ChemSpider 2D Image | Rosiglitazone | C18H19N3O3S

Rosiglitazone

  • Molecular FormulaC18H19N3O3S
  • Average mass357.427 Da
  • Monoisotopic mass357.114716 Da
  • ChemSpider ID70383

More details:






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

Rosiglitazone [INN] [Wiki]
122320-73-4 [RN]
2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- [ACD/Index Name]
2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- (9CI)
5-(4-{2-[Methyl(2-pyridinyl)amino]ethoxy}benzyl)-1,3-thiazolidin-2,4-dion [German] [ACD/IUPAC Name]
5-(4-{2-[Methyl(2-pyridinyl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione [ACD/IUPAC Name]
5-(4-{2-[Méthyl(2-pyridinyl)amino]éthoxy}benzyl)-1,3-thiazolidine-2,4-dione [French] [ACD/IUPAC Name]
5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
7662
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

05V02F2KDG [DBID]
UNII:05V02F2KDG [DBID]
3U8PBH2BON [DBID]
6L2K7RBQ5H [DBID]
BR-72839 [DBID]
BRL 49653 [DBID]
BRL-49653 [DBID]
CCRIS 4693 [DBID]
EPA Pesticide Chemical Code 079011 [DBID]
KBio2_002183 [DBID]
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  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-24041]
    • Safety:

      20/21/22 Novochemy [NC-24041]
      20/21/36/37/39 Novochemy [NC-24041]
      5 Axon Medchem 2443
      A10BG02 Wikidata Q424771
      GHS07 Biosynth Q-201681
      GHS07; GHS09 Novochemy [NC-24041]
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 2443
      H315; H319 Biosynth Q-201681
      H332; H403 Novochemy [NC-24041]
      IRRITANT Matrix Scientific 090201
      no pictogram Axon Medchem 2443
      None LKT Labs [R5773]
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 2443
      P301+P310; P337+P313 Novochemy [NC-24041]
      P305+P351+P338 Biosynth Q-201681
      R52/53 Novochemy [NC-24041]
      Warning Biosynth Q-201681
      Warning Novochemy [NC-24041]
      Warning Axon Medchem 2443
    • Target Organs:

      PPAR agonist TargetMol T0334
    • Compound Source:

      synthetic Microsource [01504263]
    • Bio Activity:

      Biochemicals & small molecules/Agonists & activators Hello Bio [HB2556]
      Cell Cycle/DNA Damage MedChem Express HY-17386
      Cell Cycle/DNA Damage; NF-KB; MedChem Express HY-17386
      Cell process/Stem cells/Differentiation Hello Bio [HB2556]
      Metabolism TargetMol T0334
      Nuclear Receptors Tocris Bioscience 5325
      Potent and selective PPARγ agonist. Potent insulin sensitizing agent which binds PPAR receptors to fat cells and making the cells more responsive to insulin. Ameliorates insulin resistance and shows antidiabetic, hypoglycemic and anti-inflammatory action. Also promotes mesenchymal stem cells (MSCs) adipocyte differentiation and enhances endogenous neural progenitor cells (NPCs) proliferation. Hello Bio [HB2556]
      Potent and selective PPARγ agonist. Promotes adipocyte differentiation and enhances NPC proliferation. Hello Bio [HB2556]
      Potent and selective PPAR? agonist (EC50 = 60 nM); exhibits no activity at PPAR? and PPAR?. Promotes differentiation of pluripotent C3H10T1/2 stem cells into adipocytes. Exhibits antihyperglycemic act ivity in diabetic ob/ob mouse model. Antidiabetic agent. Tocris Bioscience 5325
      Potent and selective PPAR? agonist (EC50 = 60 nM); exhibits no activity at PPAR? and PPAR?. Promotes differentiation of pluripotent C3H10T1/2 stem cells into adipocytes. Exhibits antihyperglycemic activity in diabetic ob/ob mouse model. Antidiabetic agent. Tocris Bioscience 5325
      Potent and selective PPAR? agonist; antidiabetic agent. Tocris Bioscience 5325
      Potent and selective PPARgamma agonist (EC50 = 60 nM); exhibits no activity at PPARalpha and PPARbeta. Promotes differentiation of pluripotent C3H10T1/2 stem cells into adipocytes. Exhibits antihyperglycemic activity in diabetic ob/ob mouse model. Antidiabetic agent. Tocris Bioscience 5325
      Potent and selective PPARgamma agonist; antidiabetic agent. Tocris Bioscience 5325
      PPAR MedChem Express HY-17386
      PPAR TargetMol T0334
      PPAR Receptors Tocris Bioscience 5325
      PPARgamma Receptors Tocris Bioscience 5325
      PPARs Tocris Bioscience 5325
      Receptors & Transporters/Nuclear hormone/PPAR/PPARγ Hello Bio [HB2556]
      Rosiglitazone(BRL-49653) is a high-affinity selective agonist of the peroxisome proliferator-activated receptor-?(PPAR?).; IC50 Value: ; Target: PPAR?; in vitro: In competition experiments, rosiglitazone (BRL-49653), a potent antihyperglycemic agent, binds with high affinity to sites in intact adipocytes (IC50 = 12, 4 and 9 nM for rat, 3T3-L1 and human adipocytes, respectively) [1]. MedChem Express HY-17386

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

Density: 1.3±0.1 g/cm3
Boiling Point: 585.0±35.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.6 mmHg at 25°C
Enthalpy of Vaporization: 87.4±3.0 kJ/mol
Flash Point: 307.6±25.9 °C
Index of Refraction: 1.642
Molar Refractivity: 98.1±0.3 cm3
#H bond acceptors: 6
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 2.56
ACD/LogD (pH 5.5): 1.67
ACD/BCF (pH 5.5): 6.05
ACD/KOC (pH 5.5): 62.16
ACD/LogD (pH 7.4): 1.66
ACD/BCF (pH 7.4): 5.87
ACD/KOC (pH 7.4): 60.35
Polar Surface Area: 97 Å2
Polarizability: 38.9±0.5 10-24cm3
Surface Tension: 60.6±3.0 dyne/cm
Molar Volume: 271.6±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) =  3.19

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  626.18  (Adapted Stein & Brown method)
    Melting Pt (deg C):  271.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.95E-014  (Modified Grain method)
    Subcooled liquid VP: 1.52E-011 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):  10.45
       log Kow used: 3.19 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1032.8 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides
       Thiazolidinones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.69E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.328E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.19  (KowWin est)
  Log Kaw used:  -12.161  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.351
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4041
   Biowin2 (Non-Linear Model)     :   0.0430
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8074  (months      )
   Biowin4 (Primary Survey Model) :   3.0339  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1526
   Biowin6 (MITI Non-Linear Model):   0.0021
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2931
 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-009 Pa (1.52E-011 mm Hg)
  Log Koa (Koawin est  ): 15.351
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.48E+003 
       Octanol/air (Koa) model:  551 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 112.9216 E-12 cm3/molecule-sec
      Half-Life =     0.095 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.137 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  3632
      Log Koc:  3.560 

 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 = 1.760 (BCF = 57.52)
       log Kow used: 3.19 (estimated)

 Volatilization from Water:
    Henry LC:  1.69E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  6.55E+010  hours   (2.729E+009 days)
    Half-Life from Model Lake : 7.145E+011  hours   (2.977E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               7.67  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     7.53  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       0.00804         2.27         1000       
   Water     10.6            1.44e+003    1000       
   Soil      89              2.88e+003    1000       
   Sediment  0.42            1.3e+004     0          
     Persistence Time: 2.52e+003 hr




                    

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