Omega-3 fatty acids

Identification

Name

Omega-3 fatty acids

Accession Number

DB11133

Description

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 acid
• Omega-3 acid triglycerides
• Omega-3 fatty acid
• Omega-3 phospholipids
• Omega-3 polyunsaturated fatty acids
• Omega-3 polyunsaturates
• Phospholipids
• ω-3 fatty acids

External IDs

• NDI 441

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.

Associated Therapies

• Dietary and Nutritional 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.

Target	Actions	Organism
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.

Affected organisms

Not Available

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
Unlock Additional Data
Abciximab	Omega-3 fatty acids may increase the antiplatelet activities of Abciximab.
Acenocoumarol	Omega-3 fatty acids may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acid	Omega-3 fatty acids may increase the antiplatelet activities of Acetylsalicylic acid.
Alteplase	Omega-3 fatty acids may increase the anticoagulant activities of Alteplase.
Anagrelide	Omega-3 fatty acids may increase the antiplatelet activities of Anagrelide.
Ancrod	Omega-3 fatty acids may increase the anticoagulant activities of Ancrod.
Anistreplase	Omega-3 fatty acids may increase the anticoagulant activities of Anistreplase.
Antithrombin Alfa	Omega-3 fatty acids may increase the anticoagulant activities of Antithrombin Alfa.
Antithrombin III human	Omega-3 fatty acids may increase the anticoagulant activities of Antithrombin III human.
Apixaban	Omega-3 fatty acids may increase the anticoagulant activities of Apixaban.

Additional Data Available

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Food Interactions

No interactions found.

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Active Moieties

Name	Kind	UNII	CAS	InChI Key
Doconexent	unknown	ZAD9OKH9JC	6217-54-5	MBMBGCFOFBJSGT-KUBAVDMBSA-N

Product Images

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Smoflipid 20%	Omega-3 fatty acids (3 g/100mL) + Medium-chain triglycerides (6 g/100mL) + Olive oil (5 g/100mL) + Soybean oil (6 g/100mL)	Emulsion	Intravenous	Fresenius Kabi	2013-05-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Animi-3	Omega-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)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable
Animi-3 with Vitamin D	Omega-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)	Capsule	Oral	Pbm Pharmaceuticals Inc.	2011-06-01	Not applicable
Bal-Care DHA	Omega-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)	Kit	Oral	Pru Gen Pharmaceuticals	2012-05-01	Not applicable
Bal-Care DHA Essential	Omega-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)	Kit	Oral	Pru Gen Pharmaceuticals	2012-05-01	Not applicable
BumP DHA	Omega-3 fatty acids (300 mg/1) + Cobamamide (500 mg/1) + Flavin adenine dinucleotide (1 mg/1) + Flavin mononucleotide (2 mg/1) + Iron (15 mg/1) + Leucovorin (1 mg/1) + Levomefolate magnesium (1 mg/1) + Magnesium oxide (125 mg/1) + NADH (25 ug/1) + Potassium Iodide (250 ug/1) + Pyridoxal phosphate (5 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Zinc glycinate (15 1/1)	Capsule	Oral	Centurion Labs	2017-03-24	2017-04-17
C-Nate DHA	Omega-3 fatty acids (200 mg/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (1 mg/1) + Cyanocobalamin (15 ug/1) + Ferrous fumarate (28 mg/1) + Folic acid (1 mg/1) + Magnesium (30 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc oxide (20 mg/1)	Capsule, gelatin coated	Oral	Centurion Labs, LLC	2013-01-01	Not applicable
Cavan Alpha	Omega-3 fatty acids (300 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (230 mg/1) + Cholecalciferol (800 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (27 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)	Kit	Oral	Seton Pharmaceuticals	2010-07-01	2013-09-30
Cavan-EC SOD DHA	Omega-3 fatty acids (440 mg/1) + Ascorbic acid (130 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (230 mg/1) + Cholecalciferol (410 [iU]/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (28 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (30 mg/1) + Zinc oxide (26 mg/1)	Kit	Oral	Physicians Total Care, Inc.	2010-08-24	2013-01-15
Cavan-EC SOD DHA	Omega-3 fatty acids (440 mg/1) + Ascorbic acid (130 mg/1) + Beta carotene (3000 [iU]/1) + Calcium (230 mg/1) + Cholecalciferol (410 [iU]/1) + Copper (2 mg/1) + Cyanocobalamin (12 ug/1) + Folic acid (1 mg/1) + Magnesium (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (28 mg/1) + Riboflavin (4 mg/1) + Sodium feredetate (30 mg/1) + Thiamine mononitrate (1.8 mg/1) + Vitamin E (30 mg/1) + Zinc (26 mg/1)	Kit	Oral	Seton Pharmaceuticals	2010-01-10	2014-07-15
Duet DHA	Omega-3 fatty acids (400 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2825 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (800 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + D-alpha-Tocopherol acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (45 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)	Kit	Oral	Wh Nutritionals, Llc	2011-09-09	2014-03-31

Categories

Drug Categories

• Diet, Food, and Nutrition
• Dietary Fats
• Dietary Fats, Unsaturated
• Fats
• Fatty Acids
• Fatty Acids, Omega-3
• Fatty Acids, Unsaturated
• Fish Oils
• Food
• Food and Beverages
• Lipids
• Membrane Lipids
• Oils
• Phospholipids
• Physiological Phenomena

Classification

Not classified

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. [PubMed:22254027]
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. [PubMed:21884130]
3. Ito MK: A Comparative Overview of Prescription Omega-3 Fatty Acid Products. P T. 2015 Dec;40(12):826-57. [PubMed:26681905]
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. [PubMed:26740832]
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. [PubMed:27063583]
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. [PubMed:1387231]
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. [PubMed:23471029]
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. [PubMed:11483627]
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. [PubMed:26097787]
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. [PubMed:17234605]
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. [PubMed:24828044]
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. [PubMed:17459764]
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]

External Links

PubChem Substance

347911131

RxNav

4301

Wikipedia

Omega-3_fatty_acid

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Diabetes Mellitus	1
4	Active Not Recruiting	Treatment	BMI >30 kg/m2 / Esophagus, Barrett	1
4	Completed	Prevention	Health	1
4	Completed	Prevention	Liver Cancer / Liver Cirrhosis	1
4	Completed	Prevention	Malignant Neoplasm of Colon	1
4	Completed	Prevention	Prodrome / Schizophrenia	1
4	Completed	Prevention	Sepsis / Severe Sepsis	1
4	Completed	Supportive Care	Gastric Resection / Malnutrition	1
4	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Dyslipidemia / Human Immunodeficiency Virus (HIV) Infections / Hypertriglyceridemias	1
4	Completed	Treatment	Attention Deficit Hyperactivity Disorder (ADHD) / Attention Deficit/Hyperactivity Disorder / Deficient Emotional Self-Regulation (DESR)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, powder, for solution
Capsule	Oral
Capsule	Oral	700 mg
Capsule, delayed release	Oral	1000 mg
Capsule, delayed release	Oral	1200 mg
Capsule, liquid filled	Oral	1200 mg
Capsule, gelatin coated	Oral	1000 mg
Capsule, gelatin coated	Oral	758 mg
Capsule, gelatin coated	Oral	744 mg
Suspension	Endotracheal	105 mg
Suspension	Endotracheal	210 mg
Capsule, liquid filled	Oral	500 mg
Injection, emulsion	Intravenous	100 g/1L
Injection, emulsion	Intravenous drip	100 g/L
Emulsion	Parenteral	80 g/l
Capsule, liquid filled	Oral	840 mg
Emulsion	Intravenous	80 g
Liquid	Oral
Emulsion	Intravenous	16 g
Emulsion	Parenteral	2.4 g/l
Emulsion	Parenteral	2.88 g/l
Injection, emulsion	Intravenous	5.82 g/1250ml
Emulsion	Intravenous	4.656 g
Emulsion	Parenteral	6.792 g
Injection, emulsion	Intravenous	4.25 g/625ml
Emulsion	Intravenous	6.792 g
Capsule	Oral	3000 IU
Capsule	Oral	1000 MG
Tablet, coated	Oral
Capsule, gelatin coated	Oral	600 mg
Kit	Oral
Pill	Oral
Capsule, gelatin coated	Oral
Emulsion	Intravenous
Capsule, coated	Oral
Capsule	Oral	1000 g
Emulsion	Oral	400 mg
Tablet, chewable	Oral
Capsule, liquid filled	Oral
Capsule	Oral	600 mg

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

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Drug created on December 03, 2015 09:51 / Updated on June 12, 2020 10:53