Ethyl eicosapentaenoic acid

Ethyl eicosapentaenoic acid
Clinical data
Trade names	Vascepa, Vazkepa
Other names	Eicosapentaenoic acid ethyl ester; Ethyl eicosapentaenoate; Eicosapent; EPA ethyl ester; E-EPA, Icosapent ethyl (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a613024
License data	EU EMA: by INN; US DailyMed: Icosapent_ethyl; US FDA: Vascepa;
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
Drug class	Antilipemic Agents
ATC code	None;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only;
Identifiers
	IUPAC name Ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate;
CAS Number	86227-47-6 ;
PubChem CID	9831415;
IUPHAR/BPS	7441;
DrugBank	DB08887;
ChemSpider	8007147 ;
UNII	6GC8A4PAYH;
KEGG	D01892; C16184;
ChEBI	CHEBI:84883 ;
ChEMBL	ChEMBL2095209;
CompTox Dashboard (EPA)	DTXSID601018686 ;
Chemical and physical data
Formula	C22H34O2
Molar mass	330.512 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OCC;
	InChI 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- ; Key:SSQPWTVBQMWLSZ-AAQCHOMXSA-N ;
	(what is this?)

Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl), sold under the brand name Vascepa among others, is a medication used to treat dyslipidemia^[4] and hypertriglyceridemia.^[3] It is used in combination with changes in diet in adults with hypertriglyceridemia ≥ 150 mg/dL. Further, it is often required to be used with a statin (maximally-tolerated dose).^[6]

The most common side effects are musculoskeletal pain, peripheral edema (swelling of legs and hands), atrial fibrillation, and arthralgia (joint pain).^[6] Other common side effects include bleeding, constipation, gout, and rash.^[4]

It is made from the omega-3 fatty acid eicosapentaenoic acid (EPA).^[6] The US Food and Drug Administration (FDA) granted the approval of icosapent ethyl in 2012 to Amarin Corporation, and it became the second fish oil-based medication after omega-3-acid ethyl esters (brand named Lovaza, itself approved in 2004).^[7] On 13 December 2019, the FDA also approved Vascepa as the first drug specifically "to reduce cardiovascular risk among people with elevated triglyceride levels".^[6] It is available as a generic medication.^[8] In 2020, it was the 285th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[9]^[10]

^ ^a ^b "Vazkepa". Therapeutic Goods Administration (TGA). 22 November 2022. Archived from the original on 5 February 2023. Retrieved 29 April 2023.
^ "Summary Basis of Decision (SBD) for Vascepa". Health Canada. 23 October 2014. Archived from the original on 31 May 2022. Retrieved 29 May 2022.
^ ^a ^b Cite error: The named reference Vascepa FDA label was invoked but never defined (see the help page).
^ ^a ^b ^c "Vazkepa EPAR". European Medicines Agency (EMA). 25 January 2021. Archived from the original on 9 July 2021. Retrieved 7 July 2021.
^ "Vazkepa Product information". Union Register of medicinal products. Archived from the original on 5 March 2023. Retrieved 3 March 2023.
^ ^a ^b ^c ^d "FDA approves use of drug to reduce risk of cardiovascular events in certain adult patient groups". U.S. Food and Drug Administration (FDA) (Press release). 13 December 2019. Archived from the original on 22 December 2019. Retrieved 21 December 2019. This article incorporates text from this source, which is in the public domain.
^ Cite error: The named reference 2015CompareRev was invoked but never defined (see the help page).
^ "Icosapent ethyl: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 19 October 2020. Retrieved 15 August 2020.
^ "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 7 October 2022.
^ "Icosapent Ethyl - Drug Usage Statistics". ClinCalc. Archived from the original on 27 September 2022. Retrieved 7 October 2022.

[Vazkepa_APMDS-1] "Vazkepa". Therapeutic Goods Administration (TGA). 22 November 2022. Archived from the original on 5 February 2023. Retrieved 29 April 2023.

[2] "Summary Basis of Decision (SBD) for Vascepa". Health Canada. 23 October 2014. Archived from the original on 31 May 2022. Retrieved 29 May 2022.

[Vascepa_FDA_label-3] Cite error: The named reference Vascepa FDA label was invoked but never defined (see the help page).

[Vazkepa_EPAR-4] "Vazkepa EPAR". European Medicines Agency (EMA). 25 January 2021. Archived from the original on 9 July 2021. Retrieved 7 July 2021.

[5] "Vazkepa Product information". Union Register of medicinal products. Archived from the original on 5 March 2023. Retrieved 3 March 2023.

[FDA_PR-6] "FDA approves use of drug to reduce risk of cardiovascular events in certain adult patient groups". U.S. Food and Drug Administration (FDA) (Press release). 13 December 2019. Archived from the original on 22 December 2019. Retrieved 21 December 2019. This article incorporates text from this source, which is in the public domain.

[2015CompareRev-7] Cite error: The named reference 2015CompareRev was invoked but never defined (see the help page).

[8] "Icosapent ethyl: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 19 October 2020. Retrieved 15 August 2020.

[9] "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 7 October 2022.

[10] "Icosapent Ethyl - Drug Usage Statistics". ClinCalc. Archived from the original on 27 September 2022. Retrieved 7 October 2022.

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