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2D Structure
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 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

2D Structure

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.