ICOSAPENT

First approved in 2008

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	5
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

InChIKey=JAZBEHYOTPTENJ-JLNKQSITSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	5
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00159
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000Lbl.pdf

Icosapent is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GO:0004144 diacylglycerol O-acyltransferase activity 4 Target ID: GO:0004144 diacylglycerol O-acyltransferase activity Sources: https://www.vascepa.com/assets/pdf/Vascepa_PI.pdf \| https://adisinsight.springer.com/drugs/800015122 \| https://www.ncbi.nlm.nih.gov/pubmed/27444154	Inhibitor 8504
GO:0004465 lipoprotein lipase activity 4 Target ID: GO:0004465 lipoprotein lipase activity Sources: https://www.vascepa.com/assets/pdf/Vascepa_PI.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/27444154	Activator 1447
fatty acid beta-oxidation 4 Target ID: GO:0006635 Sources: https://www.vascepa.com/assets/pdf/Vascepa_PI.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/27444154	Activator 1447
lipoprotein oxidation 4 Target ID: GO:0042161 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26945158	Inhibitor 8504	2.5 µM [IC50]
transformed cell apoptotic process 104 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26295255	Activator 1447	35.0 µM [IC50]
Peroxisome proliferator-activated receptor delta 30 Target ID: CHEMBL3979 Sources: http://www.drugbank.ca/drugs/DB00159	Agonist 2752
Prolyl endopeptidase 9 Target ID: CHEMBL3202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16478242	Inhibitor 8504	247.5 µM [Ki]
Receptor-mediated non-selective cation current (Icat) 4 Target ID: Receptor-mediated non-selective cation current (Icat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9105714	Inhibitor 8504	7.0 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00159	Inhibitor 8504
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00159	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Hypertriglyceridemia 20 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000Lbl.pdf	Primary	Approved 8583	Vascepa Approved Use Indicated as an adjunct to diet to reduce triglyceride (TG) levels in adult patients with severe (≥ 500 mg/dL) hypertriglyceridemia. Launch Date 2012
Major depressive disorder 179 Sources: https://clinicaltrials.gov/ct2/show/NCT02553915	Primary	Phase III 665	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://clinicaltrials.gov/ct2/show/NCT02719327	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
347 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/25428605/	4 g 2 times / day steady-state, oral dose: 4 g route of administration: Oral experiment type: STEADY-STATE co-administered:		ICOSAPENT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
6.519 μg × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/25428605/	4 g 2 times / day steady-state, oral dose: 4 g route of administration: Oral experiment type: STEADY-STATE co-administered:		ICOSAPENT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
89 h REVIEW https://pubmed.ncbi.nlm.nih.gov/25428605/	4 g 2 times / day steady-state, oral dose: 4 g route of administration: Oral experiment type: STEADY-STATE co-administered:		ICOSAPENT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://pubmed.ncbi.nlm.nih.gov/25428605/	4 g 2 times / day steady-state, oral dose: 4 g route of administration: Oral experiment type: STEADY-STATE co-administered:		ICOSAPENT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inhibitor 2438 inducer 440

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP2C8 1057 CYP2B6 926 P-gp 1741 BCRP 910 OCT2 779 OAT1 725 OATP1B1 1079 OATP1B3 961 OAT3 747	P-gp 2052 BCRP 697 OCT2 434 OAT1 395 OATP1B1 503 OATP1B3 435 OAT3 391 CYP 303	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27.0	no
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27.0	no	no (co-administration study) Comment: Vascepa did not affect the AUC or Cmax of exposure of racemic warfarin; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202057s035lbl.pdf Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27.0
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27.0	no	no (co-administration study) Comment: Vascepa did not affect the AUC or Cmax of exposure of atorvastatin; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202057s035lbl.pdf Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27.0
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28	weak [IC50 12.8 uM]	no (co-administration study) Comment: Vascepa did not affect the AUC or Cmax of exposure of rosiglitazone; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202057s035lbl.pdf Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28	weak [IC50 14 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28	weak [IC50 14 uM]	no (co-administration study) Comment: Vascepa did not affect the AUC or Cmax of exposure of racemic warfarin; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202057s035lbl.pdf Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28	weak [IC50 8.4 uM]	no (co-administration study) Comment: Vascepa did not affect the AUC or Cmax of exposure of omeprazole; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202057s035lbl.pdf Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=27 Page: 27;28
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000PharmR.pdf#page=32 Page: 32.0	yes [Inhibition 1 uM]

Drug as victim

Target	Modality	Activity
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=25 Page: 25.0	no
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=14 Page: 14.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000ClinPharmR.pdf#page=25 Page: 25.0	no

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0037XT	https://www.aablocks.com/goods/Goods/detail?id=AA0037XT
Aaron Chemicals	AR0038PL	http://www.aaronchem.com/10417-94-4
abcr GmbH	AB135514	http://www.abcr.com/shop/en/AB135514
AbMole Bioscience	M5608	http://www.abmole.com/products/eicosapentaenoic-acid.html
AHH Chemical co.,ltd	MT-11661	http://www.ahhchemical.com/product/MT-11661.html
AK Scientific, Inc. (AKSCI)	1755AH	http://www.aksci.com/item_detail.php?cat=1755AH
Alfa Chemistry	10417-94-4	https://www.alfa-chemistry.com/epa-cas-10417-94-4-item-289473.htm
Alfa Chemistry	AP10417944	https://reagents.alfa-chemistry.com/product/cis-5-8-11-14-17-eicosapentaenoic-acid-cas-10417-94-4-988.html
Alichem	490013200	http://www.alichem.com/en/products/10417-94-4.html
Allbio Pharm Co., Ltd	AB00247	http://www.allbiopharm.com/product/n/AB00247
Alsachim	978	http://www.alsachim.com/product-C3217-glo.bal-view.html
Aurora Fine Chemicals LLC	A17.876.800	http://online.aurorafinechemicals.com/info?ID=A17.876.800
AvaChem Scientific	6305	https://www.avachem.com/productSearch.asp?6305
BioSynth	J-001125	https://www.biosynth.com/en/products/all-products/products/J-001125.html
BLD Pharm	BD127342	http://www.bldpharm.com/products/10417-94-4.html
Calbiochem	324875	http://www.emdbiosciences.com/product/324875
Chem Scene	CS-2895	http://www.chemscene.com/10417-94-4.html
Chemenu	CM126647	http://www.chemenu.com/products/CM126647
Chemspace	CSSB00016999425	https://chem-space.com/CSSB00016999425
CSNpharm	CSN10913	https://www.csnpharm.com/products/eicosapentaenoic-acid.html
DC Chemicals	DC31714	http://www.dcchemicals.com//product_show-Icosapent.html
EMD Millipore	324875	http://www.emdbiosciences.com/product/324875
Glentham Life Sciences	GK4054	http://www.glentham.com/products/product/GK4054/
iChemical	EBD219836	http://www.ichemical.com/products/10417-94-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01307220	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01307220
MedChem Express	HY-B0660	https://www.medchemexpress.com/Eicosapentaenoic-Acid.html
MuseChem	I000242	https://www.musechem.com/product/I000242.html
Sigma-Aldrich	44864_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/44864?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E-113_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/e113?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E2011_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e2011?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E7006_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e7006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S530376	http://www.smolecule.com/products/s530376
TCI (Tokyo Chemical Industry)	E0441	http://www.tcichemicals.com/eshop/en/us/commodity/E0441/index.html
THE BioTek	bt-269997	https://www.thebiotek.com/product/inhibitors/bt-269997
Tocris	5979	https://www.tocris.com/products/eicosapentaenoic-acid_5979
VladaChem	VL261029-100MG	https://www.vladachem.com/product.php?products=10417-94-4

PubMed

Title	Date	PubMed
Comparison of the in vitro effect of eicosapentaenoic acid (EPA)-derived lipoxygenase metabolites on human platelet function with those of arachidonic acid.	1986 Feb 1	3010490
[Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet].	1987 Mar 1	3035811
Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid.	1992 Jul 29	1643099
Regulation of rat liver apolipoprotein A-I, apolipoprotein A-II and acyl-coenzyme A oxidase gene expression by fibrates and dietary fatty acids.	1995 Aug 15	7556148
The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes.	1996 Jun	8635279
Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration.	1996 Mar 3	8704924
Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release.	1996 Sep	8931114
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.	1997 Oct	9415022
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.	2005 Apr 8	15684433
Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts.	2005 Aug	15930517
Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids.	2005 Dec	16305726
COX-2 inhibitors and metabolism of essential fatty acids.	2005 Jul	15990700
EPA and DHA reduce LPS-induced inflammation responses in HK-2 cells: evidence for a PPAR-gamma-dependent mechanism.	2005 Mar	15698426
Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1.	2005 Mar 7	15753205
Resolvin E1, an endogenous lipid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis.	2005 May 24	15890784
Fatty acids and expression of adipokines.	2005 May 30	15949695
Alpha-tocopherol [corrected] and ascorbic acid attenuates the ribavirin [corrected] induced decrease of eicosapentaenoic acid in erythrocyte membrane in chronic hepatitis C patients.	2006 Aug	16872308
Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells.	2006 Feb	16301737
Mechanism of induction of muscle protein degradation by angiotensin II.	2006 Jul	16257180
A phase II study with antioxidants, both in the diet and supplemented, pharmaconutritional support, progestagen, and anti-cyclooxygenase-2 showing efficacy and safety in patients with cancer-related anorexia/cachexia and oxidative stress.	2006 May	16702388
Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo.	2006 May	16467281
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.	2006 Nov	17092368
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.	2006 Nov 25	16978661
Attenuation of mycotoxin-induced IgA nephropathy by eicosapentaenoic acid in the mouse: dose response and relation to IL-6 expression.	2006 Oct	16524712
Intake of fish oil, oleic acid, folic acid, and vitamins B-6 and E for 1 year decreases plasma C-reactive protein and reduces coronary heart disease risk factors in male patients in a cardiac rehabilitation program.	2007 Feb	17237316
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.	2007 Jan 15	17038422
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.	2007 Mar	16730733
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.	2008 Mar	18320257
PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression.	2008 May 19	18489776
Growth inhibition and induction of apoptosis of colon cancer cell lines by applying marine phospholipid.	2009	19116882
Relationship between fish intake, n-3 fatty acids, mercury and risk markers of CHD (National Health and Nutrition Examination Survey 1999-2002).	2009 Aug	18986590
n3 and n6 polyunsaturated fatty acids differentially modulate prostaglandin E secretion but not markers of lipogenesis in adipocytes.	2009 Jan 21	19159447
n-3 fatty acids and rosiglitazone improve insulin sensitivity through additive stimulatory effects on muscle glycogen synthesis in mice fed a high-fat diet.	2009 May	19277604
Docosahexaenoic acid increases cellular adiponectin mRNA and secreted adiponectin protein, as well as PPARγ mRNA, in 3T3-L1 adipocytes.	2010 Dec	21164549
Ethyl-eicosapentaenoate modulates changes in neurochemistry and brain lipids induced by parkinsonian neurotoxin 1-methyl-4-phenylpyridinium in mouse brain slices.	2010 Dec 15	20868657
Eicosapentaenoic acid up-regulates apelin secretion and gene expression in 3T3-L1 adipocytes.	2010 May	20352620
Eicosapentaenoic acid and rosiglitazone increase adiponectin in an additive and PPARγ-dependent manner in human adipocytes.	2011 Feb	20814411
Omega-3 fatty acid oxidation products prevent vascular endothelial cell activation by coplanar polychlorinated biphenyls.	2011 Feb 15	21130106
Protective effects of eicosapentaenoic acid on genotoxicity and oxidative stress of cyclophosphamide in mice.	2011 Jun	20052769
Eicosapentaenoic acid reduces warfarin-induced arterial calcification in rats.	2011 Mar	21193197
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).	2011 Sep 1	21683321
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.	2012	23056435
Additive, antagonistic, and synergistic effects of procyanidins and polyunsaturated fatty acids over inflammation in RAW 264.7 macrophages activated by lipopolysaccharide.	2012 Apr	22169119
Eicosapentaenoic acid and docosahexaenoic acid inhibit macrophage-induced gastric cancer cell migration by attenuating the expression of matrix metalloproteinase 10.	2012 Nov	22285823
Elevated blood pressure in cytochrome P4501A1 knockout mice is associated with reduced vasodilation to omega-3 polyunsaturated fatty acids.	2012 Nov 1	22995157
Astaxanthin and omega-3 fatty acids individually and in combination protect against oxidative stress via the Nrf2-ARE pathway.	2013 Dec	24157545
Effects of cannabinoids and related fatty acids upon the viability of P19 embryonal carcinoma cells.	2013 Nov	23552853
Fish oil and fenofibrate prevented phosphorylation-dependent hepatic sortilin 1 degradation in Western diet-fed mice.	2014 Aug 8	24986865
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.	2014 Dec 5	25451573
Effect of omega-3 fatty acid oxidation products on the cellular and mitochondrial toxicity of BDE 47.	2015 Jun	25659769

Patents

Sample Use Guides

In Vivo Use Guide

The daily dose of VASCEPA ( (icosapent) is 4 grams per day taken as 2 capsules twice daily with food.

Route of Administration: Oral

In Vitro Use Guide

The approximate 50% inhibitory concentrations (IC50) of EPA on LA-N-1 cells at 48 hours treatment was found to be 35 uM, whereas the IC50 for ALA on LA-N-1 cells at 48 hours treatment was found to be >50 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:55 GMT 2025`
Record UNII	AAN7QOV9EA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ICOSAPENT

Official Name

English

EICOSAPENTAENOIC ACID

Preferred Name

English

EPA

Common Name

English

EICOSAPENTAENOIC ACID (EPA) (C20:5) (CONSTITUENT OF KRILL OIL) [DSC]

Common Name

English

TIMNODONIC ACID

Common Name

English

Eicosapentaenoic acid [WHO-DD]

Common Name

English

ALL-CIS-FATTY ACID 20:5 OMEGA-3

Common Name

English

INCROMEGA E 7010SR

Common Name

English

ROPUFA 70

Common Name

English

icosapent [INN]

Common Name

English

(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-EICOSAPENTAENOIC ACID

Systematic Name

English

(ALL-Z)-5,8,11,14,17-EICOSAPENTAENOIC ACID

Common Name

English

EICOSAPENTAENOATE

Systematic Name

English

EICOSAPENTAENOIC ACID [MI]

Common Name

English

EICOSAPENTAENOIC ACID (EPA) (C20:5 N3)

Common Name

English

EICOSAPENTAENOIC ACID [USP-RS]

Common Name

English

C20:5 (N-3)

Common Name

English

EICOSAPENTAENOIC ACID (C20:5 N3)

Common Name

English

EICOSAPENTAENOIC ACID [VANDF]

Common Name

English

EICOSAPENTAENOIC ACID [MART.]

Common Name

English

EPA 45G

Code

English

Classification Tree Code System Code

LOINC

75097-6