Omega-3-acid ethyl esters

Identification

Name
Omega-3-acid ethyl esters
Accession Number
DB09539
Description

Omega-3-acid ethyl esters are prescription drugs that contain eicosapentaenoic acid-ethyl ester (EPA) and docosahexaenoic acid-ethyl ester (DHA) that are used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemiaLabel2. Omega-3-acid ethyl esters are currently marketed in the US, EU, and many other regions under the brand name LovazaLabel4.

Type
Small Molecule
Groups
Approved, Investigational
Synonyms
  • Omega-3 fatty acid ethyl esters
  • Omega-3-acid ethyl esters
External IDs
  • K-85
  • K85
  • TAK-085

Pharmacology

Indication

Omega-3-Acid Ethyl Esters capsules, USP are indicated as an adjunct to diet to reduce triglyceride (TG) levels in adult patients with severe (≥500 mg/dL) hypertriglyceridemia (HTG)Label2.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Omega-3-acid ethyl esters reduce triglyceride production, increase fatty acid metabolism, inhibit the release of fatty acids, increase triglyceride clearance, and decrease production of very low density lipoprotein cholesterol(VLDL-C)2.

Mechanism of action

Omega-3-acid ethyl esters reduce triglyceride production by the liver but this mechanism is not well understood2. Omega-3-acid ethyl esters inhibit acyl-CoA:1,2-diacylglycerol acyltransferase, reducing triglyceride synthesis and increasing paroxysmal beta-oxidation, which increases fatty aside metabolism2. Omega-3-acid ethyl esters also inhibit the release of fatty acids by competing for enzymes involved in the synthesis of triglycerides, increase triglyceride clearance by increasing the activity of lipoprotein lipase, and decrease production of VLDL-C2.

TargetActionsOrganism
USterol regulatory element-binding protein 1
inhibitor
Humans
Absorption

Omega-3-acid ethyl esters are rapidly hydrolysed to free fatty acids in the intestinal lumen which then become incorporated into phospholipids, cholesterol, and triglycerides so determination of bioavailability by serum concentration is not possible5,3.

Volume of distribution

82 ± 56L1

Protein binding

Because omega-3-acid ethyl esters are rapidly hydrolysed and incorporated into other processes and structures, protein binding data is scarceLabel5. However, most of EPA is bound to plasma protein6.

Metabolism

Omega-3-acid ethyl esters are hydrolysed to free fatty acids in the intestinal lumen by pancreatic lipase3. Once in enterocytes, the free fatty acids are packaged in chylomicrons which are released from cells into the circulation3. Fatty acids then enter the liver where they can be incorporated into liver stores, incorporated into lipoprotein phospholipids, or oxidised for energy5.

Route of elimination

Includes oxidative catabolism to carbon dioxide and water

Half-life

79 hours ± 47 hours1.

Clearance

757 mL/h ± 283mL/h1.

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

In rats, omega-3-acid ethyl esters are not mutagenic or clastogenic and do not lead to impairment of fertilityLabel.

Safety in human pregnancy have not been performed, however an embryocidal effect was seen in rats force fed 7 times the maximum recommended human doseLabel. The risk and benefit of treatment during pregnancy should be weighed before deciding on treatmentLabel.

Animal studies in lactating rats have shown excretion of omega-3-acid ethyl esters at concentrations 6 to 14 times higher than in the serum of the mother, however the effects of this excretion on a mother or child have not been establishedLabel.

Safety and effectiveness in pediatric patients has not been establishedLabel.

There appear to be no differences in the safety and efficacy in patients above or below 60 years of age based on limited dataLabel.

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 Omega-3-acid ethyl esters is combined with Abciximab.
AcenocoumarolThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Acenocoumarol.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Acetylsalicylic acid.
AlteplaseThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Alteplase.
AnagrelideThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Anagrelide.
AncrodThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Ancrod.
AnistreplaseThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Anistreplase.
Antithrombin AlfaThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Antithrombin Alfa.
Antithrombin III humanThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Antithrombin III human.
ApixabanThe risk or severity of bleeding can be increased when Omega-3-acid ethyl esters is combined with Apixaban.
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 a full glass of water.
  • Take with food. Take with food to reduce gastrointestinal disturbance.

Products

Active Moieties
NameKindUNIICASInChI Key
Omega-3 fatty acidsunknown71M78END5S329042-31-1Not applicable
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LovazaCapsule, liquid filled900 mg/1OralAtlantic Biologicals Corps.2016-05-19Not applicableUs
LovazaCapsule, liquid filled900 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2008-10-212012-07-30Us
LovazaCapsule, liquid filled900 mg/1OralGlaxoSmithKline LLC2016-05-19Not applicableUs
LovazaCapsule, liquid filled1 g/1OralRebel Distributors2008-10-21Not applicableUs
LovazaCapsule, liquid filled900 mg/1OralAtlantic Biologicals Corps.2008-10-21Not applicableUs17856 078320180907 15195 c4yd6l
LovazaCapsule, liquid filled900 mg/1OralGlaxoSmithKline LLC2008-10-212019-10-31Us0173 078320180907 15195 1dafxz1
LovazaCapsule, liquid filled1 g/1OralPhysicians Total Care, Inc.2008-12-11Not applicableUs00173 0783 62 nlmimage10 4a192579
LovazaCapsule, liquid filled900 mg/1OralCardinal Health2008-10-212013-11-30Us55154 113420180913 8702 1uuutqm
OmacorCapsule, liquid filled1 g/1OralGlaxosmithkline Inc2007-03-012010-01-01Us
OmtrygCapsule900 mg/1OralTrygg Pharma, Inc.2016-07-01Not applicableUs
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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Omega-3-Acid Ethyl EsterCapsule, liquid filled900 mg/1OralBionpharma Inc.2019-10-15Not applicableUs
Omega-3-acid ethyl estersCapsule, liquid filled1 g/1OralAmerican Health Packaging2016-09-19Not applicableUs
Omega-3-acid ethyl estersCapsule, liquid filled1 g/1Oralbryant ranch prepack2014-09-302017-06-30Us
Omega-3-acid Ethyl EstersCapsule1 g/1gOralInternational Brand Management, Llc2016-04-09Not applicableUs
Omega-3-acid ethyl estersCapsule, liquid filled900 mg/1OralPrasco Laboratories2016-03-312020-03-31Us
Omega-3-Acid Ethyl EstersCapsule, liquid filled900 mg/1OralQPharma Inc2014-04-07Not applicableUs
Omega-3-Acid Ethyl EstersCapsule, liquid filled1 g/1OralAmneal Pharmaceuticals LLC2015-11-30Not applicableUs65162 03420180907 15195 9m0ms9
Omega-3-Acid Ethyl EstersCapsule, liquid filled900 mg/1OralTeva Pharmaceuticals USA, Inc.2014-04-07Not applicableUs00093 5401 89 nlmimage10 8a3bc57e
Omega-3-Acid Ethyl EstersCapsule, liquid filled900 mg/1OralGolden State Medical Supply, Inc.2014-06-24Not applicableUs
Omega-3-Acid Ethyl EstersCapsule, liquid filled900 mg/1OralANI Pharmaceuticals, Inc.2020-02-19Not applicableUs
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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Omega-3 Rx CompleteOmega-3-acid ethyl esters (1 g/1) + Ascorbic acid (60 mg/1) + Biotin (.075 mg/1) + Calcium (210 mg/1) + Chromium nicotinate (.12 mg/1) + Copper (2 mg/1) + Cyanocobalamin (.018 mg/1) + Folic acid (.4 mg/1) + Lycopene (.3 mg/1) + Magnesium (140 mg/1) + Magnesium oxide (140 mg/1) + Nicotinamide (18 mg/1) + Pantothenic acid (.016 mg/1) + Phylloquinone (.020 mg/1) + Riboflavin (1.7 mg/1) + Selenium (.11 mg/1) + Thiamine chloride (1.35 mg/1) + Vitamin A (3500 [iU]/1) + Vitamin D (700 [iU]/1) + Vitamin E (22.5 [iU]/1) + Zinc oxide (15 mg/1)KitOralTmig, Inc.2015-09-01Not applicableUs
Omega-3 Well PackOmega-3-acid ethyl esters (1 g/1) + Vitamin D (1000 [iU]/1)KitOralCloverleaf Pharma Llc2015-09-01Not applicableUs
Omega-3 Well PackOmega-3-acid ethyl esters (1 g/1) + Vitamin D (1000 [iU]/1)KitOralTmig, Inc.2015-09-01Not applicableUs
Sure Result O3D3 SystemOmega-3-acid ethyl esters (1 g/1g) + Vitamin D (1000 [iU]/1)KitOralInternational Brand Management, Llc2016-03-05Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Concept DHAOmega-3-acid ethyl esters (200 mg/1) + Ascorbic acid (25 mg/1) + Biotin (300 ug/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (12.5 ug/1) + Ferrous fumarate (53.5 mg/1) + Folic acid (1 mg/1) + Iron (38 mg/1) + Magnesium sulfate (5 mg/1) + Niacin (1.8 mg/1) + Calcium pantothenate (5 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc sulfate, unspecified form (10 mg/1)Capsule, liquid filledOralUs Pharmaceutical Corporation2009-06-24Not applicableUs
DivistaOmega-3-acid ethyl esters (300 mg/1) + Biotin (2 mg/1) + Chromium picolinate (1000 ug/1) + Cyanocobalamin (15 ug/1) + Folic acid (1 mg/1) + Pyridoxine (25 mg/1)CapsuleOralUs Pharmaceutical Corporation2010-07-102011-09-30Us
LuviraOmega-3-acid ethyl esters (1220 mg/1) + (12R)-12-hydroxyeicosapentaenoic acid (465 mg/1) + Doconexent (375 mg/1)CapsuleOralSterling-Knight Pharmaceuticals, LLC2019-11-072020-01-17Us
Mi-Omega NFOmega-3-acid ethyl esters (500 mg/1) + Cyanocobalamin (500 ug/1) + Folic acid (1 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + beta-Sitosterol (200 mg/1)CapsuleOralMayne Pharma2009-01-012016-05-31Us
Multinate DHAOmega-3-acid ethyl esters (430 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (295 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (30 mg/1) + Zinc oxide (25 mg/1)KitOralRiver's Edge Pharmaceuticals, LLC2009-09-012011-04-20Us
Multinate DHAOmega-3-acid ethyl esters (400 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (275 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (30 mg/1) + Zinc oxide (25 mg/1)KitOralRiver's Edge Pharmaceuticals, LLC2009-09-012012-11-30Us
Multinate DHA ExtraOmega-3-acid ethyl esters (430 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (295 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (3 mg/1) + Zinc oxide (25 mg/1)KitOralRiver's Edge Pharmaceuticals, LLC2009-09-012012-03-31Us
Multinate DHA ExtraOmega-3-acid ethyl esters (400 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (275 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (3 mg/1) + Zinc oxide (25 mg/1)KitOralRiver's Edge Pharmaceuticals, LLC2009-09-012011-04-20Us
RenateOmega-3-acid ethyl esters (430 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (295 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (3 mg/1) + Zinc oxide (25 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2009-01-022011-08-31Us
RenateOmega-3-acid ethyl esters (430 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Doconexent (295 mg/1) + Folic acid (1 mg/1) + Iron (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (3 mg/1) + Zinc oxide (25 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2009-01-022010-12-31Us

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
D87YGH4Z0Q
CAS number
308081-97-2

References

General References
  1. Braeckman RA, Stirtan WG, Soni PN: Pharmacokinetics of Eicosapentaenoic Acid in Plasma and Red Blood Cells After Multiple Oral Dosing With Icosapent Ethyl in Healthy Subjects. Clin Pharmacol Drug Dev. 2014 Mar;3(2):101-108. Epub 2013 Oct 22. [PubMed:26097787]
  2. Koski R: Omega-3-acid Ethyl Esters (Lovaza) For Severe Hypertriglyceridemia Pharmacy and Therapeutics. 2008 May;33(5):271-303.
  3. Davidson MH: Omega-3 fatty acids: new insights into the pharmacology and biology of docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid. Curr Opin Lipidol. 2013 Dec;24(6):467-74. doi: 10.1097/MOL.0000000000000019. [PubMed:24184945]
  4. Omega-3-acid ethyl esters 90 (K85EE) [Link]
  5. Australian Public Assessment Report for Omega-3-acid ethyl esters 90 [Link]
  6. FDA reports [Link]
PubChem Substance
347910460
RxNav
484348
Wikipedia
Omega-3_acid_ethyl_esters
FDA label
Download (177 KB)
MSDS
Download (176 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionDiabetes Mellitus1
4CompletedNot AvailableMixed Dyslipidemias1
4CompletedOtherBioavailability1
4CompletedOtherHyperlipidemias2
4CompletedPreventionAtrial Fibrillation (AF)1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Dyslipidemia / Human Immunodeficiency Virus (HIV) Infections / Hypertriglyceridemias1
4CompletedTreatmentAtherosclerosis / Type 2 Diabetes Mellitus1
4CompletedTreatmentAtrial Fibrillation (AF)1
4CompletedTreatmentBipolar Disorder (BD) / High Cholesterol / High Triglycerides / Schizoaffective Disorders / Schizophrenia1
4CompletedTreatmentBMI >30 kg/m21

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, liquid filledOral
Capsule, liquid filledOral900 mg/1
CapsuleOral
KitOral
Capsule, liquid filledOral1 g/1
CapsuleOral1 g/1g
CapsuleOral900 mg/1
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)<20[MSDS]
boiling point (°C)>400[MSDS]
water solubilityNot Soluble[MSDS]
Predicted Properties
Not Available
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Transcriptional activator required for lipid homeostasis. Regulates transcription of the LDL receptor gene as well as the fatty acid and to a lesser degree the cholesterol synthesis pathway (By sim...
Gene Name
SREBF1
Uniprot ID
P36956
Uniprot Name
Sterol regulatory element-binding protein 1
Molecular Weight
121673.6 Da
References
  1. Davidson MH: Omega-3 fatty acids: new insights into the pharmacology and biology of docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid. Curr Opin Lipidol. 2013 Dec;24(6):467-74. doi: 10.1097/MOL.0000000000000019. [PubMed:24184945]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sterol o-acyltransferase activity
Specific Function
Catalyzes the formation of fatty acid-cholesterol esters, which are less soluble in membranes than cholesterol. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition ...
Gene Name
SOAT1
Uniprot ID
P35610
Uniprot Name
Sterol O-acyltransferase 1
Molecular Weight
64733.975 Da

Drug created on November 30, 2015 12:10 / Updated on June 12, 2020 10:52

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