Page last updated: 2024-11-11

cp533536

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Description

CP533536: an EP2 receptor-selective prostaglandin E2 agonist that induces bone healing; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9890801
CHEMBL ID563646
CHEBI ID177472
SCHEMBL ID533264
MeSH IDM0451567

Synonyms (50)

Synonym
CHEBI:177472
2-[3-[[(4-tert-butylphenyl)methyl-pyridin-3-ylsulonylamino]methyl]phenoxy]acetic acid
223488-57-1
cj042794
cp533536
2-[3-[[(4-tert-butylphenyl)methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid
gtpl1929
GM9 ,
evatanepag ,
cp-533536
bdbm50293496
CHEMBL563646 ,
cp-533,536
2-(3-((n-(4-tert-butylbenzyl)pyridine-3-sulfonamido)methyl)phenoxy)acetic acid
evatanepag (usan/inn)
D09613
acetic acid, 2-(3-((((4-(1,1-dimethylethyl)phenyl)methyl)(3-pyridinylsulfonyl)amino)methyl)phenoxy)-
2-(3-((((4-(1,1-dimethylethyl)phenyl)methyl)(pyridin-3-ylsulfonyl)amino)methyl)phenoxy)acetic acid
evatanepag [usan:inn]
unii-l266r6e31e
l266r6e31e ,
evatanepag [who-dd]
evatanepag [usan]
evatanepag [inn]
SCHEMBL533264
AC-33701
CS-5571
HY-14839
AKOS030526731
2-[3-({n-[(4-tert-butylphenyl)methyl]pyridine-3-sulfonamido}methyl)phenoxy]acetic acid
WOHRHWDYFNWPNG-UHFFFAOYSA-N
(3-(((4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-methyl)-phenoxy)-acetic acid
A878589
evatanepag (cp-533536)
DB12022
BCP16478
evatanepag; cp-533536 free acid
EX-A2354
2-(3-((n-(4-(tert-butyl)benzyl)pyridine-3-sulfonamido)methyl)phenoxy)acetic acid
DTXSID20945000
[3-({[(4-tert-butylphenyl)methyl](pyridine-3-sulfonyl)amino}methyl)phenoxy]acetic acid
Q27077249
cp-533536 free acid
N16936
AU-075/43517630
(3-{[(4-tert-butylbenzyl)(3-pyridinylsulfonyl)amino]methyl}phenoxy)acetic acid
BS-51414
cp-533536 free acidcp-533536 free acid
2-[3-[n-(4-tert-butylbenzyl)-n-(pyridin-3-ylsulfonyl)aminomethyl]phenoxy]acetic acid
2-[3-[[(4-~{tert}-butylphenyl)methyl-pyridin-3-ylsulfonyl-amino]methyl]phenoxy]ethanoic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy 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 (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin E2 receptor EP1 subtypeHomo sapiens (human)Ki2.80000.00910.66351.5849AID1151360
Prostaglandin E2 receptor EP4 subtypeHomo sapiens (human)Ki3.20000.00010.47443.1623AID1151362
Prostaglandin E2 receptor EP4 subtypeRattus norvegicus (Norway rat)IC50 (µMol)3.20000.00210.00210.0021AID419200
Prostaglandin E2 receptor EP3 subtypeHomo sapiens (human)Ki2.80000.00031.70816.8000AID1151361
Prostaglandin E2 receptor EP2 subtypeHomo sapiens (human)Ki0.05000.00100.54483.0000AID1151359
Prostacyclin receptorHomo sapiens (human)Ki3.20000.00320.49586.6280AID1151363
Prostaglandin E2 receptor EP2 subtypeRattus norvegicus (Norway rat)IC50 (µMol)0.05000.00520.02760.0500AID419199
[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)
Prostaglandin E2 receptor EP2 subtypeHomo sapiens (human)EC50 (µMol)0.00500.00190.96657.8000AID1151368
Prostaglandin E2 receptor EP2 subtypeRattus norvegicus (Norway rat)EC50 (µMol)0.00030.00020.00650.0190AID419201
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
adenylate cyclase-activating dopamine receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
negative regulation of cytokine productionProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of cytokine productionProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
immune responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
JNK cascadeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to mechanical stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to nematodeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
regulation of ossificationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of integrin activationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
T-helper cell differentiationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
regulation of stress fiber assemblyProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
bone developmentProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
ERK1 and ERK2 cascadeProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
cellular response to mechanical stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
negative regulation of eosinophil extravasationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
cellular response to prostaglandin E stimulusProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
cell deathProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of fever generationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
intestine smooth muscle contractionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
negative regulation of gastric acid secretionProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to nematodeProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to lipopolysaccharideProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
response to progesteroneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
regulation of cell population proliferationProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
cellular response to prostaglandin E stimulusProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
inflammatory responseProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerProstacyclin receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
cell-cell signalingProstacyclin receptorHomo sapiens (human)
negative regulation of platelet-derived growth factor receptor signaling pathwayProstacyclin receptorHomo sapiens (human)
response to lipopolysaccharideProstacyclin receptorHomo sapiens (human)
negative regulation of smooth muscle cell proliferationProstacyclin receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationProstacyclin receptorHomo sapiens (human)
inflammatory responseProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
D1 dopamine receptor bindingProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
protein bindingProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
prostaglandin E receptor activityProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
guanyl-nucleotide exchange factor activityProstacyclin receptorHomo sapiens (human)
prostacyclin receptor activityProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP1 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP4 subtypeHomo sapiens (human)
nuclear envelopeProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP3 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
plasma membraneProstaglandin E2 receptor EP2 subtypeHomo sapiens (human)
cytosolProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
plasma membraneProstacyclin receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID419204Volume of distribution at steady state in Sprague-Dawley rat at 1 mg/kg, iv2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419208Induction of bone formation in mouse assessed as total bone area at 1 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419201Agonist activity against rat EP2 receptor expressed in HEK293 cells assessed as stimulation of cAMP release2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1151376Selectivity ratio of Ki for DP1 receptor (unknown origin) to Ki for EP2 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID419213Induction of bone formation in mouse assessed as bone mineral density at 3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1151361Binding affinity to EP3 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151373Selectivity ratio of Ki for EP4 receptor (unknown origin) to Ki for EP2 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID419199Inhibition of rat EP2 receptor expressed in HEK293 cells2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419211Induction of bone formation in mouse assessed as total bone area at 3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419212Induction of bone formation in mouse assessed as bone mineral content at 3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419203Clearance in Sprague-Dawley rat at 1 mg/kg, iv2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419210Induction of bone formation in mouse assessed as bone mineral density at 1 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419200Inhibition of rat EP4 receptor expressed in HEK293 cells2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419202Half life in Sprague-Dawley rat at 1 mg/kg, iv2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1151359Binding affinity to EP2 receptor (unknown origin) by competitive binding assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID419209Induction of bone formation in mouse assessed as bone mineral content at 1 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID419206Induction of bone formation in mouse assessed as bone mineral content at 0.3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1151360Binding affinity to EP1 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID419205Induction of bone formation in mouse assessed as total bone area at 0.3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1151372Selectivity ratio of Ki for EP3 receptor (unknown origin) to Ki for EP2 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151369Agonist activity at prostanoid IP receptor (unknown origin) by functional assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151363Binding affinity to prostanoid IP receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151371Selectivity ratio of Ki for EP1 receptor (unknown origin) to Ki for EP2 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151362Binding affinity to EP4 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151374Selectivity ratio of Ki for prostanoid IP receptor (unknown origin) to Ki for EP2 receptor (unknown origin)2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID1151368Agonist activity at EP2 receptor (unknown origin) by functional assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Prostanoid receptor EP2 as a therapeutic target.
AID419207Induction of bone formation in mouse assessed as bone mineral density at 0.3 mg/kg by peripheral quantitative computerized tomography2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1346318Rat EP2 receptor (Prostanoid receptors)2009Bioorganic & medicinal chemistry letters, Apr-01, Volume: 19, Issue:7
Discovery of CP-533536: an EP2 receptor selective prostaglandin E2 (PGE2) agonist that induces local bone formation.
AID1346427Human EP4 receptor (Prostanoid receptors)2008Life sciences, Jan-16, Volume: 82, Issue:3-4
In vitro pharmacological characterization of CJ-042794, a novel, potent, and selective prostaglandin EP(4) receptor antagonist.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (66.67)29.6817
2010's4 (33.33)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: 11.81

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 Index11.81 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]