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Omega-3-Acid Ethyl Esters

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36 API Suppliers, 18 USDMF, 23 CEP/COS, 4 JDMF, 22 KDMF, 3 Listed Suppliers

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19 FDF Dossiers, 18 FDA Orange Book, 1 Listed Dossiers

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1 SPI Pharma, 7 DKSH, 1 Gangwal Healthcare, 2 Nanjing Well Pharmaceutical, 4 ACG Worldwide, 2 Actylis, 2 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 BASF, 10 Corel Pharma Chem, 1 Finar, 4 Gangwal Chemicals, 4 Ideal Cures Pvt Ltd, 13 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 1 Microlex e.U, 1 Novo Excipients, 1 Pluviaendo, 1 Qianhao Chemical (Hebei) Co., Ltd, 2 Qualicaps, 2 Roquette, 7 Seppic, 1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Sigachi Industries, 2 The Dow Chemical Company, 1 Valens Pharmachem

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Synopsis

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Chemistry

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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 90

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 Formula	C₄₆H₇₀O₄
Molecular Weight	687.0 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	31
Exact Mass	686.52741071 g/mol
Monoisotopic Mass	686.52741071 g/mol
Topological Polar Surface Area	52.6 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	916
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	11
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Lovaza
Drug Label	LOVAZA, 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 Ingredient	Omega-3-acid ethyl esters
Dosage Form	Capsule
Route	Oral
Strength	1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market Status	Prescription
Company	Smithkline Beecham

2 of 4
Drug Name	Omega-3-acid ethyl esters
Drug Label	LOVAZA, 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 Ingredient	Omega-3-acid ethyl esters
Dosage Form	Capsule
Route	Oral
Strength	1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market Status	Prescription
Company	Apotex; Teva Pharms Usa; Par Pharm

3 of 4
Drug Name	Lovaza
Drug Label	LOVAZA, 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 Ingredient	Omega-3-acid ethyl esters
Dosage Form	Capsule
Route	Oral
Strength	1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market Status	Prescription
Company	Smithkline Beecham

4 of 4
Drug Name	Omega-3-acid ethyl esters
Drug Label	LOVAZA, 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 Ingredient	Omega-3-acid ethyl esters
Dosage Form	Capsule
Route	Oral
Strength	1gm contains at least 900mg of the ethyl esters of omega-3 fatty acids
Market Status	Prescription
Company	Apotex; 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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