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
Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression.	1999 Jun	10357836
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.	2000 Jun 20	10852718
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.	2001 Dec 15	11755111
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
Vasopressin-stimulated Ca2+ spiking in vascular smooth muscle cells involves phospholipase D.	2001 Jun	11356622
p38 MAP kinase mediates stress-induced leukotriene synthesis in a human B-lymphocyte cell line.	2001 Nov	11698504
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.	2002 Apr 19	11830588
Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole.	2002 Nov	12386130
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
Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes.	2003 Feb	12538810
Genetic variation in cyclooxygenase 1: effects on response to aspirin.	2003 Jan	12545150
Regulation of selenoprotein GPx4 expression and activity in human endothelial cells by fatty acids, cytokines and antioxidants.	2003 Nov	14642406
Relationship of arachidonic acid concentration to cyclooxygenase-dependent human platelet aggregation.	2003 Sep	12971030
The ingestion of Ginkgo biloba extract (EGb 761) inhibits arachidonic acid-mediated platelet aggregation and thromboxane B2 production in healthy volunteers.	2004	15927922
Heme oxygenase-1 protects HepG2 cells against cytochrome P450 2E1-dependent toxicity.	2004 Feb 1	15036350
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
Polyunsaturated fatty acids block dendritic cell activation and function independently of NF-kappaB activation.	2005 Apr 8	15684433
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
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
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
Arachidonic acid, an omega-6 fatty acid, induces cytoplasmic phospholipase A2 in prostate carcinoma cells.	2005 Sep	15878913
Effect of enteric coating on antiplatelet activity of low-dose aspirin in healthy volunteers.	2006 Aug	16794200
Mechanism of induction of muscle protein degradation by angiotensin II.	2006 Jul	16257180
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.	2006 May	16489205

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)