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Details

Stereochemistry ACHIRAL
Molecular Formula C22H34O2
Molecular Weight 330.505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 5
Charge 0

SHOW SMILES / InChI
Structure of ICOSAPENT ETHYL

SMILES

CC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\CCCC(=O)OCC

InChI

InChIKey=SSQPWTVBQMWLSZ-AAQCHOMXSA-N
InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-

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

1.34317434E12
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
Deoxynivalenol-induced mitogen-activated protein kinase phosphorylation and IL-6 expression in mice suppressed by fish oil.
2003 Dec
Eicosapentaenoic acid in the treatment of schizophrenia and depression: rationale and preliminary double-blind clinical trial results.
2003 Dec
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
Troglitazone reduces activity of the Na+/H+ exchanger in fructose-fed borderline hypertensive rats.
2003 Jan
A pilot study of eicosapentaenoic acid therapy for ribavirin-related anemia in patients with chronic hepatitis C.
2003 Jun
The effect of supplementation with fish oil during pregnancy on breast milk immunoglobulin A, soluble CD14, cytokine levels and fatty acid composition.
2004 Aug
Essential fatty acids in erythrocyte phospholipids during pregnancy and at delivery in mothers and their neonates: comparison with plasma phospholipids.
2004 Dec
Docosahexaenoic acid and eicosapentaenoic acid, but not alpha-linolenic acid, suppress deoxynivalenol-induced experimental IgA nephropathy in mice.
2004 Jun
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
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.
2005 Apr 8
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
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
Signalling pathways in the induction of proteasome expression by proteolysis-inducing factor in murine myotubes.
2005 Jan
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
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
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
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
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
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
n3 and n6 polyunsaturated fatty acids differentially modulate prostaglandin E secretion but not markers of lipogenesis in adipocytes.
2009 Jan 21
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
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
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 ETHYL
ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
AMR-101
Code English
EICOSAPENTAENOIC ACID ETHYL ESTER [WHO-DD]
Common Name English
EICOSAPENTAENOIC ACID ETHYL ESTER
MART.   MI   WHO-DD  
Systematic Name English
AMR 101
Code English
ETHYL EICOSAPENTAENOIC ACID
Systematic Name English
ICOSAPENT ETHYL [ORANGE BOOK]
Common Name English
VASCEPA
Brand Name English
ETHYL ICOSAPENT
Common Name English
ETHYL ICOSAPENTATE
JAN  
Common Name English
ETHYL EICOSAPENTAENOATE
Systematic Name English
EICOSAPENTAENOIC ACID ETHYL ESTER [MART.]
Common Name English
5,8,11,14,17-EICOSAPENTAENOIC ACID, ETHYL ESTER, (5Z,8Z,11Z,14Z,17Z)-
Common Name English
ETHYL ALL-CIS-5,8,11,14,17-ICOSAPENTAENOIC ACID
Common Name English
TIMNODONIC ACID ETHYL ESTER
Common Name English
NSC-759597
Code English
AMR101
Code English
EPADEL
Common Name English
ICOSAPENT ETHYL [VANDF]
Common Name English
ETHYL (5Z,8Z,11Z,14Z,17Z)-ICOSA-5,8,11,14,17-PENTAENOATE
Systematic Name English
ICOSAPENT ETHYL [USAN]
Common Name English
EICOSAPENTAENOIC ACID ETHYL ESTER [USP-RS]
Common Name English
EICOSAPENTAENOIC ACID ETHYL ESTER [MI]
Common Name English
ICOSAPENT ETHYL ESTER
Common Name English
ETHYL ICOSAPENTATE [JAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 134300
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
EU-Orphan Drug EU/3/00/013
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
NCI_THESAURUS C29703
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
Code System Code Type Description
DRUG BANK
DB08887
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
PUBCHEM
9831415
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
USP_CATALOG
1234307
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL2095209
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
FDA UNII
6GC8A4PAYH
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
DRUG CENTRAL
1413
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
EVMPD
SUB32403
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
CAS
86227-47-6
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
MERCK INDEX
M4848
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1200711
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
RXCUI
1304974
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C72986
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY
WIKIPEDIA
ETHYL EICOSAPENTAENOIC ACID
Created by admin on Fri Jun 25 22:14:05 UTC 2021 , Edited by admin on Fri Jun 25 22:14:05 UTC 2021
PRIMARY