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84494-70-2 | 5,8,11,14,17-Eicosapentaenoicacid, ethyl ester
CAS No: 84494-70-2 Catalog No: AG0054QJ MDL No:MFCD00060102
Product Description
Catalog Number:
AG0054QJ
Chemical Name:
5,8,11,14,17-Eicosapentaenoicacid, ethyl ester
CAS Number:
84494-70-2
Molecular Formula:
C22H34O2
Molecular Weight:
330.5042
MDL Number:
MFCD00060102
IUPAC Name:
ethyl (5E,8E,11E,14E,17E)-icosa-5,8,11,14,17-pentaenoate
InChI:
InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5+,9-8+,12-11+,15-14+,18-17+
InChI Key:
SSQPWTVBQMWLSZ-LRKAYDMASA-N
SMILES:
CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC
Properties
Complexity:
425
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
5
Exact Mass:
330.256g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
330.512g/mol
Monoisotopic Mass:
330.256g/mol
Rotatable Bond Count:
15
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.3
Literature
| Title | Journal |
|---|---|
| Icosapent ethyl for the treatment of hypertriglyceridemia. | Expert opinion on pharmacotherapy 20130701 |
| Efficacy and safety of eicosapentaenoic acid ethyl ester (AMR101) therapy in statin-treated patients with persistent high triglycerides (from the ANCHOR study). | The American journal of cardiology 20121001 |
| A new pure ω-3 eicosapentaenoic acid ethyl ester (AMR101) for the management of hypertriglyceridemia: the MARINE trial. | Expert review of cardiovascular therapy 20120601 |
| Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on lipoprotein particle concentration and size in patients with very high triglyceride levels (the MARINE study). | Journal of clinical lipidology 20120101 |
| Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). | The American journal of cardiology 20110901 |
| Protective effects of prescription n-3 fatty acids against impairment of spatial cognitive learning ability in amyloid β-infused rats. | Food & function 20110701 |
| Ethyl-eicosapentaenoate modulates changes in neurochemistry and brain lipids induced by parkinsonian neurotoxin 1-methyl-4-phenylpyridinium in mouse brain slices. | European journal of pharmacology 20101215 |
| Eicosapentaenoic acid (EPA) from highly concentrated n-3 fatty acid ethyl esters is incorporated into advanced atherosclerotic plaques and higher plaque EPA is associated with decreased plaque inflammation and increased stability. | Atherosclerosis 20100901 |
| Eicosapentaenoic acid (EPA) from highly concentrated n-3 fatty acid ethyl esters is incorporated into advanced atherosclerotic plaques and higher plaque EPA is associated with decreased plaque inflammation and increased stability. | Atherosclerosis 20100901 |
| Effects of dietary omega-3 fatty acids on ventricular function in dogs with healed myocardial infarctions: in vivo and in vitro studies. | American journal of physiology. Heart and circulatory physiology 20100401 |
| A double-blind, randomized controlled trial of ethyl-eicosapentaenoate for major depressive disorder. | The Journal of clinical psychiatry 20091201 |
| Effects of eicosapentaenoic acid ethyl ester on visfatin and apelin in lean and overweight (cafeteria diet-fed) rats. | The British journal of nutrition 20090401 |
| Highly purified eicosapentaenoic acid prevents the progression of hepatic steatosis by repressing monounsaturated fatty acid synthesis in high-fat/high-sucrose diet-fed mice. | Prostaglandins, leukotrienes, and essential fatty acids 20090401 |
| Increased phospholipase A2 activity and inflammatory response but decreased nerve growth factor expression in the olfactory bulbectomized rat model of depression: effects of chronic ethyl-eicosapentaenoate treatment. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20090107 |
| Usefulness of colon targeted DHA and EPA as novel diabetes medications that promote intrinsic GLP-1 secretion. | Journal of controlled release : official journal of the Controlled Release Society 20081208 |
| Effects of omega-3 acid ethyl esters and aspirin, alone and in combination, on platelet function in healthy subjects. | Thrombosis and haemostasis 20081001 |
| Does eicosapentaenoic acid (EPA) inhibit cerebral vasospasm in patients after aneurysmal subarachnoid hemorrhage? | Acta neurologica Scandinavica 20080701 |
| Identification of inflammatory and proresolving lipid mediators in bone marrow and their lipidomic profiles with ovariectomy and omega-3 intake. | American journal of hematology 20080601 |
| Improving effect of ethyl eicosapentanoate on statin-induced rhabdomyolysis in Eisai hyperbilirubinemic rats. | Biochemical and biophysical research communications 20060203 |
| Effects of the addition of amino acids and peptides on lipid oxidation in a powdery model system. | Journal of agricultural and food chemistry 20051019 |
| Antitumor and antimetastatic actions of eicosapentaenoic acid ethylester and its by-products formed during accelerated stability testing. | Cancer science 20050701 |
| Effects of protein and peptide addition on lipid oxidation in powder model system. | Journal of agricultural and food chemistry 20050112 |
| Effects of eicosapentaenoic acids on oxidative stress and plasma fatty acid composition in patients with lupus nephritis. | In vivo (Athens, Greece) 20050101 |
| A pilot open case series of ethyl-EPA supplementation in the treatment of anorexia nervosa. | Prostaglandins, leukotrienes, and essential fatty acids 20041001 |
| Ethyl-eicosapentaenoate and dexamethasone resistance in therapy-refractory depression. | The international journal of neuropsychopharmacology 20040901 |
| Omega-3 fatty acid ethyl-eicosapentaenoate, but not soybean oil, attenuates memory impairment induced by central IL-1beta administration. | Journal of lipid research 20040601 |
| Dietary ethyl-eicosapentaenoic acid but not soybean oil reverses central interleukin-1-induced changes in behavior, corticosterone and immune response in rats. | Stress (Amsterdam, Netherlands) 20040301 |
| Divergent effects of eicosapentaenoic and docosahexaenoic acid ethyl esters, and fish oil on hepatic fatty acid oxidation in the rat. | Biochimica et biophysica acta 20031130 |
| Is eicosapentaenoic acid useful in the treatment of ulcerative colitis in children? | Journal of pediatric gastroenterology and nutrition 20031101 |
| Effects of highly purified eicosapentaenoic acid on erythrocyte fatty acid composition and leukocyte and colonic mucosa leukotriene B4 production in children with ulcerative colitis. | Journal of pediatric gastroenterology and nutrition 20031101 |
| Long-term administration of highly purified eicosapentaenoic acid ethyl ester improves blood coagulation abnormalities and dysfunction of vascular endothelial cells in Otsuka Long-Evans Tokushima fatty rats. | Endocrine journal 20031001 |
| The effects on plasma, red cell and platelet fatty acids of taking 12 g/day of ethyl-eicosapentaenoate for 16 months: dihomogammalinolenic, arachidonic and docosahexaenoic acids and relevance to Inuit metabolism. | Prostaglandins, leukotrienes, and essential fatty acids 20030501 |
| Omega-3 fatty acids for depression in pregnancy. | The American journal of psychiatry 20030201 |
| Resolution of typical lipoprotein glomerulopathy by intensive lipid-lowering therapy. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20030101 |
| Effects of water activity and lipid addition on secondary structure of zein in powder systems. | Journal of agricultural and food chemistry 20030101 |
| omega-3 Fatty acid treatment of women with borderline personality disorder: a double-blind, placebo-controlled pilot study. | The American journal of psychiatry 20030101 |
| omega-3 Fatty acid for schizophrenia. | The American journal of psychiatry 20030101 |
| A dose-ranging study of the effects of ethyl-eicosapentaenoate in patients with ongoing depression despite apparently adequate treatment with standard drugs. | Archives of general psychiatry 20021001 |
| Addition of omega-3 fatty acid to maintenance medication treatment for recurrent unipolar depressive disorder. | The American journal of psychiatry 20020301 |
| Effect of eicosapentaenoic acid ethyl ester v. oleic acid-rich safflower oil on insulin resistance in type 2 diabetic model rats with hypertriacylglycerolaemia. | The British journal of nutrition 20020201 |
| MRI and neuropsychological improvement in Huntington disease following ethyl-EPA treatment. | Neuroreport 20020121 |
| A dose-ranging exploratory study of the effects of ethyl-eicosapentaenoate in patients with persistent schizophrenic symptoms. | Journal of psychiatric research 20020101 |
| A new category of psychotropic drugs: neuroactive lipids as exemplified by ethyl eicosapentaenoate (E-E). | Progress in drug research. Fortschritte der Arzneimittelforschung. Progres des recherches pharmaceutiques 20020101 |
| A placebo-controlled trial of omega-3 fatty acid (ethyl eicosapentaenoic acid) supplementation for residual symptoms and cognitive impairment in schizophrenia. | The American journal of psychiatry 20011201 |
| Effect of eicosapentaenoic acid ethyl ester on hypothyroid function. | The Journal of endocrinology 20011101 |
| [A case of mitochondrial myopathy, encephalopathy, lactic acidosis and stroke-like episodes (MELAS), showing temporary improvement during the treatment with eicosapentaenoic acid ethyl ester]. | Rinsho shinkeigaku = Clinical neurology 20011001 |
| [Eicosapentaenoic acid]. | Nihon rinsho. Japanese journal of clinical medicine 20010301 |
| [A study on the contents of fat and fatty acids in five shellfishes]. | Se pu = Chinese journal of chromatography 20010301 |
| Effect of ethyl icosapentaenoate (EPA) on the concentration of tumor necrosis factor (TNF) and interleukin-1 (IL-1) in the carotid artery of cuff-sheathed rabbit models. | Journal of atherosclerosis and thrombosis 20010101 |
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