Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H19NO.H3O4P |
Molecular Weight | 315.3019 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.CCOC1=CC=C2NC(C)(C)C=C(C)C2=C1
InChI
InChIKey=HGXWAQIWVLMXFM-UHFFFAOYSA-N
InChI=1S/C14H19NO.H3O4P/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13;1-5(2,3)4/h6-9,15H,5H2,1-4H3;(H3,1,2,3,4)
Molecular Formula | C14H19NO |
Molecular Weight | 217.3068 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H3O4P |
Molecular Weight | 97.9952 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26904606Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/27350330
https://www.ncbi.nlm.nih.gov/pubmed/10853663
www.ncbi.nlm.nih.gov/pubmed/14644360
https://www.ncbi.nlm.nih.gov/pubmed/16266792
http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=573.380
https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.140
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26904606
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/27350330
https://www.ncbi.nlm.nih.gov/pubmed/10853663
www.ncbi.nlm.nih.gov/pubmed/14644360
https://www.ncbi.nlm.nih.gov/pubmed/16266792
http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=573.380
https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.140
Ethoxyquin (EQ) has been used as an antioxidant in animal feed for many years, but pharmacological use of EQ has never been evaluated in humans despite that small
amounts of EQ exist in certain food items. The level of this antioxidant in animal feeds should not be higher than 150 ppm (U.S. FDA permissions). Ethoxyquin is rapidly absorbed from gastrointestinal tract of laboratory animals like rats and mice. Peak blood concentration of the compound is observed within 1 h. Distribution of EQ in animal body is similar when it is administered orally and intravenously. Small amounts of parent EQ were detected in liver, kidney, and adipose tissue and fish muscles. It is excreted predominantly as metabolites via urine. Ethoxyquin is also registered as an antioxidant to control scald (browning) in apples and pears. EQ-induced DNA damage in human lymphocytes in a dose-dependent manner. According to the studies on dogs and laboratory animals it was shown that ethoxyquin had little acute toxicity, except when it is administered parenterally. Values of LD50 for EQ are 1700 mg kg−1 bw (rats, oral gavage), 2000 mg kg−1 bw (rats, dermal treatment, 24 h), 900 mg kg−1 bw (mice, intraperitoneal administration), and 180 mg kg−1 bw (mice, intravenous administration).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10853663
Curator's Comment: Known to be CNS active in mouse. Human data not available.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10853663
Curator's Comment: For the first time Ethoxyquin was synthesized in 1921 by Knoevenagel.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08238 Gene ID: 3326.0 Gene Symbol: HSP90AB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24127661 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Modification of chemical carcinogenesis by antioxidants. | 1983 |
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Modifying effects of butylated hydroxyanisole, ethoxyquin and acetaminophen on induction of neoplastic lesions in rat liver and kidney initiated by N-ethyl-N-hydroxyethylnitrosamine. | 1984 Apr |
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Effects of some non-steroidal anti-inflammatory drugs and other agents on cyclooxygenase and lipoxygenase activities in some enzyme preparations. | 1985 Jun |
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Inhibitory effects of ethoxyquin, 4,4'-diaminodiphenylmethane and acetaminophen on rat hepatocarcinogenesis. | 1986 Mar |
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Summation effects of uracil and other promoters on epithelial lesion development in the F344 rat urinary bladder initiated by N-butyl-N-(4-hydroxybutyl)nitrosamine. | 1991 Nov |
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Resistance to aflatoxin B1 is associated with the expression of a novel aldo-keto reductase which has catalytic activity towards a cytotoxic aldehyde-containing metabolite of the toxin. | 1993 Sep 1 |
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Regulation of aflatoxin B1-metabolizing aldehyde reductase and glutathione S-transferase by chemoprotectors. | 1994 May 15 |
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Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B1 metabolism. | 1997 Sep |
|
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats. | 2005 Aug 15 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Regulation of mouse organic anion-transporting polypeptides (Oatps) in liver by prototypical microsomal enzyme inducers that activate distinct transcription factor pathways. | 2005 Sep |
|
Simultaneous determination of five synthetic antioxidants in edible vegetable oil by GC-MS. | 2006 Nov |
|
Hepatic biotransformation and metabolite profile during a 2-week depuration period in Atlantic salmon fed graded levels of the synthetic antioxidant, ethoxyquin. | 2006 Sep |
|
Genotoxic and antioxidant activities of ethoxyquin salts evaluated by the comet assay. | 2006 Sep 25 |
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Antioxidant profile of ethoxyquin and some of its S, Se, and Te analogues. | 2007 Aug 3 |
|
Identification of unknown pesticides in fruits using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry. Imazalil as a case study of quantification. | 2007 Dec 28 |
|
Evaluation of the genotoxic and antioxidant effects of two novel feed additives (ethoxyquin complexes with flavonoids) by the comet assay and micronucleus test. | 2007 Jun |
|
Simultaneous quantitative determination of the synthetic antioxidant ethoxyquin and its major metabolite in Atlantic salmon (Salmo salar, L), ethoxyquin dimer, by reversed-phase high-performance liquid chromatography with fluorescence detection. | 2007 Mar-Apr |
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Assessment of the stability of pesticides during the cryogenic processing of fruits and vegetables. | 2007 Nov |
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[Hypersensitivity to the antioxidant ethoxyquin]. | 2007 Oct |
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Importance of hepatic induction of constitutive androstane receptor and other transcription factors that regulate xenobiotic metabolism and transport. | 2007 Oct |
|
Evaluation of PCDD/Fs characterization in animal feed and feed additives. | 2007 Sep |
|
Abstracts of papers presented at the 2008 pittsburgh conference. | 2008 |
|
The Role of PPARs in Cancer. | 2008 |
|
Induction of hepatic glutathione S-transferases in male mice by prototypes of various classes of microsomal enzyme inducers. | 2008 Dec |
|
Tissue distribution, ontogeny, and regulation of aldehyde dehydrogenase (Aldh) enzymes mRNA by prototypical microsomal enzyme inducers in mice. | 2008 Jan |
|
The combination of deoxynivalenol and zearalenone at permitted feed concentrations causes serious physiological effects in young pigs. | 2008 Mar |
|
Accumulation and depuration of the synthetic antioxidant ethoxyquin in the muscle of Atlantic salmon (Salmo salar L.). | 2008 May |
|
Stabilizing oils from smoked pink salmon (Oncorhynchus gorbuscha). | 2009 Apr |
|
Induction of mouse UDP-glucuronosyltransferase mRNA expression in liver and intestine by activators of aryl-hydrocarbon receptor, constitutive androstane receptor, pregnane X receptor, peroxisome proliferator-activated receptor alpha, and nuclear factor erythroid 2-related factor 2. | 2009 Apr |
|
Role of the tumor suppressor PTEN in antioxidant responsive element-mediated transcription and associated histone modifications. | 2009 Mar |
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Induced expression of drug metabolizing enzymes by preventive agents: role of the antioxidant response element. | 2009 Nov 10 |
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Comparison of supplements to enhance recovery of heat-injured Salmonella from egg albumen. | 2009 Oct |
|
Assessment of the Efficacy of L-Lysine Sulfate vis-à-vis L-Lysine Hydrochloride as Sources of Supplemental Lysine in Broiler Chickens. | 2010 |
|
Levels of synthetic antioxidants (ethoxyquin, butylated hydroxytoluene and butylated hydroxyanisole) in fish feed and commercially farmed fish. | 2010 Dec |
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Expression and localization of rat aldo-keto reductases and induction of the 1B13 and 1D2 isoforms by phenolic antioxidants. | 2010 Feb |
|
Determination of ethoxyquin by high-performance liquid chromatography with fluorescence detection and its application to the survey of residues in food products of animal origin. | 2010 Jan-Feb |
|
4-(8-Eth-oxy-2,3-dihydro-1H-cyclo-penta-[c]quinolin-4-yl)butane-1-peroxol. | 2010 Jun 16 |
|
Proteomic analysis of Nrf2 deficient transgenic mice reveals cellular defence and lipid metabolism as primary Nrf2-dependent pathways in the liver. | 2010 Jun 16 |
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Modulation of ethoxyquin genotoxicity by free radical scavengers and DNA damage repair in human lymphocytes. | 2010 Mar 15 |
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Screening of agrochemicals in foodstuffs using low-temperature plasma (LTP) ambient ionization mass spectrometry. | 2010 May |
|
Effects of typical inducers on olfactory xenobiotic-metabolizing enzyme, transporter, and transcription factor expression in rats. | 2010 Oct |
|
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. | 2011 Feb 27 |
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Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens. | 2011 Jun |
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Regulation of aldo-keto reductase AKR1B10 gene expression: involvement of transcription factor Nrf2. | 2011 May 30 |
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Benzo(a)pyrene induces hepatic AKR1A1 mRNA expression in tilapia fish (Oreochromis niloticus). | 2012 Jul |
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Transcription factor-mediated regulation of carboxylesterase enzymes in livers of mice. | 2012 Jun |
|
The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates. | 2012 Mar |
|
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
|
Evidence that the capacity of nongenotoxic carcinogens to induce oxidative stress is subject to marked variability. | 2015 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27350330
Curator's Comment: Cisplatin induced significant nucleolar atrophy while the co-treatment with EQ was able to maintain physiological nucleolar sizes.
Rats, 75 μg/kg/day daily
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27350330
An immortalized rat DRG neuronal cell line (50B11) was used to examine the neurotoxicity of cisplatin and the effect of EQ on its neurotoxicity by measuring cellular ATP levels. 50B11 cells were incubated with cisplatin at different concentrations, ranging from 300 pM to 10 μM. When cells were exposed to cisplatin at 3 μM concentration combined with varying amounts of EQ (1 nM to 10 μM), there was consistent neuroprotection from 30nM to 300nM.
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
L3ZFF2BRN8
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Record Status |
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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