Related CAS #
54533-86-7 (fumarate salt)
54533-85-6 (free)
Synonym
Nizofenone fumarate; NSC315856; NSC-315856; NSC 315856
IUPAC/Chemical Name
Methanone, (2-chlorophenyl)(2-(2-((diethylamino)methyl)-1H-imidazol-1-yl)-5-nitrophenyl)-, trans-2-butenedioate
InChi Key
JDQAUUIBFFFOOV-WLHGVMLRSA-N
InChi Code
InChI=1S/C21H21ClN4O3.C4H4O4/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;5-3(6)1-2-4(7)8/h5-13H,3-4,14H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
SMILES Code
O=C(C1=CC=CC=C1Cl)C2=CC([N+]([O-])=O)=CC=C2N3C=CN=C3CN(CC)CC.O=C(O)/C=C/C(O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Nizofenone fumarate is a neuroprotective drug which protects neurons from death following cerebral anoxia (interruption of oxygen supply to the brain).
In vitro activity:
Nizofenone (10 mg/kg i.p.) significantly inhibited neuronal cell death in the hippocampus CA1 pyramidal cells 7 days after 15 min of ischemia caused by 4-vessel occlusion. Nizofenone (10 mg/kg i.p.) completely inhibited the ischemic glutamate increase and post-ischemic lactate increase.
Reference: Eur J Pharmacol. 1994 Sep 1;262(1-2):157-61. https://pubmed.ncbi.nlm.nih.gov/7813567/
In vivo activity:
The present study was aimed to investigate the effects of nizofenone administration on the chronic restraint stress-induced cognitive impairments in mice. The results showed that the cognitive performances in CRS group were markedly deteriorated, accompanied by noticeable alterations in oxidative parameters, acetylcholinesterase activity and catecholamines levels in the hippocampus and the prefrontal cortex. These changes could be reversed by nizofenone treatment. Moreover, CRS group showed higher corticosterone levels and lower catecholamines levels in the serum, which were reversed in the nizofenone treatment groups.
Reference: Pharmacol Biochem Behav. 2013 Jan;103(3):474-80. https://pubmed.ncbi.nlm.nih.gov/23026061/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
528.95
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Matsumoto Y, Aihara K, Kamata T, Goto N. Nizofenone, a neuroprotective drug, suppresses glutamate release and lactate accumulation. Eur J Pharmacol. 1994 Sep 1;262(1-2):157-61. doi: 10.1016/0014-2999(94)90039-6. PMID: 7813567.
2. Kotake H, Nawada T, Matsumoto T, Kitamura H, Kaneda T, Hasegawa J, Mashiba H. Chronotropic effect of nizofenone fumarate in rabbit sino-atrial node in vitro. Br J Pharmacol. 1988 Dec;95(4):1175-80. doi: 10.1111/j.1476-5381.1988.tb11753.x. PMID: 3219485; PMCID: PMC1854257.
3. Liu Y, Zhuang X, Gou L, Ling X, Tian X, Liu L, Zheng Y, Zhang L, Yin X. Protective effects of nizofenone administration on the cognitive impairments induced by chronic restraint stress in mice. Pharmacol Biochem Behav. 2013 Jan;103(3):474-80. doi: 10.1016/j.pbb.2012.09.009. Epub 2012 Sep 28. PMID: 23026061.
4. Hayashi Y, Shimada O, Yasuda H, Ikegami K. Effect of nizofenone on experimental head trauma in mice. Arch Int Pharmacodyn Ther. 1994 Nov-Dec;328(3):251-60. PMID: 7625881.
In vitro protocol:
1. Matsumoto Y, Aihara K, Kamata T, Goto N. Nizofenone, a neuroprotective drug, suppresses glutamate release and lactate accumulation. Eur J Pharmacol. 1994 Sep 1;262(1-2):157-61. doi: 10.1016/0014-2999(94)90039-6. PMID: 7813567.
2. Kotake H, Nawada T, Matsumoto T, Kitamura H, Kaneda T, Hasegawa J, Mashiba H. Chronotropic effect of nizofenone fumarate in rabbit sino-atrial node in vitro. Br J Pharmacol. 1988 Dec;95(4):1175-80. doi: 10.1111/j.1476-5381.1988.tb11753.x. PMID: 3219485; PMCID: PMC1854257.
In vivo protocol:
1. Liu Y, Zhuang X, Gou L, Ling X, Tian X, Liu L, Zheng Y, Zhang L, Yin X. Protective effects of nizofenone administration on the cognitive impairments induced by chronic restraint stress in mice. Pharmacol Biochem Behav. 2013 Jan;103(3):474-80. doi: 10.1016/j.pbb.2012.09.009. Epub 2012 Sep 28. PMID: 23026061.
2. Hayashi Y, Shimada O, Yasuda H, Ikegami K. Effect of nizofenone on experimental head trauma in mice. Arch Int Pharmacodyn Ther. 1994 Nov-Dec;328(3):251-60. PMID: 7625881.
1: Liu Y, Zhuang X, Gou L, Ling X, Tian X, Liu L, Zheng Y, Zhang L, Yin X. Protective effects of nizofenone administration on the cognitive impairments induced by chronic restraint stress in mice. Pharmacol Biochem Behav. 2013 Jan;103(3):474-80. doi: 10.1016/j.pbb.2012.09.009. Epub 2012 Sep 28. PubMed PMID: 23026061.
2: Nakamura T, Tsumagari T. [Effects of nizofenone on experimental arrhythmia in dogs]. Nihon Yakurigaku Zasshi. 1984 Nov;84(5):441-51. Japanese. PubMed PMID: 6097519.
3: Miura Y, Inui J, Nakamura T. [Effects of nizofenone on the action potential of guinea-pig papillary muscle and S-A node and dog Purkinje fibers]. Nihon Yakurigaku Zasshi. 1985 Mar;85(3):159-65. Japanese. PubMed PMID: 4007706.
4: Saito I, Asano T, Ochiai C, Takakura K, Tamura A, Sano K. A double-blind clinical evaluation of the effect of Nizofenone (Y-9179) on delayed ischemic neurological deficits following aneurysmal rupture. Neurol Res. 1983;5(4):29-47. PubMed PMID: 6149485.
5: Yasuda H, Izumi N, Nakanishi M, Maruyama Y. Brain protection against oxygen deficiency by nizofenone. Adv Exp Med Biol. 1988;222:403-10. PubMed PMID: 3364265.
6: Kotake H, Nawada T, Matsumoto T, Kitamura H, Kaneda T, Hasegawa J, Mashiba H. Chronotropic effect of nizofenone fumarate in rabbit sino-atrial node in vitro. Br J Pharmacol. 1988 Dec;95(4):1175-80. PubMed PMID: 3219485; PubMed Central PMCID: PMC1854257.
7: Ohta T, Kikuchi H, Hashi K, Kudo Y. Nizofenone administration in the acute stage following subarachnoid hemorrhage. Results of a multi-center controlled double-blind clinical study. J Neurosurg. 1986 Mar;64(3):420-6. PubMed PMID: 3512795.
8: Mizoi K, Olca M, Fujimoto S, Abiko H, Suzuki J. [An experimental study on the protective effect of nizofenone in cerebral ischemia]. No To Shinkei. 1984 Nov;36(11):1089-93. Japanese. PubMed PMID: 6525322.
9: Yasuda H, Nakajima A. Brain protection against ischemic injury by nizofenone. Cerebrovasc Brain Metab Rev. 1993 Winter;5(4):264-76. Review. PubMed PMID: 8110594.
10: Morimoto Y, Fukuda T, Tsumagari T. [Effects of nizofenone on ischemic cerebral edema in Mongolian gerbils]. No To Shinkei. 1984 Oct;36(10):983-8. Japanese. PubMed PMID: 6518129.
