ChemSpider 2D Image | Topiramate | C12H21NO8S

Topiramate

  • Molecular FormulaC12H21NO8S
  • Average mass339.362 Da
  • Monoisotopic mass339.098785 Da
  • ChemSpider ID4447672
  • defined stereocentres - 4 of 4 defined stereocentres


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[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyr-3a-yl]methylsulfamat [German]
[(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 [ACD/IUPAC Name]
[(3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methylsulfamat [German] [ACD/IUPAC Name]
0H73WJJ391
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate
6099
97240-79-4 [RN]
RWJ 17021-000
Sulfamate de [(3aS,5aR,8aR,8bS)-2,2,7,7-tétraméthyltétrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]méthyle [French] [ACD/IUPAC Name]
Tipiramate [French]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63631 [DBID]
BRN 5988957 [DBID]
C07502 [DBID]
D00537 [DBID]
KW-6485 [DBID]
LS-69764 [DBID]
McN 4853 [DBID]
MCN-4853 [DBID]
PubChem Substance ID 329831176 [DBID]
SPBio_000995 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      white to off-white solid LGC Standards LGCFOR1348.00
    • Safety:

      GHS07 Biosynth Q-201846
      H319 Biosynth Q-201846
      N03AX11 Wikidata Q221174
      P305+P351+P338 Biosynth Q-201846
      Warning Biosynth Q-201846
      Xi Abblis Chemicals AB1009630
    • Target Organs:

      GABAR antagonist;GluR antagonist; Carbonic anhydrase inhibitor TargetMol T0675
    • Chemical Class:

      A hexose derivative that is 2,3:4,5-di-<element>O</element>-isopropylidene-<stereo>beta</stereo>-<stereo>D</stereo>-fructopyranose in which the hydroxy group has been converted to the corresponding su lfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine. ChEBI CHEBI:63631
    • Drug Status:

      approved BIONET-Key Organics KS-1122
    • Compound Source:

      synthetic; RWJ-17021 Microsource [01505801]
    • Bio Activity:

      Anticonvulsant. Antagonizes GluR5 kainate receptors (IC50 = 0.46 ?M), acts as a positive allosteric modulator of GABAA receptor-mediated currents, inhibits Nav channels (IC50 = 48.9 ?M) and inhibits L -type Ca2+ channels. Also inhibits carbonic anhydrase (CA) (Ki values are 0.1 and 0.2 ?M at rat CA II and CA IV respectively), which lowers intracellular neuronal pH. Tocris Bioscience 3620
      Anticonvulsant. Antagonizes GluR5 kainate receptors (IC50 = 0.46 ?M), acts as a positive allosteric modulator of GABAA receptor-mediated currents, inhibits Nav channels (IC50 = 48.9 ?M) and inhibits L-type Ca2+ channels. Also inhibits carbonic anhydrase (CA) (Ki values are 0.1 and 0.2 ?M at rat CA II and CA IV respectively), which lowers intracellular neuronal pH. Tocris Bioscience 3620
      Anticonvulsant. Antagonizes GluR5 kainate receptors (IC50 = 0.46 muM), acts as a positive allosteric modulator of GABAA receptor-mediated currents, inhibits Nav channels (IC50 = 48.9 muM) and inhibits L-type Ca2+ channels. Also inhibits carbonic anhydrase (CA) (Ki values are 0.1 and 0.2 muM at rat CA II and CA IV respectively), which lowers intracellular neuronal pH. Tocris Bioscience 3620
      Anticonvulsant. Antagonizes GluR5 kainate receptors (IC50 = 0.46 muM), acts as a positive allosteric modulator of GABAA receptor-mediated currents, inhibits Nav channels (IC50 = 48.9 muM) and inhibits L-type Ca2+ channels. Also inhibits carbonic anhydrase (CA) (Ki values are 0.1 and 0.2 muM at rat CA II and CA IV respectively), which lowers intracellular neuronal pH. Deuterated analog also available. Tocris Bioscience 3620
      GABAR;GluR5;Carbonic anhydrase TargetMol T0675
      GluR5 antagonist; inhibits carbonic anhydrase (CA) II and IV Tocris Bioscience 3620
      Glutamate (Ionotropic) Receptors Tocris Bioscience 3620
      GPCR/G protein MedChem Express HY-B0122
      GPCR/G protein; MedChem Express HY-B0122
      Ion Channels Tocris Bioscience 3620
      Ligand-gated Ion Channels Tocris Bioscience 3620
      mGluR MedChem Express HY-B0122
      Neuroscience TargetMol T0675
      Topiramate is an anticonvulsant that antagonizes GluR5 receptors and acts as a positive allosteric modulator of GABA receptor-mediated currents. MedChem Express
      Topiramate is an anticonvulsant that antagonizes GluR5 receptors and acts as a positive allosteric modulator of GABA receptor-mediated currents.; Target: GluR5 receptor; GABA receptor; Topiramate (Topamax) is a structurally novel broad-spectrum antiepileptic drug (AED) with established efficacy as monotherapy or adjunctive therapy in the treatment of adult and paediatric patients with generalised tonic-clonic seizures, partial seizures with or without generalised seizures, and seizures associated with Lennox-Gastaut syndrome [1]. MedChem Express HY-B0122
      Topiramate is an anticonvulsant that antagonizes GluR5 receptors and acts as a positive allosteric modulator of GABA receptor-mediated currents.;Target: GluR5 receptor; GABA receptor;Topiramate (Topamax) is a structurally novel broad-spectrum antiepileptic drug (AED) with established efficacy as monotherapy or adjunctive therapy in the treatment of adult and paediatric patients with generalised tonic-clonic seizures, partial seizures with or without generalised seizures, and seizures associated with Lennox-Gastaut syndrome [1]. topiramate has been believed to be a type of antiepileptic drug that blocks spread of seizures. Thus far, the mechanisms of its actions have been proven to include use-dependent inhibition of voltage-dependent Na+ channels in neurons, potentiation of GABA (gamma-amino-butyric acid)-induced Cl- influx, and inhibitory effects on inward currents by antagonizing kainate/alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptors [2].;Topiramate (me MedChem Express HY-B0122

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 438.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 69.6±3.0 kJ/mol
Flash Point: 219.1±31.5 °C
Index of Refraction: 1.497
Molar Refractivity: 74.3±0.4 cm3
#H bond acceptors: 9
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 2.97
ACD/LogD (pH 5.5): 2.15
ACD/BCF (pH 5.5): 25.26
ACD/KOC (pH 5.5): 351.12
ACD/LogD (pH 7.4): 2.14
ACD/BCF (pH 7.4): 24.90
ACD/KOC (pH 7.4): 346.04
Polar Surface Area: 124 Å2
Polarizability: 29.5±0.5 10-24cm3
Surface Tension: 53.4±3.0 dyne/cm
Molar Volume: 253.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -0.33

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  420.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  175.67  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7E-008  (Modified Grain method)
    Subcooled liquid VP: 2.56E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.364e+004
       log Kow used: -0.33 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.88E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.292E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.33  (KowWin est)
  Log Kaw used:  -14.440  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.110
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -1.7026
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7695  (months      )
   Biowin4 (Primary Survey Model) :   2.8491  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0209
   Biowin6 (MITI Non-Linear Model):   0.0019
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.7468
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000341 Pa (2.56E-006 mm Hg)
  Log Koa (Koawin est  ): 14.110
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00879 
       Octanol/air (Koa) model:  31.6 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.241 
       Mackay model           :  0.413 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  66.7218 E-12 cm3/molecule-sec
      Half-Life =     0.160 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.924 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.327 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.33 (estimated)

 Volatilization from Water:
    Henry LC:  8.88E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.215E+013  hours   (5.061E+011 days)
    Half-Life from Model Lake : 1.325E+014  hours   (5.521E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       1.46e-009       3.85         1000       
   Water     49.2            1.44e+003    1000       
   Soil      50.7            2.88e+003    1000       
   Sediment  0.096           1.3e+004     0          
     Persistence Time: 1.18e+003 hr




                    

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