Icosapent Ethyl
Grundinformationen
- CAS
73310-10-8- Standard-SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC- InChIKey
SSQPWTVBQMWLSZ-AAQCHOMXSA-N- Summenformel
- C22H34O2
- Durchschnittliche Molmasse
- 330,5 g/mol
- Monoisotopische Masse
- 330,25588032
Überblick
Ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate is a long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of (5Z,8Z,11Z,14Z,17Z)-icosapentaenoic acid with the hydroxy group of ethanol. It has a role as an antidepressant, an antipsychotic agent, an anticholesteremic drug, a prodrug and a marine metabolite. It is a long-chain fatty acid ethyl ester and a polyunsaturated fatty ester. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid.
Namen und Bezeichner
- Bevorzugter Name
- Icosapent Ethyl
- IUPAC
- ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
- Englischer Name
- Ethyl all cis-5,8,11,14,17-Eicosapentaenoate
- Summenformel
- C22H34O2
- Molmasse
- 330.5
Namen und Synonyme
Eicosapentaenoic acid ethyl ester86227-47-6ethyl icosapentateICOSAPENT ETHYLEpadelethyl eicosapentaenoateVascepaEPA ethyl esterTimnodonic acid ethyl esterethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoateethyl icosapentaenoateEthyl icosapent
Weitere Namen anzeigen
Ethyl icosapentanoateEPA-E(5Z,8Z,11Z,14Z,17Z)-ethyl icosa-5,8,11,14,17-pentaenoatecis-5Icosapent ethyl EPAMaxomegaTM EPA 96EEEthyl Icosapentate RSicosapent ethyl esterOMEGA 3 ACID ETHYL ESTER
AMR101Ethyl eicosapentaenoic acidcis-Eicosapentaenoic acid ethyl esterAMR 101E-EPAethyl-EPA(all-Z)-5,8,11,14,17-Eicosapentaenoic acid ethyl esterethyl-eicosapentaenoic acid
Datenbank-Bezeichner
- CAS
73310-10-8、86227-47-6
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,3
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 15
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 425
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Siedepunkt
- 417 · 417.0±34.0 °C(Predicted)
- Dichte
- 0 · 0,91 g/cm3
- Brechungsindex
- 1.485 to · 1.4850 to 1.4890
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- Wasserlöslichkeit
- Insoluble in water
- Löslichkeit
- 100 · DMF:100.0(Max Conc. mg/mL);302.56(Max Conc. mM)DMSO:66.67(Max Conc. mg/mL);201.7(Max Conc. mM)Ethanol:75.0(Max Conc. mg/mL);226.92(Max Conc. mM)PBS (pH 7.2):0.15(Max Conc. mg/mL);0.45(Max Conc. mM)
- Aggregatzustand
- Liquid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationChemical: Eicosapentaenoic acid, ethyl ester
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and CategoriesAquatic Chronic 1 (50%)
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 29161900
- safety_code
- 24/25
- Speicherklasse
- 10 - Combustible liquids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
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. 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.
Biological Half-LifeThe half life of EPA is 89 hours.
Metabolism/MetabolitesOnce converted into active EPA, it is hepatically metabolized into acetyl Coenzyme A via beta-oxidation.
MeSH Pharmacological Classification
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Substances that alter the metabolism of LIPIDS.
Absorption, Distribution and Excretion
Icosapent ethyl is de-esterfied, converted into active EPA, and then absorbed in the small intestine. It reaches peak plasma concentration in 5 hours post-oral administration. Very little (<1%) is left circulating in the plasma as EPA incorporates into phospholipids, TG's, and cholesteryl esters.
Icosapent ethyl is not renally excreted
Steady state volume of distribution of active EPA is 88 L
Total plasma clearance, EPA = 684 mL/hr
Cellular LocationsExtracellular
Anwendungen
BeschreibungEthyl icosapentate is an ester of a polyunsaturated acid derived from fish oil. It is reported to decrease platelet aggregation, reduce blood viscosity and increase erythrocyte deformability.
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