Page last updated: 2024-12-08

benzarone

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

Description

benzarone: antihemorrhagic agent; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID255968
CHEMBL ID1474963
CHEBI ID34559
SCHEMBL ID555497
MeSH IDM0045624

Synonyms (72)

Synonym
benzarona [inn-spanish]
nsc 82134
einecs 216-026-2
benzarone [inn:dcf]
benzaronum [inn-latin]
brn 0222901
venagil
2-ethyl-3-(4'-hydroxybenzoyl)benzofuran
benzofuran, (2-ethyl-3-(4'-hydroxybenzoyl))
l 2197-labaz
ethyl-2 (hydroxy-4 benzoyl)-3 benzofuranne [french]
UNM000003519301
(2-ethylbenzofuran-3-yl)-(4-hydroxyphenyl)methanone
1477-19-6
(2-ethyl-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone
fagivil
nsc82134
benzarone
l 2179-labaz
methanone, (2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-
fragivix
2-ethyl-3-benzofuranyl p-hydroxyphenyl ketone
wln: t56 boj c2 dor dq
l 2197
2-ethyl-3-(4-hydroxybenzoyl)benzofuran
2-ethyl-4'-hydroxy-3-benzoylbenzofuran
nsc-82134
benzofuran, [2-ethyl-3-(4'-hydroxybenzoyl)]
ketone, 2-ethyl-3-benzofuranyl p-hydroxyphenyl
vasoc
2-ethyl-3-p-hydroxybenzoylbenzofuran
2-ethyl-3-(p-hydroxybenzoyl)benzofuran
fragivil
benzaron
NCIOPEN2_004472
(2-ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone
chebi:34559 ,
l-2197 ,
benzaronum
5-18-02-00334 (beilstein handbook reference)
unii-23zw4bg89c
ethyl-2 (hydroxy-4 benzoyl)-3 benzofuranne
23zw4bg89c ,
benzarona
(2-ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone
chembl1474963 ,
bdbm50342278
AKOS016010825
smr001550644
MLS006010019
SCHEMBL555497
benzarone [mi]
benzarone [inn]
benzarone [mart.]
benzarone [who-dd]
DTXSID2061721
RFRXIWQYSOIBDI-UHFFFAOYSA-N
EX-A1132
SR-01000945019-1
sr-01000945019
(2-ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone (benzarone)
(2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)methanone
(2-ethylbenzo[b]furan-3-yl)(4-hydroxyphenyl)methanone
F17414
mfcd00867417
Q27116149
AS-18081
[[4-(1-methyl-1-phenylethyl)phenoxy]methyl]-oxiran
AC-36827
(2-ethyl-benzofuran-3-yl)-(4-hydroxy-phenyl)-methanone
HY-W011711
E1289

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with benzarone or benzbromarone can be associated with hepatic injury. "( Mechanisms of benzarone and benzbromarone-induced hepatic toxicity.
Gasser, R; Hänni, A; Kaufmann, P; Krähenbühl, S; Roberts, P; Török, M, 2005
)
1.04

Toxicity

ExcerptReferenceRelevance
"Many adverse drug reactions are caused by the cytochrome P450 (CYP)-dependent activation of drugs into reactive metabolites."( Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
Jones, LH; Nadanaciva, S; Rana, P; Will, Y, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" Much of the faecal 14C was attributable to 14C excreted in the bile which amounted to 59% in the 7 h bile collected from an intravenously dosed dog, and a mean of 72% in the 24 h bile of orally dosed rats."( Metabolic fate of the thrombolytic agent benzarone in man: comparison with the rat and dog.
Bonn, R; Chasseaud, LF; Darragh, A; Grote, H; John, BA; Lambe, RF; Sandrock, K; Wood, SG, 1987
)
0.54
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1-benzofuransA member of the class of benzofurans consisting of a 1-benzofuran skeleton and its substituted derivatives thereof.
[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 (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)150.00000.00053.49849.7600AID1411183; AID1622781
Solute carrier family 22 member 12Homo sapiens (human)IC50 (µMol)2.80000.02602.61527.3000AID593714
Eyes absent homolog 3Homo sapiens (human)IC50 (µMol)17.00003.40005.85008.3000AID1411181; AID1622771
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
monoatomic ion transportSolute carrier family 22 member 12Homo sapiens (human)
response to xenobiotic stimulusSolute carrier family 22 member 12Homo sapiens (human)
urate transportSolute carrier family 22 member 12Homo sapiens (human)
cellular homeostasisSolute carrier family 22 member 12Homo sapiens (human)
cellular response to insulin stimulusSolute carrier family 22 member 12Homo sapiens (human)
urate metabolic processSolute carrier family 22 member 12Homo sapiens (human)
transmembrane transportSolute carrier family 22 member 12Homo sapiens (human)
renal urate salt excretionSolute carrier family 22 member 12Homo sapiens (human)
organic anion transportSolute carrier family 22 member 12Homo sapiens (human)
double-strand break repairEyes absent homolog 3Homo sapiens (human)
chromatin remodelingEyes absent homolog 3Homo sapiens (human)
visual perceptionEyes absent homolog 3Homo sapiens (human)
anatomical structure morphogenesisEyes absent homolog 3Homo sapiens (human)
response to ionizing radiationEyes absent homolog 3Homo sapiens (human)
positive regulation of DNA repairEyes absent homolog 3Homo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway in absence of ligandEyes absent homolog 3Homo sapiens (human)
cell differentiationEyes absent homolog 3Homo sapiens (human)
anatomical structure developmentEyes absent homolog 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
urate transmembrane transporter activitySolute carrier family 22 member 12Homo sapiens (human)
PDZ domain bindingSolute carrier family 22 member 12Homo sapiens (human)
protein tyrosine phosphatase activityEyes absent homolog 3Homo sapiens (human)
protein bindingEyes absent homolog 3Homo sapiens (human)
metal ion bindingEyes absent homolog 3Homo sapiens (human)
histone H2AXY142 phosphatase activityEyes absent homolog 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
plasma membraneSolute carrier family 22 member 12Homo sapiens (human)
membraneSolute carrier family 22 member 12Homo sapiens (human)
apical plasma membraneSolute carrier family 22 member 12Homo sapiens (human)
brush border membraneSolute carrier family 22 member 12Homo sapiens (human)
extracellular exosomeSolute carrier family 22 member 12Homo sapiens (human)
nucleusEyes absent homolog 3Homo sapiens (human)
nucleoplasmEyes absent homolog 3Homo sapiens (human)
cytoplasmEyes absent homolog 3Homo sapiens (human)
centrosomeEyes absent homolog 3Homo sapiens (human)
nucleusEyes absent homolog 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID593713Inhibition of human URAT1 expressed in xenopus oocyte assessed as inhibition of [14C]-labelled urate uptake at 50 uM after 60 mins by liquid scintillation counting2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Developing potent human uric acid transporter 1 (hURAT1) inhibitors.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID593714Inhibition of human URAT1 expressed in xenopus oocyte assessed as inhibition of [14C]-labelled urate uptake after 60 mins by liquid scintillation counting2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Developing potent human uric acid transporter 1 (hURAT1) inhibitors.
AID1636379Drug activation in human Hep3B cells assessed as human CYP3A4-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 53 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of NAD2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID625293Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in LTKB-BD2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1636491Drug activation in human Hep3B cells assessed as human CYP2C9-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 47.3 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of N2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID732068Inhibition of Staphylococcus aureus AgrC12013Journal of medicinal chemistry, Feb-28, Volume: 56, Issue:4
Attenuating Staphylococcus aureus virulence gene regulation: a medicinal chemistry perspective.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID625276FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of most concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1636436Drug activation in human Hep3B cells assessed as human CYP2D6-mediated drug metabolism-induced cytotoxicity measured as decrease in cell viability at 5.8 uM pre-incubated with BSO for 18 hrs followed by incubation with compound for 3 hrs in presence of NA2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (51.52)18.7374
1990's4 (12.12)18.2507
2000's1 (3.03)29.6817
2010's10 (30.30)24.3611
2020's1 (3.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.84

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

MetricThis Compound (vs All)
Research Demand Index36.84 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index47.86 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (11.43%)5.53%
Reviews1 (2.86%)6.00%
Case Studies7 (20.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (65.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]