Page last updated: 2024-11-04

lm 4108

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

Description

indomethacin phenethylamide: a cyclooxygenase-2 inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4292
CHEMBL ID95311
CHEBI ID186335
SCHEMBL ID678111
MeSH IDM0472393

Synonyms (29)

Synonym
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1h-indol-3-yl}-n-(2-phenylethyl)acetamide
bdbm22966
chembl95311 ,
indomethacin derivative, 19
lm4108
indomethacin phenethylamide
lm 4108
2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl)-n-phenethylacetamide
lm-4108
n-(2-phenylethyl)-indomethacin amide
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-(2-phenylethyl)acetamide
CHEBI:186335
AKOS001757067
STK226516
FT-0673765
261766-32-9
n-(2-phenylethyl)indomethacinamide
n-(2-phenylethyl)indomethacin amide
SCHEMBL678111
HMS3649K21
DTXSID80274424
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-n-(2-phenylethyl)acetamide
J-016308
Z27761860
SR-01000946582-1
sr-01000946582
EN300-1266060
1h-indole-3-acetamide, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-n-(2-phenylethyl)-
CS-0084079
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylindoleA carboxamide resulting from the formal condensation of a carboxylic acid with the nitrogen of an indole.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)33.08000.00032.177410.0000AID162019; AID1798273
Prostaglandin G/H synthase 1Mus musculus (house mouse)IC50 (µMol)56.70000.00072.08445.1000AID457533
Prostaglandin G/H synthase 1Homo sapiens (human)IC50 (µMol)66.00000.00021.557410.0000AID313126
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)13.28800.00010.995010.0000AID162488; AID1798273; AID313125
Prostaglandin G/H synthase 2Mus musculus (house mouse)IC50 (µMol)16.63250.00050.40086.2000AID1798273; AID457534
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (60)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin G/H synthase 1Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 1Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 1Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 1Homo sapiens (human)
regulation of cell population proliferationProstaglandin G/H synthase 1Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 1Homo sapiens (human)
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 1Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 1Homo sapiens (human)
protein bindingProstaglandin G/H synthase 1Homo sapiens (human)
heme bindingProstaglandin G/H synthase 1Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 1Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 1Homo sapiens (human)
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 (13)

Processvia Protein(s)Taxonomy
photoreceptor outer segmentProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 1Homo sapiens (human)
Golgi apparatusProstaglandin G/H synthase 1Homo sapiens (human)
intracellular membrane-bounded organelleProstaglandin G/H synthase 1Homo sapiens (human)
extracellular exosomeProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 1Homo sapiens (human)
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 (8)

Assay IDTitleYearJournalArticle
AID313126Inhibition of COX12007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Structural and functional basis of cyclooxygenase inhibition.
AID313125Inhibition of COX22007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Structural and functional basis of cyclooxygenase inhibition.
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.
AID457534Inhibition of COX2 in mouse RAW264.7 cells by enzyme immunoassay2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
Discovery of 3-(4-bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide as a novel dual cyclooxygenase/5-lipoxygenase inhibitor that also inhibits tumor necrosis factor-alpha production.
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.
AID457533Inhibition of COX1 in mouse RAW264.7 cells by enzyme immunoassay2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
Discovery of 3-(4-bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide as a novel dual cyclooxygenase/5-lipoxygenase inhibitor that also inhibits tumor necrosis factor-alpha production.
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.
AID1798273Time-Dependent Inhibition Assay from Article 10.1073/pnas.97.2.925: \\Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors.\\2000Proceedings of the National Academy of Sciences of the United States of America, Jan-18, Volume: 97, Issue:2
Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-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's6 (85.71)29.6817
2010's1 (14.29)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: 12.54

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 Index12.54 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]