after 15 to 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID1510608Inhibition of Enterobacter cloacae beta-lactamase treated with enzyme for 10 mins following enzyme incubation with 0.7 to 2.1 M DMSO for 5 mins followed by nitrocefin substrate challenge and measured for 5 mins by DMSO perturbation assay2019ACS medicinal chemistry letters, Jun-13, Volume: 10, Issue:6
DMSO-Perturbing Assay for Identifying Promiscuous Enzyme Inhibitors.
AID1189026Inhibition of beta-lactamase OXA-24/40 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
AID1189021Inhibition of beta-lactamase CTX M-15 (unknown origin) using nitrocefin substrate by enzymatic turnover assay2014ACS medicinal chemistry letters, Aug-14, Volume: 5, Issue:8
Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (83.33)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 117.46

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index117.46 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index209.58 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (117.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]