Page last updated: 2024-11-09

sb 366791

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Description

N-(3-methoxyphenyl)-4-chlorocinnamanilide: a TRPV1 antagonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID667594
CHEMBL ID122413
CHEBI ID93038
MeSH IDM000613861

Synonyms (51)

Synonym
BRD-K59331372-001-01-2
sb-366791, >=98% (hplc), powder
bdbm20488
(2e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)prop-2-enamide
sb-366791
sb 366791
sb366791
sb-366,791
n-(3-methoxyphenyl)-4-chlorocinnamanilide
STK202522
CHEMBL122413
(e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)prop-2-enamide
3-(4-chlorophenyl)-n-(3-methoxyphenyl)prop-2-enamide
AKOS002529706
NCGC00025231-02
4'-chloro-3-methoxycinnamanilide
n-(3-methoxyphenyl)-4-chlorocinnamide
472981-92-3
2-propenamide, 3-(4-chlorophenyl)-n-(3-methoxyphenyl)-
S8238
gtpl4309
ES-0017
AC-32678
mfcd01033818
HY-12245
EX-A1109
sr-01000597592
SR-01000597592-1
CS-5658
CHEBI:93038
1649486-65-6
BCP17766
3-(4-chlorophenyl)-n-(3-methoxyphenyl)-2-propenamide
4-chloro-3-methoxycinnamanilide
(e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)acrylamide
sb366791 (sb-366791)
HMS3676N03
Q27088723
HMS3412N03
3-(4-chlorophenyl)-n-(3-methoxyphenyl)acrylamide
HMS3886F08
CCG-267355
(e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)prop-2-enamide.
XTA98192
A900888
(e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)-2-propenamide
e8ey4m2n4h ,
2-propenamide, 3-(4-chlorophenyl)-n-(3-methoxyphenyl)-, (2e)-
unii-e8ey4m2n4h
(2e)-3-(4-chlorophenyl)-n-(3-methoxyphenyl)-2-propenamide
ZEI ,

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Pre-treatment with SB 366791 (2 mg/kg, i.p.), a new TRPV1 antagonist, also abolished the hypothermia evoked by AM 404 (20 mg/kg, i.p.)."( Role of TRPV1 and cannabinoid CB1 receptors in AM 404-evoked hypothermia in rats.
Cowan, A; Ding, Z; Rawls, SM, 2006
)
0.65
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily V member 1Rattus norvegicus (Norway rat)IC50 (µMol)3.70000.00040.21474.0000AID1858391
Fatty-acid amide hydrolase 1Rattus norvegicus (Norway rat)IC50 (µMol)10.00000.00051.33138.0000AID1281385
Transient receptor potential cation channel subfamily M member 1Mus musculus (house mouse)IC50 (µMol)0.00600.00600.00600.0060AID1775866
Transient receptor potential cation channel subfamily M member 8Homo sapiens (human)IC50 (µMol)10.00000.02001.27553.9000AID1775865
Transient receptor potential cation channel subfamily V member 1Homo sapiens (human)IC50 (µMol)0.23000.00020.606010.0000AID1281384; AID1281386
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transient receptor potential cation channel subfamily V member 1Homo sapiens (human)EC50 (µMol)0.02000.00051.06746.3096AID1797977
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
intracellular calcium ion homeostasisTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
response to coldTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
positive regulation of cold-induced thermogenesisTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IITransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
fever generationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
microglial cell activationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
diet induced thermogenesisTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
peptide secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of systemic arterial blood pressureTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
lipid metabolic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cell surface receptor signaling pathwayTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chemosensory behaviorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of heart rateTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of mitochondrial membrane potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
glutamate secretionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium-mediated signalingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to heatTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of apoptotic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to peptide hormoneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
behavioral response to painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
sensory perception of mechanical stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in thermoceptionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of painTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein homotetramerizationTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory postsynaptic potentialTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
smooth muscle contraction involved in micturitionTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion transmembrane transportTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to alkaloidTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to ATPTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to tumor necrosis factorTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to acidic pHTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to temperature stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
negative regulation of establishment of blood-brain barrierTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium ion import across plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
response to capsazepineTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
cellular response to nerve growth factor stimulusTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
calcium channel activityTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
protein bindingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
ligand-gated calcium channel activityTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
transmembrane signaling receptor activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
voltage-gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
calmodulin bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
ATP bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
intracellularly gated calcium channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
chloride channel regulator activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphatidylinositol bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
identical protein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
metal ion bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
phosphoprotein bindingTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
temperature-gated ion channel activityTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
external side of plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
membrane raftTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily M member 8Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
external side of plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
dendritic spine membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
neuronal cell bodyTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
postsynaptic membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
plasma membraneTransient receptor potential cation channel subfamily V member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

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.
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.
AID1281385Inhibition of rat brain FAAH assessed as hydrolysis of [14C]AEA to [14C]Ethanolamine incubated for 30 mins by scintillation counting method2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Arylboronic acids as dual-action FAAH and TRPV1 ligands.
AID524794Antiplasmodial activity against Plasmodium falciparum GB4 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.
AID210793Antagonistic activity against human transient receptor potential vanilloid type 1 in FLIPR assay2004Bioorganic & medicinal chemistry letters, Jul-16, Volume: 14, Issue:14
Discovery of small molecule antagonists of TRPV1.
AID218332Agonistic activity against vanilloid receptor 1 (TRPV1)2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
Vanilloid receptor TRPV1 antagonists as the next generation of painkillers. Are we putting the cart before the horse?
AID1775866Inhibition of mouse TRPM1 expressed in HEK293T cells assessed as blocked of capsaicin-activated current at 10 uM by whole cell patch clamp electrophysiology relative to control2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both In Vitro and In Vivo.
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.
AID1549771Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Fluo-4-AM dye based fluorescence assay2019European journal of medicinal chemistry, May-15, Volume: 170N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.
AID1281384Antagonist activity at recombinant human TRPV1 channel expressed in HEK293 cells assessed as inhibition of capsiacin-induced Ca2+ flux preincubated for 5 mins followed by capsiacin challenge by Fluo-4-AM dye based spectrofluorimetry2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Arylboronic acids as dual-action FAAH and TRPV1 ligands.
AID1281386Antagonist activity at recombinant human TRPV1 channel expressed in CHO cells assessed as inhibition of capsiacin-induced Ca2+ flux by Fluo-3 dye based FLIPR assay2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Arylboronic acids as dual-action FAAH and TRPV1 ligands.
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.
AID1775865Inhibition of human TRPM8 expressed in HEK293T cells assessed as blocked of menthol-activated current by whole cell patch clamp electrophysiology relative to control2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both In Vitro and In Vivo.
AID1281383Agonist activity at recombinant human TRPV1 channel expressed in HEK293 cells assessed as increase in intracellular Ca2+ concentration by Fluo-4-AM dye based spectrofluorimetry2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Arylboronic acids as dual-action FAAH and TRPV1 ligands.
AID1858391Antagonist activity at rat TRPV1 expressed in human HEK293 cells assessed as inhibition of capsaicin-induced influx by measuring intracellular calcium accumulation by fura-2 dye based fluorimetric assay2022RSC medicinal chemistry, Oct-19, Volume: 13, Issue:10
AID1281382Agonist activity at recombinant human TRPV1 channel expressed in HEK293 cells assessed as increase in intracellular Ca2+ concentration by Fluo-4-AM dye based spectrofluorimetry relative to ionomycin2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Arylboronic acids as dual-action FAAH and TRPV1 ligands.
AID1797977FLIPR (Fluorescence Imaging Plate Reader)-Based Ca2+ Assay from Article 10.1016/j.bmcl.2004.05.028: \\Discovery of small molecule antagonists of TRPV1.\\2004Bioorganic & medicinal chemistry letters, Jul-16, Volume: 14, Issue:14
Discovery of small molecule antagonists of TRPV1.
AID1346617Human TRPV1 (Transient Receptor Potential channels)2004Neuropharmacology, Jan, Volume: 46, Issue:1
Identification and characterisation of SB-366791, a potent and selective vanilloid receptor (VR1/TRPV1) antagonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (117)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's41 (35.04)29.6817
2010's67 (57.26)24.3611
2020's9 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.16

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.16 (24.57)
Research Supply Index4.78 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other117 (99.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]