Eicosapentaenoic Acid ethyl ester
(Synonyms: 顺-二十碳五烯酸乙酯,EPA ethyl ester; Ethyl eicosapentaenoate) 目录号 : GC40813
An ω-3 fatty acid ethyl ester
Cas No.:86227-47-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fish oils in the diet have anti-inflammatory and cardiovascular benefits due to an abundance of ω-3 polyunsaturated fatty acids (PUFAs), including eicosapentaenoic acid (EPA). EPA ethyl ester is a stabilized ethyl ester form of this ω-3 C20:5 PUFA. EPA competitively inhibits the metabolism of (ω-6) arachidonic acid by cyclooxygenase enzymes, suggesting that EPA ethyl ester may also directly modulate the actions of enzymes involved in fatty acid metabolism. In addition, dietary EPA ethyl ester in rats increases fatty acid β-oxidation enzyme levels, indicating that EPA ethyl ester may alter the expression of genes related to fatty acid metabolism. Consistent with this concept, dietary supplementation with EPA ethyl ester in rats also down-regulates lipogenic genes, and decreases plasma cholesterol and triglyceride levels. Also, in rats fed a high-fat diet, supplementation with EPA ethyl ester blocks induced insulin resistance and corrects changes in adiponectin levels and TNF-α expression.
| Cas No. | 86227-47-6 | SDF | |
| 别名 | 顺-二十碳五烯酸乙酯,EPA ethyl ester; Ethyl eicosapentaenoate | ||
| Canonical SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(OCC)=O | ||
| 分子式 | C22H34O2 | 分子量 | 330.5 |
| 溶解度 | DMF: 100 mg/ml,DMSO: 100 mg/ml,Ethanol: 100 mg/ml,PBS (pH 7.2): 0.15 mg/ml | 储存条件 | Store at -20°C, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0257 mL | 15.1286 mL | 30.2572 mL |
| 5 mM | 0.6051 mL | 3.0257 mL | 6.0514 mL |
| 10 mM | 0.3026 mL | 1.5129 mL | 3.0257 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cardiovascular Risk Reduction with Icosapent Ethyl for Hypertriglyceridemia
N Engl J Med 2019 Jan 3;380(1):11-22.PMID:30415628DOI:10.1056/NEJMoa1812792.
Background: Patients with elevated triglyceride levels are at increased risk for ischemic events. Icosapent ethyl, a highly purified Eicosapentaenoic Acid ethyl ester, lowers triglyceride levels, but data are needed to determine its effects on ischemic events. Methods: We performed a multicenter, randomized, double-blind, placebo-controlled trial involving patients with established cardiovascular disease or with diabetes and other risk factors, who had been receiving statin therapy and who had a fasting triglyceride level of 135 to 499 mg per deciliter (1.52 to 5.63 mmol per liter) and a low-density lipoprotein cholesterol level of 41 to 100 mg per deciliter (1.06 to 2.59 mmol per liter). The patients were randomly assigned to receive 2 g of icosapent ethyl twice daily (total daily dose, 4 g) or placebo. The primary end point was a composite of cardiovascular death, nonfatal myocardial infarction, nonfatal stroke, coronary revascularization, or unstable angina. The key secondary end point was a composite of cardiovascular death, nonfatal myocardial infarction, or nonfatal stroke. Results: A total of 8179 patients were enrolled (70.7% for secondary prevention of cardiovascular events) and were followed for a median of 4.9 years. A primary end-point event occurred in 17.2% of the patients in the icosapent ethyl group, as compared with 22.0% of the patients in the placebo group (hazard ratio, 0.75; 95% confidence interval [CI], 0.68 to 0.83; P<0.001); the corresponding rates of the key secondary end point were 11.2% and 14.8% (hazard ratio, 0.74; 95% CI, 0.65 to 0.83; P<0.001). The rates of additional ischemic end points, as assessed according to a prespecified hierarchical schema, were significantly lower in the icosapent ethyl group than in the placebo group, including the rate of cardiovascular death (4.3% vs. 5.2%; hazard ratio, 0.80; 95% CI, 0.66 to 0.98; P=0.03). A larger percentage of patients in the icosapent ethyl group than in the placebo group were hospitalized for atrial fibrillation or flutter (3.1% vs. 2.1%, P=0.004). Serious bleeding events occurred in 2.7% of the patients in the icosapent ethyl group and in 2.1% in the placebo group (P=0.06). Conclusions: Among patients with elevated triglyceride levels despite the use of statins, the risk of ischemic events, including cardiovascular death, was significantly lower among those who received 2 g of icosapent ethyl twice daily than among those who received placebo. (Funded by Amarin Pharma; REDUCE-IT ClinicalTrials.gov number, NCT01492361 .).
The Diagnosis and Treatment of Hypertriglyceridemia
Dtsch Arztebl Int 2019 Dec 6;116(49):825-832.PMID:31888796DOI:10.3238/arztebl.2019.0825.
Background: Hypertriglyceridemia affects 15-20% of the adult population and is associated with overweight, metabolic syndrome, and diabetes mellitus. It is often discovered incidentally. Methods: This review is based on pertinent publications retrieved by a selective literature search, including current guidelines on hypertriglyceridemia. Results: Elevated triglyceride (TG) levels are causally linked to cardiovascular disease; TG levels above 1000 mg/dL (11.4 mmol/L) can induce acute pancreatitis. The individual risk of cardiovascular disease and of pancreatitis must be estimated in order to decide whether, and how, hypertriglyceridemia should be treated. Lifestyle modifications (cessation of alcohol consumption, reduced intake of rapidly metabolized carbohydrates), weight loss, and blood sugar control are the most effective ways to lower TG levels. The need to lower the low-density lipoprotein (LDL) concentration must be determined on the basis of the cardiovascular risk, independently of the success of the lifestyle changes. Few patients need specific drug treatment to lower the TG level. Fibrates can lower TG concentrations, but their efficacy in combination with statins has not been clearly shown in endpoint studies. A daily dose of 2-4 g omega-3 fatty acids can also lower TG levels. To date, only a single large-scale randomized, blinded trial has shown the efficacy of 4 g of Eicosapentaenoic Acid ethyl ester per day in lowering the risk in high-risk patients (number needed to treat = 21). Patients with the very rare purely genetic types of hypertriglyceridemia (familial chylomicronemia syndrome) should be treated in specialized outpatient clinics. Conclusion: Hypertriglyceridemia is causally linked to cardiovascular disease and pancreatitis. Lifestyle modifications play a paramount role in its treatment.
Eicosapentaenoic Acid ethyl ester improves endothelial dysfunction in type 2 diabetic mice
Lipids Health Dis 2018 May 22;17(1):118.PMID:29788974DOI:10.1186/s12944-018-0770-0.
Background: Eicosapentaenoic acid (EPA) is thought to have many beneficial effects, such as anti-atherosclerogenic and anti-inflammatory properties. However, few studies have reported its effects of endothelial dysfunction in diabetes and its direct effects on the aorta. Here, we investigated the effects of EPA treatment on impaired endothelium-dependent relaxation of the aorta in KKAy mice, a model of type 2 diabetes. Methods: Male KKAy mice were fed a high-fat (HF) diet for 8 weeks to induce diabetes, after which they were divided into two groups. One group was fed a HF diet, and the other group was fed a HF diet containing EPA ethyl ester (EPA-E, 10 mg/day) for 4 weeks. Then, the vascular reactivities of prepared aortic rings were measured in an organ bath to determine if EPA-E administration changed vascular function in these diabetic mice. In addition, we examined effect of EPA-E and its metabolites to vascular action using aorta separated from C57BL/6 J mice. Results: Although EPA-E administration did not change the plasma glucose and insulin levels in diabetic mice, total cholesterol levels were significantly decreased. The aorta extracted from EPA-E untreated diabetic mice showed impaired endothelium-dependent relaxation in response to acetylcholine (ACh). However, EPA-E administration improved the relaxation response to ACh to the control levels observed in non-diabetic C57BL/6 J mice. On the other hand, endothelium-independent relaxation in response to sodium nitroprusside did not significantly differ among these three groups. The enhanced contractile response by phenylephrine in diabetic mice was not altered by the administration of EPA-E. In addition, the direct administration of EPA-E metabolites such as EPA, docosahexaenoic acid, and docosapentaenoic acid led to vasodilation in the aortic rings of C57BL/6 J mice. Conclusion: These results showed that chronic EPA-E administration prevented the development of endothelial dysfunction in KKAy mice, partly via the direct action of EPA-E metabolites on the aorta.
Preparation of Eicosapentaenoic Acid ethyl ester from fish oil ethyl esters by continuous batch chromatography
J Sep Sci 2019 Dec;42(24):3697-3702.PMID:31610075DOI:10.1002/jssc.201900387.
Fish oils are rich in eicosapentaenoic acid, which has the wide-ranging biological activities. The rapid and efficient separation of Eicosapentaenoic Acid ethyl ester from fish oils ethyl ester is still regarded as a challenge. In this study, we described an effective and flexible chromatography for Eicosapentaenoic Acid ethyl ester preparation, named continuous batch chromatography, which combined the batch chromatography with the continuous chromatographic operation mode. After continuous batch chromatography experiment, the recovery of Eicosapentaenoic Acid ethyl ester was 82.01%, the average relative purity and the relative highest purity of Eicosapentaenoic Acid ethyl ester were 97.82 and 98.98%. The productivity of continuous batch chromatography was 5.48 times higher than that of batch chromatography, while the solvent consumption of Eicosapentaenoic Acid ethyl ester was 78% of the batch chromatography. This study provided a reference for the separation of the targeted chemical component from multi-component mixtures.
Long-term safety and efficacy of MND-2119 (self-emulsifying formulation of highly purified Eicosapentaenoic Acid ethyl ester) in patients with hypertriglyceridemia: Results from a multicenter, 52-week, open-label study
J Clin Lipidol 2022 Sep-Oct;16(5):737-746.PMID:36202740DOI:10.1016/j.jacl.2022.09.002.
Background: In Japan, Eicosapentaenoic Acid ethyl ester (EPA-E) is administered twice-daily or three-times-daily for dyslipidemia. We have developed MND-2119, a novel self-emulsifying formulation of highly purified EPA-E which can be administered once-daily. Objective: The objective of this study was to investigate the safety and efficacy of long-term administration of MND-2119 in hypertriglyceridemia patients. Methods: In this multicenter, 52-week, open-label study, patients with high triglyceride (TG) (TG levels between ≥ 150 and < 500 mg/dL) undergoing lifestyle modification were randomized to MND-2119 2 g/day (n=61) or MND-2119 4 g/day (n=61). Results: The incidence of adverse events in MND-2119 2 g/day and MND-2119 4 g/day was 70.5% and 62.3%, respectively, and the incidence of adverse drug reactions was 9.8% and 8.2%, respectively. There were no notable problems in the safety assessments of both treatment groups. By Week 4, TG levels had decreased from baseline in both groups, and the TG reducing effect continued up to Week 52 (mean percentage change from baseline in TG at Week 52 [two-sided 95% confidence interval]: MND-2119 2 g/day: -16.71% [-26.61, -6.81], MND-2119 4 g/day: -21.01% [-27.86, -14.16]). In both groups, plasma EPA concentration at Week 4 was maintained up until Week 52 and the plasma EPA concentration at Week 52 was 200.5 ± 54.7 μg/mL in MND-2119 2 g/day and 308.6 ± 98.6 μg/mL in MND-2119 4 g/day. Conclusion: Long-term administration of MND-2119 was not associated with any safety-related problems. TG levels decreased by Week 4, and the TG reducing effect continued up to Week 52.