Page last updated: 2024-11-07

3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5h)-furanone

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

Description

3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID127923
CHEMBL ID18264
SCHEMBL ID2159864
MeSH IDM0268475

Synonyms (19)

Synonym
3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)furan-2(5h)-one
3-(3,4-difluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-5h-furan-2-one
bdbm50078688
mf-tricyclic
162011-83-8
3-(3,4-difluorophenyl)4-(4-(methylsulfonyl)phenyl)-2-(5h)-furanone
merck frosst tricyclic
mf tricyclic
2(5h)-furanone, 3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-
3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5h)-furanone
CHEMBL18264 ,
4-(3,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one
SCHEMBL2159864
3-(3.4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5h)-furanone
3 -(3,4- difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5h)-furanone
INRQTVDUZFESAO-UHFFFAOYSA-N
3-(3,4-difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2-(5h)-furanone
DTXSID30167291
3-(3,4-difluorophenyl)-4-(4-methylsulfonylphenyl)-5h-furan-2-one

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" Thus, combination with a TP antagonist might reveal an antiinflammatory effect of a COX-2 inhibitor in this disease."( Cyclooxygenases, thromboxane, and atherosclerosis: plaque destabilization by cyclooxygenase-2 inhibition combined with thromboxane receptor antagonism.
Egan, KM; FitzGerald, GA; Fries, S; Lawson, JA; Lucitt, MB; Puré, E; Wang, M; Zukas, AM, 2005
)
0.33
" Combination with the COX-2 inhibitor failed to augment the impact of TP antagonism alone on lesion area."( Cyclooxygenases, thromboxane, and atherosclerosis: plaque destabilization by cyclooxygenase-2 inhibition combined with thromboxane receptor antagonism.
Egan, KM; FitzGerald, GA; Fries, S; Lawson, JA; Lucitt, MB; Puré, E; Wang, M; Zukas, AM, 2005
)
0.33
" Despite early intervention, selective inhibition of COX-2, alone or in combination with a TP antagonist, failed to modify disease progression but may undermine plaque stability when combined with the antagonist."( Cyclooxygenases, thromboxane, and atherosclerosis: plaque destabilization by cyclooxygenase-2 inhibition combined with thromboxane receptor antagonism.
Egan, KM; FitzGerald, GA; Fries, S; Lawson, JA; Lucitt, MB; Puré, E; Wang, M; Zukas, AM, 2005
)
0.33

Dosage Studied

ExcerptRelevanceReference
"A water soluble choline prodrug (17) of a COX-2 selective inhibitor (16) suitable for intravenous dosing in models of cerebral ischemia has been developed."( Water soluble prodrug of a COX-2 selective inhibitor suitable for intravenous administration in models of cerebral ischemia.
Chen, W; Correa, L; Cramer, M; Lorrain, D; Munoz, B; Payne, J; Prasit, P; Reger, TS; Smith, ND; Stock, N; Yang, J; Zunic, J, 2005
)
0.33
[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 1Homo sapiens (human)IC50 (µMol)54.33330.00021.557410.0000AID161484; AID161485; AID161659
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)0.38670.00010.995010.0000AID162494; AID162495; AID162650
[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 (16)

Assay IDTitleYearJournalArticle
AID161672Inhibitory potency against Prostaglandin G/H synthase 1 in human whole blood assay2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.
AID162663Inhibitory potency against cyclooxygenase-2 in human whole blood assay2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.
AID161485In vitro inhibitory activity against human whole cells Prostaglandin G/H synthase 11999Bioorganic & medicinal chemistry letters, Jul-05, Volume: 9, Issue:13
The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor.
AID241198Inhibitory concentration against prostaglandin G/H synthase 2 in human whole blood2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Water soluble prodrug of a COX-2 selective inhibitor suitable for intravenous administration in models of cerebral ischemia.
AID1595204Inhibition of COX2 in rabbit whole blood assessed as reduction of LPS-induced PGE2 accumulation at 10 to 10000 nM preincubated with LPS followed by compound addition and incubated for 6 or 24 hrs by EIA method2019European journal of medicinal chemistry, Jun-01, Volume: 171Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.
AID244119Selectivity for prostaglandin G/H synthase 2 in human whole blood2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Water soluble prodrug of a COX-2 selective inhibitor suitable for intravenous administration in models of cerebral ischemia.
AID1595205Antiinflammatory activity in carrageenan-induced C57Bl/6 mouse model of inflammation assessed as inhibition of PGE2 accumulation in air pouch at 0.1 to 10 mg/kg po pretreated with carrageenan for 20 hrs and followed by compound administration and measured2019European journal of medicinal chemistry, Jun-01, Volume: 171Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.
AID162650Inhibitory activity against recombinant human Prostaglandin G/H synthase 22004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.
AID161484In vitro inhibitory activity against human whole blood Prostaglandin G/H synthase 11999Bioorganic & medicinal chemistry letters, Jul-05, Volume: 9, Issue:13
The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor.
AID162495In vitro inhibitory activity against human whole cells (CHO) Prostaglandin G/H synthase 21999Bioorganic & medicinal chemistry letters, Jul-05, Volume: 9, Issue:13
The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor.
AID241196Inhibitory concentration against prostaglandin G/H synthase 1 in human whole blood2005Bioorganic & medicinal chemistry letters, Jul-01, Volume: 15, Issue:13
Water soluble prodrug of a COX-2 selective inhibitor suitable for intravenous administration in models of cerebral ischemia.
AID459024Analgesic activity against complete Freund's adjuvant-induced Sprague-Dawley rat inflammatory pain assessed as inhibition of chronic paw swelling2010Journal of medicinal chemistry, Mar-11, Volume: 53, Issue:5
The discovery of 4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic acid (MK-2894), a potent and selective prostaglandin E2 subtype 4 receptor antagonist.
AID162494In vitro inhibitory activity against human whole blood Prostaglandin G/H synthase 21999Bioorganic & medicinal chemistry letters, Jul-05, Volume: 9, Issue:13
The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor.
AID459023Analgesic activity in po dosed Sprague-Dawley rat assessed as inhibition of carrageenan-induced mechanical hyperalgesia relative to control2010Journal of medicinal chemistry, Mar-11, Volume: 53, Issue:5
The discovery of 4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic acid (MK-2894), a potent and selective prostaglandin E2 subtype 4 receptor antagonist.
AID1595203Inhibition of COX2 in guinea pig blood assessed as reduction of LPS-induced PGE2 accumulation at 10 to 10000 nM preincubated with LPS followed by compound addition and incubated for 6 or 24 hrs by EIA method2019European journal of medicinal chemistry, Jun-01, Volume: 171Insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore.
AID161659Inhibitory activity against recombinant human prostaglandin G/H synthase 12004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (21.74)18.2507
2000's15 (65.22)29.6817
2010's3 (13.04)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: 11.39

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 Index11.39 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.39)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (8.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (92.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]