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 2678	1.2 µM [IC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2678	1.6 µM [IC50]
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://link.springer.com/article/10.1007%2Fs00044-012-0285-6	Agonist 2678	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 8297	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 8297	1071.0 nM [IC50]
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12036355	Binding Agent 1064	180.0 nM [Kd]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669	Substrate 661

PubMed

Title	Date	PubMed
Specificity of endogenous fatty acid release during tumor necrosis factor-induced apoptosis in WEHI 164 fibrosarcoma cells.	1999 Dec	10588948
Identification of the major intestinal fatty acid transport protein.	1999 Sep	10518211
Antiallergic effects of H1-receptor antagonists.	2000	11291777
Cloning and expression of human TRAAK, a polyunsaturated fatty acids-activated and mechano-sensitive K(+) channel.	2000 Apr 14	10767409
Prostaglandin E2 and the protein kinase A pathway mediate arachidonic acid induction of c-fos in human prostate cancer cells.	2000 Jun	10864209
5-lipoxygenase is phosphorylated by p38 kinase-dependent MAPKAP kinases.	2000 May 9	10779545
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.	2000 Sep 15	10880510
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.	2001 Dec 15	11755111
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
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.	2001 Jan-Feb	11347965
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
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
Antioxidant and pro-oxidant effects of a manganese porphyrin complex against CYP2E1-dependent toxicity.	2002 Jul 1	12086689
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
Leukotriene B4 production in human mononuclear phagocytes is modulated by interleukin-4-induced 15-lipoxygenase.	2002 Mar	11861792
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
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.	2003 Aug 30	14500111
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.	2003 Feb	12576510
Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes.	2003 Feb	12538810
Aldehyde dehydrogenase 3 expression is decreased by clofibrate via PPAR gamma induction in JM2 rat hepatoma cell line.	2003 Feb 1	12604186
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
PGE(2) is generated by specific COX-2 activity and increases VEGF production in COX-2-expressing human pancreatic cancer cells.	2003 Jul 11	12821125
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
Prostaglandins and other cyclooxygenase-dependent arachidonic acid metabolites and the kidney in liver disease.	2003 Oct	14626494
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
In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG).	2004 Aug	15177302
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
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.	2005 Apr 8	15684433
Increase in heme oxygenase-1 levels ameliorates renovascular hypertension.	2005 Dec	16316349
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
Angiotensin II-induced Akt activation through the epidermal growth factor receptor in vascular smooth muscle cells is mediated by phospholipid metabolites derived by activation of phospholipase D.	2005 Mar	15525798
Fatty acids and expression of adipokines.	2005 May 30	15949695
Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin.	2005 Oct	16185265
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
[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
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

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:17:51 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:51 GMT 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)