Omega-3 acid ethyl ester 90

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General Information
Surname Omega-3 acid ethyl ester 90
other names Omega-3 acidorum esteri ethylici 90 (Ph.Eur . )
Substance properties Light yellow liquid with a faint, fish-like odor. Practically insoluble in water, very easily soluble in acetone , ethanol , heptane and methanol . The total content of omega-3 acid ethyl esters is 90%.
ATC code C10 AX06
Drug class Lipid lowering agents
Prescription requirement Yes ( D , USA )
Main components
Surname Eicosapentaenic acid ethyl ester (icosapent-ethyl) Docosahexaenoic acid ethyl ester (Doconexent-Ethyl)
Structural formula Structural formula of icosapent ethyl Structural formula of ethyl docosahexaenoate
Molecular formula C 22 H 34 O 2 C 24 H 36 O 2
CAS number 86227-47-6 73310-11-9

Omega-3 acid ethyl ester 90 is a liquid, partially synthetic mixture of substances made from fish oil and used as a drug from the active ingredient class of lipid-lowering agents.

composition

Basic structures of the triglycerides contained in fish oil : Glycerine is esterified with different saturated and unsaturated fatty acid
residues .
a – i: number of repeat units
Structures of the components EPA and DHA contained in omega-3 acid ethyl ester

The active ingredient, which requires a prescription in Germany, is one of the esters of long-chain, polyunsaturated fatty acids . It mainly consists of the ethyl esters of the two omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which in total contain at least 80%. The content of ethyl eicosapentaenoate is at least 40% and ethyl docosahexaenoate at least 34%. The total content of omega-3 acid ethyl esters is at least 90%. The name of the active ingredient also relates to this.

The omega-3 acid ethyl esters are obtained from fish oil by molecular distillation. The starting material is the body oil (muscle oil) of fatty fish species from families such as Engraulidae , Carangidae , Clupeidae , Osmeridae , Salmonidae and Scombridae . The omega-3 fatty acids are contained in natural fish oil as triglyceride esters in a proportion of approx. 20%.

These pharmacologically active substances can be isolated and concentrated up to 90% by transesterification to ethyl esters. The substances are highly purified through physico-chemical processes and are therefore free of harmful substances (such as mercury and heavy metals ) and - in contrast to natural fish oil - do not contain any triglycerides . The pharmacologically active substances from fish oil (EPA and DHA) are therefore present in this active ingredient in an isolated and highly purified form. Tocopherol is added as an antioxidant . A monograph on Omega-3 acid ethyl ester 90 is contained in the European Pharmacopoeia (Pharmacopoea Europaea).

(For occurrence, various properties and biological functions, see the main articles of the individual substances eicosapentaenoic acid and docosahexaenoic acid ).

Clinical information

application areas

  • Hypertriglyceridemia

Omega-3 acid ethyl ester 90 is used to treat high blood lipids ( hypertriglyceridemia ) when dietary measures alone are not sufficient. If not only the triglycerides are increased, but also the LDL cholesterol , the therapy is carried out in combination with HMG-CoA reductase inhibitors, so-called statins . The dosage here is 2–4 grams of omega-3 acid ethyl ester 90 per day. There is no evidence of a long-term effect (more than a year) on lipid lowering.

  • Secondary prevention after myocardial infarction

Secondary prevention after myocardial infarction was a further area of ​​application . In the literature, positive effects were discussed primarily through an antiarrhythmic effect. However, an examination by the EMA's Committee on Medicinal Products for Human Use found that omega-3 acid ethyl esters 90 were not effective in preventing further heart disease after a heart attack. The approval for this area of ​​application was revoked by the BfArM in June 2019. The dosage of 1 gram per day used for this purpose has no significant lipid-lowering effect.

Side effects

The most common side effects of omega-3 fatty acid ethyl ester 90 are a fishy aftertaste, gastrointestinal upset (e.g. diarrhea) and nausea.

Mechanism of action

Omega-3-acid ethyl esters 90 in a dose of 2 grams or more cause a reduction in triglycerides, which increases with increasing dose. The actual mechanism of action has not yet been fully clarified, but it is postulated that EPA and DHA in correspondingly high concentrations reduce the synthesis of the triglyceride-rich lipoproteins (VLDL, very low density lipoproteins) in the liver. The lipoprotein lipase is also activated and thus the breakdown of triglyceride-rich particles ( VLDL , chylomicrons) is promoted. In 2010, an omega-3 fatty acid receptor, GPR 120, was described for the first time in macrophages and adipocytes , which mediates anti-inflammatory and insulin- sensitizing effects. The triglyceride-lowering effect is between 30% and 45% depending on the initial values ​​and the dosage used. With simultaneous administration with statins, the blood lipid lowering effect of the omega-3 acid ethyl ester 90 is increased.

In addition to the lipid-lowering effects, there are also cardioprotective effects such as B. an antiarrhythmic, anti-inflammatory, antithrombotic and membrane-stabilizing effect.

Finished preparations (trade names)

Zodin ( D ), Omacor (D), Lovaza ( USA )

Individual evidence

  1. European Pharmacopoeia, Monograph 6.0 / 1250 (2008).
  2. Harold Bays: Rationale for prescription omega-3-acid ethyl ester therapy for hypertriglyceridemia: a primer for clinicians . In: Drugs of Today 2008, 44 (3): 205-246
  3. a b c Technical information Zodin 1000 mg soft capsules. Status: May 2005
  4. BfArM - Risk assessment method - Omega-3 fatty acids: EMA assesses use after a heart attack. Retrieved June 24, 2019 .
  5. ^ William S Harris et al .: Safety and efficacy of Omacor in severe hypertriglyceridemia . In: J Cardiovasc Risk . 1997; 4: 385-391
  6. Henry J Pownall et al .: Correlation of serum triglyceride and its reduction by omega-3 fatty acids with lipid transfer activity and the neutral lipid compositions of high-density and low-density lipoproteins . In: Atherosclerosis 143 (1999): 285-297
  7. William S Harris: Why do omega-3 fatty acids lower serum triglycerides? In: Curr Opin Lipidol 17: 387-393; 2006
  8. Oh da Y, Talukdar S, Bae EJ, Imamura T, Morinaga H, Fan W, Li P, Lu WJ, Watkins SM, Olefsky JM. GPR120 is an Omega-3 Fatty Acid Receptor Mediating Potent Anti-inflammatory and Insulin-Sensitizing Effects . In: Cell . 2010 Sep 3; 142 (5): 687-98.
  9. Ann C Skulas-Ray et al .: Omega-3 fatty acid concentrates in the treatment of moderate hypertriglyceridemia . In: Expert Opin Pharmacother . 2008 (7): 1237-1248.
  10. Michael H Davidson et al .: Efficacy and tolerability of adding prescription Omega-3 fatty acids 4 g / d to simvastatin 40 mg / d in hypertriglyceridemic patients: an 8-week, randomized, double-blind, placebo-controlled study. In: Clin Ther . 2007; 29: 1354-1367.