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Icosapent Ethyl

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Chemistry

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Also known as: Timnodonic acid, Icosapent, 10417-94-4, Icosapentaenoic acid, Epa, Cis-5,8,11,14,17-eicosapentaenoic acid

Molecular Formula

C₂₀H₃₀O₂

Molecular Weight

302.5 g/mol

InChI Key

JAZBEHYOTPTENJ-JLNKQSITSA-N

FDA UNII

AAN7QOV9EA

Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.

1 2D Structure

Icosapent Ethyl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

2.1.2 InChI

InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-

2.1.3 InChI Key

JAZBEHYOTPTENJ-JLNKQSITSA-N

2.1.4 Canonical SMILES

CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O

2.1.5 Isomeric SMILES

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

AAN7QOV9EA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5,8,11,14,17-eicosapentaenoic Acid

2. 5,8,11,14,17-icosapentaenoic Acid

3. Acid, Eicosapentanoic

4. Eicosapentanoic Acid

5. Icosapent

6. Omega 3 Eicosapentaenoic Acid

7. Omega-3-eicosapentaenoic Acid

8. Timnodonic Acid

2.3.2 Depositor-Supplied Synonyms

1. Timnodonic Acid

2. Icosapent

3. 10417-94-4

4. Icosapentaenoic Acid

5. Epa

6. Cis-5,8,11,14,17-eicosapentaenoic Acid

7. (5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoic Acid

8. Icosapento

9. Icosapentum

10. 5,8,11,14,17-eicosapentaenoic Acid

11. Eicosapentaenoate

12. 5z,8z,11z,14z,17z-eicosapentaenoic Acid

13. (all-z)-5,8,11,14,17-eicosapentaenoic Acid

14. Icosapent [inn]

15. (5z,8z,11z,14z,17z)-5,8,11,14,17-eicosapentaenoic Acid

16. 5,8,11,14,17-icosapentaenoic Acid

17. Ropufa 70

18. Ccris 3279

19. Incromega E 7010sr

20. Aan7qov9ea

21. (5z,8z,11z,14z,17z)-icosapentaenoic Acid

22. (5z,8z,11z,14z,17z)-eicosapentaenoic Acid

23. Omega-3-carboxylic Acids

24. Epa 45g

25. Chembl460026

26. (5z,8z,11z,14z,17z)-eicosapentaenoate

27. All-cis-5,8,11,14,17-icosapentaenoic Acid

28. Chebi:28364

29. All-cis-5,8,11,14,17-eicosapentaenoic Acid

30. All-cis-icosa-5,8,11,14,17-pentaenoic Acid

31. Icosapent (inn)

32. Cis-delta(5,8,11,14,17)-eicosapentaenoic Acid

33. 5,8,11,14,17-eicosapentaenoic Acid, (all-z)-

34. All-cis-fatty Acid 20:5 Omega-3

35. Eicosapentaenoic Acid (c20:5 N3)

36. Epa;timnodonic Acid

37. Icosapentaenoate

38. (all-z)-delta5,8,11,14,17-eicosapentaenoic Acid

39. C20:5n-3,6,9,12,15

40. Cis-5,8,11,14,17-epa

41. Fa 20:5

42. Ncgc00161344-03

43. C20:5 (n-3)

44. Eicosapentaenoic Acid (20:5 N-3)

45. Eicosa-5z,8z,11z,14z,17z-pentaenoic Acid (20:5, N-3)

46. Miraxion

47. Eicosapentanoic Acid

48. Eye Q

49. Eye-q

50. 5,8,11,14,17-eicosapentaenoic Acid, (5z,8z,11z,14z,17z)-

51. Epa [drug]

52. Unii-aan7qov9ea

53. 1553-41-9

54. Icosapentum [inn-latin]

55. Icosapento [inn-spanish]

56. (5z,8z,11z,14z,17z)-icosapentaenoate

57. Timnodonate

58. 3gwx

59. All Cis-5,8,11,14,17-eicosapentaenoic Acid

60. Mfcd00065716

61. All-cis-icosapentaenoate

62. All-cis-icosapentaenoic Acid

63. Dsstox_cid_21023

64. Dsstox_rid_79612

65. Dsstox_gsid_41023

66. Schembl20469

67. Bspbio_001328

68. Bml3-b01

69. Gtpl3362

70. Dtxsid9041023

71. Eicosapentaenoic Acid [mi]

72. Hms1361c10

73. Hms1791c10

74. Hms1989c10

75. Hms3402c10

76. Hms3649d19

77. Hy-b0660

78. Zinc4474603

79. 5,8,11,14,17-icosapentaenoate

80. Eicosapentaenoic Acid [inci]

81. Tox21_111991

82. 5,8,11,14,17-eicosapentaenoate

83. Bdbm50242349

84. Eicosapentaenoic Acid [vandf]

85. Lmfa01030759

86. S6476

87. Eicosapentaenoic Acid [mart.]

88. Akos027470327

89. Eicosapentaenoic Acid [usp-rs]

90. Eicosapentaenoic Acid [who-dd]

91. Ccg-207957

92. Ccg-208136

93. Db00159

94. Cis-5,8,11,14,17-eicosapentaenoate

95. Idi1_033798

96. Ncgc00161344-01

97. Ncgc00161344-02

98. Ncgc00161344-04

99. Ncgc00161344-07

100. 5z,8z,11z,14z,17z-eicosapentaenoate

101. Ac-31072

102. As-53730

103. Cas-10417-94-4

104. E0441

105. 5,8,11,14,17-eicosapentaenoic Acid (6ci)

106. All Cis-5,8,11,14,17-icosapentaenoic Acid

107. C06428

108. D08061

109. P16966

110. (all-cis)-5,8,11,14,17-eicosapentaenoic Acid

111. Eicosapentaenoic Acid (epa) (c20:5 N3)

112. L001256

113. Q409990

114. Sr-01000946647

115. Fa(20:5(5z,8z,11z,14z,17z))

116. J-001125

117. Sr-01000946647-1

118. Z,z,z,z,z-eicosa-5,8,11,14,17-pentaenoic Acid

119. (z,z,z,z,z)-5,8,11,14,17-eicosapentaenoic Acid

120. Brd-k47192521-001-02-1

121. Cis-5,8,11,14,17-eicosapentaenoic Acid, >=99%

122. 7f8bf016-b146-4f72-a52e-b9298ba3a9ab

123. C20h30o2 (cis-5,8,11,14,17-eicosapentaenoic Acid)

124. Eicosapentaenoic Acid, 5,8,11,14,17-(z,z,z,z,z)-

125. 5,8,11,14,17-eicosapentaenoic Acid, (all-z)- (8ci)

126. Cis-5,8,11,14,17-eicosapentaenoic Acid, >=85%, Liquid

127. Cis-5,8,11,14,17-eicosapentaenoic Acid, Analytical Standard

128. (5z,8z,11 Z,14z,17z)-icosa-5,8,11,14,17-pentaenoic Acid

129. (5z,8z,11z,14z,17z)-eicosa-5,8,11,14,17-pentaenoic Acid

130. Cis, Cis, Cis, Cis, Cis-eicosa-5,8,11,14,17-pentaenoic Acid

131. 5,8,11,14,17-eicosapentaenoic Acid, (5z,8z,11z,14z,17z)- (9ci)

132. Eicosapentaenoic Acid (epa) (c20:5) (constituent Of Krill Oil) [dsc]

133. Cis-5,8,11,14,17-eicosapentaenoic Acid, 500 Mug/ml In Ethanol, Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₀O₂
Molecular Weight	302.5 g/mol
XLogP3	5.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	13
Exact Mass	302.224580195 g/mol
Monoisotopic Mass	302.224580195 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	398
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	5
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.

FDA Label

OM3-CA is indicated as an adjunct to diet to reduce triglycerides levels in adults patients with severe hypertriglyceridemia (>500 mg/dL). The patients involved in this treatment should be laced with an appropriate lipid-lowering diet. Hypertriglyceridemia is defined as an elevated plasma triglyceride concentration. It is usually correlated to other secondary conditions such as poor diet, alcohol use, obesity, metabolic syndrome and type 2 diabetes.

FDA Label

Treatment of Familial Adenomatous Polyposis

Treatment of dyslipidaemia

5 Pharmacology and Biochemistry

5.1 Pharmacology

Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.

OM3-CA is very effective in reducing triglyceride levels. After 14 days of treatment, it is possible to observe even a 21% reduction. The reduction of the triglycerides could reach even to 25% in cases with the maximal used concentration of 4 g.

5.2 Absorption, Distribution and Excretion

Absorption

When compared to omega-3 -acid ethyl esters, OM3-CA present a 4-fold higher bioavailability. OM3-CA is absorbed directly in the small intestine and the maximal plasma concentration is reached between 4.5-5 hours after initial administration. The absorbed dosage is transferred to the general circulation via the lymphatic system and distributed within tissues throughout the body. The absorption speed and extent is highly promoted by the bile. In preclinical studies performed in dogs, the Cmax, tmax and AUC were reported to be 15.1 mcg/ml, 24 hours and 1210.3 mcg.h/ml, respectively.

Route of Elimination

OM3-CA does not go under renal excretion. After the metabolism, all the dose is excreted as CO2 and water in the form of expelled air and the rest is excreted in feces.

Volume of Distribution

This pharmacokinetic property is not available.

Clearance

The registered clearance rate at steady-state is of 548 ml/h for eicosapentaenoic acid and 518 ml/h for docohexaenoic acid.

5.3 Metabolism/Metabolites

OM3-CA is metabolized in the liver following the normal fatty acid oxidation. Once absorbed, they are incorporated into triglycerides, cholesterol esters and phospholipids in tissues. The metabolism is marked by beta-oxidation followed by tricarboxylic acid cycle. It is reported that OM3-CA is an inhibitor of several enzymes such as CYP2C9, CYP2C19 and to a lesser extent to CYP1A2, CYP2E1, CYP3A4. It is thought that the metabolism of OM3-CA is mainly done by CYP3A and CYP4F3B.

Eicosapentaenoic acid has known human metabolites that include Juniperonic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Biological Half-Life

The half-life of OM3-CA depends on the type of component in which for eicosapentaenoic acid it is estimated to be of approximately 4.7-10.8 hours while for docosahexaenoic acid is reported to be of about 7 hours. The half-life of baseline-adjusted at steady-state is of 36 and 46 hours respectively for eicosapentaenoic acid and docosahexaenoic acid.

5.5 Mechanism of Action

The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40.

The reduction of the synthesis of triglycerides in the liver may be caused because the main components of OM3-CA, eicosapentaenoic acid, and docosahexaenoic acid, are poor substrates for the enzymes responsible for the synthesis of triglycerides. These two major components inhibit the esterification of other fatty acids. OM3-CA is also thought to enhance the clearance of triglycerides from the circulating very low-density lipoprotein particles by different potential effects such as inhibition of acyl-CoA:1,2-diacylglycerol acyltransferase, increase in mitochondrial and peroxisomal beta-oxidation in the liver, decrease lipogenesis in the liver and increase lipoprotein lipase activity.

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