ARACHIDONIC ACID

Possibly Marketed Outside US

First approved in 2013

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H32O2
Molecular Weight	304.4676
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\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	304.4676
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 60 Target ID: CHEMBL239 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2470	1.2 µM [IC50]
Peroxisome proliferator-activated receptor gamma 101 Target ID: CHEMBL235 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2470	1.6 µM [IC50]
Peroxisome proliferator-activated receptor delta 22 Target ID: CHEMBL3979 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2470	3.1 µM [IC50]
Solute carrier organic anion transporter family member 1B1 30 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 7728	602.56 nM [IC50]
Solute carrier organic anion transporter family member 1B3 15 Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 7728	1071.0 nM [IC50]
Fatty acid binding protein adipocyte 11 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036355	Binding Agent 996	180.0 nM [Kd]
Cyclooxygenase-2 189 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669	Substrate 609

PubMed

Title	Date	PubMed
Butylated hydroxyanisole specifically inhibits tumor necrosis factor-induced cytotoxicity and growth enhancement.	1992 Jul	1515551
Antiallergic effects of H1-receptor antagonists.	2000	11291777
Targeted disruption of the leukotriene B(4) receptor in mice reveals its role in inflammation and platelet-activating factor-induced anaphylaxis.	2000 Aug 7	10934231
Effect of endogenous and exogenous prostaglandin E(2) on interleukin-1 beta-induced cyclooxygenase-2 expression in human airway smooth-muscle cells.	2000 Dec	11112151
Prostaglandin levels in stimulated macrophages are controlled by phospholipase A2-activating protein and by activation of phospholipase C and D.	2001 Feb 23	11094054
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
Evidence for the presence of phospholipid hydroperoxide glutathione peroxidase in human platelets: implications for its involvement in the regulatory network of the 12-lipoxygenase pathway of arachidonic acid metabolism.	2001 Jan 1	11115402
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.	2001 Jan-Feb	11347965
Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components.	2001 Jun	11356925
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
p38 MAP kinase mediates stress-induced leukotriene synthesis in a human B-lymphocyte cell line.	2001 Nov	11698504
A comparative study of the antipyretic effects of indomethacin and dipyrone in rats.	2002 Jan	11852909
Cytosolic phospholipase A2 (cPLA2) regulation of human monocyte NADPH oxidase activity. cPLA2 affects translocation but not phosphorylation of p67(phox) and p47(phox).	2002 Jul 12	12101222
Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole.	2002 Nov	12386130
On the interaction of specific prostaglandin H synthase-2 inhibitors with prostaglandin H synthase-1.	2002 Oct 25	12398900
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.	2003 Feb 1	12604186
Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation.	2003 Sep	12971030
Effects of d-003, a new substance purified from sugar cane wax, on platelet aggregation and plasma levels of arachidonic acid metabolites in healthy volunteers.	2004	15689052
2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells.	2004 Apr	15115777
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.	2004 Aug	15307955
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).	2004 Aug	15177302
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.	2004 Jul	15205388
Enhanced antiplatelet effect of clopidogrel in patients whose platelets are least inhibited by aspirin: a randomized crossover trial.	2005 Dec	16359503
Increase in heme oxygenase-1 levels ameliorates renovascular hypertension.	2005 Dec	16316349
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
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.	2005 Nov	16258897
Late-gestation rat myometrial cells express multiple isoforms of phospholipase A2 that mediate PCB 50-induced release of arachidonic acid with coincident prostaglandin production.	2005 Nov	16120751
Vasoactive prostanoids are generated from arachidonic acid by COX-1 and COX-2 in the mouse.	2005 Oct	15863457
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.	2005 Oct 28	16118212
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
Nongenomic action of progesterone inhibits oxytocin-induced phosphoinositide hydrolysis and prostaglandin F2alpha secretion in the ovine endometrium.	2006 Feb	16254031
Nitric oxide alters arachidonic acid turnover in brain cortex synaptoneurosomes.	2006 Jan	16216387
[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
Mechanism of induction of muscle protein degradation by angiotensin II.	2006 Jul	16257180
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 `Fri Jun 25 23:03:38 UTC 2021` Edited by `admin` on `Fri Jun 25 23:03:38 UTC 2021`
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)