Arachidonyl trifluoromethyl ketone

Arachidonyl trifluoromethyl ketone

Names
IUPAC name 1,1,1-Trifluoro-6Z,9Z,12Z,15Z-heneicosateraen-2-one
Other names Arachidonic acid trifluoromethyl ketone Arachidonyltrifluoromethane Arach-CF3 AACOCF3
Identifiers
CAS Number	149301-79-1
3D model (Jmol)	Interactive image
ChemSpider	4444095
PubChem	5280436
InChI 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- Key: PLWROONZUDKYKG-DOFZRALJSA-N
SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
Properties
Chemical formula	C21H31F3O
Molar mass	356.47 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Arachidonyl trifluoromethyl ketone (ATK) is an analog of arachidonic acid.^[1] that inhibits some isoforms of the enzyme phospholipase A2.^[2] Specifically it inhibits the 85 kDa cystolic PLA2 (cPLA2).^[2]

It has been studied as a neuroprotective agent after spinal cord injury,^[2][3] and in animal models of multiple sclerosis.^[4]

See also

• Spinal stenosis

References

1. Street, Ian P.; Lin, Hung Kuei; Laliberte, France; Ghomashchi, Farideh; Wang, Zhaoyin; Perrier, Helene; Tremblay, Nathalie M.; Huang, Zheng; Weech, Philip K.; Gelb, Michael H. (1993). "Slow- and tight-binding inhibitors of the 85-k Da human phospholipase A2". Biochemistry. 32 (23): 5935. doi:10.1021/bi00074a003. PMID 8018213.
2. Khan, Mushfiquddin; Shunmugavel, Anandakumar; Dhammu, Tajinder S; Matsuda, Fumiyo; Singh, Avtar K; Singh, Inderjit (2015). "Oral administration of cytosolic PLA2 inhibitor arachidonyl trifluoromethyl ketone ameliorates cauda equina compression injury in rats". Journal of Neuroinflammation. 12: 94. doi:10.1186/s12974-015-0311-y. PMC 4436116. PMID 25971887.
3. Huang, Wenlong; Bhavsar, Amar; Ward, Rachael E; Hall, Jodie C.E.; Priestley, John V.; Michael-Titus, Adina T. (2009). "Arachidonyl trifluoromethyl ketone is neuroprotective after spinal cord injury". Journal of Neurotrauma: 110306202455053. doi:10.1089/neu.2008-0835.
4. Vana, Adam C.; Li, Shihe; Ribeiro, Rachel; Tchantchou, Flaubert; Zhang, Yumin (2011). "Arachidonyl trifluoromethyl ketone ameliorates experimental autoimmune encephalomyelitis via blocking peroxynitrite formation in mouse spinal cord white matter". Experimental Neurology. 231 (1): 45–55. doi:10.1016/j.expneurol.2011.05.014. PMID 21683698.