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
Structure for Icosapent ethyl (DB08887)
- 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
- 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.
Drug Interaction Unlock Additional DataAbciximab The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Abciximab. Aceclofenac The risk or severity of bleeding can be increased when Aceclofenac is combined with Icosapent ethyl. Acemetacin The risk or severity of bleeding can be increased when Acemetacin is combined with Icosapent ethyl. Acenocoumarol The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Acenocoumarol. Acetylsalicylic acid Acetylsalicylic acid may increase the antiplatelet activities of Icosapent ethyl. Alclofenac The risk or severity of bleeding can be increased when Alclofenac is combined with Icosapent ethyl. Aldesleukin The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Aldesleukin. Alemtuzumab The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Alemtuzumab. Alteplase The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Alteplase. Altretamine The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Altretamine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
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
Name Kind UNII CAS InChI Key Icosapent unknown AAN7QOV9EA 10417-94-4 JAZBEHYOTPTENJ-JLNKQSITSA-N - International/Other Brands
- Epadel
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataVascepa Capsule 1 g Oral Hls Therapeutics Inc 2020-02-07 Not applicable Canada 
Vascepa Capsule 1000 mg/1 Oral Amarin Pharma Inc. 2012-10-01 Not applicable US 
Vascepa Capsule 1000 mg/1 Oral bryant ranch prepack 2012-10-01 Not applicable US Vascepa Capsule 1000 mg/1 Oral Amarin Pharma Inc. 2012-10-01 Not applicable US Vascepa Capsule 500 mg/1 Oral Amarin Pharma Inc. 2016-09-16 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- Drug Categories
- Antiplatelet agents
- Autacoids
- Biological Factors
- Diet, Food, and Nutrition
- Dietary Fats
- Dietary Fats, Unsaturated
- Eicosanoids
- Fats
- Fatty Acids
- Fatty Acids, Omega-3
- Fatty Acids, Unsaturated
- Fish Oils
- Food
- Food and Beverages
- Hematologic Agents
- Hypolipidemic Agents
- Inflammation Mediators
- Lipids
- Miscellaneous Antilipemic Agents
- Oils
- Physiological Phenomena
- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0039530
- KEGG Drug
- D01892
- KEGG Compound
- C16184
- PubChem Compound
- 9831415
- PubChem Substance
- 175427134
- ChemSpider
- 8007147
- 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
Phase Status Purpose Conditions Count 4 Completed Prevention Cerebral Vasospasm / Subarachnoid Hemorrhage 1 4 Completed Prevention Myocardial Infarction, Unstable Angina Pectoris, Sudden Cardiac Death, Stroke, Peripheral Artery Disease 1 4 Completed Treatment Hypertriglyceridemias 1 4 Recruiting Basic Science Cardiovascular Heart Disease / Cardiovascular Risk / Triglycerides High / Type 2 Diabetes Mellitus 1 4 Recruiting Prevention Atherosclerosis / Cardiovascular Heart Disease / Novel Coronavirus Infectious Disease (COVID-19) / Upper Respiratory Tract Infection 1 4 Unknown Status Prevention Acute Heart Failure (AHF) / Acute Myocardial Infarction (AMI) 1 3 Completed Prevention Cardiovascular Heart Disease 1 3 Completed Treatment Huntington's Disease (HD) 1 3 Completed Treatment Hypertriglyceridemias 3 3 Not Yet Recruiting Treatment Novel Coronavirus Infectious Disease (COVID-19) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Capsule Oral 1 g Capsule Oral 1000 mg/1 Capsule Oral 500 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS8293727 No 2012-10-23 2030-02-09 US US8293728 No 2012-10-23 2030-02-09 US US8314086 No 2012-11-20 2030-02-09 US US8318715 No 2012-11-27 2030-02-09 US US8357677 No 2013-01-22 2030-02-09 US US8367652 No 2013-02-05 2030-02-09 US US8377920 No 2013-02-19 2030-02-09 US US8399446 No 2013-03-19 2030-02-09 US US8415335 No 2013-04-09 2030-02-09 US US8426399 No 2013-04-23 2030-02-09 US US8431560 No 2013-04-30 2030-02-09 US US8440650 No 2013-05-14 2030-02-09 US US8445003 No 2013-05-21 2030-04-29 US US8445013 No 2013-05-21 2030-04-29 US US8501225 No 2013-08-06 2030-04-29 US US8524698 No 2013-09-03 2030-04-29 US US8551521 No 2013-10-08 2030-04-29 US US8563608 No 2013-10-22 2030-04-29 US US8617593 No 2013-12-31 2030-04-29 US US8546372 No 2013-10-01 2030-04-29 US US8518929 No 2013-08-27 2030-04-29 US US8617594 No 2013-12-31 2030-04-29 US US8623406 No 2014-01-07 2030-04-29 US US8298554 No 2012-10-30 2030-04-29 US US8188146 No 2012-05-29 2020-01-27 US US9700537 No 2017-07-11 2027-05-31 US US9198892 No 2015-12-01 2027-09-25 US US8410086 No 2013-04-02 2030-06-15 US US8454994 No 2013-06-04 2030-04-29 US US8455472 No 2013-06-04 2030-06-15 US US8618166 No 2013-12-31 2030-04-29 US US8642077 No 2014-02-04 2030-04-29 US US8669245 No 2014-03-11 2030-06-15 US US8680144 No 2014-03-25 2030-02-09 US US8703185 No 2014-04-22 2030-04-29 US US8691871 No 2014-04-08 2030-04-29 US US8709475 No 2014-04-29 2030-04-29 US US8710041 No 2014-04-29 2030-06-15 US US9603826 No 2017-03-28 2033-06-28 US US9610272 No 2017-04-04 2033-06-28 US US9623001 No 2017-04-18 2033-06-28 US US9693984 No 2017-07-04 2033-06-28 US US9693985 No 2017-07-04 2033-06-28 US US9693986 No 2017-07-04 2033-06-28 US US10010517 No 2018-07-03 2030-04-29 US US9918954 No 2018-03-20 2033-06-28 US US10278935 No 2019-05-07 2033-06-28 US US10265287 No 2019-04-23 2030-04-29 US US10278937 No 2019-05-07 2033-06-28 US US10278936 No 2019-05-07 2033-06-28 US US10383840 No 2019-08-20 2033-06-28 US US10555925 No 2013-06-28 2033-06-28 US US10555924 No 2013-06-28 2033-06-28 US US10568861 No 2013-06-28 2033-06-28 US US10576054 No 2013-06-28 2033-06-28 US US10668042 No 2013-06-28 2033-06-28 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 9.83e-05 mg/mL ALOGPS logP 6.8 ALOGPS logP 6.73 ChemAxon logS -6.5 ALOGPS pKa (Strongest Basic) -7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 26.3 Å2 ChemAxon Rotatable Bond Count 15 ChemAxon Refractivity 110.59 m3·mol-1 ChemAxon Polarizability 40.32 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9947 Blood Brain Barrier + 0.9783 Caco-2 permeable + 0.7651 P-glycoprotein substrate Non-substrate 0.7486 P-glycoprotein inhibitor I Non-inhibitor 0.8803 P-glycoprotein inhibitor II Non-inhibitor 0.812 Renal organic cation transporter Non-inhibitor 0.8776 CYP450 2C9 substrate Non-substrate 0.8606 CYP450 2D6 substrate Non-substrate 0.9069 CYP450 3A4 substrate Non-substrate 0.625 CYP450 1A2 substrate Non-inhibitor 0.5469 CYP450 2C9 inhibitor Non-inhibitor 0.9392 CYP450 2D6 inhibitor Non-inhibitor 0.9277 CYP450 2C19 inhibitor Non-inhibitor 0.9562 CYP450 3A4 inhibitor Non-inhibitor 0.9476 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6856 Ames test Non AMES toxic 0.6329 Carcinogenicity Carcinogens 0.5714 Biodegradation Ready biodegradable 0.8556 Rat acute toxicity 1.3874 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8771 hERG inhibition (predictor II) Non-inhibitor 0.897
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on May 28, 2013 14:35 / Updated on October 19, 2020 07:46
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