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5,8,11,14,17-eicosapentaenoic acid [C20:5w3]

[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: 1) effects on transcription factors: a) 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] b) EPA & DHA inhibit IL-1 beta induced transcription factor activation [2] - NF-kappa B [2,3] - C/EBP - Ets-1 2) health benefits a) EPA & DHA intake up to 0.20 grams daily is associated with decreased cardiovascular risk (odds ratio 0.64) [7] b) EPA (600 mg TID) in combination with statin, diminished acute coronary events, but not fatalities in Japanese population [6] c) reduced cardiovascular mortality & improved cardiovascular outcomes greater with EPA monotherapy than with EPA+DHA [10] d) active metabolite of ethyl icosapentate (Vascepa) e) EPA 1g/day may reduce incidence of left-sided colorectal adenomas [9] Pharmacokinetics: - 1/2life of EPA is 89 hours [8] Laboratory: - eicosapentaenoate in erythrocytes - eicosapentaenoate in serum/plasma

Interactions

molecular events

Related

eicosapentaenoate cascade fatty acid composition of brain

Specific

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

General

fatty acid, omega-3 (Epanova)

Properties

COMPARTMENT: membrane SIZE: MW = 302.4 G/MOL

Database Correlations

PUBCHEM correlations

References

  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: 12149216
  2. Bousserouel S et al, Lipid Res 44:601, 2003 PMID: 12562859
  3. Zhao Y et al, J Am Coll Nutr 23(1):71-8, 2004 PMID: 14963056
  4. Chambrier C et al, Obes Res 10(6):518-25, 2002 PMID: 12055328
  5. Xu HE et al, Mol Cell 3(3):397-403. 1999 PMID: 10198642
  6. 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: 17398308 - Mozaffarian D, JELIS, fish oil, and cardiac events. Lancet 2007, 369:1062 PMID: 17398290
  7. 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. PubChem: 9831415
  9. 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: 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: 30466865 Free Article https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(18)32322-5/fulltext
  10. 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: 34505026 PMCID: PMC8413259 Free PMC article

Component-of

alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/pyridoxine alpha tocopherol/ascorbate/calcium phosphate/docosahexaenoate/eicosapentaenoate/folic acid/pyridoxine ascorbate/calcium carbonate/cholecalciferol/choline bitartrate/cobalamin/docosahexaenoate/eicosapentaenoate/ferrous fumarate/folic acid/nicotinic acid/potassium iodide/pyridoxine/riboflavin/thiamine/vitamin e/zinc oxide ascorbate/copper gluconate/docosahexaenoate/eicosapentaenoate/lutein/zeaxanthin/zinc oxide cholecalciferol/docosahexaenoate/eicosapentaenoate/vitamin e cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/policosanol/pyridoxine cobalamin/docosahexaenoate/eicosapentaenoate/folic acid/phytosterol/pyridoxine cobalamin/docosahexaenoate/eicosapentaenoate/pyridoxine docosahexaenoate/eicosapentaenoate docosahexaenoate/eicosapentaenoate/folic acid/hypericum perforatum docosahexaenoate/eicosapentaenoate/phosphatidylserine docosahexaenoate/eicosapentaenoate/phytosterol docosahexaenoate/eicosapentaenoate/ubiquinone/vitamin e docosahexaenoate/eicosapentaenoate/vitamin e