ICOSAPENT SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H29O2.Na
Molecular Weight	324.4328
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	5
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O

InChI

InChIKey=RBZYGQJEMWGTOH-RSDXMDNYSA-M

InChI=1S/C20H30O2.Na/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);/q;+1/p-1/b4-3-,7-6-,10-9-,13-12-,16-15-;

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count	MOL RATIO 1 MOL RATIO (average)

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

Molecular Formula	C20H29O2
Molecular Weight	301.4431
Charge	-1
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 8,504
GO:0004465 lipoprotein lipase activity 4	Activator 1,447
fatty acid beta-oxidation 4	Activator 1,447
lipoprotein oxidation 4	Inhibitor 8,504	2.5 µM [IC50]
transformed cell apoptotic process 104	Activator 1,447	35.0 µM [IC50]
Peroxisome proliferator-activated receptor delta 30	Agonist 2,752
Prolyl endopeptidase 9	Inhibitor 8,504	247.5 µM [Ki]
Receptor-mediated non-selective cation current (Icat) 4	Inhibitor 8,504	7.0 µM [IC50]
Cyclooxygenase-2 201	Inhibitor 8,504
Peroxisome proliferator-activated receptor gamma 118	Agonist 2,752

Conditions

Condition	Modality	Highest Phase	Product
Hypertriglyceridemia 20	Primary	Approved 8,583	Vascepa
Major depressive disorder 179	Primary	Phase III 665	Unknown
Alzheimer’s disease 278	Primary	Phase III 665	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 1,087	inhibitor 2,438 inducer 440

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2,057 CYP2C8 1,057 CYP2B6 926 P-gp 1,741 BCRP 910 OCT2 779 OAT1 725 OATP1B1 1,079 OATP1B3 961 OAT3 747	P-gp 2,052 BCRP 697 OCT2 434 OAT1 395 OATP1B1 503 OATP1B3 435 OAT3 391 CYP 303	CYP1A2 832

Drug as perpetrator

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Target	Modality	Activity
BCRP 985	inhibitor 4,027	no
CYP1A2 2,333	inducer 1,966	no
OAT1 730	inhibitor 4,027	no
OATP1B1 1,095	inhibitor 4,027	no
OATP1B3 970	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
BCRP 697	substrate 4,014	no
CYP 303	substrate 4,014	no
OAT1 395	substrate 4,014	no
OAT3 391	substrate 4,014	no
OATP1B1 503	substrate 4,014	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
Aaron Chemicals	AR0038PL	http://www.aaronchem.com/10417-94-4
abcr GmbH	AB135514	http://www.abcr.com/shop/en/AB135514
AbMole Bioscience	M5608	http://www.abmole.com/products/eicosapentaenoic-acid.html
AHH Chemical co.,ltd	MT-11661	http://www.ahhchemical.com/product/MT-11661.html

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PubMed

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Title	Date	PubMed
Thin-layer chromatography and high-performance liquid chromatography for the assay of fatty acid compositions of individual phospholipids in platelets from non-insulin-dependent diabetes mellitus patients: effect of eicosapentaenoic acid ethyl ester administration.	1996 Mar 3	8704924
Dietary fish oil decreases superoxide generation by human neutrophils: relation to cyclooxygenase pathway and lysosomal enzyme release.	1996 Sep	8931114
Modulation in vitro of human natural cytotoxicity, lymphocyte proliferative response to mitogens and cytokine production by essential fatty acids.	1997 Oct	9415022
Eicosapentaenoic acid in treatment-resistant depression associated with symptom remission, structural brain changes and reduced neuronal phospholipid turnover.	2001 Oct	11695079
Deoxynivalenol-induced mitogen-activated protein kinase phosphorylation and IL-6 expression in mice suppressed by fish oil.	2003 Dec	14690764

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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	5PXN91KPRO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ICOSAPENT SODIUM

Common Name

English

5,8,11,14,17-EICOSAPENTAENOIC ACID, SODIUM SALT (1:1), (5Z,8Z,11Z,14Z,17Z)-

Preferred Name

English

5,8,11,14,17-EICOSAPENTAENOIC ACID, SODIUM SALT, (ALL-Z)-

Common Name

English

EICOSAPENTAENOIC ACID SODIUM SALT

Common Name

English

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Code System

Code

Type

Description

DRUG BANK

DBSALT002305

PRIMARY

PUBCHEM

23679014

PRIMARY

EPA CompTox

DTXSID10993898

PRIMARY

SMS_ID

300000017643

PRIMARY

CAS

73167-03-0

PRIMARY

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Related Record

Type

Details


					AAN7QOV9EA

ICOSAPENT

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					AAN7QOV9EA

ICOSAPENT

ACTIVE MOIETY

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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