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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
    Icosapent Ethyl
    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 Weight 302.5 g/mol
    Molecular Formula C20H30O2
    XLogP35.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count13
    Exact Mass302.224580195 g/mol
    Monoisotopic Mass302.224580195 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity398
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count5
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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    20-Sep-2021
    18-Jul-2024
    KGS
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