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Details

Stereochemistry ACHIRAL
Molecular Formula C22H34O2
Molecular Weight 330.5042
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 5
Charge 0

SHOW SMILES / InChI
Structure of ICOSAPENT ETHYL

SMILES

CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

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

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.5 µM [IC50]
35.0 µM [IC50]
247.5 µM [Ki]
7.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vascepa
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
347 μg/mL
4 g 2 times / day steady-state, oral
ICOSAPENT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.519 μg × h/mL
4 g 2 times / day steady-state, oral
ICOSAPENT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
89 h
4 g 2 times / day steady-state, oral
ICOSAPENT plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
4 g 2 times / day steady-state, oral
ICOSAPENT plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The daily dose of VASCEPA ( (icosapent) is 4 grams per day taken as 2 capsules twice daily with food.
Route of Administration: Oral
In Vitro Use Guide
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.