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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
Structure of Icosapent lysine salt

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

HIDE SMILES / InChI

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Lower levels of lipid peroxidation in human platelets incubated with eicosapentaenoic acid.
1992 Jul 29
The mechanism of inhibitory effect of eicosapentaenoic acid on phagocytic activity and chemotaxis of human neutrophil granulocytes.
1996 Jun
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
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
Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts.
2005 Aug
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
EPA and DHA reduce LPS-induced inflammation responses in HK-2 cells: evidence for a PPAR-gamma-dependent mechanism.
2005 Mar
Fatty acids and expression of adipokines.
2005 May 30
Mechanism of induction of muscle protein degradation by angiotensin II.
2006 Jul
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.
2006 Nov
Attenuation of mycotoxin-induced IgA nephropathy by eicosapentaenoic acid in the mouse: dose response and relation to IL-6 expression.
2006 Oct
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
Ethyl-eicosapentaenoate modulates changes in neurochemistry and brain lipids induced by parkinsonian neurotoxin 1-methyl-4-phenylpyridinium in mouse brain slices.
2010 Dec 15
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
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
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
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 Sat Dec 16 20:13:05 UTC 2023
Edited
by admin
on Sat Dec 16 20:13:05 UTC 2023
Record UNII
XX8KWN4FNB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Icosapent lysine salt
Common Name English
Lysine Eicosapentaenoate
Common Name English
L-Lysine, mixt. with (all-Z)-5,8,11,14,17-eicosapentaenoic acid
Common Name English
Code System Code Type Description
FDA UNII
XX8KWN4FNB
Created by admin on Sat Dec 16 20:13:05 UTC 2023 , Edited by admin on Sat Dec 16 20:13:05 UTC 2023
PRIMARY
CAS
1957202-41-3
Created by admin on Sat Dec 16 20:13:05 UTC 2023 , Edited by admin on Sat Dec 16 20:13:05 UTC 2023
PRIMARY
CAS
127963-98-8
Created by admin on Sat Dec 16 20:13:05 UTC 2023 , Edited by admin on Sat Dec 16 20:13:05 UTC 2023
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE