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
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-
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00159Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202057Orig1s000Lbl.pdf
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0004144 diacylglycerol O-acyltransferase activity |
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Target ID: GO:0004465 lipoprotein lipase activity |
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Target ID: GO:0006635 |
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Target ID: GO:0042161 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26945158 |
2.5 µM [IC50] | ||
Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26295255 |
35.0 µM [IC50] | ||
Target ID: CHEMBL3979 Sources: http://www.drugbank.ca/drugs/DB00159 |
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Target ID: CHEMBL3202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16478242 |
247.5 µM [Ki] | ||
Target ID: Receptor-mediated non-selective cation current (Icat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9105714 |
7.0 µM [IC50] | ||
Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00159 |
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Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00159 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Vascepa Approved UseIndicated as an adjunct to diet to reduce triglyceride (TG) levels in adult patients with severe (≥ 500 mg/dL) hypertriglyceridemia. Launch Date2012 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
347 μg/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
89 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
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[Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet]. | 1987 Mar 1 |
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Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis. | 1988 May |
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Effects of small concentrations of eicosapentaenoic acid on platelets. | 1989 |
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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 |
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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 |
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Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release. | 1996 Sep |
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Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids. | 1997 Oct |
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Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
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[The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis]. | 2000 |
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Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro. | 2000 Apr 13 |
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The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. | 2001 Jan |
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Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
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Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
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Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model. | 2001 Nov |
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Eicosapentaenoic acid in treatment-resistant depression associated with symptom remission, structural brain changes and reduced neuronal phospholipid turnover. | 2001 Oct |
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Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells. | 2002 Sep |
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Deoxynivalenol-induced mitogen-activated protein kinase phosphorylation and IL-6 expression in mice suppressed by fish oil. | 2003 Dec |
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Eicosapentaenoic acid in the treatment of schizophrenia and depression: rationale and preliminary double-blind clinical trial results. | 2003 Dec |
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Inhibition by eicosapentaenoic acid of IL-1beta-induced PGHS-2 expression in human microvascular endothelial cells: involvement of lipoxygenase-derived metabolites and p38 MAPK pathway. | 2003 Feb 20 |
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Troglitazone reduces activity of the Na+/H+ exchanger in fructose-fed borderline hypertensive rats. | 2003 Jan |
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Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. | 2003 Jan |
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Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients. | 2003 Jan |
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A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C. | 2003 Jun |
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The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition. | 2004 Aug |
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Essential fatty acids in erythrocyte phospholipids during pregnancy and at delivery in mothers and their neonates: comparison with plasma phospholipids. | 2004 Dec |
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Docosahexaenoic acid and eicosapentaenoic acid, but not alpha-linolenic acid, suppress deoxynivalenol-induced experimental IgA nephropathy in mice. | 2004 Jun |
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Modulation of cyclin D1 and early growth response factor-1 gene expression in interleukin-1beta-treated rat smooth muscle cells by n-6 and n-3 polyunsaturated fatty acids. | 2004 Nov |
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Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation. | 2005 Apr 8 |
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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 |
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Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
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Signalling pathways in the induction of proteasome expression by proteolysis-inducing factor in murine myotubes. | 2005 Jan |
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COX-2 inhibitors and metabolism of essential fatty acids. | 2005 Jul |
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Mechanism of induction of muscle protein degradation by angiotensin II. | 2006 Jul |
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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 |
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Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha. | 2008 Mar |
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PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression. | 2008 May 19 |
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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 |
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A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
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Elevated blood pressure in cytochrome P4501A1 knockout mice is associated with reduced vasodilation to omega-3 polyunsaturated fatty acids. | 2012 Nov 1 |
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Astaxanthin and omega-3 fatty acids individually and in combination protect against oxidative stress via the Nrf2-ARE pathway. | 2013 Dec |
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Effects of cannabinoids and related fatty acids upon the viability of P19 embryonal carcinoma cells. | 2013 Nov |
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Fish oil and fenofibrate prevented phosphorylation-dependent hepatic sortilin 1 degradation in Western diet-fed mice. | 2014 Aug 8 |
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Group VIA Phospholipase A2 (iPLA2β) Modulates Bcl-x 5'-Splice Site Selection and Suppresses Anti-apoptotic Bcl-x(L) in β-Cells. | 2015 Apr 24 |
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Effect of omega-3 fatty acid oxidation products on the cellular and mitochondrial toxicity of BDE 47. | 2015 Jun |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26295255
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
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on
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Record UNII |
AAN7QOV9EA
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88998-0
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EICOSAPENTAENOIC ACID
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CHEMBL460026
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DB00159
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID | |||
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DERIVATIVE -> PARENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
EPA is mainly metabolized by the liver via beta-oxidation similar to dietary fatty acids. Beta oxidation splits the long carbon chain of EPA into acetyl Coenzyme A, which is converted into energy via the Krebs cycle. Cytochrome P450-mediated metabolism is a minor pathway of elimination of EPA.
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |