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Showing Compound Topiramate (FDB023601)

Record Information
Version1.0
Creation date2011-09-21 00:32:15 UTC
Update date2015-07-21 06:57:47 UTC
Primary IDFDB023601
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number97240-79-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
McN-4853ChEBI
Topamax Sprinklehmdb
Topiramatehmdb
Predicted 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
Chemical FormulaC12H21NO8S
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
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 KeyKJADKKWYZYXHBB-XBWDGYHZSA-N
Isomeric SMILES[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2
Average Molecular Weight339.362
Monoisotopic Molecular Weight339.098787343
Classification
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

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTopiramate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-003r-5893000000-57939ef42b569234ad29Spectrum
Predicted GC-MSTopiramate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0239000000-994a7b97e101c455a7922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-01q9-2960000000-a11a150bcada5055d2e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0090000000-c1fa3d6ff15890fc14182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0059000000-a6337903cab01edce60e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0239000000-994a7b97e101c455a7922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01x0-1970000000-f0e80f5cc5d6fc2b6d382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-004i-9000000000-a8df5a6ea132d69b94892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-004i-9000000000-f76d8f2283f18dfa20be2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-004i-9000000000-316320612e65b9d317cb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-004i-9000000000-63d6b2cbde40b2bcd6392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9003000000-0b8ee634478a6f2f0eee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-000i-0009000000-086098dbff51e692c04f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0c0r-9850000000-ae199550ba647589f0882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9000000000-eab734dd0ed786cbba6d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1029000000-37869fd8dcd3ec0f4cc12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01po-4295000000-7cdbdca2d1d67b21879d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-9810000000-9b5c3fb12c27e09cf4502017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-4239000000-e56f7b1fecd3064e87832017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9164000000-892445ea4dcd3bf9420d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-7c64b90d0daae2c6e5b82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-9a74f9cc10019d27995c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0149000000-093e852afab8097cfa0f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-8790000000-0a33128bbe614c27cdf72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-345311bd602424b95a492021-09-24View Spectrum
NMRNot Available
ChemSpider ID4447672
ChEMBL IDCHEMBL220492
KEGG Compound IDC07502
Pubchem Compound ID5284627
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00273
HMDB IDHMDB05034
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDTOR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTopiramate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutamate receptor, ionotropic kainate 1GRIK1P39086
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference