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ChemSpider 2D Image | Tiagabine | C20H25NO2S2

Tiagabine

  • Molecular FormulaC20H25NO2S2
  • Average mass375.548 Da
  • Monoisotopic mass375.132660 Da
  • ChemSpider ID54661
  • defined stereocentres - 1 of 1 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidincarbonsäure [German] [ACD/IUPAC Name]
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid [ACD/IUPAC Name]
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid
(R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid
(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid
(R)-Tiagabine
115103-54-3 [RN]
3-Piperidinecarboxylic acid, 1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-, (3R)- [ACD/Index Name]
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A 70569 [DBID]
NO 328 [DBID]
ABT-569 [DBID]
C07503 [DBID]
PubChem Substance ID 329831176 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Toxicity:

      Organic Compound; Amine; Drug; GABA Agonist; Anticonvulsant; Neuroprotective Agent; Neurotransmitter Uptake Inhibitor; Metabolite; Synthetic Compound Toxin, Toxin-Target Database T3D2926
    • Safety:

      N03AG06 Wikidata Q907219
    • Target Organs:

      GABAR inhibitor TargetMol T2407
    • Chemical Class:

      A piperidinemonocarboxylic acid that is (<stereo>R</stereo>)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group. A GABA reuptake inhibitor, it is used (generally as the hydrochloride salt) for the treatment of epilepsy. ChEBI CHEBI:9586
    • Bio Activity:

      GABA TargetMol T2407
      Neuroscience TargetMol T2407
      Others MedChem Express HY-B0696
      Tiagabine(NO328) is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor. MedChem Express
      Tiagabine(NO328) is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor.; Target: GABA reuptake inhibitor; Tiagabine had an early onset of effect, as shown by significant reduction from baseline in mean HAM-A total score compared with placebo at week 1 (observed cases, p < .05). MedChem Express HY-B0696
      Tiagabine(NO328) is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor.;Target: GABA reuptake inhibitor;Tiagabine had an early onset of effect, as shown by significant reduction from baseline in mean HAM-A total score compared with placebo at week 1 (observed cases, p < .05). Tiagabine was generally well tolerated and not associated with changes in sexual functioning or depressive status. Symptoms of a discontinuation syndrome during taper were not observed. Tiagabine may be a useful treatment option for adult patients diagnosed with GAD [1]. Tiagabine was generally well tolerated; the most common adverse events were nausea, dizziness and headaches [2]. Tiagabine (0.1 microM), an antiepileptic drug that specifically inhibits the GAT-1 GABA transporter inhibited GABA uptake 50% in temporal cortex and 60-68% in white structures [3]. MedChem Express HY-B0696

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

Density: 1.2±0.1 g/cm3
Boiling Point: 568.0±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 89.7±3.0 kJ/mol
Flash Point: 297.3±30.1 °C
Index of Refraction: 1.605
Molar Refractivity: 107.0±0.3 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 5.68
ACD/LogD (pH 5.5): 2.45
ACD/BCF (pH 5.5): 10.74
ACD/KOC (pH 5.5): 37.05
ACD/LogD (pH 7.4): 2.45
ACD/BCF (pH 7.4): 10.74
ACD/KOC (pH 7.4): 37.05
Polar Surface Area: 97 Å2
Polarizability: 42.4±0.5 10-24cm3
Surface Tension: 49.8±3.0 dyne/cm
Molar Volume: 310.7±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) =  2.04

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  587.95  (Adapted Stein & Brown method)
    Melting Pt (deg C):  319.79  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.25E-014  (Modified Grain method)
    Subcooled liquid VP: 1.52E-010 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):  0.6634
       log Kow used: 2.04 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15.66 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines-acid
       Thiophenes-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.52E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.400E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.04  (KowWin est)
  Log Kaw used:  -10.842  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.882
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5455
   Biowin2 (Non-Linear Model)     :   0.0601
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3294  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2664  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0034
   Biowin6 (MITI Non-Linear Model):   0.0054
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6394
 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):  2.03E-008 Pa (1.52E-010 mm Hg)
  Log Koa (Koawin est  ): 12.882
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  148 
       Octanol/air (Koa) model:  1.87 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.993 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 238.7005 E-12 cm3/molecule-sec
      Half-Life =     0.045 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.538 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   163.799988 E-17 cm3/molecule-sec
      Half-Life =     0.007 Days (at 7E11 mol/cm3)
      Half-Life =     10.075 Min
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8.153E+004
      Log Koc:  4.911 

 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: 2.04 (estimated)

 Volatilization from Water:
    Henry LC:  3.52E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.223E+009  hours   (1.343E+008 days)
    Half-Life from Model Lake : 3.516E+010  hours   (1.465E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               2.28  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.19  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       0.00707         0.145        1000       
   Water     28.6            900          1000       
   Soil      71.3            1.8e+003     1000       
   Sediment  0.116           8.1e+003     0          
     Persistence Time: 894 hr




                    

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