1.0 2011-09-21 00:32:15 UTC 2015-07-21 06:57:47 UTC FDB023601 Topiramate Topiramate 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] 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acid 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamate 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acid 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acid 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamate 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acid 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acid 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamate 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acid 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acid 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamate 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acid 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acid 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamate 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acid 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamate 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acid 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamate 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acid Epitomax McN-4853 RWJ-17021 Tipiramate Tipiramato Tipiramic acid Topamax Topamax Sprinkle Topiramate Topiramato Topiramatum Topiramic acid Topomax TPM C12H21NO8S 339.362 339.098787343 [(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 topiramate 97240-79-4 [H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2 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 KJADKKWYZYXHBB-XBWDGYHZSA-N 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. Dioxolopyrans Organic compounds Organoheterocyclic compounds Dioxolopyrans Aliphatic heteropolycyclic compounds 1,3-dioxolanes Hydrocarbon derivatives Ketals Monosaccharides Organic nitrogen compounds Organic oxides Organic sulfuric acids and derivatives Oxacyclic compounds Oxanes Acetal Aliphatic heteropolycyclic compound Dioxolopyran Hydrocarbon derivative Ketal Meta-dioxolane Monosaccharide Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfuric acid or derivatives Organooxygen compound Oxacycle Oxane cyclic ketal ketohexose derivative sulfamate ester Solid logp 1.29 ALOGPS logs -1.70 ALOGPS solubility 6.80e+00 g/l ALOGPS logp 0.13 ChemAxon pka_strongest_acidic 11.09 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac [(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 ChemAxon average_mass 339.362 ChemAxon mono_mass 339.098787343 ChemAxon smiles [H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2 ChemAxon formula C12H21NO8S ChemAxon 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 ChemAxon inchikey KJADKKWYZYXHBB-XBWDGYHZSA-N ChemAxon polar_surface_area 115.54 ChemAxon refractivity 72.3 ChemAxon polarizability 32.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 7643 Specdb::CMs 146216 Specdb::NmrOneD 54922 Specdb::NmrOneD 54923 Specdb::NmrOneD 54924 Specdb::NmrOneD 54925 Specdb::NmrOneD 54926 Specdb::NmrOneD 54927 Specdb::NmrOneD 54928 Specdb::NmrOneD 54929 Specdb::NmrOneD 54930 Specdb::NmrOneD 54931 Specdb::NmrOneD 54932 Specdb::NmrOneD 54933 Specdb::NmrOneD 54934 Specdb::NmrOneD 54935 Specdb::NmrOneD 54936 Specdb::NmrOneD 54937 Specdb::NmrOneD 54938 Specdb::NmrOneD 54939 Specdb::NmrOneD 54940 Specdb::NmrOneD 54941 Specdb::MsMs 255057 Specdb::MsMs 255058 Specdb::MsMs 255059 Specdb::MsMs 274998 Specdb::MsMs 274999 Specdb::MsMs 275000 Specdb::MsMs 374230 Specdb::MsMs 374388 Specdb::MsMs 439967 Specdb::MsMs 450258 Specdb::MsMs 450259 Specdb::MsMs 450653 Specdb::MsMs 450984 Specdb::MsMs 2236308 Specdb::MsMs 2237055 Specdb::MsMs 2238474 Specdb::MsMs 2239126 Specdb::MsMs 2240569 Specdb::MsMs 2241116 Specdb::MsMs 2242638 Specdb::MsMs 2243236 Specdb::MsMs 2809142 Specdb::MsMs 2809143 Specdb::MsMs 2809144 Specdb::MsMs 2900559 HMDB05034 TOR #<Reference:0x000055ce32c55ea8> #<Reference:0x000055ce32c55cf0> bitter Glutamate receptor, ionotropic kainate 1 P39086 GRIK1