U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ICOSAPENT

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
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
[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
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
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
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
[The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis].
2000
Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro.
2000 Apr 13
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
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
Eicosapentaenoic acid in treatment-resistant depression associated with symptom remission, structural brain changes and reduced neuronal phospholipid turnover.
2001 Oct
Eicosapentaenoic acid and gamma-linolenic acid induce apoptosis in HL-60 cells.
2002 Sep
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
Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk.
2003 Jan
Effects of purified eicosapentaenoic acid and docosahexaenoic acid on platelet, fibrinolytic and vascular function in hypertensive type 2 diabetic patients.
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
Mechanism of induction of muscle protein degradation by angiotensin II.
2006 Jul
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
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
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
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:07 GMT 2023
Edited
by admin
on Fri Dec 15 16:35:07 GMT 2023
Record UNII
AAN7QOV9EA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ICOSAPENT
INN  
INN  
Official 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 [INCI]
Common 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
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official 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
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 88998-0
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
FDA ORPHAN DRUG 283409
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 90911-9
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LIVERTOX 342
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
EU-Orphan Drug EU/3/09/666
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 88996-4
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
NCI_THESAURUS C67080
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
DSLD 3820 (Number of products:4)
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 35173-4
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 90908-5
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
DSLD 1011 (Number of products:2641)
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 90909-3
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 88999-8
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 88997-2
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
LOINC 90912-7
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
Code System Code Type Description
CHEBI
36006
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
RS_ITEM_NUM
1234293
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
SMS_ID
100000079270
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
MESH
D015118
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
FDA UNII
AAN7QOV9EA
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CHEBI
28364
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
INN
6328
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CAS
10417-94-4
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
WIKIPEDIA
EICOSAPENTAENOIC ACID
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
ChEMBL
CHEMBL460026
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CHEBI
61330
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID9041023
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
DAILYMED
AAN7QOV9EA
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
DRUG CENTRAL
3174
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
EVMPD
SUB13664MIG
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CAS
25378-27-2
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
NON-SPECIFIC SUBSTITUTION
MERCK INDEX
m4848
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY Merck Index
CHEBI
58562
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CHEBI
84883
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
NCI_THESAURUS
C68434
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
CAS
1553-41-9
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
618597
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
ALTERNATIVE
IUPHAR
7441
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
RXCUI
90
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
DRUG BANK
DB00159
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
PUBCHEM
446284
Created by admin on Fri Dec 15 16:35:07 GMT 2023 , Edited by admin on Fri Dec 15 16:35:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
DERIVATIVE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
Related Record Type Details
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
Related Record Type Details
ACTIVE MOIETY