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Also known as: 97240-79-4, Topamax, Epitomax, Topamax sprinkle, Topina, Mcn-4853
Molecular Formula
C12H21NO8S
Molecular Weight
339.36  g/mol
InChI Key
KJADKKWYZYXHBB-XBWDGYHZSA-N
FDA UNII
0H73WJJ391

Topiramate
A sulfamate-substituted fructose analog that was originally identified as a hypoglycemic agent. It is used for the treatment of EPILEPSY and MIGRAINE DISORDERS, and may also promote weight loss.
The mechanism of action of topiramate is as a Cytochrome P450 3A4 Inducer, and Cytochrome P450 2C19 Inhibitor. The physiologic effect of topiramate is by means of Decreased Central Nervous System Disorganized Electrical Activity.
1 2D Structure

Topiramate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate
2.1.2 InChI
InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
2.1.3 InChI Key
KJADKKWYZYXHBB-XBWDGYHZSA-N
2.1.4 Canonical SMILES
CC1(OC2COC3(C(C2O1)OC(O3)(C)C)COS(=O)(=O)N)C
2.1.5 Isomeric SMILES
CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C
2.2 Other Identifiers
2.2.1 UNII
0H73WJJ391
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2,3-4,5-bis-o-(1-methylethylidene)-beta-d-fructopyranose Sulfamate

2. Epitomax

3. Mcn 4853

4. Mcn-4853

5. Mcn4853

6. Topamax

7. Usl255

2.3.2 Depositor-Supplied Synonyms

1. 97240-79-4

2. Topamax

3. Epitomax

4. Topamax Sprinkle

5. Topina

6. Mcn-4853

7. Tipiramate

8. Topiramatum

9. Topimax

10. Topomax

11. Tipiramato

12. Topiramato

13. Epitoma

14. Topamac

15. Mcn 4853

16. Rwj-17021

17. Rwj-17021-000

18. C12h21no8s

19. 2,3:4,5-bis-o-(1-methylethylidene)-beta-d-fructopyranose Sulfamate

20. Sincronil

21. Usl255

22. Qudexy

23. Usl-255

24. 2,3:4,5-di-o-isopropylidene-beta-d-fructopyranose Sulfamate

25. (-)-topiramate

26. [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyltetrahydro-3ah-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl Sulfamate

27. Chebi:63631

28. Tipiramate [french]

29. Tipiramato [spanish]

30. 0h73wjj391

31. ((3as,5ar,8ar,8bs)-2,2,7,7-tetramethyltetrahydro-3ah-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl Sulfamate

32. Topiramatum [inn-latin]

33. Topiramatum [latin]

34. Topiramato [inn-spanish]

35. Mfcd00865320

36. Dsstox_cid_3688

37. Dsstox_rid_77148

38. Dsstox_gsid_23688

39. ((3as,5ar,8ar,8bs)-2,2,7,7-tetramethyltetrahydro-3ah-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl Sulfamate

40. [(1r,2s,6s,9r)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl Sulfamate

41. Tpm

42. Topiragen

43. Topax

44. Trokendi Xr

45. Qudexy Xr

46. Smr000466325

47. Topiramate (tpm)

48. Tor

49. Topamax (tn)

50. Cas-97240-79-4

51. Rwj 17021

52. Brn 5988957

53. Unii-0h73wjj391

54. Hsdb 7531

55. Sulfamate 7

56. 3hku

57. 3lxe

58. Usl 255

59. Topiramate [usan:usp:inn:ban]

60. Topiramate Solution

61. Ncgc00095181-01

62. [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[5,4-b:5',3'-d]pyran-3a-yl]methyl Sulfamate

63. Topiramate- Bio-x

64. Trokendi Xr (tn)

65. Eprontia

66. Ks-1122

67. Topiramate [mi]

68. Topiramate [inn]

69. Topiramate [jan]

70. Spectrum2_001128

71. Topiramate [hsdb]

72. Topiramate [inci]

73. Topiramate [usan]

74. Beta-d-fructopyranose, 2,3:4,5-bis-o-(1-methylethylidene)-, Sulfamate

75. Topiramate [vandf]

76. Cbchromo1_000352

77. Topiramate [mart.]

78. Topiramate [usp-rs]

79. Topiramate [who-dd]

80. Bidd:pxr0127

81. Schembl34631

82. Bspbio_002306

83. Topiramate (jan/usp/inn)

84. Eprontia (liquid Formulation)

85. Mls000759431

86. Mls001424070

87. Bidd:gt0854

88. Spectrum1505801

89. Spbio_000995

90. Chembl220492

91. Gtpl6849

92. Dtxsid8023688

93. Topiramate [orange Book]

94. Bdbm10887

95. 2,3:4,5-di-o-isopropylidene-b-d-fructopyranose Sulfamate

96. Topiramate [ep Monograph]

97. Topiramate [usp Impurity]

98. Qsymia Component Topiramate

99. Hms1922h06

100. Hms2051l09

101. Hms2093d20

102. Hms2232h21

103. Hms3414c15

104. Hms3678c15

105. Hms3715i12

106. Hms3884c17

107. Pharmakon1600-01505801

108. Topiramate [usp Monograph]

109. [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyltetrahydro-3ah-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl Sulfamate (non-preferred Name)

110. Act09031

111. Albb-022457

112. Hy-b0122

113. Tox21_111472

114. Tox21_302401

115. Nsc759251

116. S1438

117. Zinc95616603

118. Topiramate Component Of Qsymia

119. .beta.-d-fructopyranose, 2,3:4,5-bis-o-(1-methylethylidene)-, Sulfamate

120. Akos000424547

121. Topiramate 1.0 Mg/ml In Acetonitrile

122. Topiramate, >=98% (hplc), Solid

123. Tox21_111472_1

124. Ccg-100940

125. Cs-1885

126. Db00273

127. Nc00190

128. Nsc 759251

129. Nsc-759251

130. Ncgc00178714-01

131. Ncgc00178714-04

132. Ncgc00178714-18

133. Ncgc00255221-01

134. Bt167048

135. Sbi-0206907.p001

136. Sw197570-3

137. C07502

138. D00537

139. F20536

140. Ab00639961-06

141. Ab00639961-08

142. Ab00639961_09

143. Ab00639961_10

144. 240t794

145. A900173

146. Q221174

147. Sr-01000759409

148. W-60376

149. Q-201845

150. Sr-01000759409-4

151. Z1522553470

152. Topiramate, United States Pharmacopeia (usp) Reference Standard

153. 2,3:4,5-bis-o-(1-methylethylidene)-?-d-fructopyranose Sulfamate

154. 2,3:4,5-di-o-isopropylidene-.beta.-d-fructopyranose Sulfamate

155. Topiramate, Pharmaceutical Secondary Standard; Certified Reference Material

156. .beta.-d-fructopyranose, 2,3:4,5-bis-o-(1-methylethylidene)-, 1-sulfamate

157. Topiramate Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

158. [(1r,2s,6s,9r)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl Sulfamate

159. [(3as,5ar,8ar,8bs)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl Sulfamate

160. 2,3:4,5-bis-o-(1-methylethylidene)-beta-d-fructopyranose 1-sulfamate;2,3:4,5-di-o-isopropylidene-beta-d-fructopyranose Sulfamate; Topamax; Tracrium; Toiramate:

2.4 Create Date
2005-11-20
3 Chemical and Physical Properties
Molecular Weight 339.36 g/mol
Molecular Formula C12H21NO8S
XLogP3-0.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass339.09878780 g/mol
Monoisotopic Mass339.09878780 g/mol
Topological Polar Surface Area124 Ų
Heavy Atom Count22
Formal Charge0
Complexity556
Isotope Atom Count0
Defined Atom Stereocenter Count4
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 6  
Drug NameTopamax
PubMed HealthTopiramate (By mouth)
Drug ClassesAnticonvulsant, Central Nervous System Agent
Drug LabelTopiramate is a sulfamate-substituted monosaccharide. TOPAMAX (topiramate) Tablets are available as 25 mg, 50 mg, 100 mg, and 200 mg round tablets for oral administration. TOPAMAX (topiramate capsules) Sprinkle Capsules are available as 15 mg and...
Active IngredientTopiramate
Dosage FormTablet; Capsule
RouteOral
Strength200mg; 25mg; 15mg; 100mg; 50mg
Market StatusPrescription
CompanyJanssen Pharms