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

MedKoo Cat#: 300330 | Name: Rufinamide

Description:

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

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

Theoretical Analysis

MedKoo Cat#: 300330

Name: Rufinamide

CAS#: 106308-44-5

Chemical Formula: C10H8F2N4O

Exact Mass: 238.0666

Molecular Weight: 238.19

Elemental Analysis: C, 50.42; H, 3.39; F, 15.95; N, 23.52; O, 6.72

Price and Availability

Size	Price	Availability
100mg	USD 450.00	2 Weeks
200mg	USD 550.00	2 Weeks
500mg	USD 650.00	2 Weeks
1g	USD 750.00	2 Weeks
2g	USD 950.00	2 Weeks
5g	USD 1,950.00	2 Weeks
10g	USD 3,450.00	2 Weeks
20g	USD 4,950.00	2 Weeks

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Related CAS #

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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

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	48.0	201.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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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Evaluation of ivermectin and vitamin E based combination with antiseizure rufinamide drug for mitigation of pentylenetetrazole-induced kindling, behavioral challenges and histopathological aberrations. J Physiol Pharmacol. 2024 Jun;75(3). doi: 10.26402/jpp.2024.3.01. Epub 2024 Jul 18. PMID: 39042385. 6: Müller P, Draguhn A, Egorov AV. Persistent sodium currents in neurons: potential mechanisms and pharmacological blockers. Pflugers Arch. 2024 Oct;476(10):1445-1473. doi: 10.1007/s00424-024-02980-7. Epub 2024 Jul 5. Erratum in: Pflugers Arch. 2024 Oct;476(10):1623. doi: 10.1007/s00424-024-02995-0. PMID: 38967655; PMCID: PMC11381486. 7: Zhang H, Ou Z, Zhang E, Liu W, Hao N, Chen Y, Liu Y, Ye H, Zhou D, Wu X. Efficacy and safety of add-on antiseizure medications for focal epilepsy: A network meta-analysis. Epilepsia Open. 2024 Aug;9(4):1550-1564. doi: 10.1002/epi4.12997. Epub 2024 Jun 18. PMID: 38888005; PMCID: PMC11296132. 8: Porwal MH, Razzak AN, Kumar V, Obeidat AZ, Sharma U. An analysis of suicidal and self-injurious behavior reports with antiseizure medications in the FDA adverse event database. Epilepsy Res. 2024 Jul;203:107382. doi: 10.1016/j.eplepsyres.2024.107382. Epub 2024 May 17. PMID: 38761467. 9: Heger K, Burns ML, Nikanorova M, Johannessen SI, Johannessen Landmark C. Pharmacokinetic Variability of Rufinamide and Stiripentol in Children With Refractory Epilepsy: A Retrospective Study of Therapeutic Drug Monitoring From the National Epilepsy Centers in Denmark and Norway. Ther Drug Monit. 2024 Oct 1;46(5):664-671. doi: 10.1097/FTD.0000000000001219. Epub 2024 May 15. PMID: 38758628. 10: Kim SM, Heo WY, Oh H, Joo EY, Shon YM, Hong SB, Lee SY, Seo DW. Therapeutic Drug Monitoring of 6 New-Generation Antiseizure Medications Using a Mass Spectrometry Method: Analysis of 2-Year Experience in a Large Cohort of Korean Epilepsy Patients. Arch Pathol Lab Med. 2024 Apr 5. doi: 10.5858/arpa.2023-0386-OA. Epub ahead of print. PMID: 38576184. 11: Chen Y, Li W, Lu C, Gao X, Song H, Zhang Y, Zhao S, Cai G, Guo Q, Zhou D, Chen Y. Efficacy, tolerability and safety of add-on third-generation antiseizure medications in treating focal seizures worldwide: a network meta-analysis of randomised, placebo-controlled trials. EClinicalMedicine. 2024 Feb 28;70:102513. doi: 10.1016/j.eclinm.2024.102513. PMID: 38449838; PMCID: PMC10915785. 12: Wang S, Xia X, Chen Q, Li K, Xiao X, Chen FE. Accelerated Diffusion of a Copper(I)-Functionalized COF Packed Bed Reactor for Efficient Continuous Flow Catalysis. ACS Appl Mater Interfaces. 2024 Jan 31;16(4):5158-5167. doi: 10.1021/acsami.3c17607. Epub 2024 Jan 18. PMID: 38238929. 13: Chen JL, Kuo CC. Inhibition of resurgent Na+ currents by rufinamide. Neuropharmacology. 2024 Apr 1;247:109835. doi: 10.1016/j.neuropharm.2024.109835. Epub 2024 Jan 14. PMID: 38228283. 14: Xue F, Zhang J, Ma Z, Wang Z. Copper Dispersed Covalent Organic Framework for Azide-Alkyne Cycloaddition and Fast Synthesis of Rufinamide in Water. Small. 2024 Jun;20(25):e2307796. doi: 10.1002/smll.202307796. Epub 2024 Jan 7. PMID: 38185802. 15: Parveen A, Alqahtani F, Javaid S, Ashraf W, Siddique F, Rawat R, Rasool MF, Ahmad T, Alasmari F, Imran I. Anxiolytic potential of resveratrol and rufinamide combination by modulating GABA-ergic transmission: insights from experiments, molecular docking and dynamics simulations. J Physiol Pharmacol. 2023 Oct;74(5). doi: 10.26402/jpp.2023.5.02. Epub 2023 Dec 6. PMID: 38085514. 16: Milosheska D, Roškar R. Simple HPLC-UV Method for Therapeutic Drug Monitoring of 12 Antiepileptic Drugs and Their Main Metabolites in Human Plasma. Molecules. 2023 Nov 28;28(23):7830. doi: 10.3390/molecules28237830. PMID: 38067559; PMCID: PMC10708341. 17: Ptolemy AS, Peake RWA, Kellogg MD. Turbulent Flow Liquid Chromatography- Tandem Mass Spectrometry Methods for Antiepileptic Drug Quantitation in Serum. Methods Mol Biol. 2024;2737:33-41. doi: 10.1007/978-1-0716-3541-4_4. PMID: 38036808. 18: Chong E, Oh H, Kim DJ, Kim SM, Lee SY. Quantification of Gabapentin, Lacosamide, Perampanel, Pregabalin, Rufinamide, and Vigabatrin in Serum Using Liquid Chromatography-Tandem Mass Spectrometry. Methods Mol Biol. 2024;2737:25-32. doi: 10.1007/978-1-0716-3541-4_3. PMID: 38036807. 19: Lumley LA, Nguyen DA, de Araujo Furtado M, Niquet J, Linz EO, Schultz CR, Stone MF, Wasterlain CG. Efficacy of Lacosamide and Rufinamide as Adjuncts to Midazolam-Ketamine Treatment Against Cholinergic-Induced Status Epilepticus in Rats. J Pharmacol Exp Ther. 2024 Jan 17;388(2):347-357. doi: 10.1124/jpet.123.001789. PMID: 37977809; PMCID: PMC10801783. 20: Sills GJ. Pharmacological diversity amongst approved and emerging antiseizure medications for the treatment of developmental and epileptic encephalopathies. Ther Adv Neurol Disord. 2023 Aug 30;16:17562864231191000. doi: 10.1177/17562864231191000. PMID: 37655228; PMCID: PMC10467199.