Np mrd loader

Record Information
Version2.0
Created at2024-09-11 14:18:24 UTC
Updated at2024-09-11 14:18:24 UTC
NP-MRD IDNP0338200
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthyl icosapentate
DescriptionEthyl icosapentate, also known as icosapent or epadel, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl icosapentate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Studies suggest that EPA reduces hepatic very low-density lipoprotein triglycerides (VLDL-TG) synthesis and/or secretion and enhances TG clearance from circulating VLDL particles. Ethyl icosapentate or Ethyl icosapentate is a synthetic derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA). Outside of the human body, Ethyl icosapentate has been detected, but not quantified in, fishes. This could make ethyl icosapentate a potential biomarker for the consumption of these foods. Potential mechanisms of action include increased β-oxidation; inhibition of acyl-CoA:1,2-Diacylglycerol acyltransferase (DGAT); decreased lipogenesis in the liver; and increased plasma lipoprotein lipase activity. It is used as adjunct therapy for severe hypertriglyceridemia (TG levels > 500 mg/dL). Once converted into active EPA, it is hepatically metabolized into acetyl Coenzyme A via beta-oxidation. Ethyl icosapentate was first documented in 2012 (PMID: 22819432). FDA approved on July 26, 2012 (PMID: 22894624) (PMID: 23312052) (PMID: 23325450) (PMID: 23701295) (PMID: 23835245) (PMID: 23992935).
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoic acid ethyl esterChEBI
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl esterChEBI
all-cis-Ethyl 5,8,11,14,17-icosapentaenoateChEBI
AMR 101ChEBI
AMR101ChEBI
cis-Eicosapentaenoic acid ethyl esterChEBI
e-EPAChEBI
Eicosapentaenoic acid ethyl esterChEBI
EpadelChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoateChEBI
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateChEBI
Ethyl (all cis)-5,8,11,14,17-icosapentaenoateChEBI
Ethyl all-cis-5,8,11,14,17-icosapentaenoateChEBI
Ethyl eicosapentaenoateChEBI
IcosapentChEBI
Icosapent ethylChEBI
Timnodonic acid ethyl esterChEBI
VascepaChEBI
EPA ethyl esterKegg
Epadel SKegg
(5Z,8Z,11Z,14Z,17Z)-Eicosapetaenoate ethyl esterGenerator
(all-Z)-5,8,11,14,17-Eicosapentaenoate ethyl esterGenerator
all-cis-Ethyl 5,8,11,14,17-icosapentaenoic acidGenerator
cis-Eicosapentaenoate ethyl esterGenerator
Eicosapentaenoate ethyl esterGenerator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acidGenerator
Ethyl (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acidGenerator
Ethyl (all cis)-5,8,11,14,17-icosapentaenoic acidGenerator
Ethyl all-cis-5,8,11,14,17-icosapentaenoic acidGenerator
Ethyl eicosapentaenoic acidGenerator
Timnodonate ethyl esterGenerator
Ethyl icosapentic acidGenerator
Eicosapentaenoic acid, ethyl esterHMDB
Epa-eHMDB
Ethyl epaHMDB
Ethyl ester(all-Z)-5,8,11,14,17-eicosapentaenoic acidHMDB
Ethyl icosapentaenoateHMDB
Ethyl icosapentate, janHMDB
MND 21HMDB
AMR-101MeSH
Ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoateMeSH
Ethyl icosapentateChEBI
Chemical FormulaC22H34O2
Average Mass330.5042 Da
Monoisotopic Mass330.25588 Da
IUPAC Nameethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Nameethyl eicosapentaenoate
CAS Registry NumberNot Available
SMILES
CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
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-
InChI KeySSQPWTVBQMWLSZ-AAQCHOMXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.8ALOGPS
logP6.73ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.59 m³·mol⁻¹ChemAxon
Polarizability40.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039530
DrugBank IDDB08887
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019145
KNApSAcK IDNot Available
Chemspider ID8007147
KEGG Compound IDC16184
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_eicosapentaenoic_acid
METLIN IDNot Available
PubChem Compound9831415
PDB IDNot Available
ChEBI ID84883
Good Scents IDNot Available
References
General References
  1. 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:22819432 ]
  2. Jacobson TA: A new pure omega-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:22894624 ]
  3. Bays HE, Braeckman RA, Ballantyne CM, Kastelein JJ, Otvos JD, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on lipoprotein particle concentration and size in patients with very high triglyceride levels (the MARINE study). J Clin Lipidol. 2012 Nov-Dec;6(6):565-72. doi: 10.1016/j.jacl.2012.07.001. Epub 2012 Jul 24. [PubMed:23312052 ]
  4. Bays HE, Ballantyne CM, Braeckman RA, Stirtan WG, Soni PN: Icosapent ethyl, a pure ethyl ester of eicosapentaenoic acid: effects on circulating markers of inflammation from the MARINE and ANCHOR studies. Am J Cardiovasc Drugs. 2013 Feb;13(1):37-46. doi: 10.1007/s40256-012-0002-3. [PubMed:23325450 ]
  5. Ballantyne CM, Braeckman RA, Soni PN: Icosapent ethyl for the treatment of hypertriglyceridemia. Expert Opin Pharmacother. 2013 Jul;14(10):1409-16. doi: 10.1517/14656566.2013.798645. Epub 2013 May 24. [PubMed:23701295 ]
  6. Brinton EA, Ballantyne CM, Bays HE, Kastelein JJ, Braeckman RA, Soni PN: Effects of icosapent ethyl on lipid and inflammatory parameters in patients with diabetes mellitus-2, residual elevated triglycerides (200-500 mg/dL), and on statin therapy at LDL-C goal: the ANCHOR study. Cardiovasc Diabetol. 2013 Jul 9;12:100. doi: 10.1186/1475-2840-12-100. [PubMed:23835245 ]
  7. Braeckman RA, Manku MS, Bays HE, Stirtan WG, Soni PN: Icosapent ethyl, a pure EPA omega-3 fatty acid: effects on plasma and red blood cell fatty acids in patients with very high triglyceride levels (results from the MARINE study). Prostaglandins Leukot Essent Fatty Acids. 2013 Sep;89(4):195-201. doi: 10.1016/j.plefa.2013.07.005. Epub 2013 Aug 1. [PubMed:23992935 ]
  8. Weintraub H: Update on marine omega-3 fatty acids: management of dyslipidemia and current omega-3 treatment options. Atherosclerosis. 2013 Oct;230(2):381-9. doi: 10.1016/j.atherosclerosis.2013.07.041. Epub 2013 Jul 31. [PubMed:24075771 ]
  9. Nelson SD, Munger MA: Icosapent ethyl for treatment of elevated triglyceride levels. Ann Pharmacother. 2013 Nov;47(11):1517-23. doi: 10.1177/1060028013504079. Epub 2013 Nov 5. [PubMed:24259598 ]
  10. Hilleman DE, Malesker MA: Potential benefits of icosapent ethyl on the lipid profile: case studies. Clin Med Insights Cardiol. 2014 Feb 2;8:13-5. doi: 10.4137/CMC.S13571. eCollection 2014. [PubMed:24516343 ]