MedKoo Cat#: 318052 | Name: Icosapent
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Icosapent is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). 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.

Chemical Structure

Icosapent
Icosapent
CAS#10417-94-4

Theoretical Analysis

MedKoo Cat#: 318052

Name: Icosapent

CAS#: 10417-94-4

Chemical Formula: C20H30O2

Exact Mass: 302.2246

Molecular Weight: 302.45

Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
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Synonym
Icosapent, Eicosapentaenoic acid, Timnodonic acid, Vascepa, Epadel, EPAX; EPA.
IUPAC/Chemical Name
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
InChi Key
JAZBEHYOTPTENJ-JLNKQSITSA-N
InChi Code
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-
SMILES Code
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
Appearance
Oily or waxy solid
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA).
In vitro activity:
EPA inhibited both porcine basilar and coronary artery contractions induced by U46619 and PGF2α in a concentration-dependent manner, but it did not affect the contractions induced by 80 mM KCl. EPA also inhibited the increase in F340/380 induced by U46619 and PGF2α in TP-293T cells. Reference: Sci Rep. 2022 Jul 27;12(1):12829. https://pubmed.ncbi.nlm.nih.gov/35896794/
In vivo activity:
These findings indicated that the anti-fibrotic effects of EPA are mediated in part by phenotypic polarization of macrophages toward anti-inflammatory M2 macrophages and increases of the anti-inflammatory cytokine, IL-10. In summary, EPA prevents the exacerbation of cardiac fibrosis and LV diastolic dysfunction in rats during sustained pressure overload. EPA could represent a novel treatment strategy for hypertensive cardiomyopathy. Reference: J Lipid Res. 2022 Oct 4:100292. https://pubmed.ncbi.nlm.nih.gov/36206854/
Solvent mg/mL mM
Solubility
Ethanol 100.0 330.63
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 302.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yoshioka K, Obara K, Oikawa S, Uemura K, Yamaguchi A, Fujisawa K, Hanazawa H, Fujiwara M, Endoh T, Suzuki T, De Dios Regadera M, Ito D, Saitoh N, Nakagome Y, Yamashita T, Kiguchi M, Saito Y, Nakao Y, Miyaji H, Ou G, Xu K, Tanaka Y. Eicosapentaenoic acid (EPA)-induced inhibitory effects on porcine coronary and cerebral arteries involve inhibition of prostanoid TP receptors. Sci Rep. 2022 Jul 27;12(1):12829. doi: 10.1038/s41598-022-16917-6. PMID: 35896794; PMCID: PMC9329469. 2. Zang T, Chen H, Shen S, Xu F, Wang R, Yin J, Chen X, Guan M, Shen L, Pan H, Ge J. Highly Purified Eicosapentaenoic Acid Alleviates the Inflammatory Response and Oxidative Stress in Macrophages during Atherosclerosis via the miR-1a-3p/sFRP1/Wnt/PCP-JNK Pathway. Oxid Med Cell Longev. 2022 Apr 13;2022:9451058. doi: 10.1155/2022/9451058. PMID: 35464772; PMCID: PMC9021996. 3. Gharraee N, Wang Z, Pflum A, Medina-Hernandez D, Herrington D, Zhu X, Meléndez GC. Eicosapentaenoic Acid Ameliorates Cardiac Fibrosis and Tissue Inflammation in Spontaneously Hypertensive Rats. J Lipid Res. 2022 Oct 4:100292. doi: 10.1016/j.jlr.2022.100292. Epub ahead of print. PMID: 36206854. 4. Kato Y, Ohsugi K, Fukuno Y, Iwatsuki K, Harada Y, Miyaji T. Vesicular nucleotide transporter is a molecular target of eicosapentaenoic acid for neuropathic and inflammatory pain treatment. Proc Natl Acad Sci U S A. 2022 Jul 26;119(30):e2122158119. doi: 10.1073/pnas.2122158119. Epub 2022 Jul 18. PMID: 35858418; PMCID: PMC9335333.
In vitro protocol:
1. Yoshioka K, Obara K, Oikawa S, Uemura K, Yamaguchi A, Fujisawa K, Hanazawa H, Fujiwara M, Endoh T, Suzuki T, De Dios Regadera M, Ito D, Saitoh N, Nakagome Y, Yamashita T, Kiguchi M, Saito Y, Nakao Y, Miyaji H, Ou G, Xu K, Tanaka Y. Eicosapentaenoic acid (EPA)-induced inhibitory effects on porcine coronary and cerebral arteries involve inhibition of prostanoid TP receptors. Sci Rep. 2022 Jul 27;12(1):12829. doi: 10.1038/s41598-022-16917-6. PMID: 35896794; PMCID: PMC9329469. 2. Zang T, Chen H, Shen S, Xu F, Wang R, Yin J, Chen X, Guan M, Shen L, Pan H, Ge J. Highly Purified Eicosapentaenoic Acid Alleviates the Inflammatory Response and Oxidative Stress in Macrophages during Atherosclerosis via the miR-1a-3p/sFRP1/Wnt/PCP-JNK Pathway. Oxid Med Cell Longev. 2022 Apr 13;2022:9451058. doi: 10.1155/2022/9451058. PMID: 35464772; PMCID: PMC9021996.
In vivo protocol:
1. Gharraee N, Wang Z, Pflum A, Medina-Hernandez D, Herrington D, Zhu X, Meléndez GC. Eicosapentaenoic Acid Ameliorates Cardiac Fibrosis and Tissue Inflammation in Spontaneously Hypertensive Rats. J Lipid Res. 2022 Oct 4:100292. doi: 10.1016/j.jlr.2022.100292. Epub ahead of print. PMID: 36206854. 2. Kato Y, Ohsugi K, Fukuno Y, Iwatsuki K, Harada Y, Miyaji T. Vesicular nucleotide transporter is a molecular target of eicosapentaenoic acid for neuropathic and inflammatory pain treatment. Proc Natl Acad Sci U S A. 2022 Jul 26;119(30):e2122158119. doi: 10.1073/pnas.2122158119. Epub 2022 Jul 18. PMID: 35858418; PMCID: PMC9335333.
1: Borow KM, Nelson JR, Mason RP. Biologic plausibility, cellular effects, and molecular mechanisms of eicosapentaenoic acid (EPA) in atherosclerosis. Atherosclerosis. 2015 Sep;242(1):357-66. doi: 10.1016/j.atherosclerosis.2015.07.035. Epub 2015 Jul 22. Review. PubMed PMID: 26253795. 2: Pappalardo G, Almeida A, Ravasco P. Eicosapentaenoic acid in cancer improves body composition and modulates metabolism. Nutrition. 2015 Apr;31(4):549-55. doi: 10.1016/j.nut.2014.12.002. Epub 2014 Dec 12. Review. PubMed PMID: 25770317. 3: Xie D, Jackson EN, Zhu Q. Sustainable source of omega-3 eicosapentaenoic acid from metabolically engineered Yarrowia lipolytica: from fundamental research to commercial production. Appl Microbiol Biotechnol. 2015 Feb;99(4):1599-610. doi: 10.1007/s00253-014-6318-y. Epub 2015 Jan 8. Review. PubMed PMID: 25567511; PubMed Central PMCID: PMC4322222. 4: Chen CT, Bazinet RP. β-oxidation and rapid metabolism, but not uptake regulate brain eicosapentaenoic acid levels. Prostaglandins Leukot Essent Fatty Acids. 2015 Jan;92:33-40. doi: 10.1016/j.plefa.2014.05.007. Epub 2014 Jun 5. Review. PubMed PMID: 24986271. 5: Fleming JA, Kris-Etherton PM. The evidence for α-linolenic acid and cardiovascular disease benefits: Comparisons with eicosapentaenoic acid and docosahexaenoic acid. Adv Nutr. 2014 Nov 14;5(6):863S-76S. doi: 10.3945/an.114.005850. Print 2014 Nov. Review. PubMed PMID: 25398754; PubMed Central PMCID: PMC4224228. 6: Gyurko R, Van Dyke TE. The role of polyunsaturated ω-3 fatty acid eicosapentaenoic acid-derived resolvin E1 (RvE1) in bone preservation. Crit Rev Immunol. 2014;34(4):347-57. Review. PubMed PMID: 24941160; PubMed Central PMCID: PMC4382917. 7: Davidson MH. Omega-3 fatty acids: new insights into the pharmacology and biology of docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid. Curr Opin Lipidol. 2013 Dec;24(6):467-74. doi: 10.1097/MOL.0000000000000019. Review. PubMed PMID: 24184945. 8: Wu L, Roe CL, Wen Z. The safety assessment of Pythium irregulare as a producer of biomass and eicosapentaenoic acid for use in dietary supplements and food ingredients. Appl Microbiol Biotechnol. 2013 Sep;97(17):7579-85. doi: 10.1007/s00253-013-5114-4. Epub 2013 Jul 31. Review. PubMed PMID: 23900800. 9: Ohnishi H, Saito Y. Eicosapentaenoic acid (EPA) reduces cardiovascular events: relationship with the EPA/arachidonic acid ratio. J Atheroscler Thromb. 2013;20(12):861-77. Epub 2013 Sep 18. Review. PubMed PMID: 24047614. 10: Kwak SM, Myung SK, Lee YJ, Seo HG; Korean Meta-analysis Study Group. Efficacy of omega-3 fatty acid supplements (eicosapentaenoic acid and docosahexaenoic acid) in the secondary prevention of cardiovascular disease: a meta-analysis of randomized, double-blind, placebo-controlled trials. Arch Intern Med. 2012 May 14;172(9):686-94. doi: 10.1001/archinternmed.2012.262. Review. PubMed PMID: 22493407. 11: Fusar-Poli P, Berger G. Eicosapentaenoic acid interventions in schizophrenia: meta-analysis of randomized, placebo-controlled studies. J Clin Psychopharmacol. 2012 Apr;32(2):179-85. doi: 10.1097/JCP.0b013e318248b7bb. Review. PubMed PMID: 22367656. 12: Hjorth E, Freund-Levi Y. Immunomodulation of microglia by docosahexaenoic acid and eicosapentaenoic acid. Curr Opin Clin Nutr Metab Care. 2012 Mar;15(2):134-43. doi: 10.1097/MCO.0b013e32835017cc. Review. PubMed PMID: 22316559. 13: Maki KC, Rains TM. Stearidonic acid raises red blood cell membrane eicosapentaenoic acid. J Nutr. 2012 Mar;142(3):626S-629S. doi: 10.3945/jn.111.153858. Epub 2012 Jan 25. Review. PubMed PMID: 22279138. 14: Jacobson TA, Glickstein SB, Rowe JD, Soni PN. Effects of eicosapentaenoic acid and docosahexaenoic acid on low-density lipoprotein cholesterol and other lipids: a review. J Clin Lipidol. 2012 Jan-Feb;6(1):5-18. doi: 10.1016/j.jacl.2011.10.018. Epub 2011 Nov 3. Review. PubMed PMID: 22264569. 15: Siriwardhana N, Kalupahana NS, Moustaid-Moussa N. Health benefits of n-3 polyunsaturated fatty acids: eicosapentaenoic acid and docosahexaenoic acid. Adv Food Nutr Res. 2012;65:211-22. doi: 10.1016/B978-0-12-416003-3.00013-5. Review. PubMed PMID: 22361189. 16: Wei MY, Jacobson TA. Effects of eicosapentaenoic acid versus docosahexaenoic acid on serum lipids: a systematic review and meta-analysis. Curr Atheroscler Rep. 2011 Dec;13(6):474-83. doi: 10.1007/s11883-011-0210-3. Review. Erratum in: Curr Atheroscler Rep. 2012 Feb;14(1):93. PubMed PMID: 21975919. 17: Murphy RA, Yeung E, Mazurak VC, Mourtzakis M. Influence of eicosapentaenoic acid supplementation on lean body mass in cancer cachexia. Br J Cancer. 2011 Nov 8;105(10):1469-73. doi: 10.1038/bjc.2011.391. Epub 2011 Oct 4. Review. PubMed PMID: 21970879; PubMed Central PMCID: PMC3242518. 18: Iwami D, Nonomura K, Shirasugi N, Niimi M. Immunomodulatory effects of eicosapentaenoic acid through induction of regulatory T cells. Int Immunopharmacol. 2011 Mar;11(3):384-9. doi: 10.1016/j.intimp.2010.11.035. Epub 2010 Dec 18. Review. PubMed PMID: 21182821. 19: Sakamoto Y, Node K. [Anti-atherosclerotic effect of fibrates and eicosapentaenoic acid]. Nihon Rinsho. 2011 Jan;69(1):87-91. Review. Japanese. PubMed PMID: 21226266. 20: Musa-Veloso K, Binns MA, Kocenas AC, Poon T, Elliot JA, Rice H, Oppedal-Olsen H, Lloyd H, Lemke S. Long-chain omega-3 fatty acids eicosapentaenoic acid and docosahexaenoic acid dose-dependently reduce fasting serum triglycerides. Nutr Rev. 2010 Mar;68(3):155-67. doi: 10.1111/j.1753-4887.2010.00272.x. Review. PubMed PMID: 20384846.