Page last updated: 2024-12-04

bml 190

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

Description

indomethacin morpholinylamide: an inverse agonist of the cannabinoid CB2 receptor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2415
CHEMBL ID72631
CHEBI ID93649
SCHEMBL ID8314320
MeSH IDM0450673

Synonyms (91)

Synonym
CBIOL_001726
CHEMBL72631 ,
HY-15420
HMS3267D16
BRD-K94379058-001-02-7
EU-0100685
2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl)-1-morpholinoethanone
NCGC00025136-01
BIO2_000763 ,
BIO1_000501
BIO2_000283
BIO1_000012
lopac-i-151
NCGC00015540-01
BIO1_000990
tocris-1383
BSPBIO_001563
IDI1_034033
NCGC00025136-03
NCGC00025136-04
KBIO2_000283
KBIOGR_000283
KBIOSS_000283
KBIO3_000566
KBIO2_002851
KBIO2_005419
KBIO3_000565
LOPAC0_000685
NCGC00025136-05
NCGC00025136-02
indomethacin morpholinylamide
NCGC00015540-03
bml-190
HMS1989O05
I-151
bdbm50090806
2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-1-morpholin-4-yl-ethanone
BML2-C04
HMS1791O05
HMS1361O05
2854-32-2
AKOS001233928
BCP9000422
CCG-204770
NCGC00015540-04
NCGC00015540-06
NCGC00015540-02
NCGC00015540-05
bml 190
bml190
BCPP000330
CS-0853
S2854
bml-190|indomethacin morpholinylamide|imma|1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1-[2-(4-morpholinyl)-2-oxoethyl]-1h-indole
SCHEMBL8314320
imma
BJSDNVVWJYDOLK-UHFFFAOYSA-N
bml 190?2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl)-1-morpholinoethanone
AC-32777
HMS3402O05
HMS3649M07
c23h23cln2o4
2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl)-1-morpholinoethan-1-one
CHEBI:93649
indomethacin morpholinylamide, solid
HMS3651P17
J-017120
SR-01000075946-3
SR-01000075946-1
sr-01000075946
SW219196-1
Q4835975
2-[1-[(4-chlorophenyl)-oxomethyl]-5-methoxy-2-methyl-3-indolyl]-1-(4-morpholinyl)ethanone
HMS3676K16
BS-16362
SR-01000075946-5
BCP02700
HMS3412K16
3-amino benzonitrile?
BRD-K94379058-001-03-5
SB19547
indomethacin morpholinamide
ethanone, 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-1-(4-morpholinyl)-
D94635
CAA85432
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-1-(morpholin-4-yl)ethan-1-one
EN300-18118631
mfcd01317813
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indolyl]-1-morpholinoethanone
SY046843
Z28251597

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" 2 Delta(9)-and Delta(8)-tetrahydrocannabinol (THC) were toxic when added directly to SH-SY5Y neuroblastoma cells."( Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor.
Bissonnette, CJ; Klegeris, A; McGeer, PL, 2003
)
0.32
[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 (39)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency28.18380.003245.467312,589.2998AID2517
Chain A, Ferritin light chainEquus caballus (horse)Potency35.48135.623417.292931.6228AID2323
Chain A, CruzipainTrypanosoma cruziPotency25.78770.002014.677939.8107AID1476
NFKB1 protein, partialHomo sapiens (human)Potency0.01780.02827.055915.8489AID895; AID928
TDP1 proteinHomo sapiens (human)Potency30.05340.000811.382244.6684AID686978; AID686979
thyroid stimulating hormone receptorHomo sapiens (human)Potency39.81070.001318.074339.8107AID926; AID938
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency14.12540.28189.721235.4813AID2326
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency0.02240.035520.977089.1251AID504332
Bloom syndrome protein isoform 1Homo sapiens (human)Potency44.66840.540617.639296.1227AID2364; AID2528
peripheral myelin protein 22 isoform 1Homo sapiens (human)Potency75.686323.934123.934123.9341AID1967
cytochrome P450 2C19 precursorHomo sapiens (human)Potency1.58490.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency39.81070.00636.904339.8107AID883
potassium voltage-gated channel subfamily H member 2 isoform dHomo sapiens (human)Potency35.48130.01789.637444.6684AID588834
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency28.18380.00798.23321,122.0200AID2551
gemininHomo sapiens (human)Potency14.12540.004611.374133.4983AID463097
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency5.01190.031610.279239.8107AID884; AID885
M-phase phosphoprotein 8Homo sapiens (human)Potency89.12510.177824.735279.4328AID488949
muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Potency17.78280.00106.000935.4813AID943
pyruvate kinase PKM isoform bHomo sapiens (human)Potency0.00792.511912.262825.1189AID954; AID958
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency39.81070.00638.235039.8107AID883
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

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)33.00000.00010.995010.0000AID162488
[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 (10)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
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)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID524796Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID524795Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
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.
AID524791Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
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.
AID521220Inhibition of neurosphere proliferation of mouse neural precursor cells by MTT assay2007Nature chemical biology, May, Volume: 3, Issue:5
Chemical genetics reveals a complex functional ground state of neural stem cells.
AID524790Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay2009Nature chemical biology, Oct, Volume: 5, Issue:10
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID493017Wombat Data for BeliefDocking2000Journal 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 (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (53.85)29.6817
2010's4 (30.77)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.81

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 Index17.81 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.81)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]