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OMEGA-3 ACID ETHYL ESTERS
Also known as: 861006-80-6, Omacor, Coromega, Lotriga, Zodin, Ethyl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate compound with ethyl (5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoate (1:1)
Molecular Formula
C46H70O4
Molecular Weight
687.0  g/mol
InChI Key
DTMGIJFHGGCSLO-FIAQIACWSA-N

Omega-3-Acid Ethyl Esters is an ethyl ester form of omega-3 fatty acid derived from fish oil, with activity in decreasing serum triglyceride levels. Although its mechanism of action isn't known, omega-3-acid ethyl esters may work by decreasing the amount of triglycerides and other fats made in the liver.
1 2D Structure

OMEGA-3 ACID ETHYL ESTERS

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate;ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
2.1.2 InChI
InChI=1S/C24H36O2.C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26-4-2;1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18,20-21H,3-4,7,10,13,16,19,22-23H2,1-2H3;5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-;6-5-,9-8-,12-11-,15-14-,18-17-
2.1.3 InChI Key
DTMGIJFHGGCSLO-FIAQIACWSA-N
2.1.4 Canonical SMILES
CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC.CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OCC
2.1.5 Isomeric SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC.CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OCC
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Omacor

2. Omega-3 Ethyl Ester 90

3. P-om3 Adjunct

2.2.2 Depositor-Supplied Synonyms

1. 861006-80-6

2. Omacor

3. Coromega

4. Lotriga

5. Zodin

6. Ethyl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate Compound With Ethyl (5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoate (1:1)

7. Omega-3 Acid Ethyl Esters

8. Omega-3-acid Ethyl Ester

9. Omega-3-acid Ethyl Esters

10. Chembl1200711

11. Tak-085

12. Omega-3-acid Ethyl Esters Type A

13. Icosapent (epa Ethyl Ester)

14. Doconexent (dha Ethyl Ester)

15. K-85

16. 4,7,10,13,16,19-docosahexaenoic Acid, Ethyl Ester, (4z,7z,10z,13z,16z,19z)-, Mixt. With (5z,8z,11z,14z,17z)-ethyl 5,8,11,14,17-eicosapentaenoate

17. Ethyl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate;ethyl (5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoate

2.3 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 687.0 g/mol
Molecular Formula C46H70O4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count31
Exact Mass686.52741071 g/mol
Monoisotopic Mass686.52741071 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count50
Formal Charge0
Complexity916
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count11
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameLovaza
Drug LabelLOVAZA, a lipid-regulating agent, is supplied as a liquid-filled gel capsule for oral administration. Each 1-gram capsule of LOVAZA contains at least 900 mg of the ethyl esters of omega-3 fatty acids sourced from fish oils. These are predominantly a...
Active IngredientOmega-3-acid ethyl esters
Dosage FormCapsule
RouteOral
Strength1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market StatusPrescription
CompanySmithkline Beecham

2 of 4  
Drug NameOmega-3-acid ethyl esters
Drug LabelLOVAZA, a lipid-regulating agent, is supplied as a liquid-filled gel capsule for oral administration. Each 1-gram capsule of LOVAZA contains at least 900 mg of the ethyl esters of omega-3 fatty acids sourced from fish oils. These are predominantly a...
Active IngredientOmega-3-acid ethyl esters
Dosage FormCapsule
RouteOral
Strength1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market StatusPrescription
CompanyApotex; Teva Pharms Usa; Par Pharm

3 of 4  
Drug NameLovaza
Drug LabelLOVAZA, a lipid-regulating agent, is supplied as a liquid-filled gel capsule for oral administration. Each 1-gram capsule of LOVAZA contains at least 900 mg of the ethyl esters of omega-3 fatty acids sourced from fish oils. These are predominantly a...
Active IngredientOmega-3-acid ethyl esters
Dosage FormCapsule
RouteOral
Strength1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market StatusPrescription
CompanySmithkline Beecham

4 of 4  
Drug NameOmega-3-acid ethyl esters
Drug LabelLOVAZA, a lipid-regulating agent, is supplied as a liquid-filled gel capsule for oral administration. Each 1-gram capsule of LOVAZA contains at least 900 mg of the ethyl esters of omega-3 fatty acids sourced from fish oils. These are predominantly a...
Active IngredientOmega-3-acid ethyl esters
Dosage FormCapsule
RouteOral
Strength1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market StatusPrescription
CompanyApotex; Teva Pharms Usa; Par Pharm

4.2 Drug 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).


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

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).


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Omega-3 Fatty Acid [EPC]; Fatty Acids, Omega-3 [CS]
5.3 Absorption, Distribution and Excretion

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 possible.


Route of Elimination

Includes oxidative catabolism to carbon dioxide and water


Volume of Distribution

82 56L


Clearance

757 mL/h 283mL/h.


5.4 Metabolism/Metabolites

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


5.5 Biological Half-Life

79 hours 47 hours.


5.6 Mechanism of Action

Omega-3-acid ethyl esters reduce triglyceride production by the liver but this mechanism is not well understood. Omega-3-acid ethyl esters inhibit acyl-CoA:1,2-diacylglycerol acyltransferase, reducing triglyceride synthesis and increasing paroxysmal beta-oxidation, which increases fatty aside metabolism. 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-C.


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