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Details

Stereochemistry ACHIRAL
Molecular Formula C20H29O2.Na
Molecular Weight 324.4328
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 5
Charge 0

SHOW SMILES / InChI
Structure of ICOSAPENT SODIUM

SMILES

[Na+].CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O

InChI

InChIKey=RBZYGQJEMWGTOH-RSDXMDNYSA-M
InChI=1S/C20H30O2.Na/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);/q;+1/p-1/b4-3-,7-6-,10-9-,13-12-,16-15-;

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.5 µM [IC50]
35.0 µM [IC50]
247.5 µM [Ki]
Target ID: Receptor-mediated non-selective cation current (Icat)
7.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
[Decreasing atherogenic risks by an eicosapentaenoic acid-rich diet].
1987 Mar 1
Effects of fasting on disease activity, neutrophil function, fatty acid composition, and leukotriene biosynthesis in patients with rheumatoid arthritis.
1988 May
Effects of small concentrations of eicosapentaenoic acid on platelets.
1989
Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid.
1992 Jul 29
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
The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes.
1996 Jun
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
Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release.
1996 Sep
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.
1997 Oct
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.
2005 Apr 8
Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts.
2005 Aug
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
COX-2 inhibitors and metabolism of essential fatty acids.
2005 Jul
EPA and DHA reduce LPS-induced inflammation responses in HK-2 cells: evidence for a PPAR-gamma-dependent mechanism.
2005 Mar
Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1.
2005 Mar 7
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
Fatty acids and expression of adipokines.
2005 May 30
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
Eicosapentaenoic acid (20:5 n-3) increases fatty acid and glucose uptake in cultured human skeletal muscle cells.
2006 Feb
Mechanism of induction of muscle protein degradation by angiotensin II.
2006 Jul
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
Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo.
2006 May
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.
2006 Nov
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
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.
2007 Jan 15
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
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.
2008 Mar
PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression.
2008 May 19
Growth inhibition and induction of apoptosis of colon cancer cell lines by applying marine phospholipid.
2009
Relationship between fish intake, n-3 fatty acids, mercury and risk markers of CHD (National Health and Nutrition Examination Survey 1999-2002).
2009 Aug
Docosahexaenoic acid increases cellular adiponectin mRNA and secreted adiponectin protein, as well as PPARγ mRNA, in 3T3-L1 adipocytes.
2010 Dec
Ethyl-eicosapentaenoate modulates changes in neurochemistry and brain lipids induced by parkinsonian neurotoxin 1-methyl-4-phenylpyridinium in mouse brain slices.
2010 Dec 15
Eicosapentaenoic acid up-regulates apelin secretion and gene expression in 3T3-L1 adipocytes.
2010 May
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
Protective effects of eicosapentaenoic acid on genotoxicity and oxidative stress of cyclophosphamide in mice.
2011 Jun
Eicosapentaenoic acid reduces warfarin-induced arterial calcification in rats.
2011 Mar
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
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
Additive, antagonistic, and synergistic effects of procyanidins and polyunsaturated fatty acids over inflammation in RAW 264.7 macrophages activated by lipopolysaccharide.
2012 Apr
Eicosapentaenoic acid and docosahexaenoic acid inhibit macrophage-induced gastric cancer cell migration by attenuating the expression of matrix metalloproteinase 10.
2012 Nov
Elevated blood pressure in cytochrome P4501A1 knockout mice is associated with reduced vasodilation to omega-3 polyunsaturated fatty acids.
2012 Nov 1
Astaxanthin and omega-3 fatty acids individually and in combination protect against oxidative stress via the Nrf2-ARE pathway.
2013 Dec
Effects of cannabinoids and related fatty acids upon the viability of P19 embryonal carcinoma cells.
2013 Nov
Fish oil and fenofibrate prevented phosphorylation-dependent hepatic sortilin 1 degradation in Western diet-fed mice.
2014 Aug 8
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
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.
Name Type Language
ICOSAPENT SODIUM
Common Name English
5,8,11,14,17-EICOSAPENTAENOIC ACID, SODIUM SALT, (ALL-Z)-
Common Name English
EICOSAPENTAENOIC ACID SODIUM SALT
Common Name English
5,8,11,14,17-EICOSAPENTAENOIC ACID, SODIUM SALT (1:1), (5Z,8Z,11Z,14Z,17Z)-
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002305
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY
PUBCHEM
23679014
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID10993898
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY
SMS_ID
300000017643
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY
CAS
73167-03-0
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY
FDA UNII
5PXN91KPRO
Created by admin on Fri Dec 15 18:29:55 GMT 2023 , Edited by admin on Fri Dec 15 18:29:55 GMT 2023
PRIMARY