Rufinamide | CGP-33101 | CAS#106308-44-5 | anticonvulsant

Rufinamide
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 300330

CAS#: 106308-44-5

Description: Rufinamide is a board spectrum anticonvulsant. It is used in combination with other medication and therapy to treat Lennox–Gastaut syndrome and various other seizure disorders. Rufinamide was approved by the US Food and Drug Administration on November 14, 2008 as adjunctive treatment of seizures associated with Lennox-Gastaut syndrome in children 4 years and older and adults. Rufinamide has efficacy for partial seizures. Rufinamide prolongs the inactivation of sodium channels and limits the frequency of action potential firing in cultured and acutely isolated neurons.

Chemical Structure

Rufinamide

CAS# 106308-44-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 300330
Name: Rufinamide
CAS#: 106308-44-5
Chemical Formula: C10H8F2N4O
Exact Mass: 238.07
Molecular Weight: 238.190
Elemental Analysis: C, 50.42; H, 3.39; F, 15.95; N, 23.52; O, 6.72

Price and Availability

Size	Price	Availability	Quantity
50g	USD -1
100mg	USD 450
200mg	USD 550
500mg	USD 650
1g	USD 750
2g	USD 950
5g	USD 1950
10g	USD 3450
20g	USD 4950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: CGP-33101; CGP 33101; CGP33101; Brand name: BANZEL; Inovelon.

IUPAC/Chemical Name: 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide

InChi Key: POGQSBRIGCQNEG-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H8F2N4O/c11-7-2-1-3-8(12)6(7)4-16-5-9(10(13)17)14-15-16/h1-3,5H,4H2,(H2,13,17)

SMILES Code: O=C(C1=CN(CC2=C(F)C=CC=C2F)N=N1)N

Appearance: XXXX 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: >2 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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Rufinamide inhibits the activation of voltage-gated sodium channel 1.1 (Nav1.1). It is an inhibitor of carbonic anhydrase VA (CAVA; Ki = 343.8 nM) that is selective for CAVA over CAI and CAII (Kis = >10,000 nM for both). Rufinamide inhibits seizures induced by pentylenetetrazole (ED50 = 54 mg/kg, i.p.) and reduces kainic acid-induced neuronal cell death in the mouse hippocampal CA3 region.
In vitro activity:	Rufinamide is not a substrate of human P-glycoprotein (Pgp). Rufinamide was not transported by MDR1-transfected cells from basolateral to apical sides in concentration equilibrium transport assays. Reference: Epilepsy Res. 2014 Mar;108(3):359-66. https://pubmed.ncbi.nlm.nih.gov/24530088/
In vivo activity:	In addition to inhibiting the INa, rufinamide effectively modifies the IK(Ca), which suggests that it has an impact on neuronal function and excitability. Rufinamide increased the amplitude of Ca2+-activated K+ currents (IK(Ca)) in pituitary GH3 lactotrophs. Rufinamide increased the strength of the hysteresis exhibited by the BKCa channels and induced by an inverted isosceles-triangular ramp pulse. Reference: Int J Mol Sci. 2022 Nov 8;23(22):13677. https://pubmed.ncbi.nlm.nih.gov/36430153/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	48.0	201.52

Preparing Stock Solutions

The following data is based on the product molecular weight 238.19 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. Skov M, de Paoli FV, Nielsen OB, Pedersen TH. The anti-convulsants lacosamide, lamotrigine, and rufinamide reduce myotonia in isolated human and rat skeletal muscle. Muscle Nerve. 2017 Jul;56(1):136-142. doi: 10.1002/mus.25452. Epub 2017 Feb 23. PMID: 27783415. 2. Chan PS, Zhang C, Zuo Z, Kwan P, Baum L. In vitro transport assays of rufinamide, pregabalin, and zonisamide by human P-glycoprotein. Epilepsy Res. 2014 Mar;108(3):359-66. doi: 10.1016/j.eplepsyres.2014.01.011. Epub 2014 Jan 30. PMID: 24530088. 3. Lai MC, Wu SN, Huang CW. Rufinamide, a Triazole-Derived Antiepileptic Drug, Stimulates Ca2+-Activated K+ Currents While Inhibiting Voltage-Gated Na+ Currents. Int J Mol Sci. 2022 Nov 8;23(22):13677. doi: 10.3390/ijms232213677. PMID: 36430153; PMCID: PMC9697614. 4. Lin YC, Lai YC, Lin TH, Yang YC, Kuo CC. Selective stabilization of the intermediate inactivated Na+ channel by the new-generation anticonvulsant rufinamide. Biochem Pharmacol. 2022 Mar;197:114928. doi: 10.1016/j.bcp.2022.114928. Epub 2022 Jan 19. PMID: 35063442.
In vitro protocol:	1. Skov M, de Paoli FV, Nielsen OB, Pedersen TH. The anti-convulsants lacosamide, lamotrigine, and rufinamide reduce myotonia in isolated human and rat skeletal muscle. Muscle Nerve. 2017 Jul;56(1):136-142. doi: 10.1002/mus.25452. Epub 2017 Feb 23. PMID: 27783415. 2. Chan PS, Zhang C, Zuo Z, Kwan P, Baum L. In vitro transport assays of rufinamide, pregabalin, and zonisamide by human P-glycoprotein. Epilepsy Res. 2014 Mar;108(3):359-66. doi: 10.1016/j.eplepsyres.2014.01.011. Epub 2014 Jan 30. PMID: 24530088.
In vivo protocol:	1. Lai MC, Wu SN, Huang CW. Rufinamide, a Triazole-Derived Antiepileptic Drug, Stimulates Ca2+-Activated K+ Currents While Inhibiting Voltage-Gated Na+ Currents. Int J Mol Sci. 2022 Nov 8;23(22):13677. doi: 10.3390/ijms232213677. PMID: 36430153; PMCID: PMC9697614. 2. Lin YC, Lai YC, Lin TH, Yang YC, Kuo CC. Selective stabilization of the intermediate inactivated Na+ channel by the new-generation anticonvulsant rufinamide. Biochem Pharmacol. 2022 Mar;197:114928. doi: 10.1016/j.bcp.2022.114928. Epub 2022 Jan 19. PMID: 35063442.

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1: Coppola G, Besag F, Cusmai R, Dulac O, Kluger G, Moavero R, Nabbout R, Nikanorova M, Pisani F, Verrotti A, von Stülpnagel C, Curatolo P. Current role of rufinamide in the treatment of childhood epilepsy: literature review and treatment guidelines. Eur J Paediatr Neurol. 2014 Nov;18(6):685-90. doi: 10.1016/j.ejpn.2014.05.008. Epub 2014 May 28. Review. PubMed PMID: 24929673.

2: Bentué-Ferrer D, Tribut O, Verdier MC. [Therapeutic drug monitoring of rufinamide]. Therapie. 2012 Mar-Apr;67(2):161-5. doi: 10.2515/therapie/2012013. Epub 2012 Aug 2. Review. French. PubMed PMID: 22850104.

3: McCormack PL. Rufinamide: a pharmacoeconomic profile of its use as adjunctive therapy in Lennox-Gastaut syndrome. Pharmacoeconomics. 2012 Mar;30(3):247-56. doi: 10.2165/11208630-000000000-00000. Review. PubMed PMID: 22332960.

4: Chung SS, Kelly K, Schusse C. New and emerging treatments for epilepsy: review of clinical studies of lacosamide, eslicarbazepine acetate, ezogabine, rufinamide, perampanel, and electrical stimulation therapy. J Epilepsy Res. 2011 Dec 30;1(2):35-46. doi: 10.14581/jer.11008. eCollection 2011 Dec. Review. PubMed PMID: 24649444; PubMed Central PMCID: PMC3952328.

5: Resnick T, Arzimanoglou A, Brown LW, Flamini R, Kerr M, Kluger G, Kothare S, Philip S, Harrison M, Narurkar M. Rufinamide from clinical trials to clinical practice in the United States and Europe. Epileptic Disord. 2011 May;13 Suppl 1:S27-43. doi: 10.1684/epd.2011.0421. Review. PubMed PMID: 21669560.

6: Wier HA, Cerna A, So TY. Rufinamide for pediatric patients with Lennox-Gastaut syndrome: a comprehensive overview. Paediatr Drugs. 2011 Apr 1;13(2):97-106. doi: 10.2165/11586920-000000000-00000. Review. PubMed PMID: 21351809.

7: Besag FM. Rufinamide for the treatment of Lennox-Gastaut syndrome. Expert Opin Pharmacother. 2011 Apr;12(5):801-6. doi: 10.1517/14656566.2011.560836. Epub 2011 Feb 24. Review. PubMed PMID: 21348771.

8: Joseph JR, Schultz RJ, Wilfong AA. Rufinamide for refractory epilepsy in a pediatric and young adult population. Epilepsy Res. 2011 Jan;93(1):87-9. doi: 10.1016/j.eplepsyres.2010.10.017. Epub 2010 Dec 15. Review. PubMed PMID: 21111576.

9: Ferrie CD. Rufinamide: a new antiepileptic drug treatment for Lennox-Gastaut syndrome. Expert Rev Neurother. 2010 Jun;10(6):851-60. doi: 10.1586/ern.10.51. Review. PubMed PMID: 20518600.

10: Wisniewski CS. Rufinamide: a new antiepileptic medication for the treatment of seizures associated with lennox-gastaut syndrome. Ann Pharmacother. 2010 Apr;44(4):658-67. doi: 10.1345/aph.1M679. Epub 2010 Mar 16. Review. PubMed PMID: 20233912.

11: Herranz JL. [Rufinamide. A review of its pharmacokinetic and pharmacodynamic properties]. Rev Neurol. 2008 Oct 1-15;47(7):369-73. Review. Spanish. PubMed PMID: 18841549.

12: Kreutzkamp B. [Rufinamide. An orphan drug for treatment of Lennox-Gastaut syndrome]. Med Monatsschr Pharm. 2007 Oct;30(10):358-61. Review. German. PubMed PMID: 17966284.

13: Heaney D, Walker MC. Rufinamide. Drugs Today (Barc). 2007 Jul;43(7):455-60. Review. PubMed PMID: 17728846.

14: Hakimian S, Cheng-Hakimian A, Anderson GD, Miller JW. Rufinamide: a new anti-epileptic medication. Expert Opin Pharmacother. 2007 Aug;8(12):1931-40. Review. PubMed PMID: 17696794.

15: Arroyo S. Rufinamide. Neurotherapeutics. 2007 Jan;4(1):155-62. Review. PubMed PMID: 17199032.

16: Cheng-Hakimian A, Anderson GD, Miller JW. Rufinamide: Pharmacology, clinical trials, and role in clinical practice. Int J Clin Pract. 2006 Nov;60(11):1497-501. Review. PubMed PMID: 17073844.

17: Deeks ED, Scott LJ. Rufinamide. CNS Drugs. 2006;20(9):751-60; discussion 761. Review. PubMed PMID: 16953653.

18: Rufinamide: CGP 33101, E 2080, RUF 331, Xilep. Drugs R D. 2005;6(4):249-52. Review. PubMed PMID: 15991887.

19: Jain KK. An assessment of rufinamide as an anti-epileptic in comparison with other drugs in clinical development. Expert Opin Investig Drugs. 2000 Apr;9(4):829-40. Review. PubMed PMID: 11060713.

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