NAV

Omega-3 fatty acids

Identification

Summary

Omega-3 fatty acids is an ingredient found in a variety of supplements and vitamins.

Brand Names
Animi-3 With Vitamin D, Vitafol-one
Generic Name
Omega-3 fatty acids
DrugBank Accession Number
DB11133
Background

Omega-3 fatty acids are polyunsaturated fatty acids (PUFAs) with a double bond at the third carbon atom from the end of the carbon chain. The three types of omega-3 fatty acids involved in human physiology are α-linolenic acid (ALA) (found in plant oils), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) (both commonly found in fish oil that originally come from microalgae that is further consumed by phytoplankton, a source of diet for fish). Omega-3 fatty acids play a critical role in metabolism and cellular function and they are available as daily supplements. On September 8, 2004, the U.S. Food and Drug Administration gave "qualified health claim" status to EPA and DHA omega-3 fatty acids. Therapeutic products containing omega-3 fatty acid and its derivatives for treatment of hypertriglyceridemia include Lovaza, Omtryg, Epanova, and Vascepa.

Type
Small Molecule
Groups
Approved, Nutraceutical
Synonyms
  • n-3 fatty acids
  • Omega 3 fatty acids
  • Omega-3
  • Omega-3 (n-3) polyunsaturated fatty acids
  • Omega-3 acid
  • Omega-3 acid triglycerides
  • Omega-3 fatty acid
  • Omega-3 phospholipids
  • Omega-3 polyunsaturated fatty acids
  • Omega-3 polyunsaturates
  • Omega-3-acid triglycerides
  • Phospholipids
  • ω-3 fatty acids
External IDs
  • NDI 441
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Pharmacology

Indication

Provided as daily supplements. Aa preparation of omega-3-acid ethyl esters is licensed in UK for prevention of recurrent events after myocardial infarction in addition to treatment of hypertriglyceridaemia.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Omega-3 fatty acids are triglycerides that get broken down into smaller fatty acid units. They act to reduce plasma triglyceride levels however increase the cholesterol levels and are thought to possess potent antiarrythmic effects. Polyunsaturated fatty acids including eicosapentaenoic and docosahexaenoic acid mediate important cellular function such as inhibition of platelet function, prolongation of bleeding time, anti-inflammatory effects and reduction of plasma fibrinogen. Polyunsaturated fatty acids are components of the phospholipids that form the structures of the cell membranes and also serve as energy source. They form eicosanoids which are important signalling molecules with wide-ranging functions in the body's cardiovascular, pulmonary, immune and endocrine systems. DHA tends to exist in high concentrations in the retina, brain (via uptake by Mfsd2a as a transporter), and sperm.

Mechanism of action

Omega-3 fatty acids mediate anti-inflammatory effects and increased levels of EPA or DHA has shown to decrease the levels of PGE2 and 4 series-LT. Eicosapentaenoic acids compete with constitutive levels of arachidonic acid in cell membranes for the same desaturation enzymes and produce 3-series prostaglandins and thromboxanes, and 5-series leukotrienes which have low pro-inflammatory potential. The alteration in leukotriene biosynthesis due to higher concentration of omega-3 fatty acids compared to arachidonic acid underlies the anti-inflammatory effects. EPA and DHA also give rise to resolvins and related lipid signalling molecules such as protectins via cyclooxygenase and lipoxygenase pathways, which have anti-inflammatory effects. They inhibit transendothelial migration of neutrophils and inhibit TNF and IL-1β production. Omega-3 fatty acids also decrease adhesion molecule expression on leukocytes and on endothelial cells and decrease intercellular adhesive interactions. Omega-3 (or n-3) polyunsaturated fatty acids (PUFAs) and their metabolites are natural ligands for peroxisome proliferator-activated receptor (PPAR) gamma that regulates inflammatory gene expression and NFκB activation. PPAR alpha activation is also associated with induction of COX-2 expression. The role of EPA and DHA in reducing triglyceride levels include inhibition of acyl-CoA:1,2-diacylglycerol acyltransferase, increased mitochondrial and peroxisomal-beta-oxidation in the liver, decreased lipogenesis in the liver, and increased plasma lipoprotein lipase activity. They also may reduce triglyceride synthesis because they are poor substrates for the enzymes responsible for TG synthesis, and EPA and DHA inhibit esterification of other fatty acids.

TargetActionsOrganism
APeroxisome proliferator-activated receptor gamma
ligand
Humans
UPeroxisome proliferator-activated receptor alpha
activator
Humans
USterol regulatory element-binding protein 1
inhibitor
Humans
Absorption

After ingestion, dietary lipids are hydrolyzed in the intestinal lumen. The hydrolysis products—monoglycerides and free fatty acids—are then incorporated into bile-salt– containing micelles and absorbed into enterocytes, largely by passive diffusion. The absorption rate is about 95%. Within intestinal cells, free fatty acids are primarily incorporated into chylomicrons and enter the circulation via the lymphatic system where they are delivered to various tissues for metabolism, oxidation and storage.

Volume of distribution

Vd of EPA is aproximately 82L

Protein binding

Not Available

Metabolism

ALA, DHA and EPA are metabolized and oxidized in the liver, which is the site of biosynthesis of n-3 fatty acid intermediates, synthesizing VLDL that transport fatty acids in the plasma to tissues. Major enzymes that generate lipid signalling molecules from EPA, DHA and ALA are lipoxygenases and cyclooxygenase.

Route of elimination

Not Available

Half-life

Approximate half-life values in a compartmental study of ALA, EPA and DHA are 1h, 39-67h and 20h, respectively 8,10.

Clearance

Clearance of EPA is approximately 757mL/h 9.

Adverse Effects
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Toxicity

Some adverse effects experienced in patients include gastrointestinal disturbances such as vomiting and constipation, metabolic disorders and skin reactions.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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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
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interactions in your software
AbciximabOmega-3 fatty acids may increase the antiplatelet activities of Abciximab.
AcenocoumarolOmega-3 fatty acids may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidOmega-3 fatty acids may increase the antiplatelet activities of Acetylsalicylic acid.
AlteplaseOmega-3 fatty acids may increase the anticoagulant activities of Alteplase.
AnagrelideOmega-3 fatty acids may increase the antiplatelet activities of Anagrelide.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
DoconexentunknownZAD9OKH9JC6217-54-5MBMBGCFOFBJSGT-KUBAVDMBSA-N
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ESSIVEROmega-3 fatty acids (175 mg) + Cyanocobalamin (3 mcg) + Nicotinamide (15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3 mg) + Thiamine mononitrate (3 mg) + Vitamin E (3.3 mg)Capsuleบริษัท ฟาร์มาแลนด์ (1982) จำกัด2008-03-24Not applicableThailand flag
Furryden Dental Easy OrangeOmega-3 fatty acids (0.06 g/100mL) + Salmon, unspecified (6 g/100mL)Gum, chewingOralWelpenschutz Inc.2023-02-17Not applicableUS flag
Lipidem 20%, Emulsion for infusionOmega-3 fatty acids (20 g/L) + Medium-chain triglycerides (100 g/L) + Soybean oil (80 g/L)Injection, emulsionIntravenous dripB.BRAUN MEDICAL INDUSTRIES SDN BHD2020-09-08Not applicableMalaysia flag
Lipidem 200mg/ml Emulsion for InfusionOmega-3 fatty acids (20 g/1000ml) + Medium-chain triglycerides (100 g/1000ml) + Soybean oil (80 g/1000ml)EmulsionIntravenousB. BRAUN SINGAPORE PTE LTD2009-03-16Not applicableSingapore flag
Lipidem Emulsion zur InfusionOmega-3 fatty acids (20 g/l) + Medium-chain triglycerides (100 g/l) + Soybean oil (80 g/l)EmulsionParenteralB. Braun Melsungen Ag2005-04-20Not applicableAustria flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Animi-3Omega-3 fatty acids (500 mg/1) + Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUS flag
Animi-3 with Vitamin DOmega-3 fatty acids (500 mg/1) + Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUS flag
Bal-Care DHAOmega-3 fatty acids (430 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
Bal-Care DHA EssentialOmega-3 fatty acids (374 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
BP Vit 3Omega-3 fatty acids (500 mg/1) + Cyanocobalamin (500 ug/1) + Doconexent (350 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + beta-Sitosterol (200 mg/1)Capsule, coatedOralAcella Pharmaceuticals, LLC2009-04-17Not applicableUS flag

Categories

ATC Codes
A05BA10 — Phospholipids
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
71M78END5S
CAS number
329042-31-1
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

References

General References
  1. Calder PC: Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar;2(3):355-74. doi: 10.3390/nu2030355. Epub 2010 Mar 18. [Article]
  2. Mahaffey KR, Sunderland EM, Chan HM, Choi AL, Grandjean P, Marien K, Oken E, Sakamoto M, Schoeny R, Weihe P, Yan CH, Yasutake A: Balancing the benefits of n-3 polyunsaturated fatty acids and the risks of methylmercury exposure from fish consumption. Nutr Rev. 2011 Sep;69(9):493-508. doi: 10.1111/j.1753-4887.2011.00415.x. [Article]
  3. Ito MK: A Comparative Overview of Prescription Omega-3 Fatty Acid Products. P T. 2015 Dec;40(12):826-57. [Article]
  4. Forbes SC, Holroyd-Leduc JM, Poulin MJ, Hogan DB: Effect of Nutrients, Dietary Supplements and Vitamins on Cognition: a Systematic Review and Meta-Analysis of Randomized Controlled Trials. Can Geriatr J. 2015 Dec 23;18(4):231-45. doi: 10.5770/cgj.18.189. eCollection 2015 Dec. [Article]
  5. Burckhardt M, Herke M, Wustmann T, Watzke S, Langer G, Fink A: Omega-3 fatty acids for the treatment of dementia. Cochrane Database Syst Rev. 2016 Apr 11;4:CD009002. doi: 10.1002/14651858.CD009002.pub3. [Article]
  6. Marsen TA, Pollok M, Oette K, Baldamus CA: Pharmacokinetics of omega-3-fatty acids during ingestion of fish oil preparations. Prostaglandins Leukot Essent Fatty Acids. 1992 Jul;46(3):191-6. [Article]
  7. Dobson EP, Barrow CJ, Kralovec JA, Adcock JL: Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase. J Lipid Res. 2013 May;54(5):1439-47. doi: 10.1194/jlr.M036186. Epub 2013 Mar 7. [Article]
  8. Pawlosky RJ, Hibbeln JR, Novotny JA, Salem N Jr: Physiological compartmental analysis of alpha-linolenic acid metabolism in adult humans. J Lipid Res. 2001 Aug;42(8):1257-65. [Article]
  9. 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. [Article]
  10. Pawlosky RJ, Hibbeln JR, Salem N Jr: Compartmental analyses of plasma n-3 essential fatty acids among male and female smokers and nonsmokers. J Lipid Res. 2007 Apr;48(4):935-43. Epub 2007 Jan 17. [Article]
  11. Nguyen LN, Ma D, Shui G, Wong P, Cazenave-Gassiot A, Zhang X, Wenk MR, Goh EL, Silver DL: Mfsd2a is a transporter for the essential omega-3 fatty acid docosahexaenoic acid. Nature. 2014 May 22;509(7501):503-6. doi: 10.1038/nature13241. Epub 2014 May 14. [Article]
  12. Chene G, Dubourdeau M, Balard P, Escoubet-Lozach L, Orfila C, Berry A, Bernad J, Aries MF, Charveron M, Pipy B: n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells. Biochim Biophys Acta. 2007 May;1771(5):576-89. Epub 2007 Mar 16. [Article]
  13. 23. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 291-2). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  14. National Institutes of Health (NIH) Office of Dietary Supplements: Omega-3 Fatty Acids Fact Sheet for Health Professionals [Link]
  15. Lovaza FDA Label [Link]
PubChem Substance
347911131
RxNav
4301
Wikipedia
Omega-3_fatty_acid

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionDiabetes Mellitus1
4CompletedPreventionCirrhosis of the Liver / Liver Cancer1
4CompletedPreventionColon Cancer1
4CompletedPreventionHealth1
4CompletedPreventionProdrome / Schizophrenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, delayed releaseOral1000 mg
Capsule; kit; tablet, film coatedOral
Injection, powder, for solution
CapsuleOral
Capsule, gelatin coated; kit; tabletOral
Capsule, delayed releaseOral1200 mg
Capsule, liquid filledOral1200 mg
Capsule, liquid filledOral120000000 mg
Gum, chewingOral
CapsuleOral
CapsuleOral1000 mg
SuspensionEndotracheal105 mg
SuspensionEndotracheal210 mg
Injection, emulsionIntravenous drip
EmulsionParenteral
LiquidOral
EmulsionIntravenous
Injection, emulsionIntravenous4.656 g/1000ml
Injection, emulsionIntravenous6.792 g/1000ml
Injection, emulsionIntravenous
CapsuleOral1000.000 mg
Tablet, coatedOral
Capsule, gelatin coatedOral
KitOral
PillOral
Capsule, gelatin coatedOral
SolutionEndotracheal25 mg/ml
Capsule, coatedOral
CapsuleOral1000 g
Capsule; kit; tabletOral
EmulsionOral
Tablet, chewableOral
Capsule, liquid filledOral
Capsule
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Varga T, Czimmerer Z, Nagy L: PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation. Biochim Biophys Acta. 2011 Aug;1812(8):1007-22. doi: 10.1016/j.bbadis.2011.02.014. Epub 2011 Mar 5. [Article]
  2. Edwards IJ, O'Flaherty JT: Omega-3 Fatty Acids and PPARgamma in Cancer. PPAR Res. 2008;2008:358052. doi: 10.1155/2008/358052. [Article]
Details2. Peroxisome proliferator-activated receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Rudkowska I, Garenc C, Couture P, Vohl MC: Omega-3 fatty acids regulate gene expression levels differently in subjects carrying the PPARalpha L162V polymorphism. Genes Nutr. 2009 Sep;4(3):199-205. doi: 10.1007/s12263-009-0129-2. Epub 2009 Jul 8. [Article]
  2. Liu M, Montgomery MK, Fiveash CE, Osborne B, Cooney GJ, Bell-Anderson K, Turner N: PPARalpha-independent actions of omega-3 PUFAs contribute to their beneficial effects on adiposity and glucose homeostasis. Sci Rep. 2014 Jul 2;4:5538. doi: 10.1038/srep05538. [Article]
Details3. Sterol regulatory element-binding protein 1
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. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [Article]

Enzymes

Details1. Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. doi: 10.1074/jbc.M110.119867. Epub 2010 May 12. [Article]
Details2. Arachidonate 5-lipoxygenase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Calder PC: Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar;2(3):355-74. doi: 10.3390/nu2030355. Epub 2010 Mar 18. [Article]

Drug created at December 03, 2015 16:51 / Updated at July 18, 2023 22:56