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 adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL). FDA approved on July 26, 2012.

Type

Small Molecule

Groups

Approved, Investigational, Nutraceutical

Structure

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

Pharmacology

Indication

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

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Associated Conditions

Severe Hypertriglyceridemia

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.

Drug	Interaction
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Abciximab	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.

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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
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
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	1000 mg/1	Oral	bryant ranch prepack	2012-10-01	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 Ethyl	Capsule	1 g/1	Oral	Hikma Pharmaceuticals USA Inc.	2020-11-04	Not applicable

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. [Article]

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	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	Bipolar Disorder (BD)	1
4	Recruiting	Basic Science	Cardiovascular Disease (CVD) / Cardiovascular Risk / High Triglyceride Level / Type 2 Diabetes Mellitus	1
4	Recruiting	Prevention	Atherosclerosis / Cardiovascular Disease (CVD) / Coronavirus Disease 2019 (COVID‑19) / Upper Respiratory Tract Infection	1
4	Unknown Status	Prevention	Acute Heart Failure (AHF) / Acute Myocardial Infarction (AMI)	1
3	Completed	Prevention	Cardiovascular Disease (CVD)	1
3	Completed	Treatment	Huntington's Disease (HD)	1
3	Completed	Treatment	Hypertriglyceridemias	3

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

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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	2013-06-28	2033-06-28
US10555924	No	2013-06-28	2033-06-28
US10568861	No	2013-06-28	2033-06-28
US10576054	No	2013-06-28	2033-06-28
US10668042	No	2013-06-28	2033-06-28
US10792270	No	2013-06-28	2033-06-28
US10786478	No	2013-06-28	2033-06-28
US10792267	No	2010-04-29	2030-04-29
US10842768	No	2010-06-15	2030-06-15
US10842766	No	2010-04-29	2030-04-29
US10881632	No	2010-04-29	2030-04-29
US10894028	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

Drug created on May 28, 2013 20:35 / Updated on July 24, 2021 14:57

Icosapent ethyl

Identification

Structure for Icosapent ethyl (DB08887)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra