Nizofenone

Nizofenone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N06BX10 (WHO) ;
Identifiers
	IUPAC name (2-chlorophenyl)(2-{2-[(diethylamino)methyl]-1H-imidazol-1-yl}-5-nitrophenyl)methanone;
CAS Number	54533-85-6;
PubChem CID	4514;
ChemSpider	4357 ;
UNII	7A2NOC3R88;
CompTox Dashboard (EPA)	DTXSID401014745 DTXSID5048637, DTXSID401014745 ;
Chemical and physical data
Formula	C21H21ClN4O3
Molar mass	412.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccccc1C(=O)c3cc([N+]([O-])=O)ccc3n2ccnc2CN(CC)CC;
	InChI InChI=1S/C21H21ClN4O3/c1-3-24(4-2)14-20-23-11-12-25(20)19-10-9-15(26(28)29)13-17(19)21(27)16-7-5-6-8-18(16)22/h5-13H,3-4,14H2,1-2H3 ; Key:WZGBZLHGOVJDET-UHFFFAOYSA-N ;
	(verify)

Nizofenone (Ekonal, Midafenone) is a neuroprotective drug which protects neurons from death following cerebral anoxia (interruption of oxygen supply to the brain). It might thus be useful in the treatment of acute neurological conditions such as stroke.^[1]^[2]^[3]^[4]

References

^ Ohta T, Kikuchi H, Hashi K, Kudo Y (March 1986). "Nizofenone administration in the acute stage following subarachnoid hemorrhage. Results of a multi-center controlled double-blind clinical study". Journal of Neurosurgery. 64 (3): 420–426. doi:10.3171/jns.1986.64.3.0420. PMID 3512795.
^ Yasuda H, Izumi N, Nakanishi M, Maruyama Y (1988). "Brain Protection Against Oxygen Deficiency by Nizofenone". Oxygen Transport to Tissue X. Advances in Experimental Medicine and Biology. Vol. 222. pp. 403–10. doi:10.1007/978-1-4615-9510-6_48. ISBN 978-1-4615-9512-0. PMID 3364265.
^ Yasuda H, Nakajima A (1993). "Brain protection against ischemic injury by nizofenone". Cerebrovascular and Brain Metabolism Reviews. 5 (4): 264–276. PMID 8110594.
^ Matsumoto Y, Aihara K, Kamata T, Goto N (September 1994). "Nizofenone, a neuroprotective drug, suppresses glutamate release and lactate accumulation". European Journal of Pharmacology. 262 (1–2): 157–161. doi:10.1016/0014-2999(94)90039-6. PMID 7813567.

Yasuda H (1999). "Prevention of neurodegeneration by a neuroprotective radical scavenger". Annals of the New York Academy of Sciences. 893 (1): 430–433. Bibcode:1999NYASA.893..430Y. doi:10.1111/j.1749-6632.1999.tb07871.x. PMID 10672283. S2CID 21398803.
Hayashi Y, Shimada O, Yasuda H, Ikegami K (1994). "Effect of nizofenone on experimental head trauma in mice". Archives Internationales de Pharmacodynamie et de Therapie. 328 (3): 251–260. PMID 7625881.
Yasuda H, Kishiro K, Izumi N, Nakanishi M (July 1985). "Biphasic liberation of arachidonic and stearic acids during cerebral ischemia". Journal of Neurochemistry. 45 (1): 168–172. doi:10.1111/j.1471-4159.1985.tb05489.x. PMID 2987409. S2CID 24857145.
Yasuda H, Ochi H, Tsumagari T (September 1984). "Stimulation of prostacyclin synthesis by nizofenone". Biochemical Pharmacology. 33 (17): 2707–2709. doi:10.1016/0006-2952(84)90684-1. PMID 6431991.
Saito I, Asano T, Ochiai C, Takakura K, Tamura A, Sano K (1983). "A double-blind clinical evaluation of the effect of Nizofenone (Y-9179) on delayed ischemic neurological deficits following aneurysmal rupture". Neurological Research. 5 (4): 29–47. doi:10.1080/01616412.1983.11739654. PMID 6149485.
Ochiai C, Asano T, Takakura K, Fukuda T, Horizoe H, Morimoto Y (1982). "Mechanisms of cerebral protection by pentobarbital and nizofenone correlated with the course of local cerebral blood flow changes". Stroke. 13 (6): 788–796. doi:10.1161/01.str.13.6.788. PMID 7147293.
Yasuda H, Shimada O, Nakajima A, Asano T (October 1981). "Cerebral protective effect and radical scavenging action". Journal of Neurochemistry. 37 (4): 934–938. doi:10.1111/j.1471-4159.1981.tb04480.x. PMID 7320731. S2CID 22484255.
Yasuda H, Nakanishi M, Tsumagari T, Nakajima A, Nakanishi M (November 1979). "The mechanism of action of a novel cerebral protective drug against anoxia I. The effect on cerebral energy demand". Archives Internationales de Pharmacodynamie et de Therapie. 242 (1): 77–85. PMID 543750.
Tamura A, Asano T, Sano K, Tsumagari T, Nakajima A (1979). "Protection from cerebral ischemia by a new imidazole derivative (Y-9179) and pentobarbital. A comparative study in chronic middle cerebral artery occlusion in cats". Stroke. 10 (2): 126–134. doi:10.1161/01.str.10.2.126. PMID 442136.

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[1] Ohta T, Kikuchi H, Hashi K, Kudo Y (March 1986). "Nizofenone administration in the acute stage following subarachnoid hemorrhage. Results of a multi-center controlled double-blind clinical study". Journal of Neurosurgery. 64 (3): 420–426. doi:10.3171/jns.1986.64.3.0420. PMID 3512795.

[2] Yasuda H, Izumi N, Nakanishi M, Maruyama Y (1988). "Brain Protection Against Oxygen Deficiency by Nizofenone". Oxygen Transport to Tissue X. Advances in Experimental Medicine and Biology. Vol. 222. pp. 403–10. doi:10.1007/978-1-4615-9510-6_48. ISBN 978-1-4615-9512-0. PMID 3364265.

[3] Yasuda H, Nakajima A (1993). "Brain protection against ischemic injury by nizofenone". Cerebrovascular and Brain Metabolism Reviews. 5 (4): 264–276. PMID 8110594.

[4] Matsumoto Y, Aihara K, Kamata T, Goto N (September 1994). "Nizofenone, a neuroprotective drug, suppresses glutamate release and lactate accumulation". European Journal of Pharmacology. 262 (1–2): 157–161. doi:10.1016/0014-2999(94)90039-6. PMID 7813567.

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References

Further reading