Icosapent ethyl

Identification

Name
Icosapent ethyl
Accession Number
DB08887
Description

Icosapent ethyl or ethyl eicosapentaenoic acid is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). It is used as adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL). FDA approved on July 26, 2012.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Thumb
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

Pharmacology

Indication

Icosapent ethyl is used as adjunct therapy to reduce triglyceride (TG) levels in adults with severe (>500 mg/dL) hypertriglyceridemia.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
AbciximabThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Abciximab.
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.
Acetylsalicylic acidAcetylsalicylic acid may increase the antiplatelet activities of Icosapent ethyl.
AlclofenacThe risk or severity of bleeding can be increased when Alclofenac is combined with Icosapent ethyl.
AldesleukinThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Aldesleukin.
AlemtuzumabThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Alemtuzumab.
AlteplaseThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Alteplase.
AltretamineThe risk or severity of bleeding can be increased when Icosapent ethyl is combined with Altretamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take with food.

Products

Active Moieties
NameKindUNIICASInChI Key
IcosapentunknownAAN7QOV9EA10417-94-4JAZBEHYOTPTENJ-JLNKQSITSA-N
International/Other Brands
Epadel
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VascepaCapsule1 gOralHls Therapeutics Inc2020-02-07Not applicableCanada flag
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
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

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)

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. [PubMed:23701295]
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
AHFS Codes
  • 24:06.92 — Miscellaneous Antilipemic Agents
FDA label
Download (275 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionCerebral Vasospasm / Subarachnoid Hemorrhage1
4CompletedPreventionMyocardial Infarction, Unstable Angina Pectoris, Sudden Cardiac Death, Stroke, Peripheral Artery Disease1
4CompletedTreatmentHypertriglyceridemias1
4RecruitingBasic ScienceCardiovascular Heart Disease / Cardiovascular Risk / Triglycerides High / Type 2 Diabetes Mellitus1
4RecruitingPreventionAtherosclerosis / Cardiovascular Heart Disease / Novel Coronavirus Infectious Disease (COVID-19) / Upper Respiratory Tract Infection1
4Unknown StatusPreventionAcute Heart Failure (AHF) / Acute Myocardial Infarction (AMI)1
3CompletedPreventionCardiovascular Heart Disease1
3CompletedTreatmentHuntington's Disease (HD)1
3CompletedTreatmentHypertriglyceridemias3
3Not Yet RecruitingTreatmentNovel Coronavirus Infectious Disease (COVID-19)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
CapsuleOral1 g
CapsuleOral1000 mg/1
CapsuleOral500 mg/1
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
US10555925No2013-06-282033-06-28US flag
US10555924No2013-06-282033-06-28US flag
US10568861No2013-06-282033-06-28US flag
US10576054No2013-06-282033-06-28US flag
US10668042No2013-06-282033-06-28US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on May 28, 2013 14:35 / Updated on October 19, 2020 07:46

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates