icosapent ethyl Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1413 86227-47-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ethyl-eicosapent
  • ethyl eicosapent
  • ethyl-eicosapentaenoic acid
  • icosapent ethyl
  • vascepa
  • ethyl eicosapentaenoate
  • ethyl icosapentate
  • timnodonic acid ethyl ester
Icosapent ethyl is a stable ethyl ester of the omega-3 fatty acid, eicosapentaenoic acid (EPA). The mechanisms of action contributing to reduction of cardiovascular events with icosapent ethyl are not completely understood. The mechanisms are likely multi-factorial including improved lipoprotein profile with reduction of triglyceride-rich lipoproteins, anti-inflammatory, and antioxidant effects, reduction of macrophage accumulation, improved endothelial function, increased fibrous cap thickness/stability, and antiplatelet effects. Each of these mechanisms can beneficially alter the development, progression, and stabilisation of atherosclerotic plaque, as well as the implications of plaque rupture, and preclinical and clinical studies support such benefits with EPA. Systemic and localised anti-inflammatory effects of EPA may result from displacement of pro-inflammatory arachidonic acid (AA), directing catabolism away from eicosanoids (2-series prostaglandins and thromboxanes, and 4-series leukotrienes) to non- or anti-inflammatory mediators. However, the direct clinical meaning of individual findings is not clear.
  • Molecular weight: 330.51
  • Formula: C22H34O2
  • CLOGP: 7.81
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 26.30
  • ALOGS: -6.53
  • ROTB: 15

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
March 26, 2021 EMA Amarin Pharmaceuticals Ireland Limited
July 26, 2012 FDA AMARIN PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Product odour abnormal 88.13 26.16 17 1435 1119 46683491
Blood triglycerides increased 60.49 26.16 20 1432 11763 46672847
Interstitial lung disease 31.36 26.16 20 1432 53929 46630681
Product taste abnormal 31.09 26.16 8 1444 1955 46682655
Hepatic function abnormal 28.42 26.16 16 1436 34405 46650205
Product physical issue 27.84 26.16 9 1443 4918 46679692
Prescribed underdose 26.58 26.16 11 1441 12042 46672568

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Product odour abnormal 202.51 22.56 35 1958 565 29949920
Blood triglycerides increased 130.86 22.56 45 1948 13972 29936513
Product physical issue 69.05 22.56 18 1975 2156 29948329
Product taste abnormal 59.45 22.56 14 1979 1104 29949381
Prescribed underdose 57.44 22.56 21 1972 7738 29942747
Hyperkinetic heart syndrome 39.79 22.56 7 1986 125 29950360
Cerebral infarction 38.05 22.56 23 1970 26350 29924135
Hepatic function abnormal 34.95 22.56 26 1967 41919 29908566
Eructation 31.72 22.56 11 1982 3473 29947012
Echocardiogram abnormal 27.84 22.56 7 1986 725 29949760
Product adhesion issue 27.37 22.56 8 1985 1457 29949028
Stress cardiomyopathy 22.64 22.56 7 1986 1542 29948943

Pharmacologic Action:

SourceCodeDescription
MeSH PA D006401 Hematologic Agents
MeSH PA D057847 Lipid Regulating Agents
MeSH PA D010975 Platelet Aggregation Inhibitors
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:35476 grosser tranquilizer
CHEBI has role CHEBI:35821 hypocholesteremic agent
CHEBI has role CHEBI:50266 prodrugs
CHEBI has role CHEBI:76507 marine metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertriglyceridemia indication 302870006

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
1GM VASCEPA AMARIN PHARMS N202057 July 26, 2012 RX CAPSULE ORAL Dec. 13, 2022 ADJUNCT TO MAX TOLERATED STATIN TX TO REDUCE RISK OF MI, STROKE, CORONULLRY REVASCULARIZATION, & UNSTABLE ANGINULL REQUIRING HOSPITALIZATION IN ADULTS W/ ELEVATED TG LEVELS & ESTABLISHED CV DISEASE OR DIABETES MELLITUS & 2+ RISK FACTORS FOR CV DISEASE
500MG VASCEPA AMARIN PHARMS N202057 Feb. 16, 2017 RX CAPSULE ORAL Dec. 13, 2022 ADJUNCT TO MAX TOLERATED STATIN TX TO REDUCE RISK OF MI, STROKE, CORONULLRY REVASCULARIZATION, & UNSTABLE ANGINULL REQUIRING HOSPITALIZATION IN ADULTS W/ ELEVATED TG LEVELS & ESTABLISHED CV DISEASE OR DIABETES MELLITUS & 2+ RISK FACTORS FOR CV DISEASE

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Diacylglycerol O-acyltransferase 1 Enzyme INHIBITOR DRUG LABEL DRUG LABEL

External reference:

IDSource
4032044 VUID
N0000186143 NUI
D01892 KEGG_DRUG
4032044 VANDF
C0058978 UMLSCUI
CHEBI:84883 CHEBI
CHEMBL2095209 ChEMBL_ID
DB08887 DRUGBANK_ID
9831415 PUBCHEM_CID
C035276 MESH_SUPPLEMENTAL_RECORD_UI
6GC8A4PAYH UNII
1304974 RXNORM
192321 MMSL
28709 MMSL
340526 MMSL
014642 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Icosapent Ethyl HUMAN PRESCRIPTION DRUG LABEL 1 0054-0508 CAPSULE 1 g ORAL ANDA 26 sections
Icosapent HUMAN PRESCRIPTION DRUG LABEL 1 43598-267 CAPSULE 1000 mg ORAL ANDA 22 sections
Vascepa HUMAN PRESCRIPTION DRUG LABEL 1 52937-001 CAPSULE 1000 mg ORAL NDA 25 sections
Vascepa HUMAN PRESCRIPTION DRUG LABEL 1 52937-003 CAPSULE 500 mg ORAL NDA 25 sections
Vascepa HUMAN PRESCRIPTION DRUG LABEL 1 52937-101 CAPSULE 1000 mg ORAL NDA 25 sections
Vascepa HUMAN PRESCRIPTION DRUG LABEL 1 63629-8247 CAPSULE 1000 mg ORAL NDA 25 sections