Topiramate sodiumProduct ingredient for Topiramate
- Name
- Topiramate sodium
- Drug Entry
- Topiramate
Topiramate is a anti-epileptic drug used to manage seizures and prevent migraines.4 It was initially approved by the FDA in 1996. In 2004, topiramate was approved for the prevention of migraine in adults.6,19,23 Since 2012, the extended-release formulation has been approved in combination with phentermine for chronic weight management therapy in adults.21
Characteristics that distinguish topiramate from other antiepileptic drugs are a monosaccharide chemical structure containing a sulfamate, and 40% of its mass accounted for by oxygen.4 Interestingly, topiramate was discovered by chance when attempts were made to formulate a novel antidiabetic drug.8
- Accession Number
- DBSALT002318
- Structure
Structure for Topiramate sodium (DBSALT002318)
- Synonyms
- Not Available
- UNII
- N808MSN0PT
- CAS Number
- 488127-49-7
- Weight
- Average: 361.34
Monoisotopic: 361.08073206 - Chemical Formula
- C12H20NNaO8S
- InChI Key
- ZUWVVMMRNQEJMW-WGAVTJJLSA-N
- InChI
- InChI=1S/C12H20NO8S.Na/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,(H-,13,14,15);/q-1;+1/t7-,8-,9+,12+;/m1./s1
- IUPAC Name
- sodium (1R,2S,6S,9R)-6-{[(azanidylsulfonyl)oxy]methyl}-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecane
- SMILES
- [Na+].CC1(C)O[C@@H]2CO[C@@]3(COS([NH-])(=O)=O)OC(C)(C)O[C@H]3[C@@H]2O1
- External Links
- ChemSpider
- 8100733
- Predicted Properties
Property Value Source Water Solubility 12.3 mg/mL ALOGPS logP 1.26 ALOGPS logP 0.13 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 11.09 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 109.75 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 71.5 m3·mol-1 Chemaxon Polarizability 31.88 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon