Compounds > indomethacin ethyl ester
Page last updated: 2024-12-06

indomethacin ethyl ester

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Description

indomethacin ethyl ester: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID27861
CHEMBL ID328864
SCHEMBL ID4549122
MeSH IDM0494293

Synonyms (21)

Synonym
CHEMBL328864 ,
brn 0497742
indomethacin ethyl ester
1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid ethyl ester
indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-, ethyl ester
1h-indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, ethyl ester
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-acetic acid ethyl ester
bdbm50090784
ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
unii-8aon0u1ubt
8aon0u1ubt ,
indomethacin ethyl
16401-99-3
SCHEMBL4549122
indomethacin, ethyl ester
COIRSVPTDJIIKY-UHFFFAOYSA-N
DTXSID50167697
ethyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]acetate (indomethacin ethyl ester)
1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-acetic acid ethyl ester; indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-, ethyl ester (8ci); ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetate; ethyl 1-(p-chlorobenzoyl)-2-methyl-
indometacin impurity i [ep impurity]
A899368

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In conclusion, after oral dosing of NC-IndOEt, IndOEt is converted into IndOH in the intestinal lumen and wall before reaching the blood stream."( Lipid-core nanocapsules restrained the indomethacin ethyl ester hydrolysis in the gastrointestinal lumen and wall acting as mucoadhesive reservoirs.
Cattani, VB; Colomé, LM; Dalla Costa, T; Fiel, LA; Guterres, SS; Jäger, A; Jäger, E; Pohlmann, AR; Stefani, V; Uchoa, F, 2010)		0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)66.00000.00032.177410.0000AID162019
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)0.10000.00010.995010.0000AID162488
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (59)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID162488In vitro inhibitory activity against human Prostaglandin G/H synthase 2 (66 nM) using [14C]AA (50 uM) was determined2000Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15
Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors.
AID162019In vitro inhibitory activity against ovine Prostaglandin G/H synthase 1 (44 nM) using [14C]AA (50 uM) was determined2000Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15
Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors.
AID235519Selectivity ratio of IC50s from COX-1 and COX-22000Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15
Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (71.43)29.6817
2010's2 (28.57)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: 12.70

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

MetricThis Compound (vs All)
Research Demand Index12.70 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.70)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
bml 190
indomethacin morpholinylamide: an inverse agonist of the cannabinoid CB2 receptor		210N-acylindole
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		4.3470aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
lm 4108
indomethacin phenethylamide: a cyclooxygenase-2 inhibitor; structure in first source		210N-acylindole
propidium
Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.		2.9610phenanthridines;
quaternary ammonium ion		fluorochrome;
intercalator
fluorescein-5-isothiocyanate
Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.		2.1310fluorescein isothiocyanate
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Exacerbation
[description not available]		02.1310
Benign Neoplasms, Brain
[description not available]		03.3920
Astrocytoma, Grade IV
[description not available]		02.1310
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		03.3920
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		02.1310
Glial Cell Tumors
[description not available]		02.9610
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		07.9610