ICOSAPENT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	5
Charge	0

SHOW SMILES / InChI

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI

InChIKey=JAZBEHYOTPTENJ-JLNKQSITSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	5
Optical Activity	NONE

Description

Icosapent is an 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. EPA 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GO:0004144 diacylglycerol O-acyltransferase activity 4	Inhibitor 8,297
GO:0004465 lipoprotein lipase activity 4	Activator 1,430
fatty acid beta-oxidation 4	Activator 1,430
lipoprotein oxidation 4	Inhibitor 8,297	2.5 µM [IC50]
transformed cell apoptotic process 108	Activator 1,430	35.0 µM [IC50]
Peroxisome proliferator-activated receptor delta 29	Agonist 2,678
Prolyl endopeptidase 9	Inhibitor 8,297	247.5 µM [Ki]
Receptor-mediated non-selective cation current (Icat) 4	Inhibitor 8,297	7.0 µM [IC50]
Cyclooxygenase-2 196	Inhibitor 8,297
Peroxisome proliferator-activated receptor gamma 111	Agonist 2,678

Conditions

Condition	Modality	Highest Phase	Product
Hypertriglyceridemia 17	Primary	Approved 8,429	Vascepa
Major depressive disorder 173	Primary	Phase III 656	Unknown
Alzheimer’s disease 272	Primary	Phase III 656	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
347 μg/mL	4 g 2 times / day steady-state, oral		ICOSAPENT plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
6.519 μg × h/mL	4 g 2 times / day steady-state, oral		ICOSAPENT plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
89 h	4 g 2 times / day steady-state, oral		ICOSAPENT plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%	4 g 2 times / day steady-state, oral		ICOSAPENT plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781	inhibitor 1,767 inducer 389

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 CYP2C8 911 CYP2B6 810 P-gp 1,461 BCRP 699 OCT2 647 OAT1 599 OATP1B1 788 OATP1B3 706 OAT3 642	P-gp 1,537 BCRP 561 OCT2 355 OAT1 326 OATP1B1 406 OATP1B3 350 OAT3 339 CYP 270	CYP1A2 701

Drug as perpetrator

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Target	Modality	Activity
BCRP 773	inhibitor 3,277	no
CYP1A2 1,692	inducer 1,573	no
OAT1 603	inhibitor 3,277	no
OATP1B1 803	inhibitor 3,277	no
OATP1B3 715	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
BCRP 561	substrate 3,367	no
CYP 270	substrate 3,367	no
OAT1 326	substrate 3,367	no
OAT3 339	substrate 3,367	no
OATP1B1 406	substrate 3,367	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
AA Blocks	AA0037XT	https://www.aablocks.com/goods/Goods/detail?id=AA0037XT
AHH Chemical co.,ltd	MT-11661	http://www.ahhchemical.com/product/MT-11661.html
AK Scientific, Inc. (AKSCI)	1755AH	http://www.aksci.com/item_detail.php?cat=1755AH
Aaron Chemicals	AR0038PL	http://www.aaronchem.com/10417-94-4
AbMole Bioscience	M5608	http://www.abmole.com/products/eicosapentaenoic-acid.html

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PubMed

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Title	Date	PubMed
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.	1997 Oct	9415022
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.	1999 Jul 14	10403814
[The role of arachidonic and eicosapentaenoic acid lipoxygenase products in the pathogenesis of generalized parodontosis].	2000	11424554
Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro.	2000 Apr 13	10753628
The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells.	2001 Jan	11172467

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Patents

Sample Use Guides

In Vivo Use Guide

The daily dose of VASCEPA ( (icosapent) is 4 grams per day taken as 2 capsules twice daily with food.

Route of Administration: Oral

In Vitro Use Guide

The approximate 50% inhibitory concentrations (IC50) of EPA on LA-N-1 cells at 48 hours treatment was found to be 35 uM, whereas the IC50 for ALA on LA-N-1 cells at 48 hours treatment was found to be >50 uM.

Substance Class	Chemical
Record UNII	AAN7QOV9EA
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ICOSAPENT

Official Name

English

EPA

Common Name

English

EICOSAPENTAENOIC ACID (EPA) (C20:5) (CONSTITUENT OF KRILL OIL) [DSC]

Common Name

English

TIMNODONIC ACID

Common Name

English

Eicosapentaenoic acid [WHO-DD]

Common Name

English

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Classification Tree

Code System

Code

RBC

LOINC

75097-6

Ser/Plas

LOINC

88998-0

Designated

FDA ORPHAN DRUG

283409

Bld

LOINC

90911-9

lipid lowering agent

LIVERTOX

342

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Code System

Code

Type

Description

CHEBI

36006

PRIMARY

RS_ITEM_NUM

1234293

PRIMARY

SMS_ID

100000079270

PRIMARY

MESH

D015118

PRIMARY

FDA UNII

AAN7QOV9EA

PRIMARY

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Related Record

Type

Details


					V0I3IBX33C

KRILL OIL

PARENT -> CONSTITUENT ALWAYS PRESENT

Qualification:

USP


					5PXN91KPRO

ICOSAPENT SODIUM

SALT/SOLVATE -> PARENT


					XGF7L72M0F

FISH OIL

LIPID -> FATTY ACID


					562599X5JL

ICOSABUTATE

DERIVATIVE -> PARENT

Amount:


					BBL281NWFG

COD LIVER OIL

PARENT -> CONSTITUENT ALWAYS PRESENT

Qualification:

USP

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Related Record

Type

Details


					6GC8A4PAYH

ICOSAPENT ETHYL

PARENT -> METABOLITE ACTIVE

Comments:

EPA is mainly metabolized by the liver via beta-oxidation similar to dietary fatty acids. Beta oxidation splits the long carbon chain of EPA into acetyl Coenzyme A, which is converted into energy via the Krebs cycle. Cytochrome P450-mediated metabolism is a minor pathway of elimination of EPA.

Interaction Type:

MAJOR

Qualification:

PLASMA

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Related Record

Type

Details


					AAN7QOV9EA

ICOSAPENT

ACTIVE MOIETY

Showing 1 to 1 of 1 entries

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator