Omega-3 carboxylic acids explained

Omega-3 carboxylic acids[1] (Epanova) is a formerly marketed yet still not an Food And Drug Administration (FDA) approved prescription medication–since taken off market by the manufacturer–used alongside a low fat and low cholesterol diet that lowers high triglyceride (fat) levels in adults with very high levels. This was the third class of fish oil-based drug, after omega-3 acid ethyl esters (Lovaza and Omtryg) and ethyl eicosapentaenoic acid (Vascepa), to be approved for use as a drug.[2] The first approval by US Food and Drug Administration was granted 05 May 2014.[3] These fish oil drugs are similar to fish oil dietary supplements, but the ingredients are better controlled and have been tested in clinical trials. Specifically, Epanova contained at least 850 mg omega-3-acid ethyl esters per 1 g capsule.

Following phase III clinical trial in mixed dyslipidaemia, AstraZeneca announced on 13 January 2019 that their clinical trials were terminated for futility because no medical benefit of the medication could be found.[4]

Medical uses

Omega-3 carboxylic acids are used in addition to changes in diet to reduce triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia.[5]

Intake of large doses (2.0 to 4.0 g/day) of long-chain omega-3 fatty acids as prescription drugs or dietary supplements are generally required to achieve significant (> 15%) lowering of triglycerides, and at those doses the effects can be significant (from 20% to 35% and even up to 45% in individuals with levels greater that 500 mg/dL). It appears that both eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) lower triglycerides. However, DHA appears to raise LDL cholesterol more than EPA, and further, DHA raises HDL cholesterol while EPA does not.[6]

Other fish-oil based drugs

There are other omega-3 fish oil based drugs on the market that have similar uses and mechanisms of action.

Dietary supplements

There are many fish oil dietary supplements on the market. There appears to be little difference in effect between dietary supplement and prescription forms of omega-3 fatty acids. Importantly, EPA and DHA ethyl esters (prescription forms) work better when taken with a mildly fattening meal of about 350 calories.[6] The ingredients of dietary supplements are not as carefully controlled as prescription products and have not been fixed and tested in clinical trials, as prescription drugs have.[11] Furthermore, the prescription forms are more concentrated, requiring fewer capsules to be taken and increasing the likelihood of compliance.[12]

Side effects

Special caution should be taken with people who have with fish and shellfish allergies.[5] In addition, as with other omega-3 fatty acids, taking omega-3 carboxylic acids puts people who are on anticoagulants at risk for prolonged bleeding time.[5] [6]

Side effects include diarrhea, nausea, abdominal pain, and burping.[5]

Omega-3 carboxylic acids have not been tested in pregnant women and are rated pregnancy category C because it is excreted in breast milk and the effects on infants are not known.[5]

Pharmacology

Omega-3 carboxylic acids are directly absorbed in the small intestine. Maximum plasma concentrations are achieved between 5–8 hours after dosing for total EPA and between 5–9 hours after dosing for total DHA. Both DHA and EPA are metabolized primarily in the liver, just like other fatty acids derived from food. The half-life of EPA from Omega-3 carboxylic acids is about 37 hours. For DHA, the half-life is about 46 hours.[5]

Mechanism of action

Omega-3 carboxylic acids, like other omega-3 fatty acid based drugs, appears to reduce production of triglycerides in the liver and to enhance clearance of triglycerides from circulating very low-density lipoprotein (VLDL) particles. The way it does that is not clear, but potential mechanisms include increased breakdown of fatty acids; inhibition of diglyceride acyltransferase, which is involved in biosynthesis of triglycerides in the liver; and increased activity of lipoprotein lipase in blood.[13]

Physical and chemical properties

Omega-3 carboxylic acids are derived from fish oil and are a purified mixture of the polyunsaturated free fatty acids docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA).[12] The drug contains a concentration of DHA at 15–25% and a concentration of EPA at 50–60%.[5]

History

Omega-3 carboxylic acids was approved by the US FDA in May 2014,[14] and such formulation(s) was the third prescription form of an omega-3 product approved in the United States. A notable difference is that the carboxylic acid treatment was the first approved in free fatty acid form.[15] Development was completed and regulatory approval was obtained by AstraZeneca,[14] but omega-3 carboxylic acids were first created at Chrysalis Pharma in Switzerland. Later, Princeton-based Omthera obtained rights from Chysalis, and Astrazeneca acquired Omthera in 2013 for $323 million in cash along with up to $120 million in milestones.[16] At the time Epanova was approved, AstraZeneca's plan was to develop a combination product with rosuvastatin, the patent on which was set to expire in 2016.[16]

Clinical trials of Epanova for severe hypertriglyceridemia showed good results.[15] [17] However, a clinical trial on mixed dyslipidaemia (hypertriglyceridemia with hypocholesterolemia) was started on 30 October 2014,[18] which was terminated after Phase III clinical trials, on 13 January 2019, due to lack of medical benefit in the results.[4]

External links

Notes and References

  1. "Omega-3 carboxylic acids" is the USAN, see here under 2014 and the proposed INN - see 3.8 here
  2. Skulas-Ray . Ann C. . Wilson . Peter W.F. . Harris . William S. . Brinton . Eliot A. . Kris-Etherton . Penny M.. Penny M. Kris-Etherton . Richter . Chesney K. . Jacobson . Terry A. . Engler . Mary B. . Miller . Michael . Robinson . Jennifer G. . Blum . Conrad B. . Rodriguez-Leyva . Delfin . de Ferranti . Sarah D. . Welty . Francine K. . Omega-3 Fatty Acids for the Management of Hypertriglyceridemia: A Science Advisory From the American Heart Association . Circulation . 2019 . 140 . 12 . 10.1161/CIR.0000000000000709 . 31422671 . 8 . e673–e691. free .
  3. Book: Food and Drug Administration, Center for Drug Evaluation and Research . 2021 . Approved Drug Products with Therapeutic Equivalence Evaluations . 41st . Food and Drug Administration . 830.
  4. News: AstraZeneca to discontinue Epanova trial, expects $100 million writedown . 15 January 2020 . Reuters . 13 January 2020 . en.
  5. http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205060s000lbl.pdf Epanova label
  6. 26699442 . 10.1016/j.jacl.2015.09.002 . 9 . National Lipid Association Recommendations for Patient-Centered Management of Dyslipidemia: Part 2 . 2015 . J Clin Lipidol . S1–122.e1 . Jacobson . TA . Maki . KC . Orringer . CE . Jones . PH . Kris-Etherton . P . Sikand . G . La Forge . R . Daniels . SR . Wilson . DP . Morris . PB . Wild . RA . Grundy . SM . Daviglus . M . Ferdinand . KC . Vijayaraghavan . K . Deedwania . PC . Aberg . JA . Liao . KP . McKenney . JM . Ross . JL . Braun . LT . Ito . MK . Bays . HE . Brown . WV . Underberg . JA . 6 . free .
  7. http://pharmacyservices.utah.edu/alerts/251.html University of Utah Pharmacy Services (August 15, 2007) "Omega-3-acid Ethyl Esters Brand Name Changed from Omacor to Lovaza"
  8. https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204977s000lbl.pdf Omtryg Label
  9. http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=OMEGA-3-ACID%20ETHYL%20ESTERS FDA Omega-3 acid ethyl esters products
  10. CenterWatch Vascepa (icosapent ethyl) Page accessed March 31, 2016
  11. Sweeney MET. Hypertriglyceridemia Pharmacologic Therapy for Medscape Drugs & Diseases, Ed. Khardori R. Updated: Apr 14, 2015, page accessed April 1, 2016
  12. 26681905 . 40 . A Comparative Overview of Prescription Omega-3 Fatty Acid Products . 4671468 . 2015 . P T . 826–57 . Ito . MK. 12 .
  13. Weintraub. HS. Overview of prescription omega-3 fatty acid products for hypertriglyceridemia. Postgrad Med. 2014. 126. 7. 7–18. 10.3810/pgm.2014.11.2828. 25387209. 12524547.
  14. Web site: Epanova (omega-3-carboxylic acids). CenterWatch. 15 December 2014.
  15. Blair . Hannah A. . Dhillon . Sohita . Omega-3 Carboxylic Acids (Epanova®): A Review of Its Use in Patients with Severe Hypertriglyceridemia . American Journal of Cardiovascular Drugs . 2014 . 14 . 5 . 393–400 . 10.1007/s40256-014-0090-3 . 25234378. 23706094 .
  16. John Carroll for FierceBiotech.May 6, 2014. AstraZeneca wins FDA OK for another fish-oil heart pill, enters crowded market
  17. Stroes . Erik S.G. . Susekov . Andrey V. . de Bruin . Tjerk W.A. . Kvarnström . Mats . Yang . Hong . Davidson . Michael H. . Omega-3 carboxylic acids in patients with severe hypertriglyceridemia: EVOLVE II, a randomized, placebo-controlled trial . Journal of Clinical Lipidology . 2018 . 12 . 2 . 321–330 . 10.1016/j.jacl.2017.10.012 . 29289538. free .
  18. Nicholls . Stephen J. . Lincoff . A. Michael . Bash . Dianna . Ballantyne . Christie M. . Barter . Philip J. . Davidson . Michael H. . Kastelein . John J. P. . Koenig . Wolfgang . McGuire . Darren K. . Mozaffarian . Dariush . Pedersen . Terje R. . Ridker . Paul M. . Ray . Kausik . Karlson . Björn W. . Lundström . Torbjörn . Wolski . Kathy . Nissen . Steven E. . Assessment of omega-3 carboxylic acids in statin-treated patients with high levels of triglycerides and low levels of high-density lipoprotein cholesterol: Rationale and design of the STRENGTH trial . Clinical Cardiology . 2018 . 41 . 10 . 1281–1288 . 10.1002/clc.23055 . 30125052 . 8 . 6489732.