Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H30O2.C6H14N2O2 |
| Molecular Weight | 448.6386 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 5 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI
InChIKey=OSZMRUUDBQFIEL-DTAHNJQXSA-N
InChI=1S/C20H30O2.C6H14N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22;7-4-2-1-3-5(8)6(9)10/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22);5H,1-4,7-8H2,(H,9,10)/b4-3-,7-6-,10-9-,13-12-,16-15-;/t;5-/m.0/s1
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 |
|---|---|---|---|
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:0042161 |
2.5 µM [IC50] | ||
Target ID: GO:0006927 |
35.0 µM [IC50] | ||
Target ID: CHEMBL3979 Sources: http://www.drugbank.ca/drugs/DB00159 |
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Target ID: CHEMBL3202 |
247.5 µM [Ki] | ||
Target ID: Receptor-mediated non-selective cation current (Icat) |
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 |
|---|---|---|---|---|
| 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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| 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 Page: 27.0 |
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| 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 Page: 27.0 |
|||
| 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 Page: 27;28 |
|||
| weak [IC50 14 uM] | ||||
| 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 Page: 27;28 |
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| 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 Page: 27;28 |
|||
| yes [Inhibition 1 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
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 |
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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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| Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid. | 1992 Jul 29 |
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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 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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| Eicosapentaenoic acid in the treatment of schizophrenia and depression: rationale and preliminary double-blind clinical trial results. | 2003 Dec |
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| Troglitazone reduces activity of the Na+/H+ exchanger in fructose-fed borderline hypertensive rats. | 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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| 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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| 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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| 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 |
|
| Mechanism of induction of muscle protein degradation by angiotensin II. | 2006 Jul |
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| 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 |
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| Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo. | 2006 May |
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| Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. | 2006 Nov |
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| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
|
| Attenuation of mycotoxin-induced IgA nephropathy by eicosapentaenoic acid in the mouse: dose response and relation to IL-6 expression. | 2006 Oct |
|
| 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 |
|
| TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
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| 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 |
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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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| Relationship between fish intake, n-3 fatty acids, mercury and risk markers of CHD (National Health and Nutrition Examination Survey 1999-2002). | 2009 Aug |
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| Eicosapentaenoic acid up-regulates apelin secretion and gene expression in 3T3-L1 adipocytes. | 2010 May |
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| Eicosapentaenoic acid and rosiglitazone increase adiponectin in an additive and PPARγ-dependent manner in human adipocytes. | 2011 Feb |
|
| Omega-3 fatty acid oxidation products prevent vascular endothelial cell activation by coplanar polychlorinated biphenyls. | 2011 Feb 15 |
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| Protective effects of eicosapentaenoic acid on genotoxicity and oxidative stress of cyclophosphamide in mice. | 2011 Jun |
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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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| Fish oil and fenofibrate prevented phosphorylation-dependent hepatic sortilin 1 degradation in Western diet-fed mice. | 2014 Aug 8 |
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| Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal. | 2014 Dec 5 |
|
| 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 |
|
| 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
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XX8KWN4FNB
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1957202-41-3
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127963-98-8
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ALTERNATIVE |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
