Identification
- Summary
Rufinamide is an antiepileptic drug used as adjunctive therapy to treat seizures associated with Lennox-Gastaut Syndrome (LGS).
- Brand Names
- Banzel, Inovelon
- Generic Name
- Rufinamide
- DrugBank Accession Number
- DB06201
- Background
Rufinamide is a triazole derivative and an anticonvulsant medication to treat seizure disorders like Lennox-Gastuat syndrome, a form of childhood epilepsy. Clinical trials suggest its efficacy in the treatment of partial seizures.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Rufinamide (DB06201)
- Weight
- Average: 238.1935
Monoisotopic: 238.066617308 - Chemical Formula
- C10H8F2N4O
- Synonyms
- Rufinamida
- Rufinamide
- Xilep
- External IDs
- CGP 33101
- E 2080
- E-2080
- E2080
- RUF 331
Pharmacology
- Indication
Adjunct therapy for treatment of seizures associated with Lennox-Gastaut syndrome.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in management of Lennox-gastaut syndrome •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
At high concentrations will inhibit action of mGluR5 subtype receptors thus preventing the production of glutamate.
- Mechanism of action
Rufinamide is a triazole derivative antiepileptic that prolongs the inactive state of voltage gated sodium channels thus stabilizing membranes, ultimately blocking the spread of partial seizure activity.
Target Actions Organism USodium channel protein type 9 subunit alpha modulatorHumans UMetabotropic glutamate receptor 5 inhibitorHumans - Absorption
The oral suspension and tablet are bioequivalent on a mg per mg basis. Rufinamide is well absorbed but the rate is slow and the extent of absorption decreases as dose is increases. Based on urinary excretion, the extent of absorption was at least 85% following oral administration of a single dose of 600 mg rufinamide tablet under fed conditions. Bioavailability= 70%-85% (decreases with increasing doses); Tmax, fed and fasted states= 4-6 hours; Cmax, 10 mg/kg/day= 4.01 µL/mL; Cmax, 30mg/kg/day= 8.68 µL/mL; AUC (0h-12h), 10mg/kg/day= 37.8±47 µg·h/mL; AUC (0h-12h), 30mg/kg/day= 89.3±59 µg·h/mL.
- Volume of distribution
Rufinamide was evenly distributed between erythrocytes and plasma. The apparent volume of distribution is dependent upon dose and varies with body surface area. The apparent volume of distribution was about 50 L at 3200 mg/day. Volume of distribution is similar between adults and children and is non-linear.
- Protein binding
26.3% - 34.8% with 90% binding to albumin (27%).
- Metabolism
Rufinamide is extensively metabolized but has no active metabolites. Metabolism by carboxyesterases into inactive metabolite CGP 47292, a carboxylic acid derivative, via hydrolysis is the primary biotransformation pathway. A few minor additional metabolites were detected in urine, which appeared to be acyl-glucuronides of CGP 47292. The cytochrome P450 enzyme system or glutathiones are not involved with the metabolism of rufinamide. Rufinamide is a weak inhibitor of CYP 2E1. Rufinamide is a weak inducer of CYP 3A4 enzymes.
Hover over products below to view reaction partners
- Route of elimination
Renally (91%; 66% as CGP 47292, 2% as unchanged drug) and fecally (9%) eliminated.
- Half-life
Elimination half-life, healthy subjects and patients with epilepsy = 6-10 hours.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The most commonly observed adverse reactions (≥10% and greater than placebo) were headache, dizziness, fatigue, somnolence, and nausea.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Rufinamide is combined with 1,2-Benzodiazepine. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Rufinamide. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Rufinamide. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Rufinamide. Acetaminophen Rufinamide may increase the hepatotoxic activities of Acetaminophen. - Food Interactions
- Take with food. Food can increase the absorption of rufinamide.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Banzel Tablet, film coated 400 mg/1 Oral Eisai Inc. 2008-11-14 Not applicable US 
Banzel Tablet 400 mg Oral Eisai Limited 2011-09-01 Not applicable Canada 
Banzel Tablet, film coated 200 mg/1 Oral Eisai Inc. 2008-11-14 Not applicable US 
Banzel Tablet 200 mg Oral Eisai Limited 2011-08-29 Not applicable Canada Banzel Suspension 40 mg/1mL Oral Eisai Inc. 2011-03-03 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Rufinamide Suspension 40 mg/1mL Oral Lupin Pharmaceuticals, Inc. 2023-06-22 Not applicable US Rufinamide Tablet, film coated 400 mg/1 Oral Hikma Pharmaceuticals USA Inc. 2021-05-30 Not applicable US Rufinamide Suspension 40 mg/1mL Oral Hikma Pharmaceuticals USA Inc. 2020-11-01 Not applicable US Rufinamide Tablet, film coated 200 mg/1 Oral Mylan Pharmaceuticals Inc. 2021-06-01 Not applicable US Rufinamide Suspension 40 mg/1mL Oral Camber Pharmaceuticals, Inc. 2023-12-05 Not applicable US
Categories
- ATC Codes
- N03AF03 — Rufinamide
- Drug Categories
- Anticonvulsants
- Carboxamide Derivatives
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (weak)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Membrane Transport Modulators
- Miscellaneous Anticonvulsants
- Nervous System
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 2-heteroaryl carboxamides. These are compounds containing a heteroaromatic ring that carries a carboxamide group.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Carboxylic acid derivatives
- Direct Parent
- 2-heteroaryl carboxamides
- Alternative Parents
- Fluorobenzenes / Aryl fluorides / Vinylogous amides / Triazoles / Heteroaromatic compounds / Primary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds show 3 more
- Substituents
- 1,2,3-triazole / 2-heteroaryl carboxamide / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Fluorobenzene / Halobenzene show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- WFW942PR79
- CAS number
- 106308-44-5
- InChI Key
- POGQSBRIGCQNEG-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide
- SMILES
- NC(=O)C1=CN(CC2=C(F)C=CC=C2F)N=N1
References
- Synthesis Reference
Emanuele ATTOLINO, Lino COLOMBO, Ilaria MORMINO, Pietro ALLEGRINI, "METHOD FOR THE PREPARATION OF RUFINAMIDE." U.S. Patent US20100234616, issued September 16, 2010.
US20100234616- General References
- Arroyo S: Rufinamide. Neurotherapeutics. 2007 Jan;4(1):155-62. [Article]
- Hakimian S, Cheng-Hakimian A, Anderson GD, Miller JW: Rufinamide: a new anti-epileptic medication. Expert Opin Pharmacother. 2007 Aug;8(12):1931-40. [Article]
- Authors unspecified: Rufinamide: CGP 33101, E 2080, RUF 331, Xilep. Drugs R D. 2005;6(4):249-52. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D05775
- PubChem Compound
- 129228
- PubChem Substance
- 175427055
- ChemSpider
- 114471
- 69036
- ChEBI
- 134966
- ChEMBL
- CHEMBL1201754
- ZINC
- ZINC000000007782
- PharmGKB
- PA166131606
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Rufinamide
- FDA label
- Download (562 KB)
- MSDS
- Download (76.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Epilepsy 1 3 Completed Treatment Epilepsy 1 3 Completed Treatment Lennox-Gastaut Syndrome 3 3 Terminated Treatment Refractory Partial Onset Seizures 1 3 Withdrawn Treatment Refractory Partial Onset Seizures 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suspension Oral 40 mg / mL Tablet Oral 100 mg Tablet Oral 200 mg Tablet Oral 400 mg Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 400 mg/1 Suspension Oral 40 MG/ML Tablet, film coated Oral Tablet, film coated Oral 100 MG Tablet, film coated Oral 400 MG Tablet, film coated Oral 200 mg Tablet, coated Oral 400 mg Suspension Oral 40 mg/1mL Tablet Oral 200 mg/1 Tablet Oral 400 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, coated Oral 200 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7750028 Yes 2010-07-06 2019-04-19 US US8076362 Yes 2011-12-13 2018-12-08 US US6740669 Yes 2004-05-25 2023-05-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Insoluble FDA label logP 0.835 MSDS - Predicted Properties
Property Value Source Water Solubility 0.642 mg/mL ALOGPS logP 0.95 ALOGPS logP 1.27 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 12.64 Chemaxon pKa (Strongest Basic) -1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 73.8 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.07 m3·mol-1 Chemaxon Polarizability 20.42 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9777 Caco-2 permeable - 0.5301 P-glycoprotein substrate Non-substrate 0.7407 P-glycoprotein inhibitor I Non-inhibitor 0.9422 P-glycoprotein inhibitor II Non-inhibitor 0.9633 Renal organic cation transporter Non-inhibitor 0.6685 CYP450 2C9 substrate Non-substrate 0.8452 CYP450 2D6 substrate Non-substrate 0.8723 CYP450 3A4 substrate Non-substrate 0.5567 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Non-inhibitor 0.8201 CYP450 2D6 inhibitor Non-inhibitor 0.8454 CYP450 2C19 inhibitor Non-inhibitor 0.5561 CYP450 3A4 inhibitor Non-inhibitor 0.7995 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5438 Ames test AMES toxic 0.6126 Carcinogenicity Non-carcinogens 0.8415 Biodegradation Not ready biodegradable 0.9945 Rat acute toxicity 2.5067 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9484 hERG inhibition (predictor II) Non-inhibitor 0.7869
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 150.44136 predictedDeepCCS 1.0 (2019) [M+H]+ 152.81679 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.89249 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
- Gene Name
- SCN9A
- Uniprot ID
- Q15858
- Uniprot Name
- Sodium channel protein type 9 subunit alpha
- Molecular Weight
- 226370.175 Da
References
- Suter MR, Kirschmann G, Laedermann CJ, Abriel H, Decosterd I: Rufinamide attenuates mechanical allodynia in a model of neuropathic pain in the mouse and stabilizes voltage-gated sodium channel inactivated state. Anesthesiology. 2013 Jan;118(1):160-72. doi: 10.1097/ALN.0b013e318278cade. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Glutamate receptor activity
- Specific Function
- G-protein coupled receptor for glutamate. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down...
- Gene Name
- GRM5
- Uniprot ID
- P41594
- Uniprot Name
- Metabotropic glutamate receptor 5
- Molecular Weight
- 132467.635 Da
References
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Triglyceride lipase activity
- Specific Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Williams ET, Carlson JE, Lai WG, Wong YN, Yoshimura T, Critchley DJ, Narurkar M: Investigation of the metabolism of rufinamide and its interaction with valproate. Drug Metab Lett. 2011 Dec;5(4):280-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Perucca E, Cloyd J, Critchley D, Fuseau E: Rufinamide: clinical pharmacokinetics and concentration-response relationships in patients with epilepsy. Epilepsia. 2008 Jul;49(7):1123-41. doi: 10.1111/j.1528-1167.2008.01665.x. [Article]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
Drug created at March 19, 2008 16:17 / Updated at February 20, 2024 23:55