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97240-79-4 molecular structure
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[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate

ChemBase ID: 158
Molecular Formular: C12H21NO8S
Molecular Mass: 339.36204
Monoisotopic Mass: 339.09878764
SMILES and InChIs

SMILES:
S(=O)(=O)(OC[C@]12OC[C@H]3OC(O[C@H]3[C@@H]2OC(O1)(C)C)(C)C)N
Canonical SMILES:
NS(=O)(=O)OC[C@]12OC[C@@H]3[C@H]([C@@H]2OC(O1)(C)C)OC(O3)(C)C
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
InChIKey:
KJADKKWYZYXHBB-XBWDGYHZSA-N

Cite this record

CBID:158 http://www.chembase.cn/molecule-158.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate
[(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
IUPAC Traditional name
topiramate
Brand Name
Topamax
Topamax Sprinkle
Synonyms
Tipiramate [French]
Tipiramato [Spanish]
Topiramato [INN-Spanish]
Topiramatum [INN-Latin]
Topiramic acid
topiramate tablet
Topiramate
Topamax
2,3:4,5-Bis-O-(1-methylethylidene)-36-D-fructo-pyranose sulfamate
McN 4853
RWJ 17021
Topiramate
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fuctopyranose 1-Sulfamate
Epitoma
Epitomax
TPM
Topamac
Topimax
Topina
Topomax
CAS Number
97240-79-4
MDL Number
MFCD00865320
PubChem SID
160963621
24724627
46508334
PubChem CID
5284627

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.087058  H Acceptors
H Donor LogD (pH = 5.5) 0.12695874 
LogD (pH = 7.4) 0.12688065  Log P 0.12695974 
Molar Refractivity 72.302 cm3 Polarizability 30.44525 Å3
Polar Surface Area 115.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.29  LOG S -1.7 
Solubility (Water) 6.80e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
9.8 mg/mL expand Show data source
Chloroform expand Show data source
DMSO: ~44 mg/mL expand Show data source
Ethyl Acetate expand Show data source
Hexane expand Show data source
Methanol expand Show data source
Apperance
white solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
125-126°C expand Show data source
Hydrophobicity(logP)
-0.7 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
LS7083000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
carbonic anhydrase(CA) expand Show data source
Gene Information
human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768)mouse ... Car5a(12352)rat ... Car2(54231), Car4(29242) expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C12H21NO8S expand Show data source
Classification
Derivatives & analogs of Natural Compounds expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S1438 external link
Research Area: Post-traumatic stress disorder, Alcoholism
Biological Activity:
Topiramate is an anticonvulsant drug. The exact mechanism of action is unknown, but four properties that may contribute to topiramate’s antiepileptic and antimigraine efficacy include a blockage of voltage-dependent sodium channels, an augmentation of gamma- aminobutyrate acid activity at some subtypes of the GABA- A receptors, antagonism of AMPA/kainate subtype of the glutamate receptor, and inhibition of the carbonic anhydrase enzyme, particularly isozymes II and IV . [1] 
DrugBank - DB00273 external link
Item Information
Drug Groups approved; investigational
Description Topiramate (brand name Topamax) is an anticonvulsant drug produced by Ortho-McNeil Neurologics, 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. [Wikipedia]
Indication Used for the treatment and control of partial seizures and severe tonic-clonic (grand mal) seizures and also for the prevention of migraine headaches. In children it is also used for treatment of Lennox-Gastaut syndrome.
Pharmacology Topiramate is an anticonvulsant indicated in the treatment of epilepsy and migraine. 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, particular 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 secundarily generalized tonic-clonic seizures in the kindling model, findings predective of a broad spectrum of antiseizure activities clinically.
Toxicity Symptoms 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.
Affected Organisms
Humans and other mammals
Biotransformation Not extensively metabolized, 70% of the dose is eliminated unchanged in the urine. The other 30% is metabolized hepatically to six metabolites (formed by hydroxylation, hydrolysis, and glucuronidation), none of which constitute more than 5% of an administered dose.
Absorption Rapid with pleak plasma concentrations occurring after 2 hours and a bioavailability of 80%.
Half Life 19 to 23 hours
Protein Binding 15-41% (over the blood concentration range of 0.5 - 250 mg/mL).
Elimination Topiramate is not extensively metabolized and is primarily eliminated unchanged in the urine (approximately 70% of an administered dose).
Clearance * Oral plasma cl=20 - 30 mL/min [in humans following oral administration]
References
Blum D, Meador K, Biton V, Fakhoury T, Shneker B, Chung S, Mills K, Hammer A, Isojarvi J: Cognitive effects of lamotrigine compared with topiramate in patients with epilepsy. Neurology. 2006 Aug 8;67(3):400-6. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - T0575 external link
Biochem/physiol Actions
Kainate GluR5 receptor antagonist; anticonvulsant.
Toronto Research Chemicals - T540250 external link
Used as an anticonvulsant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Blum D, Meador K, Biton V, Fakhoury T, Shneker B, Chung S, Mills K, Hammer A, Isojarvi J: Cognitive effects of lamotrigine compared with topiramate in patients with epilepsy. Neurology. 2006 Aug 8;67(3):400-6. Pubmed
  • •  http://en.wikipedia.org/wiki/Topiramate
  • • Maryanoff, B.E., et al.: J. Med. Chem., 30, 880 (1987)
  • • Bialer, M.: Clin. Pharmacokinet., 24, 441 (1987)
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PATENTS

PATENTS

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INTERNET

INTERNET

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