ARACHIDONYLTRIFLUOROMETHANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H31F3O
Molecular Weight	356.4654
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure of ARACHIDONYLTRIFLUOROMETHANE

Structure Search

SMILES

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

InChI

InChIKey=PLWROONZUDKYKG-DOFZRALJSA-N

InChI=1S/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25971887

Arachidonyltrifluoromethane (more known as arachidonyl trifluoromethyl ketone) is a potent and selective slow binding inhibitor of the cytosolic phospholipase A2 (cPLA2). This compound is commonly used in the study of cPLA2-related neurodegenerative diseases. It was shown, that arachidonyl trifluoromethyl ketone decreased the levels of injurious lipid mediators, reduced pain, improved functional deficits, and conferred protection against lumbar spinal canal stenosis (LSS) injury. Thus, it shows potential for preclinical evaluation in LSS.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytosolic phospholipase A2 7 Target ID: P47712 Gene ID: 5321.0 Gene Symbol: PLA2G4A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8195210	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lumbar spinal canal stenosis 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25971887	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Characterization of the pattern of the nongenomic signaling pathway through which TCDD-induces early inflammatory responses in U937 human macrophages.	2009-03	19162293
Significance of the nongenomic, inflammatory pathway in mediating the toxic action of TCDD to induce rapid and long-term cellular responses in 3T3-L1 adipocytes.	2008-12-30	19063610
Initial and extended inflammatory messages of the nongenomic signaling pathway of the TCDD-activated Ah receptor in U937 macrophages.	2008-12-15	18938131
Simultaneous stimulation of spinal NK1 and NMDA receptors produces LPC which undergoes ATX-mediated conversion to LPA, an initiator of neuropathic pain.	2008-12	19014389
Arachidonic acid signaling is involved in the mechanism of imidazoline-induced KATP channel-independent stimulation of insulin secretion.	2007-11	17922229
The role of arachidonic acid and its metabolites in insulin secretion from human islets of langerhans.	2007-01	17192482
Oxidant-mediated activation of cytosolic phospholipase a(2) in pulmonary endothelium: role of protein kinase C alpha and a pertussis toxin-sensitive protein.	2005-11-18	16291515
Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine.	2005-09-15	16148147
Prolonged extracellular signal-regulated kinase 1/2 activation during fibroblast growth factor 1- or heregulin beta1-induced antiestrogen-resistant growth of breast cancer cells is resistant to mitogen-activated protein/extracellular regulated kinase kinase inhibitors.	2004-07-01	15231676
Prostacyclin production in rat aortic smooth muscle cells: role of protein kinase C, phospholipase D and cyclooxygenase-2 expression.	2003-11-01	14613874
Tumor necrosis factor-alpha selectively induces MnSOD expression via mitochondria-to-nucleus signaling, whereas interleukin-1beta utilizes an alternative pathway.	2001-06-08	11264281

Patents

Sample Use Guides

In Vivo Use Guide

in rats: arachidonyl trifluoromethyl ketone, ATK (7.5 mg/kg) was administered by oral gavage at 2 h following the cauda equina compression (CEC). ATK treatment of CEC animals reduced the phosphorylation of cPLA2 (pcPLA2) determined by Western blot, improved locomotor function evaluated by rotarod task, and reduced pain threshold evaluated by mechanical hyperalgesia method.

Route of Administration: Oral

In Vitro Use Guide

Arachidonyl trifluoromethyl ketone (AACOCF3) inhibited the release of AA from calcium ionophore-challenged U937 cells (IC50 = 8 microM, 2 x 10(6) cells ml-1) and from platelets (IC50 = 2 microM, 4 x 10(7) cells ml-1). AACH(OH)CF3 did not inhibit the production of AA in the ionophore-challenged cells. In addition to the release of AA, AACOCF3 also inhibited the production of 12-hydroxyeicosatetraenoic acid (12-HETE) and thromboxane B2, two of the major metabolites of AA produced by platelets

Name

Type

Language

AN-20579

Preferred Name

English

ARACHIDONYLTRIFLUOROMETHANE

Systematic Name

English

6,9,12,15-HENEICOSATETRAEN-2-ONE, 1,1,1-TRIFLUORO-, (6Z,9Z,12Z,15Z)-

Systematic Name

English

AACOCF3

Common Name

English

ATFMK

Common Name

English

L-734575

Code

English

BM-162353

Code

English

ARACHIDONYL TRIFLUOROMETHYL KETONE

Systematic Name

English

Code System Code Type Description

CAS

149301-79-1