Page last updated: 2024-11-08

3-((3-trifluoromethyl)phenyl)-5-((3-carboxyphenyl)methylene)-2-thioxo-4-thiazolidinone

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

Description

3-((3-trifluoromethyl)phenyl)-5-((3-carboxyphenyl)methylene)-2-thioxo-4-thiazolidinone: a cystic fibrosis transmembrane conductance regulator inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1554208
CHEMBL ID461939
MeSH IDM0462907

Synonyms (28)

Synonym
BIM-0044592.P001
3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone
EC-000.1908
3-((3-trifluoromethyl)phenyl)-5-((3-carboxyphenyl)methylene)-2-thioxo-4-thiazolidinone
bdbm50244767
4-[[4-oxo-2-thioxo-3-[3-(trifluoromethyl)phenyl]-5-thiazolidinylidene]methyl]benzoic acid
4-((4-oxo-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-5-ylidene)methyl)benzoic acid
STL032754
4-[(z)-{4-oxo-2-thioxo-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene}methyl]benzoic acid
AKOS000365470
CHEMBL461939 ,
CFTR INHIBITOR 172 ,
cfinh-172
4-[4-oxo-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-5z)-ylidenemethyl]-benzoic acid
4-{[(5z)-4-oxo-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-5-ylidene]methyl}benzoic acid
4-[4-oxo-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-(5z)-ylidenemethyl]-benzoic acid
CS-3185
HY-16671
cftr inh-172
AC-32674
benzoic acid, 4-[[4-oxo-2-thioxo-3-[3-(trifluoromethyl)phenyl]-5-thiazolidinylidene]methyl]-
J-018109
(z)-4-((4-oxo-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-5-ylidene)methyl)benzoic acid
cftrinh 172; cftr(inh)-172; cftr inhibitor-172
EX-A2298
BS-16477
C74583
4-[4-oxo-2-thioxo-3-(3-trifluoromethyl-phenyl)-thiazolidin-5-ylidenemethyl]-benzoic acid;
[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)
Cystic fibrosis transmembrane conductance regulatorHomo sapiens (human)IC50 (µMol)0.32670.30000.32670.3800AID363622; AID501144; AID619066
NACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)IC50 (µMol)6.39000.00502.180410.0000AID1667043
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (49)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
vesicle docking involved in exocytosisCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
bicarbonate transportCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cholesterol transportCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
response to endoplasmic reticulum stressCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
transepithelial water transportCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
positive regulation of insulin secretion involved in cellular response to glucose stimulusCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
positive regulation of exocytosisCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
sperm capacitationCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
multicellular organismal-level water homeostasisCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
intracellular pH elevationCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
establishment of localization in cellCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
transmembrane transportCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
membrane hyperpolarizationCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
positive regulation of enamel mineralizationCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cellular response to cAMPCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
amelogenesisCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
positive regulation of cyclic nucleotide-gated ion channel activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
chloride transmembrane transportCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
positive regulation of voltage-gated chloride channel activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cellular response to forskolinCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
pattern recognition receptor signaling pathwayNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of acute inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of type 2 immune responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
apoptotic processNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
defense responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
osmosensory signaling pathwayNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
detection of biotic stimulusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of interleukin-1 beta productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of interleukin-1 beta productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of interleukin-4 productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
NLRP3 inflammasome complex assemblyNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
innate immune responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of T-helper 2 cell differentiationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of inflammatory responseNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of NF-kappaB transcription factor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein homooligomerizationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein maturationNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
pyroptosisNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cellular response to lipopolysaccharideNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cellular response to virusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
negative regulation of non-canonical NF-kappaB signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of T-helper 2 cell cytokine productionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
positive regulation of cysteine-type endopeptidase activity involved in apoptotic processNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (30)

Processvia Protein(s)Taxonomy
chloride channel activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
intracellularly ATP-gated chloride channel activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
protein bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
ATP bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
bicarbonate transmembrane transporter activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
chloride transmembrane transporter activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
isomerase activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
ATP hydrolysis activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
chloride channel regulator activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
chloride channel inhibitor activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
enzyme bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
PDZ domain bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
protein-folding chaperone bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
Sec61 translocon complex bindingCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
ABC-type transporter activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
ATPase-coupled transmembrane transporter activityCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
protein bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ATP bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ATP hydrolysis activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
protein-macromolecule adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
signaling adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
identical protein bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
peptidoglycan bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
ADP bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
sequence-specific DNA bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
molecular adaptor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
phosphatidylinositol-4-phosphate bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
DNA-binding transcription factor bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
small molecule sensor activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cysteine-type endopeptidase activator activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
molecular condensate scaffold activityNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
phosphatidylinositol phosphate bindingNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (25)

Processvia Protein(s)Taxonomy
nucleusCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cytoplasmCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
lysosomal membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
early endosomeCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
endoplasmic reticulum membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cytosolCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
plasma membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cell surfaceCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
endosome membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
apical plasma membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
Golgi-associated vesicle membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
clathrin-coated endocytic vesicle membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
early endosome membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
recycling endosomeCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
recycling endosome membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
protein-containing complexCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
chloride channel complexCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cytosolCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
plasma membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
apical plasma membraneCystic fibrosis transmembrane conductance regulatorHomo sapiens (human)
cytoplasmNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytosolNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
membraneNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
Golgi membraneNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
extracellular regionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
nucleusNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytoplasmNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
mitochondrionNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
endoplasmic reticulumNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
microtubule organizing centerNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
cytosolNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
interphase microtubule organizing centerNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
NLRP3 inflammasome complexNACHT, LRR and PYD domains-containing protein 3 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1667040Inhibition of NLRP3 inflammasome (unknown origin) activation in LPS-primed bone marrow derived macrophage cells at 10 uM in presence of mono sodium urate relative to control2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID363624Cytotoxicity against rat FRT cells assessed as cell viability at 20 uM after 48 hrs by crystal violet staining2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Thiazolidinone CFTR inhibitors with improved water solubility identified by structure-activity analysis.
AID501144Inhibition of CFTR2009Journal of medicinal chemistry, Oct-22, Volume: 52, Issue:20
Nanomolar potency pyrimido-pyrrolo-quinoxalinedione CFTR inhibitor reduces cyst size in a polycystic kidney disease model.
AID1667046Half life in mouse liver microsomes in presence of NADPH2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID363623Solubility in phosphate buffered saline2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Thiazolidinone CFTR inhibitors with improved water solubility identified by structure-activity analysis.
AID1667047Clearance in mouse liver microsomes in presence of NADPH2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID363622Inhibition of human wild type CFTR expressed in rat FRT cells assessed as chloride current by short-circuit current measurements2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
Thiazolidinone CFTR inhibitors with improved water solubility identified by structure-activity analysis.
AID619066Inhibition of CFTR2011Journal of medicinal chemistry, Aug-11, Volume: 54, Issue:15
Potent, metabolically stable benzopyrimido-pyrrolo-oxazine-dione (BPO) CFTR inhibitors for polycystic kidney disease.
AID1667045Clearance in human liver microsomes in presence of NADPH2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667041Inhibition of CFTR in human HT-29 cells assessed as effect on intracellular chloride efflux at 20 uM relative to control2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667043Inhibition of NLRP3 inflammasome (unknown origin) activation in LPS-primed bone marrow derived macrophage cells assessed as effect on IL-1beta production in presence of nigericin by ELISA2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667044Half life in human liver microsomes in presence of NADPH2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667064Inhibition of NLRP3 inflammasome (unknown origin) assessed as suppression of mono sodium urate-induced caspase 1 activation by immunoblot analysis2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667065Inhibition of NLRP3 inflammasome (unknown origin) assessed as suppression of mono sodium urate-induced IL-1beta level by immunoblot analysis2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
AID1667042Selectivity index, ratio of inhibition of NLRP3 inflammasome (unknown origin) activation in bone marrow derived macrophage cells at 10 uM to inhibition of CFTR in human HT-29 cells at 20 uM2020Bioorganic & medicinal chemistry letters, 04-01, Volume: 30, Issue:7
Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (66)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's21 (31.82)29.6817
2010's41 (62.12)24.3611
2020's4 (6.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.52%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other65 (98.48%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]