Arachidonyl trifluoromethyl ketone

Names
Preferred IUPAC name

(6Z,9Z,12Z,15Z)-1,1,1-Trifluorohenicosa-6,9,12,15-teraen-2-one

Other names

* Arachidonic acid trifluoromethyl ketone
* Arachidonyltrifluoromethane
* Arach-CF3
* AACOCF3

Identifiers

CAS Number

* 149301-79-1

3D model (JSmol)

* Interactive image

ChemSpider |

* 4444095

PubChem CID

* 5280436

UNII |

* 00XIW1CR0F Y

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 | 356.473 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

Tracking categories (test):

* SizeSet

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 et al. (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. ↑ 2.0 2.1 2.2 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. 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. http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1042&context=usuhs.

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*[CID]: Compound ID