Page last updated: 2024-12-07

4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile

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Description

4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile: a non-steroidal antiandrogen; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID132581
CHEMBL ID1099140
SCHEMBL ID1435262
MeSH IDM0238447

Synonyms (20)

Synonym
benzonitrile, 2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-
143782-25-6
4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile
unii-l6rt6e57ls
l6rt6e57ls ,
ru 56187
CHEMBL1099140 ,
ru-56187
2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-thioxoimidazolidin-1-yl)benzonitrile
bdbm50317664
2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl)benzonitrile
benzonitrile,2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-
SCHEMBL1435262
DTXSID90162545
2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxo-2-thioxo-1-imidazolidinyl)benzonitrile
hlbuakqnkjteiu-uhfffaoysa-n
2-(trifluoromethyl)-4-(3,4,4-trimethyl-5-oxidanylidene-2-sulfanylidene-imidazolidin-1-yl)benzenecarbonitrile
ru56187
4-(5-oxo-2-thioxo-3,4,4-trimethyl-1-imidazolidinyl)-2-trifluoromethylbenzonitrile
AKOS040749371

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Both compounds disappear relatively rapidly from the plasma (elimination half-life of the order of 1 h), but they form a common metabolite, the N-desalkyl derivative, RU 56279, which is eliminated much more slowly."( Preliminary pharmacokinetics and metabolism of novel non-steroidal antiandrogens in the rat: relation of their systemic activity to the formation of a common metabolite.
Battmann, T; Bergaud, B; Branche, C; Bruyant, MC; Cousty-Berlin, D; Philibert, D, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorHomo sapiens (human)IC50 (µMol)0.01500.00000.875310.0000AID478366
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorHomo sapiens (human)EC5 (µMol)0.00050.00010.05120.2000AID478367; AID478368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
MAPK cascadeAndrogen receptorHomo sapiens (human)
in utero embryonic developmentAndrogen receptorHomo sapiens (human)
regulation of systemic arterial blood pressureAndrogen receptorHomo sapiens (human)
epithelial cell morphogenesisAndrogen receptorHomo sapiens (human)
transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
signal transductionAndrogen receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAndrogen receptorHomo sapiens (human)
cell-cell signalingAndrogen receptorHomo sapiens (human)
spermatogenesisAndrogen receptorHomo sapiens (human)
single fertilizationAndrogen receptorHomo sapiens (human)
positive regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
negative regulation of cell population proliferationAndrogen receptorHomo sapiens (human)
positive regulation of gene expressionAndrogen receptorHomo sapiens (human)
male somatic sex determinationAndrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
intracellular receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of intracellular estrogen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
Leydig cell differentiationAndrogen receptorHomo sapiens (human)
multicellular organism growthAndrogen receptorHomo sapiens (human)
positive regulation of phosphorylationAndrogen receptorHomo sapiens (human)
positive regulation of MAPK cascadeAndrogen receptorHomo sapiens (human)
positive regulation of insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
positive regulation of cell differentiationAndrogen receptorHomo sapiens (human)
negative regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of integrin biosynthetic processAndrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIAndrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIIAndrogen receptorHomo sapiens (human)
insulin-like growth factor receptor signaling pathwayAndrogen receptorHomo sapiens (human)
regulation of developmental growthAndrogen receptorHomo sapiens (human)
animal organ formationAndrogen receptorHomo sapiens (human)
male genitalia morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell proliferationAndrogen receptorHomo sapiens (human)
negative regulation of epithelial cell proliferationAndrogen receptorHomo sapiens (human)
positive regulation of NF-kappaB transcription factor activityAndrogen receptorHomo sapiens (human)
activation of prostate induction by androgen receptor signaling pathwayAndrogen receptorHomo sapiens (human)
morphogenesis of an epithelial foldAndrogen receptorHomo sapiens (human)
lateral sprouting involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
prostate gland growthAndrogen receptorHomo sapiens (human)
prostate gland epithelium morphogenesisAndrogen receptorHomo sapiens (human)
epithelial cell differentiation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
tertiary branching involved in mammary gland duct morphogenesisAndrogen receptorHomo sapiens (human)
mammary gland alveolus developmentAndrogen receptorHomo sapiens (human)
positive regulation of epithelial cell proliferation involved in prostate gland developmentAndrogen receptorHomo sapiens (human)
cellular response to steroid hormone stimulusAndrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusAndrogen receptorHomo sapiens (human)
cellular response to testosterone stimulusAndrogen receptorHomo sapiens (human)
seminiferous tubule developmentAndrogen receptorHomo sapiens (human)
non-membrane-bounded organelle assemblyAndrogen receptorHomo sapiens (human)
positive regulation of miRNA transcriptionAndrogen receptorHomo sapiens (human)
regulation of protein localization to plasma membraneAndrogen receptorHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathwayAndrogen receptorHomo sapiens (human)
male gonad developmentAndrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingAndrogen receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
RNA polymerase II general transcription initiation factor bindingAndrogen receptorHomo sapiens (human)
transcription coactivator bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificAndrogen receptorHomo sapiens (human)
chromatin bindingAndrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityAndrogen receptorHomo sapiens (human)
nuclear receptor activityAndrogen receptorHomo sapiens (human)
G protein-coupled receptor activityAndrogen receptorHomo sapiens (human)
signaling receptor bindingAndrogen receptorHomo sapiens (human)
steroid bindingAndrogen receptorHomo sapiens (human)
androgen bindingAndrogen receptorHomo sapiens (human)
protein bindingAndrogen receptorHomo sapiens (human)
beta-catenin bindingAndrogen receptorHomo sapiens (human)
zinc ion bindingAndrogen receptorHomo sapiens (human)
enzyme bindingAndrogen receptorHomo sapiens (human)
ATPase bindingAndrogen receptorHomo sapiens (human)
molecular adaptor activityAndrogen receptorHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingAndrogen receptorHomo sapiens (human)
POU domain bindingAndrogen receptorHomo sapiens (human)
molecular condensate scaffold activityAndrogen receptorHomo sapiens (human)
estrogen response element bindingAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
plasma membraneAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
nucleoplasmAndrogen receptorHomo sapiens (human)
cytoplasmAndrogen receptorHomo sapiens (human)
cytosolAndrogen receptorHomo sapiens (human)
nuclear speckAndrogen receptorHomo sapiens (human)
chromatinAndrogen receptorHomo sapiens (human)
protein-containing complexAndrogen receptorHomo sapiens (human)
nucleusAndrogen receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID478371Agonist activity at AR in bicalutamide-resistant human LNCAP cells assessed as effect on cell proliferation after 6 days2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478368Activity at human AR expressed in human HeLa cells after 48 hrs by stable-luciferase reporter gene assay2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478367Activity at human AR expressed in human HeLa cells after 48 hrs by transient-luciferase reporter gene assay2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478366Displacement of [3H]mibolerone from human AR expressed in CHO-K1 cells after 2 hrs by scintillation counting2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478370Antagonist activity at AR in human LNCAP cells assessed as effect on cell proliferation after 6 days2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478372Antagonist activity at AR in bicalutamide-resistant human LNCAP cells assessed as effect on cell proliferation after 6 days2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
AID478369Agonist activity at AR in human LNCAP cells assessed as effect on cell proliferation after 6 days2010Bioorganic & medicinal chemistry, May-01, Volume: 18, Issue:9
Structure-activity relationships of bioisosteric replacement of the carboxylic acid in novel androgen receptor pure antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (71.43)18.2507
2000's1 (14.29)29.6817
2010's1 (14.29)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: 12.15

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 Index12.15 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]