Drug Details

General Information of the Drug (ID: DR8164)
Name
Eicosapentaenoic acid
Synonyms
Icosapent; Timnodonic acid; 10417-94-4; Icosapentaenoic acid; cis-5,8,11,14,17-Eicosapentaenoic acid; EPA; 5,8,11,14,17-EICOSAPENTAENOIC ACID; Icosapento; Icosapentum; (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid; UNII-AAN7QOV9EA; Icosapent [INN]; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid; 5,8,11,14,17-Icosapentaenoic acid; CCRIS 3279; AAN7QOV9EA; (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid; CHEMBL460026; (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate; CHEBI:28364; all-cis-icosa-5,8,11,14,17-pentaenoic acid; Icosapent (INN); cis-Delta(5,8,11,14,17)-eicosapentaenoic acid; 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)-; Icosapentaenoate; (all-Z)-delta5,8,11,14,17-Eicosapentaenoic acid; C20:5n-3,6,9,12,15; MFCD00065716; eicosapentaenoate; cis-5,8,11,14,17-EPA; NCGC00161344-03; EICOSAPENTAENOIC ACID (20:5 n-3); all-cis-5,8,11,14,17-icosapentaenoic acid; all-cis-5,8,11,14,17-eicosapentaenoic acid; Miraxion; Eicosapentanoic acid; Eye Q; Eye-Q; 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)-; EPA [drug]; Icosapentum [INN-Latin]; C20:5 omega-3; Icosapento [INN-Spanish]; (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate; Timnodonate; 3gwx; FA 20:5; all-cis-icosapentaenoate; all-cis-icosapentaenoic acid; DSSTox_CID_21023; DSSTox_RID_79612; DSSTox_GSID_41023; SCHEMBL20469; BSPBio_001328; EPA 45G; Eicosa-5Z,8Z,11Z,14Z,17Z-pentaenoic Acid (20:5, n-3); BML3-B01; GTPL3362; DTXSID9041023; HMS1361C10; HMS1791C10; HMS1989C10; HMS3402C10; HMS3649D19; HY-B0660; ZINC4474603; 5,8,11,14,17-Icosapentaenoate; Tox21_111991; 1755AH; 5,8,11,14,17-Eicosapentaenoate; BDBM50242349; LMFA01030759; s6476; AKOS027470327; CCG-207957; CCG-208136; DB00159; cis-5,8,11,14,17-eicosapentaenoate; IDI1_033798; NCGC00161344-01; NCGC00161344-02; NCGC00161344-04; NCGC00161344-07; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoate; AC-31072; AS-53730; CAS-10417-94-4; E0441; 5,8,11,14,17-Eicosapentaenoic acid (6CI); all cis-5,8,11,14,17-Eicosapentaenoic Acid; all cis-5,8,11,14,17-Icosapentaenoic Acid; C06428; D08061; (all-cis)-5,8,11,14,17-Eicosapentaenoic acid; L001256; Q409990; SR-01000946647; J-001125; SR-01000946647-1; z,z,z,z,z-eicosa-5,8,11,14,17-pentaenoic acid; (Z,Z,Z,Z,Z)-5,8,11,14,17-eicosapentaenoic acid; BRD-K47192521-001-02-1; cis-5,8,11,14,17-Eicosapentaenoic acid, >=99%; 7F8BF016-B146-4F72-A52E-B9298BA3A9AB; C20H30O2 (cis-5,8,11,14,17-eicosapentaenoic acid); Eicosapentaenoic acid, 5,8,11,14,17-(Z,Z,Z,Z,Z)-; 5,8,11,14,17-Eicosapentaenoic acid, (all-Z)- (8CI); cis-5,8,11,14,17-Eicosapentaenoic acid, >=85%, liquid; UNII-317SQ4W8IJ component JAZBEHYOTPTENJ-JLNKQSITSA-N; UNII-71M78END5S component JAZBEHYOTPTENJ-JLNKQSITSA-N; UNII-9B22238JYI component JAZBEHYOTPTENJ-JLNKQSITSA-N; UNII-F85N2YHE4E component JAZBEHYOTPTENJ-JLNKQSITSA-N; cis-5,8,11,14,17-Eicosapentaenoic acid, analytical standard; (5Z,8Z,11 Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoic acid; cis, cis, cis, cis, cis-eicosa-5,8,11,14,17-pentaenoic acid; 5,8,11,14,17-Eicosapentaenoic acid, (5Z,8Z,11Z,14Z,17Z)- (9CI); cis-5,8,11,14,17-Eicosapentaenoic acid, 500 mug/mL in ethanol, certified reference material
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Molecular Type
Small molecule
Disease Inherited coagulation factor deficiency [ICD-11: 3B14] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C20H30O2
PubChem CID
446284
Canonical SMILES
CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
InChI
1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey
JAZBEHYOTPTENJ-JLNKQSITSA-N
CAS Number
CAS 10417-94-4
ChEBI ID
CHEBI:28364
TTD Drug ID
D0G2MW
DrugBank ID
DB00159
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Lycopene      Daucus carota     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression FAS  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation mTOR  Molecule Info 
Pathway MAP
                    In-vitro Model HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Low concentration of lycopene and EPA could synergistically inhibit the proliferation of colon cancer cells. The inhibitory mechanism was associated with suppression of phosphatidylinositol 3-kinase/Akt signaling pathway.
Target and Pathway
Target(s) Prostaglandin-endoperoxide synthas (COX)  Molecule Info  [3]
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Concomitant supplementation of lycopene and eicosapentaenoic acid inhibits the proliferation of human colon cancer cells. J Nutr Biochem. 2009 Jun;20(6):426-34.
Reference 3 Differential modulation of Toll-like receptors by fatty acids: preferential inhibition by n-3 polyunsaturated fatty acids. J Lipid Res. 2003 Mar;44(3):479-86.
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