5,8,11,14,17-eicosapentaenoic acid [C20:5w3]
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Introduction
[C20:5w3]
Function
- EPA is a substrate in the cyclooxygenase cascade & the lipoxygenase cascade
- properties of its metabolites are in general less inflammatory than those derived from arachidonic acid
Pharmacology
- effects on transcription factors:
- several effects on PPAR
- oxidized EPA activates PPAR-alpha[1]
- EPA increases PPAR-gamma mRNA[4]
- EPA binds to the ligand-binding domain of PPAR-delta[5]
- EPA & DHA inhibit IL-1 beta induced transcription factor activation[2]
- several effects on PPAR
- health benefits
- EPA & DHA intake up to 0.20 grams daily is associated with decreased cardiovascular risk (odds ratio 0.64)[7]
- EPA (600 mg TID) in combination with statin, diminished acute coronary events, but not fatalities in Japanese population[6]
- reduced cardiovascular mortality & improved cardiovascular outcomes greater with EPA monotherapy than with EPA+DHA[10]
- active metabolite of ethyl icosapentate (Vascepa)
- EPA 1g/day may reduce incidence of left-sided colorectal adenomas[9]
Pharmacokinetics
Laboratory
More general terms
More specific terms
- 12-hydroperoxy-eicosapentaenoate
- 12-hydroxy-eicosapentaenoate
- 15-hydroperoxy-eicosapentaenoate
- 15-hydroxy-eicosapentaenoate
- 5-hydroperoxy-eicosapentaenoate
- 5-hydroxy-eicosapentaenoate
- leukotriene A5
- leukotriene B5
- leukotriene C5
- leukotriene D5
- leukotriene E5
- leukotriene F5
- prostaglandin A3
- prostaglandin D3
- prostaglandin E3
- prostaglandin F3-alpha
- prostaglandin G3
- prostaglandin H3
- prostaglandin I3
- thromboxane A3
- thromboxane B3
Additional terms
Component of
- docosahexaenoate/eicosapentaenoate/ubiquinone/vitamin e
- docosahexaenoate/eicosapentaenoate/phytosterol
- docosahexaenoate/eicosapentaenoate/phosphatidylserine
- docosahexaenoate/eicosapentaenoate/folic acid/hypericum perforatum
- docosahexaenoate/eicosapentaenoate
- cobalamin/docosahexaenoate/eicosapentaenoate/pyridoxine
- cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/policosanol/pyridoxine
- cholecalciferol/docosahexaenoate/eicosapentaenoate/vitamin e
- ascorbate/copper gluconate/docosahexaenoate/eicosapentaenoate/lutein/zeaxanthin/zinc oxide
- ascorbate/calcium carbonate/cholecalciferol/choline bitartrate/cobalamin/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/nicotinic acid/potassium iodide/pyridoxine/riboflavin/thiamine/vitamin e/zinc oxide
- alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/pyridoxine
- cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/pyridoxine
- docosahexaenoate/eicosapentaenoate/vitamin e
- alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/folic acid/pyridoxine
References
- ↑ 1.0 1.1 Sethi S, Ziouzenkova O, Ni H, Wagner DD, Plutzky J, Mayadas TN. Oxidized omega-3 fatty acids in fish oil inhibit leukocyte- endothelial interactions through activation of PPAR alpha. Blood. 2002 Aug 15;100(4):1340-6. PMID: https://www.ncbi.nlm.nih.gov/pubmed/12149216
- ↑ 2.0 2.1 2.2 Bousserouel S et al, Lipid Res 44:601, 2003 PMID: https://www.ncbi.nlm.nih.gov/pubmed/12562859
- ↑ 3.0 3.1 Zhao Y et al, J Am Coll Nutr 23(1):71-8, 2004 PMID: https://www.ncbi.nlm.nih.gov/pubmed/14963056
- ↑ 4.0 4.1 Chambrier C et al, Obes Res 10(6):518-25, 2002 PMID: https://www.ncbi.nlm.nih.gov/pubmed/12055328
- ↑ 5.0 5.1 Xu HE et al, Mol Cell 3(3):397-403. 1999 PMID: https://www.ncbi.nlm.nih.gov/pubmed/10198642
- ↑ 6.0 6.1 Yokoyama M et al, Effects of eicosapentaenoic acid on major coronary events in hypercholesterolaemic patients (JELIS): A randomised open- label, blinded endpoint analysis. Lancet 2007, 369:1090 PMID: https://www.ncbi.nlm.nih.gov/pubmed/17398308
Mozaffarian D, JELIS, fish oil, and cardiac events. Lancet 2007, 369:1062 PMID: https://www.ncbi.nlm.nih.gov/pubmed/17398290 - ↑ 7.0 7.1 Office of Dietary Supplements, National Institutes of Health Nutritional Research Series: Advancing the Role of Evidence- based Reviews in Nutrition Research and Applications Volume 4: Effects of Eicosapentanoic Acid and Docosahexanoic Acid on Mortality Across Diverse Settings: Systematic Review and Meta-Analysis of Randomized Trials and Prospective Cohorts http://www.ahrq.gov/clinic/tp/nutritn4tp.htm
- ↑ 8.0 8.1 PubChem: 9831415
- ↑ 9.0 9.1 Hull MA, Sprange K, Hepburn T et al. Eicosapentaenoic acid and aspirin, alone and in combination, for the prevention of colorectal adenomas (seAFOod Polyp Prevention trial): A multicentre, randomised, double-blind, placebo-controlled, 2 2 factorial trial. Lancet 2018 Dec 15; 392:2583. PMID: https://www.ncbi.nlm.nih.gov/pubmed/30466866 Free full text https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(18)31775-6/fulltext
Dekker E, Kaminski MF. Take a pill for no more polyps: Is it that simple? Lancet 2018 Dec 15; 392:2519. PMID: https://www.ncbi.nlm.nih.gov/pubmed/30466865 Free Article https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(18)32322-5/fulltext - ↑ 10.0 10.1 Khan SU, Lone AN, Khan MS, Virani SS et al Effect of omega-3 fatty acids on cardiovascular outcomes: A systematic review and meta-analysis. EClinicalMedicine. 2021 Jul 8;38:100997 PMID: https://www.ncbi.nlm.nih.gov/pubmed/34505026 PMCID: PMC8413259 Free PMC article
Database
- PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3209
- PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=135002
- PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=446284
- PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5282846
- PubChem: http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5282847