TOR

[(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate

Created: 2009-06-03
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count4
Bond Count45
Aromatic Bond Count0
2D diagram of TOR

Chemical Component Summary

Name[(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate
Synonymstopiramate
Systematic Name (OpenEye OEToolkits)n/a
FormulaC12 H21 N O8 S
Molecular Weight339.362
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=S(=O)(OCC23OCC1OC(OC1C3OC(O2)(C)C)(C)C)N
SMILESCACTVS3.341CC1(C)O[CH]2CO[C]3(CO[S](N)(=O)=O)OC(C)(C)O[CH]3[CH]2O1
SMILESOpenEye OEToolkits1.5.0CC1(OC2COC3(C(C2O1)OC(O3)(C)C)COS(=O)(=O)N)C
Canonical SMILESCACTVS3.341 CC1(C)O[C@@H]2CO[C@@]3(CO[S](N)(=O)=O)OC(C)(C)O[C@H]3[C@@H]2O1
Canonical SMILESOpenEye OEToolkits1.5.0 CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C
InChIInChI1.03 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
InChIKeyInChI1.03 KJADKKWYZYXHBB-XBWDGYHZSA-N

Drug Info: DrugBank

DrugBank IDDB00273 
NameTopiramate
Groups approved
DescriptionTopiramate is a anti-epileptic drug used to manage seizures and prevent migraines.[A175249] It was initially approved by the FDA in 1996. In 2004, topiramate was approved for the prevention of migraine in adults.[A188309,L10544,L43478] Since 2012, the extended-release formulation has been approved in combination with [phentermine] for chronic weight management therapy in adults.[L10550] 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.[A175249] Interestingly, topiramate was discovered by chance when attempts were made to formulate a novel antidiabetic drug.[A188330]
Synonyms
  • Topiramate sodium
  • 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
  • Tipiramato
  • Topiramatum
  • Topiramate calcium
Brand Names
  • Ipg-topiramate
  • Toiramate
  • Gd-topiramate
  • Ag-topiramate Tablets
  • Mar-topiramate
IndicationTopiramate is indicated for the following conditions: 1)Monotherapy for partial onset or primary generalized tonic-clonic seizures for patients 2 years of age and above 2)Adjunctive therapy for partial onset seizures or primary generalized tonic-clonic seizures for both adult and pediatric patients above 2 years old 3)Adjunctive therapy for seizures associated with Lennox-Gastaut syndrome in patients above 2 years of age 4)Prophylaxis of migraine in children 12 years of age and older and adults.[L10544] Topiramate is also used off-label as an adjunct therapy for weight management[L10550] and for mood disorders.[A188312]
Categories
  • Alimentary Tract and Metabolism
  • Anti-Obesity Agents
  • Anticonvulsants
  • Antiobesity Preparations, Excl. Diet Products
  • Carbohydrates
ATC-Code
  • A08AA51
  • N03AX11
CAS number97240-79-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Gamma-aminobutyric acid receptor subunit alpha-1MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownagonist
Voltage-gated sodium channel alpha subunitMEQTVLVPPGPDSFNFFTRESLAAIERRIAEEKAKNPKPDKKDDDENGPK...unknowninhibitor
Kainate receptorsMEHGTLLAQPGLWTRDTSWALLYFLCYILPQTAPQVLRIGGIFETVENEP...unknownantagonist
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Carbonic anhydrase 4MRMLLALLALSAARPSASAESHWCYEVQAESSNYPCLVPVKWGGNCQKDR...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL220492
PubChem 5284627
ChEMBL CHEMBL220492
ChEBI CHEBI:63631
CCDC/CSD SEQKAA02, SEQKAA01, SEQKAA