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    Chemistry

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    Also known as: 106308-44-5, Banzel, Inovelon, 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide, Cgp 33101, Cgp-33101
    Molecular Formula
    C10H8F2N4O
    Molecular Weight
    238.19  g/mol
    InChI Key
    POGQSBRIGCQNEG-UHFFFAOYSA-N
    FDA UNII
    WFW942PR79
    Rufinamide
    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.
    1 2D Structure

    Rufinamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(2,6-difluorophenyl)methyl]triazole-4-carboxamide
    2.1.2 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)
    2.1.3 InChI Key
    POGQSBRIGCQNEG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C(=C1)F)CN2C=C(N=N2)C(=O)N)F
    2.2 Other Identifiers
    2.2.1 UNII
    WFW942PR79
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide

    2. Cgp 33101

    3. Cgp-33101

    4. Inovelon

    2.3.2 Depositor-Supplied Synonyms

    1. 106308-44-5

    2. Banzel

    3. Inovelon

    4. 1-(2,6-difluorobenzyl)-1h-1,2,3-triazole-4-carboxamide

    5. Cgp 33101

    6. Cgp-33101

    7. 1-[(2,6-difluorophenyl)methyl]-1h-1,2,3-triazole-4-carboxamide

    8. Ruf 331

    9. Xilep

    10. Ruf-331

    11. 1-[(2,6-difluorophenyl)methyl]triazole-4-carboxamide

    12. E-2080

    13. E2080

    14. E 2080

    15. Wfw942pr79

    16. 1h-1,2,3-triazole-4-carboxamide, 1-[(2,6-difluorophenyl)methyl]-

    17. Ncgc00165883-02

    18. 1h-1,2,3-triazole-4-carboxamide, 1-((2,6-difluorophenyl)methyl)-

    19. Dsstox_cid_26506

    20. Dsstox_rid_81675

    21. Dsstox_gsid_46506

    22. 1-[(2,6-difluorophenyl)methyl]-1h-1,2,3-triazole-4 Carboxamide

    23. Smr000857122

    24. C10h8f2n4o

    25. Cas-106308-44-5

    26. Unii-wfw942pr79

    27. Rufinamide [usan:inn:ban]

    28. Syn111

    29. Syn-111

    30. Cgp33101

    31. Banzel (tn)

    32. Mfcd00865314

    33. Rufinamide (banzel)

    34. Cgp 33,101

    35. Rufinamide [mi]

    36. Rufinamide [inn]

    37. Rufinamide [jan]

    38. Rufinamide [usan]

    39. Rufinamide [vandf]

    40. Rufinamide [mart.]

    41. Rufinamide [usp-rs]

    42. Rufinamide [who-dd]

    43. Rufinamide (jan/usp/inn)

    44. Mls001332513

    45. Mls001332514

    46. Rufinamide [ema Epar]

    47. Schembl230448

    48. Gtpl7470

    49. Zinc7782

    50. Chembl1201754

    51. Dtxsid1046506

    52. Rufinamide [orange Book]

    53. Chebi:134966

    54. Hms2232m19

    55. Hms3262o14

    56. Hms3371a06

    57. Hms3651o05

    58. Hms3884g07

    59. Rufinamide [usp Monograph]

    60. Bcp21828

    61. Hy-a0042

    62. Tox21 112267

    63. Tox21_112267

    64. Tox21_500796

    65. Bdbm50515492

    66. S1256

    67. Akos005145897

    68. Rufinamide, >=98% (hplc), Powder

    69. Tox21_112267_1

    70. Ac-1429

    71. Ccg-222100

    72. Cs-1455

    73. Db06201

    74. Lp00796

    75. Sb18904

    76. Sdccgsbi-0633757.p001

    77. Ncgc00165883-01

    78. Ncgc00165883-03

    79. Ncgc00165883-04

    80. Ncgc00165883-11

    81. Ncgc00261481-01

    82. As-13861

    83. Ft-0656828

    84. Ft-0674479

    85. R0143

    86. Sw219770-1

    87. C71253

    88. D05775

    89. Ab00918347-05

    90. Ab00918347_06

    91. 308r445

    92. A801414

    93. Q408565

    94. Sr-01000842156

    95. J-001568

    96. Sr-01000842156-4

    97. 1-[(2,6-difluorophenyl)methyl]-4-triazolecarboxamide

    98. F0001-2404

    99. Z1541638521

    100. 1-(2,6-difluorobenzyl)-1h-1,2,3-triazol-4-carboxamide

    101. Rufinamide, United States Pharmacopeia (usp) Reference Standard

    102. 1-[[2,6-bis(fluoranyl)phenyl]methyl]-1,2,3-triazole-4-carboxamide

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 238.19 g/mol
    Molecular Formula C10H8F2N4O
    XLogP30.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass238.06661722 g/mol
    Monoisotopic Mass238.06661722 g/mol
    Topological Polar Surface Area73.8 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity282
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameBanzel
    PubMed HealthRufinamide (By mouth)
    Drug ClassesAnticonvulsant
    Drug LabelBANZEL (rufinamide) is a triazole derivative structurally unrelated to currently marketed antiepileptic drugs (AEDs). Rufinamide has the chemical name 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4 carboxamide. It has an empirical formula of C10H...
    Active IngredientRufinamide
    Dosage FormTablet; Suspension
    RouteOral
    Strength200mg; 40mg/ml; 400mg
    Market StatusPrescription
    CompanyEisai

    2 of 2  
    Drug NameBanzel
    PubMed HealthRufinamide (By mouth)
    Drug ClassesAnticonvulsant
    Drug LabelBANZEL (rufinamide) is a triazole derivative structurally unrelated to currently marketed antiepileptic drugs (AEDs). Rufinamide has the chemical name 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4 carboxamide. It has an empirical formula of C10H...
    Active IngredientRufinamide
    Dosage FormTablet; Suspension
    RouteOral
    Strength200mg; 40mg/ml; 400mg
    Market StatusPrescription
    CompanyEisai

    4.2 Drug Indication

    Adjunct therapy for treatment of seizures associated with Lennox-Gastaut syndrome.

    FDA Label

    Inovelon is indicated as adjunctive therapy in the treatment of seizures associated with Lennox Gastaut syndrome in patients 4 years of age and older.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    At high concentrations will inhibit action of mGluR5 subtype receptors thus preventing the production of glutamate.

    5.2 MeSH Pharmacological Classification

    Voltage-Gated Sodium Channel Blockers

    A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    5.3 ATC Code

    N03AF03

    N03AF03

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N03 - Antiepileptics

    N03A - Antiepileptics

    N03AF - Carboxamide derivatives

    N03AF03 - Rufinamide

    5.4 Absorption, Distribution and Excretion

    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 L/mL; Cmax, 30mg/kg/day= 8.68 L/mL; AUC (0h-12h), 10mg/kg/day= 37.847 gh/mL; AUC (0h-12h), 30mg/kg/day= 89.359 gh/mL.

    Route of Elimination

    Renally (91%; 66% as CGP 47292, 2% as unchanged drug) and fecally (9%) eliminated.

    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.

    5.5 Metabolism/Metabolites

    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.

    5.6 Biological Half-Life

    Elimination half-life, healthy subjects and patients with epilepsy = 6-10 hours.

    5.7 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.

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    20-Jan-2021
    05-Jul-2024
    KGS
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    Average Price (USD/KGS)

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    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - SUSPENSION;ORAL - 40MG/ML

    USFDA APPLICATION NUMBER - 201367

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    DOSAGE - TABLET;ORAL - 100MG **Federal Regist...DOSAGE - TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21911

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    DOSAGE - TABLET;ORAL - 200MG

    USFDA APPLICATION NUMBER - 21911

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    DOSAGE - TABLET;ORAL - 400MG

    USFDA APPLICATION NUMBER - 21911

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