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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:50:34 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005034
Secondary Accession Numbers
  • HMDB05034
Metabolite Identification
Common NameTopiramate
DescriptionTopiramate is an anticonvulsant drug used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm; Chemically, topiramate is a sulfamate-substituted monosaccharide, related to fructose, a rather unusual chemical structure for an anticonvulsant. Topiramate is quickly absorbed after oral use. Most of the drug (70%) is excreted in the urine as unchanged drug. The remainder is extensively metabolized by hydroxylation, hydrolysis, and glucuronidation. Six metabolites have been identified in humans, none of which constitutes more than 5% of an administered dose. Topiramate enhances GABA-activated chloride channels. In addition, topiramate inhibits excitatory neurotransmission, through actions on kainate and AMPA receptors. There is evidence that topiramate has a specific effect on GluR5 kainate receptors. It is also an inhibitor of carbonic anhydrase, particularly subtypes II and IV, but this action is weak and unlikely to be related to its anticonvulsant actions, but may account for the bad taste and the development of renal stones seen during treatment. Its possible effect as a mood stabilizer seems to occur before anticonvulsant qualities at lower dosages. Topiramate inhibits maximal electroshock and pentylenetetrazol-induced seizures as well as partial and secondarily generalized tonic-clonic seizures in the kindling model, findings predictive of a broad spectrum of antiseizure activities clinically; Johnson. It is used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved for, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics; Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Johnson. It is used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved for, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics.
Structure
Data?1582752341
Synonyms
ValueSource
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamateChEBI
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamateChEBI
MCN-4853ChEBI
RWJ-17021ChEBI
TipiramateChEBI
TipiramatoChEBI
TopamaxChEBI
TopiramatoChEBI
TopiramatumChEBI
TPMChEBI
Trokendi XRKegg
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamateGenerator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamateGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acidGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamateGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acidGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamateGenerator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acidGenerator
Tipiramic acidGenerator
Topiramic acidGenerator
EpitomaxHMDB
Topamax sprinkleHMDB
TopomaxHMDB
2,3-4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamateHMDB
Chemical FormulaC12H21NO8S
Average Molecular Weight339.362
Monoisotopic Molecular Weight339.098787343
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
Traditional Nametopiramate
CAS Registry Number97240-79-4
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 Identifier
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
InChI KeyKJADKKWYZYXHBB-XBWDGYHZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxolopyrans
Sub ClassNot Available
Direct ParentDioxolopyrans
Alternative Parents
Substituents
  • Dioxolopyran
  • Ketal
  • Oxane
  • Monosaccharide
  • Organic sulfuric acid or derivatives
  • Meta-dioxolane
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 - 126 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.8 g/LALOGPS
logP1.29ALOGPS
logP0.13ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.09ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.3 m³·mol⁻¹ChemAxon
Polarizability32.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.96731661259
DarkChem[M-H]-173.05931661259
DeepCCS[M-2H]-214.68930932474
DeepCCS[M+Na]+191.19230932474
AllCCS[M+H]+175.232859911
AllCCS[M+H-H2O]+172.332859911
AllCCS[M+NH4]+177.832859911
AllCCS[M+Na]+178.632859911
AllCCS[M-H]-175.432859911
AllCCS[M+Na-2H]-175.532859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Topiramate[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O23039.0Standard polar33892256
Topiramate[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O22252.4Standard non polar33892256
Topiramate[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O22240.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Topiramate,1TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12305.4Semi standard non polar33892256
Topiramate,1TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12477.2Standard non polar33892256
Topiramate,1TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O13219.1Standard polar33892256
Topiramate,2TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12370.4Semi standard non polar33892256
Topiramate,2TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12685.7Standard non polar33892256
Topiramate,2TMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O13161.8Standard polar33892256
Topiramate,1TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12539.6Semi standard non polar33892256
Topiramate,1TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12791.0Standard non polar33892256
Topiramate,1TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O13268.3Standard polar33892256
Topiramate,2TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O12771.3Semi standard non polar33892256
Topiramate,2TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O13223.3Standard non polar33892256
Topiramate,2TBDMS,isomer #1CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O13257.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Topiramate GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-5893000000-57939ef42b569234ad292017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Topiramate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate LC-ESI-qTof , Positive-QTOFsplash10-03di-0239000000-994a7b97e101c455a7922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate LC-ESI-qTof , Positive-QTOFsplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate Linear Ion Trap , negative-QTOFsplash10-01q9-2960000000-a11a150bcada5055d2e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate Linear Ion Trap , positive-QTOFsplash10-014i-0090000000-c1fa3d6ff15890fc14182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate Linear Ion Trap , positive-QTOFsplash10-00di-0059000000-a6337903cab01edce60e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate , positive-QTOFsplash10-03di-0239000000-994a7b97e101c455a7922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate , positive-QTOFsplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 60V, Negative-QTOFsplash10-004i-9000000000-a8df5a6ea132d69b94892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 45V, Negative-QTOFsplash10-004i-9000000000-f76d8f2283f18dfa20be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 75V, Negative-QTOFsplash10-004i-9000000000-316320612e65b9d317cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 90V, Negative-QTOFsplash10-004i-9000000000-63d6b2cbde40b2bcd6392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 30V, Negative-QTOFsplash10-004i-9003000000-0b8ee634478a6f2f0eee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 15V, Negative-QTOFsplash10-000i-0009000000-086098dbff51e692c04f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 35V, Positive-QTOFsplash10-0c0r-9850000000-ae199550ba647589f0882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Topiramate 35V, Negative-QTOFsplash10-004i-9000000000-eab734dd0ed786cbba6d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 10V, Positive-QTOFsplash10-0006-1029000000-37869fd8dcd3ec0f4cc12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 20V, Positive-QTOFsplash10-01po-4295000000-7cdbdca2d1d67b21879d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 40V, Positive-QTOFsplash10-03fr-9810000000-9b5c3fb12c27e09cf4502017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 10V, Negative-QTOFsplash10-002r-4239000000-e56f7b1fecd3064e87832017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 20V, Negative-QTOFsplash10-004j-9164000000-892445ea4dcd3bf9420d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 40V, Negative-QTOFsplash10-004i-9100000000-7c64b90d0daae2c6e5b82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 10V, Positive-QTOFsplash10-0006-0009000000-9a74f9cc10019d27995c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 20V, Positive-QTOFsplash10-0006-0149000000-093e852afab8097cfa0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 40V, Positive-QTOFsplash10-03dm-8790000000-0a33128bbe614c27cdf72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topiramate 10V, Negative-QTOFsplash10-000i-0019000000-345311bd602424b95a492021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Brain
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.47 +/- 0.03 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00273
Phenol Explorer Compound IDNot Available
FooDB IDFDB023601
KNApSAcK IDNot Available
Chemspider ID4447672
KEGG Compound IDC07502
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTopiramate
METLIN IDNot Available
PubChem Compound5284627
PDB IDTOR
ChEBI ID63631
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMaryanoff, Bruce E.; Gardocki, Joseph F. Anticonvulsant sulfamate derivatives. U.S. (1985), CODEN: USXXAM US 4513006 A 19850423 CAN 103:37701 AN 1985:437701
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus
Gene Name:
GRIK1
Uniprot ID:
P39086
Molecular weight:
103979.7
General function:
Involved in carbonate dehydratase activity
Specific function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
General function:
Involved in ion channel activity
Specific function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:
SCN1A
Uniprot ID:
P35498
Molecular weight:
228969.5