NAV

Icosapent ethyl

Identification

Summary

Icosapent ethyl is an ethyl ester of eicosapentaenoic acid (EPA) that reduces synthesis and enhances clearance of triglycerides that is used to treat patients with severe hypertriglyceridemia.

Brand Names
Vascepa
Generic Name
Icosapent ethyl
DrugBank Accession Number
DB08887
Background

Icosapent ethyl or ethyl eicosapentaenoic acid is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). It is used as an adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL) and to reduce the risk of cardiovascular events in certain patients with elevated triglycerides. FDA approved on July 26, 2012.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
3D
Similar Structures
Weight
Average: 330.5042
Monoisotopic: 330.255880332
Chemical Formula
C22H34O2
Synonyms
  • (all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl ester
  • all-cis-ethyl 5,8,11,14,17-icosapentaenoate
  • cis-Eicosapentaenoic acid ethyl ester
  • E-EPA
  • Eicosapentaenoic acid ethyl ester
  • ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate
  • ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate
  • ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate
  • Ethyl (all cis)-5,8,11,14,17-icosapentaenoate
  • Ethyl all-cis-5,8,11,14,17-icosapentaenoate
  • Ethyl eicosapentaenoate
  • Ethyl icosapentate
  • ethyl-eicosapentaenoic acid
  • Ethyl-EPA
  • Icosapent ethyl
  • Timnodonic acid ethyl ester
External IDs
  • AMR 101
  • AMR-101
  • AMR101
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Icosapent ethyl is indicated as an adjunct to maximally tolerated statin therapy to reduce the risk of myocardial infarction, stroke, coronary revascularization, and unstable angina requiring hospitalizing in adult patients with elevated triglycerides (≥150 mg/dL) and established cardiovascular disease or who have diabetes mellitus and ≥2 other risk factors for cardiovascular disease.2 It is also indicated as an adjunct to diet to reduce triglyceride levels in adult patients with severe (≥500 mg/dL) hypertriglyceridemia.2

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in prevention ofHospitalizations••••••••••••••••••••••••• ••••••••• ••• •••• •••••••• ••••••••• •• ••••• •••••••••••• •••••••••••••
Adjunct therapy in prevention ofHospitalizations•••••••••••••••••••••••••••• •••••••••••••• •••••••• ••••••••• •• ••••• •••••••••••• •••••••••••••
Adjunct therapy in treatment ofSevere hypertriglyceridemias••••••••••••••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Studies suggest that EPA reduces hepatic very low-density lipoprotein triglycerides (VLDL-TG) synthesis and/or secretion and enhances TG clearance from circulating VLDL particles. Potential mechanisms of action include increased β-oxidation; inhibition of acyl-CoA:1,2-diacylglycerol acyltransferase (DGAT); decreased lipogenesis in the liver; and increased plasma lipoprotein lipase activity.

Absorption

Icosapent ethyl is de-esterfied, converted into active EPA, and then absorbed in the small intestine. It reaches peak plasma concentration in 5 hours post-oral administration. Very little (<1%) is left circulating in the plasma as EPA incorporates into phospholipids, TG's, and cholesteryl esters.

Volume of distribution

Steady state volume of distribution of active EPA is 88 L

Protein binding

Not Available

Metabolism

Once converted into active EPA, it is hepatically metabolized into acetyl Coenzyme A via beta-oxidation.

Hover over products below to view reaction partners

  • Icosapent ethyl
Route of elimination

Icosapent ethyl is not renally excreted

Half-life

The half life of EPA is 89 hours.

Clearance

Total plasma clearance, EPA = 684 mL/hr

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Icosapent ethyl is generally well tolerated and adverse effects are unrelated to treatment.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbciximabThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Abciximab.
AbrocitinibThe risk or severity of bleeding and thrombocytopenia can be increased when Icosapent ethyl is combined with Abrocitinib.
AceclofenacThe risk or severity of bleeding can be increased when Aceclofenac is combined with Icosapent ethyl.
AcemetacinThe risk or severity of bleeding can be increased when Acemetacin is combined with Icosapent ethyl.
AcenocoumarolThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Acenocoumarol.
Food Interactions
  • Take with food.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Active Moieties
NameKindUNIICASInChI Key
IcosapentunknownAAN7QOV9EA10417-94-4JAZBEHYOTPTENJ-JLNKQSITSA-N
International/Other Brands
Epadel
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VascepaCapsule1000 mg/1OralAmarin Pharma Inc.2012-10-01Not applicableUS flag
VascepaCapsule1000 mg/1Oralbryant ranch prepack2012-10-01Not applicableUS flag
VascepaCapsule1000 mg/1OralAmarin Pharma Inc.2012-10-01Not applicableUS flag
VascepaCapsule500 mg/1OralAmarin Pharma Inc.2016-09-16Not applicableUS flag
VascepaCapsule1 gOralHls Therapeutics Inc2020-02-07Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IcosapentCapsule1000 mg/1OralDr. Reddy's Laboratories, Inc.2021-06-21Not applicableUS flag
IcosapentCapsule1000 mg/1Oralbryant ranch prepack2021-06-21Not applicableUS flag
IcosapentCapsule1000 mg/1OralAvKARE2024-01-24Not applicableUS flag
Icosapent EthylCapsule0.5 g/1OralHikma Pharmaceuticals USA Inc.2020-11-04Not applicableUS flag
Icosapent EthylCapsule, liquid filled1 g/1OralEpic Pharma, LLC2023-12-22Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
OMEGOILIcosapent ethyl (460 mg) + Doconexent (380 MG)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
OMEGOILIcosapent ethyl (460 mg) + Doconexent (380 MG)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
OMEGOILIcosapent ethyl (460 mg) + Doconexent (380 MG)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
OMEGOILIcosapent ethyl (460 mg) + Doconexent (380 MG)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
OMEGOILIcosapent ethyl (460 mg) + Doconexent (380 MG)CapsuleOralIbsa Farmaceutici Italia S.R.L.2018-08-112022-01-12Italy flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acid esters
Direct Parent
Fatty acid esters
Alternative Parents
Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Fatty acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain fatty acid ethyl ester (CHEBI:84883)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6GC8A4PAYH
CAS number
86227-47-6
InChI Key
SSQPWTVBQMWLSZ-AAQCHOMXSA-N
InChI
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-
IUPAC Name
ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
SMILES
CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

References

General References
  1. Ballantyne CM, Braeckman RA, Soni PN: Icosapent ethyl for the treatment of hypertriglyceridemia. Expert Opin Pharmacother. 2013 Jul;14(10):1409-16. doi: 10.1517/14656566.2013.798645. Epub 2013 May 24. [Article]
  2. FDA Approved Drug Products: Vascepa (icosapent ethyl) capsules for oral use [Link]
Human Metabolome Database
HMDB0039530
KEGG Drug
D01892
KEGG Compound
C16184
PubChem Compound
9831415
PubChem Substance
175427134
ChemSpider
8007147
RxNav
1304974
ChEBI
84883
ChEMBL
CHEMBL2095209
ZINC
ZINC000003785276
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ethyl_eicosapentaenoic_acid
FDA label
Download (275 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk / High Triglyceride Level / Type 2 Diabetes Mellitus1
4CompletedPreventionCerebral Vasospasm / Subarachnoid Hemorrhage1
4CompletedPreventionMyocardial Infarction, Unstable Angina Pectoris, Sudden Cardiac Death, Stroke, Peripheral Artery Disease1
4CompletedTreatmentHypertriglyceridemias1
4TerminatedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronavirus Disease 2019 (COVID‑19) / Upper Respiratory Tract Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
CapsuleOral0.5 g/1
CapsuleOral1 g/1
Capsule, liquid filledOral0.5 g/1
Capsule, liquid filledOral1 g/1
Capsule, liquid filledOral500 mg/1
CapsuleOral1 g
CapsuleOral1000 mg/1
CapsuleOral500 mg/1
CapsuleOral998 mg
CapsuleOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8293727No2012-10-232030-02-09US flag
US8293728No2012-10-232030-02-09US flag
US8314086No2012-11-202030-02-09US flag
US8318715No2012-11-272030-02-09US flag
US8357677No2013-01-222030-02-09US flag
US8367652No2013-02-052030-02-09US flag
US8377920No2013-02-192030-02-09US flag
US8399446No2013-03-192030-02-09US flag
US8415335No2013-04-092030-02-09US flag
US8426399No2013-04-232030-02-09US flag
US8431560No2013-04-302030-02-09US flag
US8440650No2013-05-142030-02-09US flag
US8445003No2013-05-212030-04-29US flag
US8445013No2013-05-212030-04-29US flag
US8501225No2013-08-062030-04-29US flag
US8524698No2013-09-032030-04-29US flag
US8551521No2013-10-082030-04-29US flag
US8563608No2013-10-222030-04-29US flag
US8617593No2013-12-312030-04-29US flag
US8546372No2013-10-012030-04-29US flag
US8518929No2013-08-272030-04-29US flag
US8617594No2013-12-312030-04-29US flag
US8623406No2014-01-072030-04-29US flag
US8298554No2012-10-302030-04-29US flag
US8188146No2012-05-292020-01-27US flag
US9700537No2017-07-112027-05-31US flag
US9198892No2015-12-012027-09-25US flag
US8410086No2013-04-022030-06-15US flag
US8454994No2013-06-042030-04-29US flag
US8455472No2013-06-042030-06-15US flag
US8618166No2013-12-312030-04-29US flag
US8642077No2014-02-042030-04-29US flag
US8669245No2014-03-112030-06-15US flag
US8680144No2014-03-252030-02-09US flag
US8703185No2014-04-222030-04-29US flag
US8691871No2014-04-082030-04-29US flag
US8709475No2014-04-292030-04-29US flag
US8710041No2014-04-292030-06-15US flag
US9603826No2017-03-282033-06-28US flag
US9610272No2017-04-042033-06-28US flag
US9623001No2017-04-182033-06-28US flag
US9693984No2017-07-042033-06-28US flag
US9693985No2017-07-042033-06-28US flag
US9693986No2017-07-042033-06-28US flag
US10010517No2018-07-032030-04-29US flag
US9918954No2018-03-202033-06-28US flag
US10278935No2019-05-072033-06-28US flag
US10265287No2019-04-232030-04-29US flag
US10278937No2019-05-072033-06-28US flag
US10278936No2019-05-072033-06-28US flag
US10383840No2019-08-202033-06-28US flag
US10555925No2020-02-112033-06-28US flag
US10555924No2020-02-112033-06-28US flag
US10568861No2020-02-252033-06-28US flag
US10576054No2020-03-032033-06-28US flag
US10668042No2020-06-022033-06-28US flag
US10792270No2020-10-062033-06-28US flag
US10786478No2020-09-292033-06-28US flag
US10792267No2020-10-062030-04-29US flag
US10842768No2020-11-242030-06-15US flag
US10842766No2020-11-242030-04-29US flag
US10881632No2021-01-052030-04-29US flag
US10894028No2021-01-192033-06-28US flag
US11000499No2021-05-112033-06-28US flag
US11154526No2021-10-262030-04-29US flag
US11103477No2021-08-312030-04-29US flag
US11116742No2021-09-142033-06-28US flag
US11213504No2010-04-292030-04-29US flag
US11298333No2013-06-282033-06-28US flag
US11369582No2013-06-282033-06-28US flag
US11717504No2010-04-292030-04-29US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.83e-05 mg/mLALOGPS
logP6.8ALOGPS
logP6.73Chemaxon
logS-6.5ALOGPS
pKa (Strongest Basic)-7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.3 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity110.59 m3·mol-1Chemaxon
Polarizability40.32 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.9783
Caco-2 permeable+0.7651
P-glycoprotein substrateNon-substrate0.7486
P-glycoprotein inhibitor INon-inhibitor0.8803
P-glycoprotein inhibitor IINon-inhibitor0.812
Renal organic cation transporterNon-inhibitor0.8776
CYP450 2C9 substrateNon-substrate0.8606
CYP450 2D6 substrateNon-substrate0.9069
CYP450 3A4 substrateNon-substrate0.625
CYP450 1A2 substrateNon-inhibitor0.5469
CYP450 2C9 inhibitorNon-inhibitor0.9392
CYP450 2D6 inhibitorNon-inhibitor0.9277
CYP450 2C19 inhibitorNon-inhibitor0.9562
CYP450 3A4 inhibitorNon-inhibitor0.9476
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6856
Ames testNon AMES toxic0.6329
CarcinogenicityCarcinogens 0.5714
BiodegradationReady biodegradable0.8556
Rat acute toxicity1.3874 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8771
hERG inhibition (predictor II)Non-inhibitor0.897
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-056r-4291000000-18f886cd2e21c8d674eb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-2895000000-27a0c86a05d8c9cd1931
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0049000000-d22bb03b137a2817c1bb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2290000000-13ed308c166d4ce04a11
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00s9-2960000000-f2cb4732c2c9633259f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-6191000000-cf9f6b9db3b8297aba5e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-9620000000-c59eef01a5b2739753af
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-235.8080281
predicted
DarkChem Lite v0.1.0
[M-H]-188.24776
predicted
DeepCCS 1.0 (2019)
[M+H]+237.0700281
predicted
DarkChem Lite v0.1.0
[M+H]+190.60577
predicted
DeepCCS 1.0 (2019)
[M+Na]+235.9422281
predicted
DarkChem Lite v0.1.0
[M+Na]+197.71721
predicted
DeepCCS 1.0 (2019)

Drug created at May 28, 2013 20:35 / Updated at December 05, 2023 12:31