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 2752	1.2 µM [IC50]
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2752	1.6 µM [IC50]
Peroxisome proliferator-activated receptor delta 30 Target ID: CHEMBL3979 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2752	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 8504	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 8504	1071.0 nM [IC50]
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036355	Binding Agent 1076	180.0 nM [Kd]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669	Substrate 661

PubMed

Title	Date	PubMed
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.	2001 Dec 15	11755111
Mechanisms of regulation of agonist efficacy at the 5-HT(1A) receptor by phospholipid-derived signaling components.	2001 Jun	11356925
Vasopressin-stimulated Ca2+ spiking in vascular smooth muscle cells involves phospholipase D.	2001 Jun	11356622
Stimulative effect of cadmium on prostaglandin E2 production in primary mouse osteoblastic cells.	2001 Mar	11351503
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
Acute effects of the cys-leukotriene-1 receptor antagonist, montelukast, on experimental colitis in rats.	2001 Oct 19	11698051
TRA-418, a novel compound having both thromboxane A(2) receptor antagonistic and prostaglandin I(2) receptor agonistic activities: its antiplatelet effects in human and animal platelets.	2003 Aug	12911598
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.	2003 Aug 30	14500111
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.	2003 Feb 1	12604186
Genetic variation in cyclooxygenase 1: effects on response to aspirin.	2003 Jan	12545150
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
Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology.	2003 Oct	14626496
Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease.	2003 Oct	14626494
The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers.	2004	15927922
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
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
Effects of dietary supplementation with arachidonic acid on platelet and renal function in patients with cirrhosis.	2004 Jan	12877651
Platelet inhibition by aspirin is diminished in patients during carotid surgery: a form of transient aspirin resistance?	2004 Jul	15213849
The effect of isoniazid on CYP2E1- and CYP4A-mediated hydroxylation of arachidonic acid in the rat liver and kidney.	2004 Jul	15205388
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
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
COX-2 inhibitors and metabolism of essential fatty acids.	2005 Jul	15990700
Fatty acids and expression of adipokines.	2005 May 30	15949695
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
Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin.	2005 Oct	16185265
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
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
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
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
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
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 `Mon Mar 31 17:53:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:15 GMT 2025`
Record UNII	27YG812J1I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ARA

Preferred Name

English

ARACHIDONIC ACID

Official 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

Classification Tree Code System Code

DSLD

1467 (Number of products:46)