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

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Icosapent ethyl (DB08887)

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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 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

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Associated Conditions

• Hospitalizations
• Severe Hypertriglyceridemias

Contraindications & Blackbox Warnings

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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
  • EPA

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

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Toxicity

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

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abciximab	The risk or severity of bleeding can be increased when Icosapent ethyl is combined with Abciximab.
Abrocitinib	The risk or severity of bleeding and thrombocytopenia can be increased when Icosapent ethyl is combined with Abrocitinib.
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.

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Food Interactions

• Take with food.

Products

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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
Vascepa	Capsule	1000 mg/1	Oral	Amarin Pharma Inc.	2012-10-01	Not applicable
Vascepa	Capsule	1000 mg/1	Oral	bryant ranch prepack	2012-10-01	Not applicable
Vascepa	Capsule	1 g	Oral	Hls Therapeutics Inc	2020-02-07	Not applicable
Vascepa	Capsule	1000 mg/1	Oral	Amarin Pharma Inc.	2012-10-01	Not applicable
Vascepa	Capsule	500 mg/1	Oral	Amarin Pharma Inc.	2016-09-16	Not applicable
Vazkepa	Capsule	998 mg	Oral	Amarin Pharmaceuticals Ireland Limited	2021-10-07	Not applicable
Vazkepa	Capsule	998 mg	Oral	Amarin Pharmaceuticals Ireland Limited	2022-05-04	Not applicable
Vazkepa	Capsule	998 mg	Oral	Amarin Pharmaceuticals Ireland Limited	2021-10-07	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Icosapent	Capsule	1000 mg/1	Oral	Dr. Reddy's Laboratories, Inc.	2021-06-21	Not applicable
Icosapent	Capsule	1000 mg/1	Oral	bryant ranch prepack	2021-06-21	Not applicable
Icosapent Ethyl	Capsule	1 g/1	Oral	bryant ranch prepack	2020-11-04	Not applicable
Icosapent Ethyl	Capsule	1 g/1	Oral	Hikma Pharmaceuticals USA Inc.	2020-11-04	Not applicable
Icosapent Ethyl	Capsule	1 g/1	Oral	Apotex Corp	2021-12-16	Not applicable

Categories

Drug Categories

• Antiplatelet agents
• Dietary Fats
• Dietary Fats, Unsaturated
• Eicosanoids
• Fats
• Fatty Acids
• Fatty Acids, Omega-3
• Fatty Acids, Unsaturated
• Fish Oils
• Hematologic Agents
• Hypolipidemic Agents
• Lipid Regulating Agents
• Lipids
• Miscellaneous Antilipemic Agents
• Oils

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Atherosclerosis / Cardiovascular Disease (CVD) / Coronavirus Disease 2019 (COVID‑19) / Upper Respiratory Tract Infection	1
4	Completed	Prevention	Myocardial Infarction, Unstable Angina Pectoris, Sudden Cardiac Death, Stroke, Peripheral Artery Disease	1
4	Completed	Prevention	Subarachnoid Hemorrhage / Vasospasm, Cerebral	1
4	Completed	Treatment	Hypertriglyceridemias	1
4	Recruiting	Basic Science	Bipolar Disorder (BD)	1
4	Recruiting	Basic Science	Cardiovascular Disease (CVD) / Cardiovascular Risk / High Triglyceride Level / Type 2 Diabetes Mellitus	1
4	Unknown Status	Prevention	Acute Heart Failure (AHF) / Acute Myocardial Infarction (AMI)	1
3	Completed	Prevention	Cardiovascular Disease (CVD)	1
3	Completed	Treatment	Coronavirus Disease 2019 (COVID‑19)	1
3	Completed	Treatment	Huntington's Disease (HD)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, coated	Oral
Capsule	Oral	1 g/1
Capsule	Oral	1 g
Capsule	Oral	1000 mg/1
Capsule	Oral	500 mg/1
Capsule	Oral	998 mg
Capsule	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8293727	No	2012-10-23	2030-02-09
US8293728	No	2012-10-23	2030-02-09
US8314086	No	2012-11-20	2030-02-09
US8318715	No	2012-11-27	2030-02-09
US8357677	No	2013-01-22	2030-02-09
US8367652	No	2013-02-05	2030-02-09
US8377920	No	2013-02-19	2030-02-09
US8399446	No	2013-03-19	2030-02-09
US8415335	No	2013-04-09	2030-02-09
US8426399	No	2013-04-23	2030-02-09
US8431560	No	2013-04-30	2030-02-09
US8440650	No	2013-05-14	2030-02-09
US8445003	No	2013-05-21	2030-04-29
US8445013	No	2013-05-21	2030-04-29
US8501225	No	2013-08-06	2030-04-29
US8524698	No	2013-09-03	2030-04-29
US8551521	No	2013-10-08	2030-04-29
US8563608	No	2013-10-22	2030-04-29
US8617593	No	2013-12-31	2030-04-29
US8546372	No	2013-10-01	2030-04-29
US8518929	No	2013-08-27	2030-04-29
US8617594	No	2013-12-31	2030-04-29
US8623406	No	2014-01-07	2030-04-29
US8298554	No	2012-10-30	2030-04-29
US8188146	No	2012-05-29	2020-01-27
US9700537	No	2017-07-11	2027-05-31
US9198892	No	2015-12-01	2027-09-25
US8410086	No	2013-04-02	2030-06-15
US8454994	No	2013-06-04	2030-04-29
US8455472	No	2013-06-04	2030-06-15
US8618166	No	2013-12-31	2030-04-29
US8642077	No	2014-02-04	2030-04-29
US8669245	No	2014-03-11	2030-06-15
US8680144	No	2014-03-25	2030-02-09
US8703185	No	2014-04-22	2030-04-29
US8691871	No	2014-04-08	2030-04-29
US8709475	No	2014-04-29	2030-04-29
US8710041	No	2014-04-29	2030-06-15
US9603826	No	2017-03-28	2033-06-28
US9610272	No	2017-04-04	2033-06-28
US9623001	No	2017-04-18	2033-06-28
US9693984	No	2017-07-04	2033-06-28
US9693985	No	2017-07-04	2033-06-28
US9693986	No	2017-07-04	2033-06-28
US10010517	No	2018-07-03	2030-04-29
US9918954	No	2018-03-20	2033-06-28
US10278935	No	2019-05-07	2033-06-28
US10265287	No	2019-04-23	2030-04-29
US10278937	No	2019-05-07	2033-06-28
US10278936	No	2019-05-07	2033-06-28
US10383840	No	2019-08-20	2033-06-28
US10555925	No	2020-02-11	2033-06-28
US10555924	No	2020-02-11	2033-06-28
US10568861	No	2020-02-25	2033-06-28
US10576054	No	2020-03-03	2033-06-28
US10668042	No	2020-06-02	2033-06-28
US10792270	No	2020-10-06	2033-06-28
US10786478	No	2020-09-29	2033-06-28
US10792267	No	2020-10-06	2030-04-29
US10842768	No	2020-11-24	2030-06-15
US10842766	No	2020-11-24	2030-04-29
US10881632	No	2021-01-05	2030-04-29
US10894028	No	2021-01-19	2033-06-28
US11000499	No	2021-05-11	2033-06-28
US11154526	No	2021-10-26	2030-04-29
US11103477	No	2021-08-31	2030-04-29
US11116742	No	2021-09-14	2033-06-28
US11213504	No	2010-04-29	2030-04-29
US11298333	No	2013-06-28	2033-06-28

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

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Drug created at May 28, 2013 20:35 / Updated at August 09, 2022 10:05