Nafimidone

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MedKoo CAT#: 584884

CAS#: 64212-22-2

Description: Nafimidone is an imidazole anticonvulsant.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-09-22. Prices are subject to change without notice.

Nafimidone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584884
Name: Nafimidone
CAS#: 64212-22-2
Chemical Formula: C15H12N2O
Exact Mass: 236.095
Molecular Weight: 236.274
Elemental Analysis: C, 76.25; H, 5.12; N, 11.86; O, 6.77


Synonym: Nafimidone

IUPAC/Chemical Name: Ethanone, 2-(1H-imidazol-1-yl)-1-(1-naphthalenyl)-

InChi Key: OQYTVTMYRAGJMK-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12N2O/c18-15(10-17-9-8-16-11-17)14-7-3-5-12-4-1-2-6-13(12)14/h1-9,11H,10H2

SMILES Code: O=C(C1=C2C=CC=CC2=CC=C1)CN3C=CN=C3


Technical Data

Appearance:
Solid powder

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:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

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


References

1: Rush WR, Alexander OF, Hall DJ, Dow RJ, Tokes L, Kurz L, Graham DJ. The metabolism of nafimidone hydrochloride in the dog, primates and man. Xenobiotica. 1990 Jan;20(1):123-32. PubMed PMID: 2109431.

2: Treiman DM, Gunawan S. Pharmacokinetics of nafimidone in patients with chronic intractable epilepsy. Clin Pharmacokinet. 1987 Jun;12(6):433-9. PubMed PMID: 3608344.

3: Robertson DW, Krushinski JH, Beedle EE, Leander JD, Wong DT, Rathbun RC. Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol. J Med Chem. 1986 Sep;29(9):1577-86. PubMed PMID: 3746810.

4: Kapetanovic IM, Kupferberg HJ. Nafimidone, an imidazole anticonvulsant, and its metabolite as potent inhibitors of microsomal metabolism of phenytoin and carbamazepine. Drug Metab Dispos. 1984 Sep-Oct;12(5):560-4. PubMed PMID: 6149905.

5: Taylor RB, Durham DG, Shivji AS, Reid R. Development of a stability-indicating assay for nafimidone [1-(2-naphthoylmethyl)imidazole hydrochloride] by high-performance liquid chromatography. J Chromatogr. 1986 Feb 26;353:51-9. PubMed PMID: 3700525.

6: Kamışlı S, Karakurt A, Uyumlu AB, Satılmış B, Alagöz A, Genç MF, Batcıoğlu K. Evaluation of the effects of novel nafimidone derivatives on thermal hypoalgesia in mice with diabetic neuropathy. Balkan Med J. 2013 Mar;30(1):94-8. doi: 10.5152/balkanmedj.2012.067. Epub 2013 Mar 1. PubMed PMID: 25207077; PubMed Central PMCID: PMC4116014.

7: Albertson TE, Walby WF. The anticonvulsant action of nafimidone on kindled amygdaloid seizures in rats. Epilepsy Res. 1988 Jan-Feb;2(1):20-6. PubMed PMID: 3197675.

8: Treiman DM, Wilensky AJ, Ben-Menachem E, Ojemann L, Yerby M, Barber KO, McCormick KB, Cereghino JJ, White BG, Swisher K. Efficacy of nafimidone in the treatment of intractable partial seizures: report of a two-center pilot study. Epilepsia. 1985 Nov-Dec;26(6):607-11. PubMed PMID: 3935425.

9: Gunawan S, Treiman DM. High-performance liquid chromatographic determination of nafimidone and its major metabolite nafimidone alcohol in human plasma and urine. J Chromatogr. 1987 Mar 6;414(2):389-98. PubMed PMID: 3571406.

10: Graham DJ, Hama KM, Smith SA, Kurz L, Chaplin MD, Hall DJ. Disposition of nafimidone in rats. Drug Metab Dispos. 1987 Jul-Aug;15(4):565-70. PubMed PMID: 2888632.

11: Rush WR, Smith SA, Mulvey JH, Graham DJ, Chaplin MD. Inhibition and induction of hepatic drug metabolism in rats and mice by nafimidone and its major metabolite nafimidone alcohol. Drug Metab Dispos. 1987 Jul-Aug;15(4):571-8. PubMed PMID: 2888633.

12: Salmona M, Conti I, Testa R, Fracasso C, Caccia S. Interaction of the anticonvulsants, denzimol and nafimidone, with liver cytochrome P450 in the rat. J Pharm Pharmacol. 1988 Jan;40(1):17-21. PubMed PMID: 2896768.

13: Kapetanovic IM, Kupferberg HJ. Inhibition of microsomal phenytoin metabolism by nafimidone and related imidazoles. Potency and structural considerations. Drug Metab Dispos. 1985 Jul-Aug;13(4):430-7. PubMed PMID: 2863106.

14: Sari S, Kaynak FB, Dalkara S. Synthesis and anticonvulsant screening of 1,2,4-triazole derivatives. Pharmacol Rep. 2018 Dec;70(6):1116-1123. doi: 10.1016/j.pharep.2018.06.007. Epub 2018 Jun 23. PubMed PMID: 30316046.

15: Sari S, Karakurt A, Uslu H, Kaynak FB, Çalış Ü, Dalkara S. New (arylalkyl)azole derivatives showing anticonvulsant effects could have VGSC and/or GABA(A)R affinity according to molecular modeling studies. Eur J Med Chem. 2016 Nov 29;124:407-416. doi: 10.1016/j.ejmech.2016.08.032. Epub 2016 Aug 25. PubMed PMID: 27597416.

16: Sari S, Dalkara S, Kaynak FB, Reynisson J, Saraç S, Karakurt A. New Anti-Seizure (Arylalkyl)azole Derivatives: Synthesis, In Vivo and In Silico Studies. Arch Pharm (Weinheim). 2017 Jun;350(6). doi: 10.1002/ardp.201700043. Epub 2017 May 2. PubMed PMID: 28464338.

17: Karakurt A, Dalkara S, Ozalp M, Ozbey S, Kendi E, Stables JP. Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities. Eur J Med Chem. 2001 May;36(5):421-33. PubMed PMID: 11451531.

18: Karakurt A, Ozalp M, Işik S, Stables JP, Dalkara S. Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives. Bioorg Med Chem. 2010 Apr 15;18(8):2902-11. doi: 10.1016/j.bmc.2010.03.010. Epub 2010 Mar 9. PubMed PMID: 20363141.

19: Kerr BM, Boddy AV, Moreland TA, Levy RH. Pharmacokinetic consequences of product stereoselectivity in the metabolism of nafimidone: estimation of fraction metabolized. J Pharm Sci. 1991 Aug;80(8):812-4. PubMed PMID: 1791547.

20: Acar MF, Sari S, Dalkara S. Synthesis, in vivo anticonvulsant testing, and molecular modeling studies of new nafimidone derivatives. Drug Dev Res. 2019 Apr 11. doi: 10.1002/ddr.21538. [Epub ahead of print] PubMed PMID: 30973979.