Page last updated: 2024-11-13

thiouredopyrenetrisulfonate

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

Description

N-[1-(methanesulfonyl)piperidin-4-yl]-N'-[4-(trifluoromethoxy)phenyl]urea : A phenylurea that is urea substituted by 1-(methylsulfonyl)piperidin-4-yl and 4-(trifluoromethoxy)phenyl groups at positions 1 and 3 respectively. [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]

Cross-References

ID SourceID
PubMed CID25093353
CHEMBL ID1257634
CHEBI ID142793
SCHEMBL ID1913735
MeSH IDM0334076

Synonyms (18)

Synonym
urea-based compound, 26
bdbm25745
3-(1-methanesulfonylpiperidin-4-yl)-1-[4-(trifluoromethoxy)phenyl]urea
smr001339075
MLS002415560
n-[1-(methylsulfonyl)piperidin-4-yl]-n'-[4-(trifluoromethoxy)phenyl]urea
n-[1-(methanesulfonyl)piperidin-4-yl]-n'-[4-(trifluoromethoxy)phenyl]urea
CHEBI:142793
n-(1-mesylpiperidin-4-yl)-n'-[4-(trifluoromethoxy)phenyl]urea
sehi, #1709
CHEMBL1257634
SCHEMBL1913735
HMS2199F22
1-(1-(methylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea
tups
1-(1-methanesulfonyl-piperidin-4-yl)-3-(4-trifluoromethoxy-phenyl)-urea
950184-27-7
1-(1-methylsulfonylpiperidin-4-yl)-3-[4-(trifluoromethoxy)phenyl]urea

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors in mice revealed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors."( 1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain.
Hammock, BD; Inceoglu, B; Jones, PD; Liu, JY; Morisseau, C; Rose, TE; Sanborn, JR, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 3.3.2.10 (soluble epoxide hydrolase) inhibitorAny inhibitor of soluble epoxide hydrolase, a bifunctional enzyme that in humans is encoded by the EPHX2 gene.Found in both the cytosol and peroxisomes it binds to specific epoxides and converts them into the corresponding diols.
[role 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]

Drug Classes (1)

ClassDescription
phenylureasAny member of the class of ureas in which at least one of the nitrogens of the urea moiety is substituted by a phenyl or substituted phenyl group.
[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 (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency39.81070.631035.7641100.0000AID504339
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency23.72460.000811.382244.6684AID686978; AID686979
importin subunit beta-1 isoform 1Homo sapiens (human)Potency1.83565.804836.130665.1308AID540253
snurportin-1Homo sapiens (human)Potency1.83565.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency1.83565.804816.996225.9290AID540253
[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)
RAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)IC50 (µMol)10.00000.00100.33498.9000AID756116
Bifunctional epoxide hydrolase 2Homo sapiens (human)IC50 (µMol)0.00290.00000.54509.1000AID517036; AID756127
Bifunctional epoxide hydrolase 2Mus musculus (house mouse)IC50 (µMol)0.00200.00170.05670.4220AID517038
Epoxide hydrolase BMycobacterium tuberculosis CDC1551IC50 (µMol)27.90000.01900.66403.4000AID1798579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
apoptotic processRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
protein phosphorylationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
signal transductionRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
activation of adenylate cyclase activityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
negative regulation of cell population proliferationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
insulin receptor signaling pathwayRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
extrinsic apoptotic signaling pathway via death domain receptorsRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
Schwann cell developmentRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
thyroid gland developmentRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
negative regulation of protein-containing complex assemblyRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
somatic stem cell population maintenanceRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
regulation of Rho protein signal transductionRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
insulin secretion involved in cellular response to glucose stimulusRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
response to muscle stretchRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
ERBB2-ERBB3 signaling pathwayRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
wound healingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
myelinationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
regulation of apoptotic processRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
negative regulation of apoptotic processRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
negative regulation of cysteine-type endopeptidase activity involved in apoptotic processRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
positive regulation of MAPK cascadeRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
type B pancreatic cell proliferationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
intermediate filament cytoskeleton organizationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
regulation of cell differentiationRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
insulin-like growth factor receptor signaling pathwayRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
neurotrophin TRK receptor signaling pathwayRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
thymus developmentRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
face developmentRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
type II interferon-mediated signaling pathwayRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
death-inducing signaling complex assemblyRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptorsRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
regulation of cell motilityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
MAPK cascadeRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
response to toxic substanceBifunctional epoxide hydrolase 2Homo sapiens (human)
positive regulation of gene expressionBifunctional epoxide hydrolase 2Homo sapiens (human)
dephosphorylationBifunctional epoxide hydrolase 2Homo sapiens (human)
cholesterol homeostasisBifunctional epoxide hydrolase 2Homo sapiens (human)
stilbene catabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
phospholipid dephosphorylationBifunctional epoxide hydrolase 2Homo sapiens (human)
regulation of cholesterol metabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
epoxide metabolic processBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (18)

Processvia Protein(s)Taxonomy
small GTPase bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
protein kinase activityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
protein serine/threonine kinase activityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
protein bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
ATP bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
enzyme bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
identical protein bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
metal ion bindingRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
protein serine kinase activityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
MAP kinase kinase kinase activityRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
magnesium ion bindingBifunctional epoxide hydrolase 2Homo sapiens (human)
epoxide hydrolase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
toxic substance bindingBifunctional epoxide hydrolase 2Homo sapiens (human)
phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
10-hydroxy-9-(phosphonooxy)octadecanoate phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
lipid phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
protein homodimerization activityBifunctional epoxide hydrolase 2Homo sapiens (human)
lysophosphatidic acid phosphatase activityBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
nucleusRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
cytoplasmRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
mitochondrial outer membraneRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
Golgi apparatusRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
cytosolRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
plasma membraneRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
pseudopodiumRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
cytosolRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
mitochondrionRAF proto-oncogene serine/threonine-protein kinaseHomo sapiens (human)
peroxisomeBifunctional epoxide hydrolase 2Homo sapiens (human)
peroxisomal matrixBifunctional epoxide hydrolase 2Homo sapiens (human)
cytosolBifunctional epoxide hydrolase 2Homo sapiens (human)
extracellular exosomeBifunctional epoxide hydrolase 2Homo sapiens (human)
peroxisomeBifunctional epoxide hydrolase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID517037Antiinflammatory activity in Sprague-Dawley rat assessed as reduction in carrageenan-induced inflammatory pain at 10 uL, intraplanter2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain.
AID756114Cytotoxicity against human HepG2 cells by MTT assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.
AID517035Lipophilicity, log P of the compound2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain.
AID756112Antiproliferative activity against HUVEC after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.
AID1186234Tmax in Swiss Webster mouse at 0.3 mg/kg, po administered as cassette dosing2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.
AID756127Inhibition of human recombinant soluble epoxide hydrolase assessed as cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxyran-2-yl)methyl] carbonate conversion to 6-methoxy-2-naphthaldehyde preincubated for 5 mins prior to substrate addition by fluo2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.
AID1186232Cmax in Swiss Webster mouse at 0.3 mg/kg, po administered as cassette dosing2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.
AID756116Inhibition of full length recombinant c-RAF (unknown origin) using MEK1 as substrate after 1 hr by luminescence assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.
AID756113Cytotoxicity against human HuH7 cells by MTT assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.
AID517036Inhibition of human recombinant soluble epoxide hydrolase by fluorescence assay2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain.
AID517038Inhibition of mouse recombinant soluble epoxide hydrolase by fluorescence assay2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain.
AID1186231AUC in Swiss Webster mouse at 0.3 mg/kg, po administered as cassette dosing2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.
AID1186233Half life in Swiss Webster mouse at 0.3 mg/kg, po administered as cassette dosing2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.
AID1186230Inhibition of human recombinant soluble epoxide hydrolase assessed as half-life of enzyme-inhibitor complex by FRET-based ACPU displacement assay2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.
AID1798579Mtb EHB Inhibition Assay from Article 10.1016/j.jmb.2008.06.030: \\The molecular structure of epoxide hydrolase B from Mycobacterium tuberculosis and its complex with a urea-based inhibitor.\\2008Journal of molecular biology, Sep-12, Volume: 381, Issue:4
The molecular structure of epoxide hydrolase B from Mycobacterium tuberculosis and its complex with a urea-based inhibitor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's6 (66.67)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.02

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 Index12.02 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]