Page last updated: 2024-12-08

sc 57666

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

Cross-References

ID SourceID
PubMed CID443373
CHEMBL ID274893
CHEBI ID8982
SCHEMBL ID213008
MeSH IDM0285961

Synonyms (24)

Synonym
(sc-57666)1-[2-(4-fluorophenyl)-1-cyclopentenyl]-4-methylsulfonylbenzene
bdbm50029614
1-fluoro-4-[2-(4-methylsulfonylphenyl)-1-cyclopentenyl]benzene
1-fluoro-4-{2-[4-(methylsulfonyl)phenyl]cyclopent-1-en-1-yl}benzene
1-[2-(4-fluorophenyl)-1-cyclopentenyl]-4-methylsulfonylbenzene
1-[2(4-flurophenyl)-1-cyclopentyl]4-methylsulfonylbenzene
sc-57666 ,
CHEMBL274893 ,
chebi:8982 ,
AC1L9EJK ,
1-fluoro-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene
SCHEMBL213008
1-[2-(4-fluorophenyl) cyclopenten-1-yl]-4- (methylsulfonyl)benzene
GJGZQTGPOKPFES-UHFFFAOYSA-N
1-[2-(4-fluorophenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene
dnc003789
surecn213008
HY-U00129
CS-7166
sc57666
Q27108201
158959-32-1
MS-24667
AKOS040737690

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Methyl sulfone 55 and sulfonamide 24 were shown to have superior in vivo pharmacological profiles, low GI toxicity, and good oral bioavailability and duration of action."( Diarylspiro[2.4]heptenes as orally active, highly selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationships.
Anderson, GD; Burton, EG; Chamberlain, TS; Cogburn, JN; Garland, DJ; Gregory, SA; Huang, HC; Isakson, PC; Koboldt, CM; Li, JJ; Manning, RE; Perkins, WE; Reinhard, EJ; Reitz, DB; Seibert, K; Veenhuizen, AW; Zhang, Y, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Homo sapiens (human)IC50 (µMol)455.71430.00021.557410.0000AID161335; AID161655; AID161661; AID161674; AID161679; AID161680
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)0.12580.00010.995010.0000AID1532167; AID160237; AID160434; AID162346; AID162645; AID162653; AID162665; AID162671
[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 (22)

Assay IDTitleYearJournalArticle
AID161674Tested for inhibition against Prostaglandin G/H synthase 11994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Selective cyclooxygenase inhibitors: novel 1,2-diarylcyclopentenes are potent and orally active COX-2 inhibitors.
AID13999Oral bioavailability in rat (dose 10 mg/kg)1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Diarylspiro[2.4]heptenes as orally active, highly selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationships.
AID234944Ratio of IC50 for COX-1 and COX-2 binding inhibitors1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Selective cyclooxygenase inhibitors: novel 1,2-diarylcyclopentenes are potent and orally active COX-2 inhibitors.
AID162337Effective dose for inhibition of Prostaglandin G/H synthase 21994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Selective cyclooxygenase inhibitors: novel 1,2-diarylcyclopentenes are potent and orally active COX-2 inhibitors.
AID161680Inhibition of Prostaglandin G/H synthase 1 (COX-1).1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
New cyclooxygenase-2/5-lipoxygenase inhibitors. 2. 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations of the dihydrobenzofuran ring.
AID234481Ratio IC50 for binding to COX-1 and COX-21998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
New cyclooxygenase-2/5-lipoxygenase inhibitors. 2. 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations of the dihydrobenzofuran ring.
AID162665Tested for inhibition against Prostaglandin G/H synthase 21994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
Selective cyclooxygenase inhibitors: novel 1,2-diarylcyclopentenes are potent and orally active COX-2 inhibitors.
AID160237Inhibition of Prostaglandin G/H synthase 2 (COX-2).1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
New cyclooxygenase-2/5-lipoxygenase inhibitors. 2. 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations of the dihydrobenzofuran ring.
AID19338Half life in rat1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Diarylspiro[2.4]heptenes as orally active, highly selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationships.
AID160434Inhibition of human Prostaglandin G/H synthase 22001Journal of medicinal chemistry, Sep-27, Volume: 44, Issue:20
Three-dimensional quantitative structure-activity relationships of cyclo-oxygenase-2 (COX-2) inhibitors: a comparative molecular field analysis.
AID162346In vitro inhibition of prostaglandin G/H synthase 2 (COX-2).1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.
AID162653Inhibitory activity against prostaglandin G/H synthase 2 (COX-2).1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Diarylspiro[2.4]heptenes as orally active, highly selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationships.
AID162671Concentration (in uM) to inhibit 50% of Prostaglandin G/H synthase 2 (COX-2) and is expressed in IC50.1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
New cyclooxygenase-2/5-lipoxygenase inhibitors. 1. 7-tert-buty1-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: discovery and variation of the 5-keto substituent.
AID161655Inhibitory activity against prostaglandin G/H synthase 1 (COX-1)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
New cyclooxygenase-2/5-lipoxygenase inhibitors. 3. 7-tert-butyl-2, 3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations at the 5 position.
AID162645Inhibitory activity against prostaglandin G/H synthase 2 (COX-2)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
New cyclooxygenase-2/5-lipoxygenase inhibitors. 3. 7-tert-butyl-2, 3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations at the 5 position.
AID161679Concentration (in uM) to inhibit 50% of Prostaglandin G/H synthase 1 (COX-1) and is expressed in IC50.1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
New cyclooxygenase-2/5-lipoxygenase inhibitors. 1. 7-tert-buty1-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: discovery and variation of the 5-keto substituent.
AID161335In vitro inhibition of prostaglandin G/H synthase 1.1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.
AID1532167Inhibition of recombinant human COX-2 expressed in Baculovirus infected sf9 cells using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 10 mins by ELISA2019European journal of medicinal chemistry, Jan-15, Volume: 162Medicinal chemistry of vicinal diaryl scaffold: A mini review.
AID182550Compound was tested for the inhibition of Carrageenan-induced Paw Edema in rat at 30 mg/kg1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.
AID233584Ratio of IC50 of COX-1 to COX-2.1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.
AID185616compound was tested for the inhibition of Adjuvant-Induced Arthritis in Rat in Rat at 1 mg/kg1995Journal of medicinal chemistry, Oct-27, Volume: 38, Issue:22
1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.
AID161661Inhibitory activity against prostaglandin G/H synthase 1 (COX-1).1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Diarylspiro[2.4]heptenes as orally active, highly selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationships.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's6 (75.00)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)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: 12.16

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 Index12.16 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]