Eicosapentaenoic Acid Ethyl Ester | Epadel | AMR-101 | CAS#86227-47-6 | Omega-3 Fatty Acid Agent

Eicosapentaenoic Acid Ethyl Ester
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 329001

CAS#: 86227-47-6

Description: Eicosapentaenoic Acid Ethyl Ester, also known as Epadel and AMR-101, is an omega-3 fatty acid agent used as adjunct therapy for severe hypertriglyceridemia. Eicosapentaenoic acid lowers triglyceride levels without increasing low-density lipoprotein cholesterol levels.

Chemical Structure

Eicosapentaenoic Acid Ethyl Ester

CAS# 86227-47-6

Instruction

Theoretical Analysis

MedKoo Cat#: 329001
Name: Eicosapentaenoic Acid Ethyl Ester
CAS#: 86227-47-6
Chemical Formula: C22H34O2
Exact Mass: 330.26
Molecular Weight: 330.512
Elemental Analysis: C, 79.95; H, 10.37; O, 9.68

Price and Availability

Size	Price	Availability
50mg	USD 275	2 weeks
100mg	USD 450	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Eicosapentaenoic Acid Ethyl Ester; AMR-101; EPA-E; LAX-101; MND-21; AMR 101; EPA E; LAX 101; MND 21; AMR101; EPAE; LAX101; MND21; Epadel; Miraxion

IUPAC/Chemical Name: ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

InChi Key: SSQPWTVBQMWLSZ-AAQCHOMXSA-N

InChi Code: 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-

SMILES Code: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(OCC)=O

Appearance: Solid powder

Purity: >98% (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

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:

Instruction:

View handling instruction

Biological target:	Eicosapentaenoic acid ethyl ester is an omega-3 fatty acid agent.
In vitro activity:	Finally, testing autocrine and paracrine effects in an avascular tumor spheroid growth assay, both exogenous MAG-EPA (monoacylglyceride eicosapantaenoic acid) and endogenous ω3 reduced VEGF secretion and in vitro endothelial cell tube formation and blocked tumor spheroid growth, suggesting that ω3 molecules can directly hinder prostate cancer cell growth. Reference: Mol Cancer Res. 2021 Mar;19(3):516-527. https://pubmed.ncbi.nlm.nih.gov/33262291/
In vivo activity:	EPA (eicosapantaenoic acid) supplementation effectively reversed the increasing trend of M1 microglial markers and the decreased expression of M2 microglial markers in the hippocampus mediated by Aβ1-42 and normalized the Aβ-induced upregulation of proinflammatory cytokines and the downregulation of anti-inflammatory factors. Consistent with these findings, EPA significantly improved cognitive function and inhibited apoptotic neuronal death in the hippocampus. Reference: Neuro Endocrinol Lett. 2021 May 4;42(2):91-98. https://pubmed.ncbi.nlm.nih.gov/34217166/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	66.7	201.72
	DMF	100.0	302.56
	Ethanol	75.0	226.92
	PBS (pH 7.2)	0.2	0.45

Preparing Stock Solutions

The following data is based on the product molecular weight 330.51 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.

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. Gevariya N, Lachance G, Robitaille K, Joly Beauparlant C, Beaudoin L, Fournier É, Fradet Y, Droit A, Julien P, Marette A, Bergeron A, Fradet V. Omega-3 Eicosapentaenoic Acid Reduces Prostate Tumor Vascularity. Mol Cancer Res. 2021 Mar;19(3):516-527. doi: 10.1158/1541-7786.MCR-20-0316. Epub 2020 Dec 1. PMID: 33262291. 2. Ando N, Hara M, Shiga K, Yanagita T, Takasu K, Nakai N, Maeda Y, Hirokawa T, Takahashi H, Ishiguro H, Matsuo Y, Takiguchi S. Eicosapentaenoic acid suppresses angiogenesis via reducing secretion of IL‑6 and VEGF from colon cancer‑associated fibroblasts. Oncol Rep. 2019 Jul;42(1):339-349. doi: 10.3892/or.2019.7141. Epub 2019 May 2. PMID: 31059084. 3. Miller EK, Pahlavani M, Ramalingam L, Scoggin S, Moustaid-Moussa N. Uncoupling Protein 1-Independent Effects of Eicosapentaenoic Acid in Brown Adipose Tissue of Diet-Induced Obese Female Mice. J Nutr Biochem. 2021 Jul 13:108819. doi: 10.1016/j.jnutbio.2021.108819. Epub ahead of print. PMID: 34271101. 4. Dong Y, Long S, Gu Y, Liu W. Eicosapentaenoic acid attenuates Aβ-induced neurotoxicity by decreasing neuroinflammation through regulation of microglial polarization. Neuro Endocrinol Lett. 2021 May 4;42(2):91-98. Epub ahead of print. PMID: 34217166.
In vitro protocol:	1. Gevariya N, Lachance G, Robitaille K, Joly Beauparlant C, Beaudoin L, Fournier É, Fradet Y, Droit A, Julien P, Marette A, Bergeron A, Fradet V. Omega-3 Eicosapentaenoic Acid Reduces Prostate Tumor Vascularity. Mol Cancer Res. 2021 Mar;19(3):516-527. doi: 10.1158/1541-7786.MCR-20-0316. Epub 2020 Dec 1. PMID: 33262291. 2. Ando N, Hara M, Shiga K, Yanagita T, Takasu K, Nakai N, Maeda Y, Hirokawa T, Takahashi H, Ishiguro H, Matsuo Y, Takiguchi S. Eicosapentaenoic acid suppresses angiogenesis via reducing secretion of IL‑6 and VEGF from colon cancer‑associated fibroblasts. Oncol Rep. 2019 Jul;42(1):339-349. doi: 10.3892/or.2019.7141. Epub 2019 May 2. PMID: 31059084.
In vivo protocol:	1. Miller EK, Pahlavani M, Ramalingam L, Scoggin S, Moustaid-Moussa N. Uncoupling Protein 1-Independent Effects of Eicosapentaenoic Acid in Brown Adipose Tissue of Diet-Induced Obese Female Mice. J Nutr Biochem. 2021 Jul 13:108819. doi: 10.1016/j.jnutbio.2021.108819. Epub ahead of print. PMID: 34271101. 2. Dong Y, Long S, Gu Y, Liu W. Eicosapentaenoic acid attenuates Aβ-induced neurotoxicity by decreasing neuroinflammation through regulation of microglial polarization. Neuro Endocrinol Lett. 2021 May 4;42(2):91-98. Epub ahead of print. PMID: 34217166.

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1: Bays HE, Ballantyne CM, Braeckman RA, Stirtan WG, Doyle RT Jr, Philip S, Soni PN, Juliano RA. Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester): Effects Upon High-Sensitivity C-Reactive Protein and Lipid Parameters in Patients With Metabolic Syndrome. Metab Syndr Relat Disord. 2015 Aug;13(6):239-47. doi: 10.1089/met.2014.0137. Epub 2015 Apr 20. PubMed PMID: 25893544.

2: Ballantyne CM, Bays HE, Philip S, Doyle RT, Braeckman RA, Stirtan WG, Soni PN, Juliano RA. Icosapent ethyl (eicosapentaenoic acid ethyl ester): Effects on remnant-like particle cholesterol from the MARINE and ANCHOR studies. Atherosclerosis. 2016 Oct;253:81-87. doi: 10.1016/j.atherosclerosis.2016.08.005. PubMed PMID: 27596132.

3: Ballantyne CM, Bays HE, Braeckman RA, Philip S, Stirtan WG, Doyle RT Jr, Soni PN, Juliano RA. Icosapent ethyl (eicosapentaenoic acid ethyl ester): Effects on plasma apolipoprotein C-III levels in patients from the MARINE and ANCHOR studies. J Clin Lipidol. 2016 May-Jun;10(3):635-645.e1. doi: 10.1016/j.jacl.2016.02.008. Epub 2016 Feb 23. PubMed PMID: 27206952.

4: Braeckman RA, Stirtan WG, Soni PN. Effect of concomitant icosapent ethyl (eicosapentaenoic acid ethyl ester) on the pharmacokinetics of atorvastatin. Clin Drug Investig. 2015 Jan;35(1):45-51. doi: 10.1007/s40261-014-0252-8. PubMed PMID: 25471740; PubMed Central PMCID: PMC4281350.

5: Braeckman RA, Stirtan WG, Soni PN. Effects of Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester) on Pharmacokinetic Parameters of Rosiglitazone in Healthy Subjects. Clin Pharmacol Drug Dev. 2015 Mar;4(2):143-148. Epub 2014 Dec 3. PubMed PMID: 26097794; PubMed Central PMCID: PMC4467261.

6: Braeckman RA, Stirtan WG, Soni PN. Effect of icosapent ethyl (eicosapentaenoic acid ethyl ester) on omeprazole plasma pharmacokinetics in healthy adults. Drugs R D. 2014 Sep;14(3):159-64. doi: 10.1007/s40268-014-0053-9. PubMed PMID: 24973042; PubMed Central PMCID: PMC4153963.

7: 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 PMID: 22819432.

8: Jacobson TA. A new pure ω-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 PMID: 22894624.

9: Bays HE, Ballantyne CM, Kastelein JJ, Isaacsohn JL, Braeckman RA, Soni PN. Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). Am J Cardiol. 2011 Sep 1;108(5):682-90. doi: 10.1016/j.amjcard.2011.04.015. Epub 2011 Jun 16. PubMed PMID: 21683321.

10: Saito H, Chang KJ, Tamura Y, Yoshida S. Ingestion of eicosapentaenoic acid-ethyl ester renders rabbit LDL less susceptible to Cu2(+)-catalyzed-oxidative modification. Biochem Biophys Res Commun. 1991 Feb 28;175(1):61-7. PubMed PMID: 1998520.

11: Chang KJ, Saito H, Tamura Y, Watanabe K, Yoshida S. Effect of oral ingestion of eicosapentaenoic acid-ethyl ester on natural killer cell activity in rat spleen cells. Prostaglandins Leukot Essent Fatty Acids. 1989 Jul;37(1):31-5. PubMed PMID: 2548219.

12: Tatsuno I. Omega-3 polyunsaturated fatty acids and cardiovascular disease: an emphasis on omega-3-acid ethyl esters 90 for the treatment of hypertriglyceridemia. Expert Rev Cardiovasc Ther. 2014 Nov;12(11):1261-8. doi: 10.1586/14779072.2014.971756. Epub 2014 Oct 16. Review. PubMed PMID: 25319059.

13: Fujikawa M, Yamazaki K, Hamazaki T, Wakaki K, Koizumi F, Yano S, Kobayashi M. Effect of eicosapentaenoic acid ethyl ester on albuminuria in streptozotocin-induced diabetic rats. J Nutr Sci Vitaminol (Tokyo). 1994 Feb;40(1):49-61. PubMed PMID: 8089771.

14: Mori Y, Nobukata H, Harada T, Kasahara T, Tajima N. Long-term administration of highly purified eicosapentaenoic acid ethyl ester improves blood coagulation abnormalities and dysfunction of vascular endothelial cells in Otsuka Long-Evans Tokushima fatty rats. Endocr J. 2003 Oct;50(5):603-11. PubMed PMID: 14614217.

15: Hattori Y, Matsuda M, Eizawa T, Nakajima K. [A case of mitochondrial myopathy, encephalopathy, lactic acidosis and stroke-like episodes (MELAS), showing temporary improvement during the treatment with eicosapentaenoic acid ethyl ester]. Rinsho Shinkeigaku. 2001 Oct;41(10):668-72. Japanese. PubMed PMID: 11993186.

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