Page last updated: 2024-12-05

ethoxyresorufin

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

Description

Ethoxyresorufin (EROD) is a synthetic substrate used in biochemical assays to measure the activity of cytochrome P450 enzymes, specifically CYP1A1 and CYP1A2. These enzymes are involved in the metabolism of various xenobiotics (foreign compounds) including environmental pollutants, drugs, and carcinogens. EROD is metabolized by CYP1A enzymes to resorufin, a fluorescent compound. The rate of resorufin formation is directly proportional to the activity of the CYP1A enzymes. EROD is used in research to study the induction and inhibition of CYP1A activity, the effects of environmental pollutants on enzyme activity, and the role of these enzymes in drug metabolism and toxicity. EROD assays are also used in toxicology and environmental monitoring.'

ethoxyresorufin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3294
CHEMBL ID1080002
CHEBI ID34480
SCHEMBL ID104497
MeSH IDM0050977

Synonyms (32)

Synonym
CHEBI:34480 ,
AKOS005428988
7-ethoxyphenoxazone
7-ethoxyresorufin
5725-91-7
7-ethoxy-3h-phenoxazin-3-one
ethoxyresorufin
bdbm21360
STK299139
resorufin ethyl ether
3h-phenoxazin-3-one, 7-ethoxy-
FT-0668125
CHEMBL1080002
7-ethoxyphenoxazin-3-one
unii-59af853sw7
59af853sw7 ,
SCHEMBL104497
7-ethoxy-3-phenoxazinone
J-100239
DTXSID90205860
mfcd00037661
AS-59402
HY-D0145
CS-0010054
7-ethoxy resorufin
Q27116097
resorufinethylether
3,5-bis(benzyloxy)benzylbromide
D97845
7-er
resorufinethyl ether
o-ethylresorufin

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Analysis of the e-waste site samples using AAS and GC-MS techniques revealed the presence of a range of toxic metals as well as persistent and toxic organic pollutants, respectively, in the vicinity of the e-waste sites."( Occurrence of chemical pollutants in major e-waste sites in West Africa and usefulness of cytotoxicity and induction of ethoxyresorufin-O-deethylase (EROD) in determining the effects of some detected brominated flame retardants and e-waste soil-derived ex
Eze, CT; Eze, OO; Ibraheem, O; Michelangeli, F; Ogbuene, EB; Ogunwole, GA; Otitoloju, AA, 2021
)
0.83

Bioavailability

ExcerptReferenceRelevance
" Members of a group of derivatives from this series showed good oral bioavailability and brain penetration and very high in vitro affinity and selectivity for the DA D(3) receptor, as well as high in vitro potency for antagonism at this receptor."( 1,2,4-Triazolyl azabicyclo[3.1.0]hexanes: a new series of potent and selective dopamine D(3) receptor antagonists.
Arista, L; Ashby, CR; Blaney, FE; Bonanomi, G; Braggio, S; Capelli, AM; Checchia, A; Damiani, F; Di-Fabio, R; Fontana, S; Gentile, G; Griffante, C; Hamprecht, D; Heidbreder, C; Marchioro, C; Micheli, F; Mugnaini, M; Piner, J; Ratti, E; Tarsi, L; Tedesco, G; Terreni, S; Worby, A, 2010
)
0.36
" The resident fish with apparently normal liver demonstrated induction of hepatic EROD and GST activities and increase in biliary FACs irrespective of the sampling period indicating bioavailability of PAHs."( Assessment of biological effects of pollutants in a hyper eutrophic tropical water body, Lake Beira, Sri Lanka using multiple biomarker responses of resident fish, Nile tilapia (Oreochromis niloticus).
De Seram, PK; Pathiratne, A; Pathiratne, KA, 2010
)
0.36

Dosage Studied

The dose-response estrogenic effects of NP (25, 100, 1000 microg/l) on hepatic VTG transcript and plasma protein levels were assessed. Ethoxyresorufin deethylation was induced in the liver by both ethanol treatments. In the lung the bolus dosing ip increased the activity four-fold.

ExcerptRelevanceReference
" Ethoxyresorufin deethylation was induced in the liver by both ethanol treatments, and in the lung the bolus dosing ip increased the activity four-fold."( Influence of ethanol on microsomal p-nitrophenol hydroxylation and ethoxyresorufin deethylation in rat liver and lung.
Carlson, GP, 1991
)
1.43
"The O-dealkylation of pentoxyresorufin, a substrate for P450 2B1, was decreased in lung microsomes from rats dosed with O,O,S-trimethylphosphorodithioate, O,O,O-trimethylphosphorothioate, bromophos, fenitrothion, p-xylene and 2,4-dichloro-(6-phenylphonoxy)ethylamine."( Inhibition and induction of cytochrome P450 isoenzymes in rat lung.
Dinsdale, D; Verschoyle, RD; Wolf, CR, 1993
)
0.29
" The dose-response estrogenic effects of NP (25, 100, 1000 microg/l) on hepatic VTG transcript and plasma protein levels, as well as on CYP1A1 transcription and its associated ethoxyresorufin O-deethylase (EROD) activity, were assessed in juvenile Liza aurata; 17beta-estradiol (E2; 2 microg/l) treatment for 1 week served as positive control."( Effects of nonylphenol on juveniles and adults in the grey mullet, Liza aurata.
Carnevali, O; Cionna, C; Maradonna, F; Olivotto, I; Pizzonia, G, 2006
)
0.53
" Lipid deposition in livers of patients with the metabolic syndrome may necessitate dosage adjustments for toxic drugs, including CLZ."( Impaired microsomal oxidation of the atypical antipsychotic agent clozapine in hepatic steatosis.
Murray, M; Ramzan, I; Zhang, WV, 2007
)
0.34
" Fish dosed with 10mg/kg BaP had increased EROD activity in the mitochondrial fraction compared to controls."( Identification of mitochondrial cytochrome P450 induced in response to polycyclic aromatic hydrocarbons in the mummichog (Fundulus heteroclitus).
Di Giulio, RT; Jung, D, 2010
)
0.36
" The use of the BMD(T) implies a focus on the change of structure in the parameter's dose-response rather than a particular percentage change in the response in such a parameter."( The point of transition on the dose-effect curve as a reference point in the evaluation of in vitro toxicity data.
Håkansson, H; Öberg, M; Ringblom, J; Sand, S, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenoxazine
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 1A2Homo sapiens (human)IC50 (µMol)0.50000.00011.774010.0000AID471150; AID517699
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID471150Inhibition of human CYP1A22010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
1,2,4-Triazolyl azabicyclo[3.1.0]hexanes: a new series of potent and selective dopamine D(3) receptor antagonists.
AID517699Inhibition of human CYP1A22010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Exploration of the amine terminus in a novel series of 1,2,4-triazolo-3-yl-azabicyclo[3.1.0]hexanes as selective dopamine D3 receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (229)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (19.65)18.7374
1990's69 (30.13)18.2507
2000's68 (29.69)29.6817
2010's43 (18.78)24.3611
2020's4 (1.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.99

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 Index32.99 (24.57)
Research Supply Index5.49 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index34.93 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.41%)5.53%
Reviews1 (0.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other239 (99.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]