Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 14:18:24 UTC |
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Updated at | 2024-09-11 14:18:24 UTC |
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NP-MRD ID | NP0338200 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Ethyl icosapentate |
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Description | Ethyl icosapentate, also known as icosapent or epadel, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl icosapentate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Studies suggest that EPA reduces hepatic very low-density lipoprotein triglycerides (VLDL-TG) synthesis and/or secretion and enhances TG clearance from circulating VLDL particles. Ethyl icosapentate or Ethyl icosapentate is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). Outside of the human body, Ethyl icosapentate has been detected, but not quantified in, fishes. This could make ethyl icosapentate a potential biomarker for the consumption of these foods. Potential mechanisms of action include increased β-oxidation; inhibition of acyl-CoA:1,2-Diacylglycerol acyltransferase (DGAT); decreased lipogenesis in the liver; and increased plasma lipoprotein lipase activity. It is used as adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL). Once converted into active EPA, it is hepatically metabolized into acetyl Coenzyme A via beta-oxidation. Ethyl icosapentate was first documented in 2012 (PMID: 22819432). FDA approved on July 26, 2012 (PMID: 22894624) (PMID: 23312052) (PMID: 23325450) (PMID: 23701295) (PMID: 23835245) (PMID: 23992935). |
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Structure | CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17- |
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Synonyms | Value | Source |
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(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoic acid ethyl ester | ChEBI | (all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl ester | ChEBI | all-cis-Ethyl 5,8,11,14,17-icosapentaenoate | ChEBI | AMR 101 | ChEBI | AMR101 | ChEBI | cis-Eicosapentaenoic acid ethyl ester | ChEBI | e-EPA | ChEBI | Eicosapentaenoic acid ethyl ester | ChEBI | Epadel | ChEBI | Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate | ChEBI | Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate | ChEBI | Ethyl (all cis)-5,8,11,14,17-icosapentaenoate | ChEBI | Ethyl all-cis-5,8,11,14,17-icosapentaenoate | ChEBI | Ethyl eicosapentaenoate | ChEBI | Icosapent | ChEBI | Icosapent ethyl | ChEBI | Timnodonic acid ethyl ester | ChEBI | Vascepa | ChEBI | EPA ethyl ester | Kegg | Epadel S | Kegg | (5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoate ethyl ester | Generator | (all-Z)-5,8,11,14,17-Eicosapentaenoate ethyl ester | Generator | all-cis-Ethyl 5,8,11,14,17-icosapentaenoic acid | Generator | cis-Eicosapentaenoate ethyl ester | Generator | Eicosapentaenoate ethyl ester | Generator | Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid | Generator | Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid | Generator | Ethyl (all cis)-5,8,11,14,17-icosapentaenoic acid | Generator | Ethyl all-cis-5,8,11,14,17-icosapentaenoic acid | Generator | Ethyl eicosapentaenoic acid | Generator | Timnodonate ethyl ester | Generator | Ethyl icosapentic acid | Generator | Eicosapentaenoic acid, ethyl ester | HMDB | Epa-e | HMDB | Ethyl epa | HMDB | Ethyl ester(all-Z)-5,8,11,14,17-eicosapentaenoic acid | HMDB | Ethyl icosapentaenoate | HMDB | Ethyl icosapentate, jan | HMDB | MND 21 | HMDB | AMR-101 | MeSH | Ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate | MeSH | Ethyl icosapentate | ChEBI |
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Chemical Formula | C22H34O2 |
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Average Mass | 330.5042 Da |
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Monoisotopic Mass | 330.25588 Da |
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IUPAC Name | ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate |
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Traditional Name | ethyl eicosapentaenoate |
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CAS Registry Number | Not Available |
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SMILES | CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17- |
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InChI Key | SSQPWTVBQMWLSZ-AAQCHOMXSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acid esters |
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Direct Parent | Fatty acid esters |
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Alternative Parents | |
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Substituents | - Fatty acid ester
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ballantyne CM, Bays HE, Kastelein JJ, Stein E, Isaacsohn JL, Braeckman RA, Soni PN: Efficacy and safety of eicosapentaenoic acid ethyl ester (AMR101) therapy in statin-treated patients with persistent high triglycerides (from the ANCHOR study). Am J Cardiol. 2012 Oct 1;110(7):984-92. doi: 10.1016/j.amjcard.2012.05.031. Epub 2012 Jul 20. [PubMed:22819432 ]
- Jacobson TA: A new pure omega-3 eicosapentaenoic acid ethyl ester (AMR101) for the management of hypertriglyceridemia: the MARINE trial. Expert Rev Cardiovasc Ther. 2012 Jun;10(6):687-95. doi: 10.1586/erc.12.56. [PubMed:22894624 ]
- Bays HE, Braeckman RA, Ballantyne CM, Kastelein JJ, Otvos JD, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on lipoprotein particle concentration and size in patients with very high triglyceride levels (the MARINE study). J Clin Lipidol. 2012 Nov-Dec;6(6):565-72. doi: 10.1016/j.jacl.2012.07.001. Epub 2012 Jul 24. [PubMed:23312052 ]
- Bays HE, Ballantyne CM, Braeckman RA, Stirtan WG, Soni PN: Icosapent ethyl, a pure ethyl ester of eicosapentaenoic acid: effects on circulating markers of inflammation from the MARINE and ANCHOR studies. Am J Cardiovasc Drugs. 2013 Feb;13(1):37-46. doi: 10.1007/s40256-012-0002-3. [PubMed:23325450 ]
- Ballantyne CM, Braeckman RA, Soni PN: Icosapent ethyl for the treatment of hypertriglyceridemia. Expert Opin Pharmacother. 2013 Jul;14(10):1409-16. doi: 10.1517/14656566.2013.798645. Epub 2013 May 24. [PubMed:23701295 ]
- Brinton EA, Ballantyne CM, Bays HE, Kastelein JJ, Braeckman RA, Soni PN: Effects of icosapent ethyl on lipid and inflammatory parameters in patients with diabetes mellitus-2, residual elevated triglycerides (200-500 mg/dL), and on statin therapy at LDL-C goal: the ANCHOR study. Cardiovasc Diabetol. 2013 Jul 9;12:100. doi: 10.1186/1475-2840-12-100. [PubMed:23835245 ]
- Braeckman RA, Manku MS, Bays HE, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on plasma and red blood cell fatty acids in patients with very high triglyceride levels (results from the MARINE study). Prostaglandins Leukot Essent Fatty Acids. 2013 Sep;89(4):195-201. doi: 10.1016/j.plefa.2013.07.005. Epub 2013 Aug 1. [PubMed:23992935 ]
- Weintraub H: Update on marine omega-3 fatty acids: management of dyslipidemia and current omega-3 treatment options. Atherosclerosis. 2013 Oct;230(2):381-9. doi: 10.1016/j.atherosclerosis.2013.07.041. Epub 2013 Jul 31. [PubMed:24075771 ]
- Nelson SD, Munger MA: Icosapent ethyl for treatment of elevated triglyceride levels. Ann Pharmacother. 2013 Nov;47(11):1517-23. doi: 10.1177/1060028013504079. Epub 2013 Nov 5. [PubMed:24259598 ]
- Hilleman DE, Malesker MA: Potential benefits of icosapent ethyl on the lipid profile: case studies. Clin Med Insights Cardiol. 2014 Feb 2;8:13-5. doi: 10.4137/CMC.S13571. eCollection 2014. [PubMed:24516343 ]
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