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Identification
NameIcosapent
Accession NumberDB00159  (NUTR00024)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. [PubChem]

Structure
Thumb
Synonyms
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoate
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
(all-Z)-5,8,11,14,17-Eicosapentaenoic acid
5,8,11,14,17-EICOSAPENTAENOIC acid
5,8,11,14,17-Icosapentaenoic acid
all-cis-5,8,11,14,17-eicosapentaenoic acid
all-cis-5,8,11,14,17-icosapentaenoic acid
all-cis-icosa-5,8,11,14,17-pentaenoic acid
cis-5,8,11,14,17-Eicosapentaenoic acid
cis-5,8,11,14,17-EPA
cis-delta(5,8,11,14,17)-Eicosapentaenoic acid
cis, cis, cis, cis, cis-Eicosa-5,8,11,14,17-pentaenoic acid
Eicosapentaenoic acid
EPA
Icosapent
Icosapentaenoic acid
Icosapento
Icosapentum
Timnodonic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Animi-3PBM Pharmaceuticals, Inc
Animi-3 With Vitamin DPBM Pharmaceuticals, Inc
Citranatal AssureMission Pharmacal Company
Folcaps Care OneMidlothian Laboratories
Folcaps Omega-3Midlothian Laboratories
HerbalifelineHerbalife International Of Luxembourg S À R L
Natelle OneMEDA Pharmaceuticals
Prenate EssentialAvion Pharmaceuticals, Llc
Se-tan DHASeton Pharmaceuticals
Ultimatecare One NfTrigen Laboratories, Inc.
Virt-bal DHA PlusVirtus Pharmaceuticals
Virt-PN PlusVirtus Pharmaceuticals LLC
Vp-CH-pnvVirtus Pharmaceuticals
SaltsNot Available
Categories
UNIIAAN7QOV9EA
CAS number10417-94-4
WeightAverage: 302.451
Monoisotopic: 302.224580204
Chemical FormulaC20H30O2
InChI KeyInChIKey=JAZBEHYOTPTENJ-JLNKQSITSA-N
InChI
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-
IUPAC Name
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationEPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
PharmacodynamicsEicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.
Mechanism of actionThe anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Alpha Linolenic Acid and Linoleic Acid MetabolismMetabolicSMP00018
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9896
Blood Brain Barrier+0.9314
Caco-2 permeable+0.7735
P-glycoprotein substrateNon-substrate0.6766
P-glycoprotein inhibitor INon-inhibitor0.9499
P-glycoprotein inhibitor IINon-inhibitor0.9025
Renal organic cation transporterNon-inhibitor0.9311
CYP450 2C9 substrateNon-substrate0.7735
CYP450 2D6 substrateNon-substrate0.9081
CYP450 3A4 substrateNon-substrate0.6884
CYP450 1A2 substrateInhibitor0.6915
CYP450 2C9 inhibitorNon-inhibitor0.8798
CYP450 2D6 inhibitorNon-inhibitor0.9631
CYP450 2C19 inhibitorNon-inhibitor0.9638
CYP450 3A4 inhibitorNon-inhibitor0.9465
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9426
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6502
BiodegradationReady biodegradable0.7808
Rat acute toxicity1.4499 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8818
hERG inhibition (predictor II)Non-inhibitor0.9315
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
  • V Sab Medical Labs Inc.
Dosage forms
FormRouteStrength
Capsuleoral
Kit
Capsule, gelatin coatedoral
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
logP6.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000289 mg/mLALOGPS
logP6.53ALOGPS
logP6.23ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.07 m3·mol-1ChemAxon
Polarizability35.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004l-9700000000-09ea61ed836b88205028View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
MSMass Spectrum (Electron Ionization)splash10-05ox-9400000000-567226e93d65502352cdView in MoNA
References
Synthesis Reference

Akira Seto, Shoko Yamashita, “Method of preparing fatty acid composition containing high concentration of eicosapentaenoic acid.” U.S. Patent US4615839, issued March, 1983.

US4615839
General References
  1. Bays HE, Ballantyne CM, Kastelein JJ, Isaacsohn JL, Braeckman RA, Soni PN: Eicosapentaenoic acid ethyl ester (AMR101) therapy in patients with very high triglyceride levels (from the Multi-center, plAcebo-controlled, Randomized, double-blINd, 12-week study with an open-label Extension [MARINE] trial). Am J Cardiol. 2011 Sep 1;108(5):682-90. doi: 10.1016/j.amjcard.2011.04.015. Epub 2011 Jun 16. [PubMed:21683321 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 88:30.00*
PDB Entries
FDA labelDownload (173 KB)
MSDSDownload (23.2 KB)
Interactions
Drug Interactions
Drug
AbciximabIcosapent may increase the anticoagulant activities of Abciximab.
AcenocoumarolIcosapent may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Icosapent.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Icosapent.
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Icosapent.
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Icosapent.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Icosapent.
CitalopramCitalopram may increase the antiplatelet activities of Icosapent.
Citric AcidIcosapent may increase the anticoagulant activities of Citric Acid.
ClomipramineClomipramine may increase the antiplatelet activities of Icosapent.
CorticotropinThe risk or severity of adverse effects can be increased when Corticotropin is combined with Icosapent.
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Icosapent.
DalteparinIcosapent may increase the anticoagulant activities of Dalteparin.
DesogestrelIcosapent may increase the thrombogenic activities of Desogestrel.
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Icosapent.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Icosapent.
DicoumarolIcosapent may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Icosapent.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Icosapent.
DoxepinDoxepin may increase the antiplatelet activities of Icosapent.
Edetic AcidIcosapent may increase the anticoagulant activities of Edetic Acid.
EnoxaparinIcosapent may increase the anticoagulant activities of Enoxaparin.
EscitalopramEscitalopram may increase the antiplatelet activities of Icosapent.
EstradiolIcosapent may increase the thrombogenic activities of Estradiol.
Estrone sulfateIcosapent may increase the thrombogenic activities of Estropipate.
Ethinyl EstradiolIcosapent may increase the thrombogenic activities of Ethinyl Estradiol.
Ethyl biscoumacetateIcosapent may increase the anticoagulant activities of Ethyl biscoumacetate.
Ethynodiol diacetateIcosapent may increase the thrombogenic activities of Ethynodiol.
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Icosapent.
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Icosapent.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Icosapent.
FluoxetineFluoxetine may increase the antiplatelet activities of Icosapent.
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Icosapent.
FluvoxamineFluvoxamine may increase the antiplatelet activities of Icosapent.
Fondaparinux sodiumIcosapent may increase the anticoagulant activities of Fondaparinux sodium.
HeparinIcosapent may increase the anticoagulant activities of Heparin.
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Icosapent.
IbrutinibIcosapent may increase the antiplatelet activities of Ibrutinib.
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Icosapent.
ImipramineImipramine may increase the antiplatelet activities of Icosapent.
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Icosapent.
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Icosapent.
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Icosapent.
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Icosapent.
MestranolIcosapent may increase the thrombogenic activities of Mestranol.
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Icosapent.
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Icosapent.
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Icosapent.
NorethisteroneIcosapent may increase the thrombogenic activities of Norethindrone.
NorgestimateIcosapent may increase the thrombogenic activities of Norgestimate.
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Icosapent.
ParoxetineParoxetine may increase the antiplatelet activities of Icosapent.
PhenindioneIcosapent may increase the anticoagulant activities of Phenindione.
PhenprocoumonIcosapent may increase the anticoagulant activities of Phenprocoumon.
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Icosapent.
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Icosapent.
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Icosapent.
Repository corticotropinThe risk or severity of adverse effects can be increased when Repository corticotropin is combined with Icosapent.
SertralineSertraline may increase the antiplatelet activities of Icosapent.
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Icosapent.
SulodexideIcosapent may increase the anticoagulant activities of Sulodexide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Icosapent.
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Icosapent.
TreprostinilIcosapent may increase the anticoagulant activities of Treprostinil.
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Icosapent.
TrimipramineTrimipramine may increase the antiplatelet activities of Icosapent.
VilazodoneVilazodone may increase the antiplatelet activities of Icosapent.
VortioxetineVortioxetine may increase the antiplatelet activities of Icosapent.
WarfarinIcosapent may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: 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. Epub 2002 Dec 1. [PubMed:12562875 ]
  2. Ait-Said F, Elalamy I, Werts C, Gomard MT, Jacquemin C, Couetil JP, Hatmi M: Inhibition by eicosapentaenoic acid of IL-1beta-induced PGHS-2 expression in human microvascular endothelial cells: involvement of lipoxygenase-derived metabolites and p38 MAPK pathway. Biochim Biophys Acta. 2003 Feb 20;1631(1):77-84. [PubMed:12573452 ]
  3. Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. [PubMed:16141635 ]
  4. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. [PubMed:16190133 ]
  5. Chene G, Dubourdeau M, Balard P, Escoubet-Lozach L, Orfila C, Berry A, Bernad J, Aries MF, Charveron M, Pipy B: n-3 and n-6 polyunsaturated fatty acids induce the expression of COX-2 via PPARgamma activation in human keratinocyte HaCaT cells. Biochim Biophys Acta. 2007 May;1771(5):576-89. Epub 2007 Mar 16. [PubMed:17459764 ]
  6. Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. doi: 10.1074/jbc.M110.119867. Epub 2010 May 12. [PubMed:20463020 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Malkowski MG, Thuresson ED, Lakkides KM, Rieke CJ, Micielli R, Smith WL, Garavito RM: Structure of eicosapentaenoic and linoleic acids in the cyclooxygenase site of prostaglandin endoperoxide H synthase-1. J Biol Chem. 2001 Oct 5;276(40):37547-55. Epub 2001 Jul 27. [PubMed:11477109 ]
  2. Machida T, Hiramatsu M, Hamaue N, Minami M, Hirafuji M: Docosahexaenoic acid enhances cyclooxygenase-2 induction by facilitating p44/42, but not p38, mitogen-activated protein kinase activation in rat vascular smooth muscle cells. J Pharmacol Sci. 2005 Sep;99(1):113-6. Epub 2005 Sep 1. [PubMed:16141635 ]
  3. Das UN: COX-2 inhibitors and metabolism of essential fatty acids. Med Sci Monit. 2005 Jul;11(7):RA233-7. Epub 2005 Jun 29. [PubMed:15990700 ]
  4. Das UN: Can COX-2 inhibitor-induced increase in cardiovascular disease risk be modified by essential fatty acids? J Assoc Physicians India. 2005 Jul;53:623-7. [PubMed:16190133 ]
  5. Yang P, Chan D, Felix E, Cartwright C, Menter DG, Madden T, Klein RD, Fischer SM, Newman RA: Formation and antiproliferative effect of prostaglandin E(3) from eicosapentaenoic acid in human lung cancer cells. J Lipid Res. 2004 Jun;45(6):1030-9. Epub 2004 Mar 1. [PubMed:14993240 ]
  6. Vecchio AJ, Simmons DM, Malkowski MG: Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63. doi: 10.1074/jbc.M110.119867. Epub 2010 May 12. [PubMed:20463020 ]
  7. Lee JY, Plakidas A, Lee WH, Heikkinen A, Chanmugam P, Bray G, Hwang DH: 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. Epub 2002 Dec 1. [PubMed:12562875 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation...
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Chambrier C, Bastard JP, Rieusset J, Chevillotte E, Bonnefont-Rousselot D, Therond P, Hainque B, Riou JP, Laville M, Vidal H: Eicosapentaenoic acid induces mRNA expression of peroxisome proliferator-activated receptor gamma. Obes Res. 2002 Jun;10(6):518-25. [PubMed:12055328 ]
  2. Selvaraj RK, Klasing KC: Lutein and eicosapentaenoic acid interact to modify iNOS mRNA levels through the PPARgamma/RXR pathway in chickens and HD11 cell lines. J Nutr. 2006 Jun;136(6):1610-6. [PubMed:16702329 ]
  3. Iwata Y, Miyamoto S, Takamura M, Yanagisawa H, Kasuya A: Interaction between peroxisome proliferator-activated receptor gamma and its agonists: docking study of oximes having 5-benzyl-2,4-thiazolidinedione. J Mol Graph Model. 2001;19(6):536-42, 598-600. [PubMed:11552681 ]
  4. Horia E, Watkins BA: Complementary actions of docosahexaenoic acid and genistein on COX-2, PGE2 and invasiveness in MDA-MB-231 breast cancer cells. Carcinogenesis. 2007 Apr;28(4):809-15. Epub 2006 Oct 19. [PubMed:17052999 ]
  5. Ramakers JD, Mensink RP, Schaart G, Plat J: Arachidonic acid but not eicosapentaenoic acid (EPA) and oleic acid activates NF-kappaB and elevates ICAM-1 expression in Caco-2 cells. Lipids. 2007 Aug;42(8):687-98. Epub 2007 Jul 3. [PubMed:17610002 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as ...
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular Weight:
49902.99 Da
References
  1. Iwata Y, Miyamoto S, Takamura M, Yanagisawa H, Kasuya A: Interaction between peroxisome proliferator-activated receptor gamma and its agonists: docking study of oximes having 5-benzyl-2,4-thiazolidinedione. J Mol Graph Model. 2001;19(6):536-42, 598-600. [PubMed:11552681 ]
  2. Xu HE, Lambert MH, Montana VG, Parks DJ, Blanchard SG, Brown PJ, Sternbach DD, Lehmann JM, Wisely GB, Willson TM, Kliewer SA, Milburn MV: Molecular recognition of fatty acids by peroxisome proliferator-activated receptors. Mol Cell. 1999 Mar;3(3):397-403. [PubMed:10198642 ]
  3. Kondo H, Misaki R, Gelman L, Watabe S: Ligand-dependent transcriptional activities of four torafugu pufferfish Takifugu rubripes peroxisome proliferator-activated receptors. Gen Comp Endocrinol. 2007 Oct-Dec;154(1-3):120-7. Epub 2007 Jun 12. [PubMed:17632107 ]
  4. Inoue I, Shino K, Noji S, Awata T, Katayama S: Expression of peroxisome proliferator-activated receptor alpha (PPAR alpha) in primary cultures of human vascular endothelial cells. Biochem Biophys Res Commun. 1998 May 19;246(2):370-4. [PubMed:9610365 ]
  5. Caldari-Torres C, Rodriguez-Sallaberry C, Greene ES, Badinga L: Differential effects of n-3 and n-6 fatty acids on prostaglandin F2alpha production by bovine endometrial cells. J Dairy Sci. 2006 Mar;89(3):971-7. [PubMed:16507691 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Oxidoreductase activity
Specific Function:
Isoform 2 does not exhibit any catalytic activity toward 20:3n-6, but it may enhance FADS2 activity (By similarity). Isoform 1 is a component of a lipid metabolic pathway that catalyzes biosynthesis of highly unsaturated fatty acids (HUFA) from precursor essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3). Catalyzes the desaturation...
Gene Name:
FADS1
Uniprot ID:
O60427
Molecular Weight:
51963.945 Da
References
  1. Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH: Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans. J Nutr. 2000 Aug;130(8):1925-31. [PubMed:10917903 ]
  2. Navarro E, Esteve M, Olive A, Klaassen J, Cabre E, Tena X, Fernandez-Banares F, Pastor C, Gassull MA: Abnormal fatty acid pattern in rheumatoid arthritis. A rationale for treatment with marine and botanical lipids. J Rheumatol. 2000 Feb;27(2):298-303. [PubMed:10685788 ]
  3. Engler MM, Bellenger-Germain SH, Engler MB, Narce MM, Poisson JP: Dietary docosahexaenoic acid affects stearic acid desaturation in spontaneously hypertensive rats. Lipids. 2000 Sep;35(9):1011-5. [PubMed:11026622 ]
  4. Chavali SR, Zhong WW, Forse RA: Dietary alpha-linolenic acid increases TNF-alpha, and decreases IL-6, IL-10 in response to LPS: effects of sesamin on the delta-5 desaturation of omega6 and omega3 fatty acids in mice. Prostaglandins Leukot Essent Fatty Acids. 1998 Mar;58(3):185-91. [PubMed:9610840 ]
  5. Watts JL, Browse J: Isolation and characterization of a Delta 5-fatty acid desaturase from Caenorhabditis elegans. Arch Biochem Biophys. 1999 Feb 1;362(1):175-82. [PubMed:9917342 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Very long-chain fatty acid-coa ligase activity
Specific Function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses arachidonate and eicosapentaenoate as substrates.
Gene Name:
ACSL4
Uniprot ID:
O60488
Molecular Weight:
79187.38 Da
References
  1. Heimli H, Hollung K, Drevon CA: Eicosapentaenoic acid-induced apoptosis depends on acyl CoA-synthetase. Lipids. 2003 Mar;38(3):263-8. [PubMed:12784866 ]
  2. Covault J, Pettinati H, Moak D, Mueller T, Kranzler HR: Association of a long-chain fatty acid-CoA ligase 4 gene polymorphism with depression and with enhanced niacin-induced dermal erythema. Am J Med Genet B Neuropsychiatr Genet. 2004 May 15;127B(1):42-7. [PubMed:15108178 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Protein kinase binding
Specific Function:
Acyl-CoA synthetases (ACSL) activates long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. ACSL3 mediates hepatic lipogenesis (By similarity). Preferentially uses myristate, laurate, arachidonate and eicosapentaenoate as substrates (By similarity). Has mainly an anabolic role in energy metabolism. Required for the incorporation of fatty acids into ph...
Gene Name:
ACSL3
Uniprot ID:
O95573
Molecular Weight:
80419.415 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Lipid binding
Specific Function:
G-protein coupled receptor for medium and long chain saturated and unsaturated fatty acids that plays an important role in glucose homeostasis. Fatty acid binding increases glucose-stimulated insulin secretion, and may also enhance the secretion of glucagon-like peptide 1 (GLP-1). May also play a role in bone homeostasis; receptor signaling activates pathways that inhibit osteoclast differentia...
Gene Name:
FFAR1
Uniprot ID:
O14842
Molecular Weight:
31456.645 Da
References
  1. Itoh Y, Hinuma S: GPR40, a free fatty acid receptor on pancreatic beta cells, regulates insulin secretion. Hepatol Res. 2005 Oct;33(2):171-3. Epub 2005 Oct 6. [PubMed:16214394 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ion channel binding
Specific Function:
Mediates the exchange of one Ca(2+) ion against three to four Na(+) ions across the cell membrane, and thereby contributes to the regulation of cytoplasmic Ca(2+) levels and Ca(2+)-dependent cellular processes (PubMed:1374913, PubMed:11241183, PubMed:1476165). Contributes to Ca(2+) transport during excitation-contraction coupling in muscle. In a first phase, voltage-gated channels mediate the r...
Gene Name:
SLC8A1
Uniprot ID:
P32418
Molecular Weight:
108546.06 Da
References
  1. Xiao YF, Ke Q, Chen Y, Morgan JP, Leaf A: Inhibitory effect of n-3 fish oil fatty acids on cardiac Na+/Ca2+ exchange currents in HEK293t cells. Biochem Biophys Res Commun. 2004 Aug 13;321(1):116-23. [PubMed:15358223 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Transmembrane signaling receptor activity
Specific Function:
Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. Involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which in...
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular Weight:
94955.33 Da
References
  1. Matta JA, Miyares RL, Ahern GP: TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. J Physiol. 2007 Jan 15;578(Pt 2):397-411. Epub 2006 Oct 12. [PubMed:17038422 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
yes
General Function:
Transporter activity
Specific Function:
B-FABP could be involved in the transport of a so far unknown hydrophobic ligand with potential morphogenic activity during CNS development. It is required for the establishment of the radial glial fiber system in developing brain, a system that is necessary for the migration of immature neurons to establish cortical layers (By similarity).
Gene Name:
FABP7
Uniprot ID:
O15540
Molecular Weight:
14888.855 Da
References
  1. Balendiran GK, Schnutgen F, Scapin G, Borchers T, Xhong N, Lim K, Godbout R, Spener F, Sacchettini JC: Crystal structure and thermodynamic analysis of human brain fatty acid-binding protein. J Biol Chem. 2000 Sep 1;275(35):27045-54. [PubMed:10854433 ]
  2. Liu YE, Pu W, Wang J, Kang JX, Shi YE: Activation of Stat5 and induction of a pregnancy-like mammary gland differentiation by eicosapentaenoic and docosapentaenoic omega-3 fatty acids. FEBS J. 2007 Jul;274(13):3351-62. Epub 2007 Jun 5. [PubMed:17547694 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08