Eicosapentaenoic acid

Eicosapentaenoic acid
Names
	Preferred IUPAC name (5Z,8Z,11Z,14Z,17Z)-Icosa-5,8,11,14,17-pentaenoic acid
	Other names (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid
Identifiers
CAS Number	10417-94-4 ;
3D model (JSmol)	Interactive image;
3DMet	B00962;
Beilstein Reference	1714433
ChEBI	CHEBI:28364 ;
ChEMBL	ChEMBL460026 ;
ChemSpider	393682 ;
DrugBank	DB00159 ;
ECHA InfoCard	100.117.069
IUPHAR/BPS	3362;
KEGG	C06428;
PubChem CID	446284;
UNII	AAN7QOV9EA ;
CompTox Dashboard (EPA)	DTXSID9041023 ;
	InChI InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15- Key: JAZBEHYOTPTENJ-JLNKQSITSA-N ; InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15- Key: JAZBEHYOTPTENJ-JLNKQSITBZ;
	SMILES O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC;
Properties
Chemical formula	C20H30O2
Molar mass	302.451 g/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Eicosapentaenoic acid (EPA; also icosapentaenoic acid) is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). It also has the trivial name timnodonic acid. In chemical structure, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.

EPA is a polyunsaturated fatty acid (PUFA) that acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 eicosanoids. EPA is both a precursor and the hydrolytic breakdown product of eicosapentaenoyl ethanolamide (EPEA: C₂₂H₃₅NO₂; 20:5,n-3).^[1] Although studies of fish oil supplements, which contain both docosahexaenoic acid (DHA) and EPA, have failed to support claims of preventing heart attacks or strokes,^[2]^[3]^[4] a recent multi-year study of Vascepa (ethyl eicosapentaenoate, the ethyl ester of the free fatty acid), a prescription drug containing only EPA, was shown to reduce heart attack, stroke, and cardiovascular death by 25% relative to a placebo in those with statin-resistant hypertriglyceridemia.^[5]^[6]

^ Lucanic M, Held JM, Vantipalli MC, Klang IM, Graham JB, Gibson BW, Lithgow GJ, Gill MS (May 2011). "N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans". Nature. 473 (7346): 226–9. Bibcode:2011Natur.473..226L. doi:10.1038/nature10007. PMC 3093655. PMID 21562563.
^ Zimmer C (September 17, 2015). "Inuit Study Adds Twist to Omega-3 Fatty Acids' Health Story". The New York Times. Archived from the original on January 9, 2019. Retrieved October 11, 2015.
^ O'Connor A (March 30, 2015). "Fish Oil Claims Not Supported by Research". The New York Times. Archived from the original on May 28, 2018. Retrieved October 11, 2015.
^ Grey A, Bolland M (March 2014). "Clinical trial evidence and use of fish oil supplements". JAMA Internal Medicine. 174 (3): 460–2. doi:10.1001/jamainternmed.2013.12765. PMID 24352849. Archived from the original on 2016-06-08. Retrieved 2015-10-12.
^ Bhatt DL, Steg PG, Miller M, Brinton EA, Jacobson TA, Ketchum SB, Doyle RT, Juliano RA, Jiao L, Granowitz C, Tardif JC, Ballantyne CM (January 3, 2019). "Cardiovascular Risk Reduction with Icosapent Ethyl for Hypertriglyceridemia". New England Journal of Medicine. 380 (1): 11–22. doi:10.1056/NEJMoa1812792. PMID 30415628.
^ "Vascepa® (icosapent ethyl) 26% Reduction in Key Secondary Composite Endpoint of Cardiovascular Death, Heart Attacks and Stroke Demonstrated in REDUCE-IT™". November 10, 2018. Archived from the original on May 23, 2019. Retrieved January 21, 2019.

[1] Lucanic M, Held JM, Vantipalli MC, Klang IM, Graham JB, Gibson BW, Lithgow GJ, Gill MS (May 2011). "N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans". Nature. 473 (7346): 226–9. Bibcode:2011Natur.473..226L. doi:10.1038/nature10007. PMC 3093655. PMID 21562563.

[NYT-20150917-cz-2] Zimmer C (September 17, 2015). "Inuit Study Adds Twist to Omega-3 Fatty Acids' Health Story". The New York Times. Archived from the original on January 9, 2019. Retrieved October 11, 2015.

[NYT-20150330-3] O'Connor A (March 30, 2015). "Fish Oil Claims Not Supported by Research". The New York Times. Archived from the original on May 28, 2018. Retrieved October 11, 2015.

[JAMA-201403-4] Grey A, Bolland M (March 2014). "Clinical trial evidence and use of fish oil supplements". JAMA Internal Medicine. 174 (3): 460–2. doi:10.1001/jamainternmed.2013.12765. PMID 24352849. Archived from the original on 2016-06-08. Retrieved 2015-10-12.

[5] Bhatt DL, Steg PG, Miller M, Brinton EA, Jacobson TA, Ketchum SB, Doyle RT, Juliano RA, Jiao L, Granowitz C, Tardif JC, Ballantyne CM (January 3, 2019). "Cardiovascular Risk Reduction with Icosapent Ethyl for Hypertriglyceridemia". New England Journal of Medicine. 380 (1): 11–22. doi:10.1056/NEJMoa1812792. PMID 30415628.

[REDUCE-IT-6] "Vascepa® (icosapent ethyl) 26% Reduction in Key Secondary Composite Endpoint of Cardiovascular Death, Heart Attacks and Stroke Demonstrated in REDUCE-IT™". November 10, 2018. Archived from the original on May 23, 2019. Retrieved January 21, 2019.

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Eicosapentaenoic acid

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