Page last updated: 2024-12-11

era-923

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Description

2-(4-hydroxyphenyl)-3-methyl-1-(4-(2-piperidin-1-yl-ethoxy)-benzyl)-1H-indol-5-ol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6433099
CHEMBL ID44426
SCHEMBL ID134583
MeSH IDM0405387

Synonyms (26)

Synonym
era-923
pipendoxifene
2-(4-hydroxyphenyl)-3-methyl-1-(4-(2-piperidin-1-yl-ethoxy)-benzyl)-1h-indol-5-ol
CHEMBL44426 ,
us8815934, no. 97
2-(4-hydroxy-phenyl)-3-methyl-1-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-1h-indol-5-ol
bdbm50099587
us8815934, no. 107
2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol
198480-55-6
1h-indol-5-ol, 2-(4-hydroxyphenyl)-3-methyl-1-((4-(2-(1-piperidinyl)ethoxy)phenyl)methyl)-
era 923
pipendoxifene [inn]
unii-tpc5q8496g
2-(p-hydroxyphenyl)-3-methyl-1-(p-(2-piperidinoethoxy)benzyl)indol-5-ol
tpc5q8496g ,
JICOGKJOQXTAIP-UHFFFAOYSA-N
DB05414
SCHEMBL134583
pipendoxifene [who-dd]
2-(4-hydroxyphenyl)-3-methyl-1-(4-(2-(piperidin-1-yl)ethoxy)benzyl)-1h-indol-5-ol.
Q27095593
DTXSID40870209
CS-0007753
2-(4-hydroxyphenyl)-3-methyl-1-[[4-[2-(1-piperidinyl)ethoxy]phenyl]methyl]-1h-indol-5-ol
HY-13724

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" ERA-923 was well tolerated, and adverse events were mild and reversible."( Multiple-dose, safety, pharmacokinetics, and pharmacodynamics of a new selective estrogen receptor modulator, ERA-923, in healthy postmenopausal women.
Burghart, PH; Cotreau, MM; Dykstra, KH; Gandhi, T; Gutierrez, M; Park, Y; Schwertschlag, US; Stonis, L; Xu, J, 2002
)
1.44

Pharmacokinetics

ExcerptReferenceRelevance
" In addition, pharmacokinetic analysis showed that a high-fat breakfast increased the extent of absorption."( Multiple-dose, safety, pharmacokinetics, and pharmacodynamics of a new selective estrogen receptor modulator, ERA-923, in healthy postmenopausal women.
Burghart, PH; Cotreau, MM; Dykstra, KH; Gandhi, T; Gutierrez, M; Park, Y; Schwertschlag, US; Stonis, L; Xu, J, 2002
)
0.53

Bioavailability

ExcerptReferenceRelevance
" We describe the identification and characterization of a series of small-molecule, orally bioavailable SERDs which are potent antagonists and degraders of ER-α and in which the ER-α degrading properties were prospectively optimized."( Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
Aparicio, A; Bonnefous, C; Brigham, D; Darimont, B; Douglas, K; Govek, S; Grillot, K; Hager, JH; Heyman, R; Joseph, JD; Julien, J; Kahraman, M; Kaufman, J; Lai, A; Lee, KJ; Lu, N; Moon, MJ; Nagasawa, J; Prudente, R; Qian, J; Rix, PJ; Sensintaffar, J; Shao, G; Smith, ND, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" Overall, ERA-923 was safe and well tolerated in postmenopausal women dosed for 28 days."( Multiple-dose, safety, pharmacokinetics, and pharmacodynamics of a new selective estrogen receptor modulator, ERA-923, in healthy postmenopausal women.
Burghart, PH; Cotreau, MM; Dykstra, KH; Gandhi, T; Gutierrez, M; Park, Y; Schwertschlag, US; Stonis, L; Xu, J, 2002
)
0.93
[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)
Estrogen receptorHomo sapiens (human)IC50 (µMol)0.00780.00000.723732.7000AID102611; AID70008
Estrogen receptor betaHomo sapiens (human)IC50 (µMol)0.04000.00010.529432.7000AID70176
[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)
Estrogen receptorHomo sapiens (human)EC50 (µMol)0.00010.00000.53054.4000AID1228205
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (44)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
antral ovarian follicle growthEstrogen receptorHomo sapiens (human)
epithelial cell developmentEstrogen receptorHomo sapiens (human)
chromatin remodelingEstrogen receptorHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
signal transductionEstrogen receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEstrogen receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEstrogen receptorHomo sapiens (human)
androgen metabolic processEstrogen receptorHomo sapiens (human)
male gonad developmentEstrogen receptorHomo sapiens (human)
negative regulation of gene expressionEstrogen receptorHomo sapiens (human)
positive regulation of phospholipase C activityEstrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayEstrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptorHomo sapiens (human)
response to estradiolEstrogen receptorHomo sapiens (human)
regulation of toll-like receptor signaling pathwayEstrogen receptorHomo sapiens (human)
negative regulation of smooth muscle cell apoptotic processEstrogen receptorHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionEstrogen receptorHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
response to estrogenEstrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
fibroblast proliferationEstrogen receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEstrogen receptorHomo sapiens (human)
stem cell differentiationEstrogen receptorHomo sapiens (human)
regulation of inflammatory responseEstrogen receptorHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
RNA polymerase II preinitiation complex assemblyEstrogen receptorHomo sapiens (human)
uterus developmentEstrogen receptorHomo sapiens (human)
vagina developmentEstrogen receptorHomo sapiens (human)
prostate epithelial cord elongationEstrogen receptorHomo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesisEstrogen receptorHomo sapiens (human)
regulation of branching involved in prostate gland morphogenesisEstrogen receptorHomo sapiens (human)
mammary gland branching involved in pregnancyEstrogen receptorHomo sapiens (human)
mammary gland alveolus developmentEstrogen receptorHomo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongationEstrogen receptorHomo sapiens (human)
protein localization to chromatinEstrogen receptorHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptorHomo sapiens (human)
negative regulation of miRNA transcriptionEstrogen receptorHomo sapiens (human)
regulation of epithelial cell apoptotic processEstrogen receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptor betaHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptor betaHomo sapiens (human)
signal transductionEstrogen receptor betaHomo sapiens (human)
cell-cell signalingEstrogen receptor betaHomo sapiens (human)
negative regulation of cell growthEstrogen receptor betaHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptor betaHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptor betaHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptor betaHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptor betaHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptor betaHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
TFIIB-class transcription factor bindingEstrogen receptorHomo sapiens (human)
transcription coregulator bindingEstrogen receptorHomo sapiens (human)
transcription corepressor bindingEstrogen receptorHomo sapiens (human)
transcription coactivator bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
chromatin bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
nuclear receptor activityEstrogen receptorHomo sapiens (human)
steroid bindingEstrogen receptorHomo sapiens (human)
protein bindingEstrogen receptorHomo sapiens (human)
calmodulin bindingEstrogen receptorHomo sapiens (human)
beta-catenin bindingEstrogen receptorHomo sapiens (human)
zinc ion bindingEstrogen receptorHomo sapiens (human)
TBP-class protein bindingEstrogen receptorHomo sapiens (human)
enzyme bindingEstrogen receptorHomo sapiens (human)
protein kinase bindingEstrogen receptorHomo sapiens (human)
nitric-oxide synthase regulator activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor bindingEstrogen receptorHomo sapiens (human)
estrogen response element bindingEstrogen receptorHomo sapiens (human)
identical protein bindingEstrogen receptorHomo sapiens (human)
ATPase bindingEstrogen receptorHomo sapiens (human)
14-3-3 protein bindingEstrogen receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingEstrogen receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptor betaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptor betaHomo sapiens (human)
DNA bindingEstrogen receptor betaHomo sapiens (human)
nuclear steroid receptor activityEstrogen receptor betaHomo sapiens (human)
nuclear receptor activityEstrogen receptor betaHomo sapiens (human)
steroid bindingEstrogen receptor betaHomo sapiens (human)
protein bindingEstrogen receptor betaHomo sapiens (human)
zinc ion bindingEstrogen receptor betaHomo sapiens (human)
enzyme bindingEstrogen receptor betaHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptor betaHomo sapiens (human)
estrogen response element bindingEstrogen receptor betaHomo sapiens (human)
receptor antagonist activityEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
nucleusEstrogen receptorHomo sapiens (human)
nucleoplasmEstrogen receptorHomo sapiens (human)
transcription regulator complexEstrogen receptorHomo sapiens (human)
cytoplasmEstrogen receptorHomo sapiens (human)
Golgi apparatusEstrogen receptorHomo sapiens (human)
cytosolEstrogen receptorHomo sapiens (human)
plasma membraneEstrogen receptorHomo sapiens (human)
membraneEstrogen receptorHomo sapiens (human)
chromatinEstrogen receptorHomo sapiens (human)
euchromatinEstrogen receptorHomo sapiens (human)
protein-containing complexEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptor betaHomo sapiens (human)
nucleoplasmEstrogen receptor betaHomo sapiens (human)
mitochondrionEstrogen receptor betaHomo sapiens (human)
intracellular membrane-bounded organelleEstrogen receptor betaHomo sapiens (human)
chromatinEstrogen receptor betaHomo sapiens (human)
nucleusEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1228205Induction of estrogen receptor-alpha degradation in human MCF7 cells after 4 hrs by in-cell western assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228239Antagonist activity at estrogen receptor in human MCF7 cells assessed as inhibition of 17beta-estradiol-mediated transcriptional activation after 24 hrs by luciferase reporter gene assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID70176In vitro inhibitory concentration against [3H]17-beta-estradiol binding to human estrogen receptor 22001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.
AID70008In vitro inhibition of [3H]17-beta-estradiol binding to human estrogen receptor alpha2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.
AID1228231Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by CellTiter-Glo assay2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228237Displacement of [3H]-E2 from estrogen receptor-beta (unknown origin) by scintillation counting analysis2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228236Displacement of [3H]-E2 from estrogen receptor-alpha (unknown origin) by scintillation counting analysis2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228206Induction of estrogen receptor-alpha degradation in human MCF7 cells at 5.12 x 10'-12 to 10'-5 M after 4 hrs by in-cell western assay relative to control2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228310AUC in 17-beta estradiol pellets supplemented nu/nu mouse xenografted with tamoxifen-resistant human MCF7 cells at 100 mg/kg/day, po administered for 4 weeks measured on day 282015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228235Cytotoxicity against human MCF7 cells assessed as cell viability at 0.000005 to 10 uM after 5 days by CellTiter-Glo assay relative to fulvestrant2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228306Antitumor activity against tamoxifen-resistant human MCF7 cells xenografted in nu/nu mouse supplemented with 17-beta estradiol pellets assessed as tumor volume at 100 mg/kg/day, po administered for 4 weeks measured twice weekly during compound dosing rela2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID1228208Induction of estrogen receptor-alpha degradation in human MCF7 cells at 5.12 x 10'-12 to 10'-5 M after 4 hrs by in-cell western assay relative to fulvestrant2015Journal of medicinal chemistry, Jun-25, Volume: 58, Issue:12
Identification of GDC-0810 (ARN-810), an Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) that Demonstrates Robust Activity in Tamoxifen-Resistant Breast Cancer Xenografts.
AID102611In vitro antagonist effect on estrogen receptor alpha transcriptional activation in MCF-7 cells against 10 pM 17-beta-estradiol2001Journal of medicinal chemistry, May-24, Volume: 44, Issue:11
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (80.00)29.6817
2010's1 (20.00)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: 12.22

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 Index12.22 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (16.67%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (66.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]