Topiramate (CED0002098)

Record Information
Version1.0
Creation Date2009-07-21 20:26:27 UTC
Update Date2026-08-18 20:28:44 UTC
Accession NumberCHEM002157
Identification
Common NameTopiramate
ClassSmall Molecule
Description
Topiramate belongs to the dioxolopyrans, a class of organoheterocyclic compounds within the organic compounds. It has the chemical formula C12H21NO8S and an average molecular weight of 339.36 g/mol. This exogenous compound is a solid at room temperature. It has been detected in the brain and prostate tissues. Topiramate is used as an anticonvulsant and functions biologically as a sodium channel blocker. Its recorded sources include antiepileptics, antiobesity preparations (excluding diet products), healthcare, pharmaceuticals and veterinary products, electrical and electronic equipment such as magnets, relays and electric hearing aids, food, food processing and cookware specifically the preparation of wine or sparkling wine, and household cleaning and consumer products including other smoking requisites and non-electric simulated smoking devices. The recorded exposure route for this compound is oral. The compound interacts with 30 recorded protein targets. These include the gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1), sodium channel protein type 1 subunit alpha (SCN1A), carbonic anhydrase 2 (CA2), and carbonic anhydrase 4 (CA4). It also acts as an antagonist or inhibitor of carbonic anhydrase 1 (CA1), carbonic anhydrase 3 (CA3), carbonic anhydrase 5A mitochondrial (CA5A), and sodium channel protein type 4 subunit alpha (SCN4A), among 21 other proteins. While the precise mechanism of action is not known, studies indicate that topiramate blocks action potentials elicited repetitively by a sustained depolarization of neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Additionally, it augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor, which controls an integral chloride channel.
Contaminant Type
  • Anti-Obesity Agent
  • Anticonvulsant
  • Drug
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Neuroprotective Agent
  • Organic Compound
  • Synthetic Compound
Chemical Structure
SynonymsNot Available
Chemical FormulaC12H21NO8S
Average Molecular Mass339.362 g/mol
Monoisotopic Mass339.099 g/mol
CAS Registry Number97240-79-4
IUPAC NameNot Available
Traditional NameNot Available
SMILES[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2
InChI IdentifierInChI=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
InChI KeyInChIKey=KJADKKWYZYXHBB-XBWDGYHZSA-N
Chemical Taxonomy
ClassificationNot classified
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Prostate
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point125 - 126°C
Boiling PointNot Available
Solubility9.8 mg/mL
Predicted PropertiesNot Available
Spectra
SpectraNot Available
Toxicity Profile
Mechanism of ToxicityThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamate excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include abdominal pain, agitation, blurred vision, convulsions, depression, dizziness, double vision, drowsiness, impaired coordination, impaired mental activity, low blood pressure, reduced consciousness, severe diarrhea, sluggishness, and speech problems.
TreatmentIn acute Topiramate overdose, if the ingestion is recent, the stomach should be emptied immediately by lavage or by induction of emesis. Activated charcoal has been shown to adsorb topiramate in vitro. Treatment should be appropriately supportive. Hemodialysis is an effective means of removing topiramate from the body. (5)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2476.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
260Antiobesity preparations, excl. diet productsHealthcare, pharmaceuticals & veterinary productsNot Available
371AntiepilepticsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCarbonic anhydrase 2P27139Rattus norvegicusPredicted (SEA)0.0778492
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)1.63483
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)2.02408
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)0.622794
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)0.544945
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)0.467095
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)0.778492
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)10.1204
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)5.44945
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)15.5698
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)3.11397
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)30.8283
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)31.5289
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)53.0932
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)49.3564
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)52.3147
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)44.2962
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)36.0442
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)33.3973
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)28.8042
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)33.3195
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)69.1301
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)34.9543
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)34.7208
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)33.553
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansKnownThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamat excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Sodium channel protein type 1 subunit alpha structureClick to view 3D structureSodium channel protein type 1 subunit alphaP35498HumansKnownThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamat excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansKnownThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamat excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P39086HumansKnownThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamat excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansKnownThe precise mechanism of action of topiramate is not known. However, studies have shown that topiramate blocks the action potentials elicited repetitively by a sustained depolarization of the neurons in a time-dependent manner, suggesting a state-dependent sodium channel blocking action. Topiramate also augments the activity of the neurotransmitter gamma-aminobutyrate (GABA) at some subtypes of the GABAA receptor (controls an integral chloride channel), indicating a possible mechanism through potentiation of the activity of GABA. Topiramate also demonstrates antagonism of the AMPA/kainate subtype of the glutamat excitatory amino acid receptor. It also inhibits carbonic anhydrase (particularly isozymes II and IV), but this action is weak and unlikely to be related to its anticonvulsant actions.
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansKnownNot Available
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansKnownNot Available
Concentrations
Not Available
External Links
IdentifiersNot Available
References
Synthesis Reference

Orn Almarsson, “Topiramate salts and compositions comprising and methods of making and using the same.” U.S. Patent US20040053853, issued March 18, 2004.

MSDSLink
General ReferencesNot Available