ARACHIDONIC ACID

Possibly Marketed Outside US

First approved in 2013

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H32O2
Molecular Weight	304.4669
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YZXBAPSDXZZRGB-DOFZRALJSA-N

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

HIDE SMILES / InChI

Molecular Formula	C20H32O2
Molecular Weight	304.4669
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	4
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2662	1.2 µM [IC50]
Peroxisome proliferator-activated receptor gamma 109 Target ID: CHEMBL235 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2662	1.6 µM [IC50]
Peroxisome proliferator-activated receptor delta 27 Target ID: CHEMBL3979 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2662	3.1 µM [IC50]
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8228	602.56 nM [IC50]
Solute carrier organic anion transporter family member 1B3 16 Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8228	1071.0 nM [IC50]
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036355	Binding Agent 1059	180.0 nM [Kd]
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669	Substrate 656

PubMed

Title	Date	PubMed
Nicotine depresses the functions of multiple cardiac potassium channels.	1999	10503950
Characterization of arachidonic acid-induced apoptosis.	1999	10403056
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.	2001 Jan-Feb	11347965
Direct activation of an inwardly rectifying potassium channel by arachidonic acid.	2001 May	11306688
Arachidonic acid-induced inhibition of Ca2+ channel currents in retinal glial (Müller) cells.	2001 Nov	11789867
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.	2002 Apr 19	11830588
LTRPC2 Ca2+-permeable channel activated by changes in redox status confers susceptibility to cell death.	2002 Jan	11804595
Induction of MnSOD gene by arachidonic acid is mediated by reactive oxygen species and p38 MAPK signaling pathway in human HepG2 hepatoma cells.	2002 Jun 1	12031898
Leukotriene B4 production in human mononuclear phagocytes is modulated by interleukin-4-induced 15-lipoxygenase.	2002 Mar	11861792
Metallothionein 2A induction by zinc protects HEPG2 cells against CYP2E1-dependent toxicity.	2003 Feb 15	12566070
Genetic variation in cyclooxygenase 1: effects on response to aspirin.	2003 Jan	12545150
Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells.	2003 Jun 6	12757841
Effect of the lipid peroxidation product acrolein on tau phosphorylation in neural cells.	2003 Mar 15	12605413
Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants.	2003 Nov	14642406
The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers.	2004	15927922
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).	2004 Aug	15177302
Heme oxygenase-1 protects HepG2 cells against cytochrome P450 2E1-dependent toxicity.	2004 Feb 1	15036350
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.	2004 Jul	15205388
Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.	2004 Mar 25	15046718
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation.	2005	15822183
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.	2005 Dec	16141368
Fenamates and diltiazem modulate lipid-sensitive mechano-gated 2P domain K(+) channels.	2005 Dec	16075240
A Thrombelastograph whole blood assay for clinical monitoring of NSAID-insensitive transcellular platelet activation by arachidonic acid.	2005 Jul	16025089
Vasoactive prostanoids are generated from arachidonic acid by COX-1 and COX-2 in the mouse.	2005 Oct	15863457
Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells.	2005 Sep	15878913
How dietary arachidonic- and docosahexaenoic- acid rich oils differentially affect the murine hepatic transcriptome.	2006 Apr 20	16623957
Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers.	2006 Aug	16794200
Induction of CYP1A and cyp2-mediated arachidonic acid epoxygenation and suppression of 20-hydroxyeicosatetraenoic acid by imidazole derivatives including the aromatase inhibitor vorozole.	2006 Aug	16714371
[Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques].	2006 Jan-Apr	16617398
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.	2006 Jul	16582421
Protective effects of a standard extract of Mangifera indica L. (VIMANG) against mouse ear edemas and its inhibition of eicosanoid production in J774 murine macrophages.	2006 Jun	16716910
Cytoglobin overexpression protects against damage-induced fibrosis.	2006 Jun	16581302
Residual arachidonic acid-induced platelet activation via an adenosine diphosphate-dependent but cyclooxygenase-1- and cyclooxygenase-2-independent pathway: a 700-patient study of aspirin resistance.	2006 Jun 27	16785341
High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome.	2006 Mar	16371119
Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin?	2006 May	16635110
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.	2006 May	16489205
Metabolites of arachidonic acid in activating platelets and their estimation by radionuclide techniques.	2006 May-Aug	16894418
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.	2006 Nov 25	16978661
Arachidonic acid-induced gene expression in colon cancer cells.	2006 Oct	16704987
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.	2007 Mar	16730733

Patents

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:48:58 UTC 2023` Edited by `admin` on `Wed Jul 05 22:48:58 UTC 2023`
Record UNII	27YG812J1I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARACHIDONIC ACID

Official Name

English

ARACHIDONIC ACID [INCI]

Common Name

English

(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAENOIC ACID

Systematic Name

English

ARACHIDONIC ACID [MART.]

Common Name

English

ARACHIDONATE

Common Name

English

ARACHIDONIC ACID [MI]

Common Name

English

Arachidonic acid [WHO-DD]

Common Name

English

ARA

Common Name

English

Classification Tree Code System Code

DSLD

1467 (Number of products:46)