Page last updated: 2024-11-08

ibuprofen acyl glucuronide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

ibuprofen acyl glucuronide: structure given in first source; metabolite of ibuprofen; 13% of ibuprofen administered to humans is excreted in urine as its acyl glucuronide [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID163959
CHEMBL ID3526740
CHEBI ID88735
MeSH IDM0216827

Synonyms (16)

Synonym
ibuprofen acyl glucuronide
chebi:88735 ,
chembl3526740 ,
bdbm50088514
115075-59-7
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]oxane-2-carboxylic acid
beta-d-glucopyranuronic acid, 1-(alpha-methyl-4-(2-methylpropyl)benzeneacetate)
1-(alpha-methyl-4-(2-methylpropyl)benzeneacetate)-beta-d-glucopyranuronic acid
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid
ibuprofen acyl-beta-d-glucuronide, analytical standard
DTXSID30921613
Q27160661
beta-d-glucopyranuronic acid, 1-[alpha-methyl-4-(2-methylpropyl)benzeneacetate]
ibuprofen acyl-beta-d-glucuronide(mixture of diastereomers)
ibuprofen acyl-beta-d-glucuronide (mixture of diastereomers)
CS-0059364

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
terpene glycosideA terpenoid in which one or more hydroxy functions are glycosylated.
[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]

Pathways (2)

PathwayProteinsCompounds
Ibuprofen Action Pathway5076
Ibuprofen Metabolism Pathway2414

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Liver carboxylesterase 1Homo sapiens (human)Ki355.00000.00252.01368.4800AID1222891
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1222897Activity of human CES2 assessed as compound hydrolysis at 100 uM measured up to 60 mins by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1221802Activity of human UGT1A3 expressed in HEK293 cells assessed as enzyme-mediated compound formation per 2 x 10'5 cells treated with ibuprofen at 1 mM measured at 24 hrs by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1221841Drug level in cell culture medium treated with ibuprofen at 1 mM measured at 6 hrs by LC-MS/MS analysis in absence of acyl glucuronidation inhibitor (-)-borneol2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1221787Ratio of drug level in human hepatocytes to HEK293 cells expressing UGT1A3 treated with ibuprofen at 1 mM2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1222891Reversible inhibition of human CES1 assessed as hydrolysis of 4NPA to 4NP2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222887Half life in buffer at pH 7.4 by 1H NMR spectroscopic analysis in presence of human urine2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1221838Drug level in human hepatocytes assessed per 2 x 10'5 cells treated with ibuprofen at 1 mM measured at 6 hrs by LC-MS/MS analysis in absence of acyl glucuronidation inhibitor (-)-borneol2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1222890Activity of human CES1 assessed as compound hydrolysis at 100 uM measured up to 60 mins by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1221810Activity of human UGT1A3 expressed in HEK293 cells assessed as enzyme-mediated compound formation in cell culture medium treated with ibuprofen at 1 mM by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1221823Drug level in human hepatocytes assessed per 2 x 10'5 cells treated with ibuprofen at 1 mM measured at 6 hrs by LC-MS/MS analysis in presence of acyl glucuronidation inhibitor (-)-borneol2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1221845Drug level in cell culture medium treated with ibuprofen at 1 mM measured at 6 hrs by LC-MS/MS analysis in presence of acyl glucuronidation inhibitor (-)-borneol2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
AID1222886Inhibition of human CES2 assessed as hydrolysis of 4NPA to 4NP at 1 mM by spectrophotometric analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222885Half life in phosphate buffer at 10 uM at pH 7.4 by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1221806Activity of human UGT1A3 expressed in HEK293 cells assessed as enzyme-mediated compound formation in cell culture medium treated with ibuprofen at 1 mM measured at 6 to 24 hrs by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, Jan, Volume: 39, Issue:1
Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (33.33)18.2507
2000's1 (11.11)29.6817
2010's5 (55.56)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.59

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.59 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.15 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.59)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]