ChemSpider 2D Image | Tazarotene | C21H21NO2S

Tazarotene

  • Molecular FormulaC21H21NO2S
  • Average mass351.462 Da
  • Monoisotopic mass351.129303 Da
  • ChemSpider ID5188

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118292-40-3 [RN]
3-pyridinecarboxylic acid, 6-[(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester
3-Pyridinecarboxylic acid, 6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester [ACD/Index Name]
6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester
6-[(4,4-Diméthyl-3,4-dihydro-2H-thiochromén-6-yl)éthynyl]nicotinate d'éthyle [French] [ACD/IUPAC Name]
6-[(4,4-diméthyl-3,4-dihydro-2H-thiochromén-6-yl)éthynyl]pyridine-3-carboxylate d'éthyle
Avage [Trade name]
Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]nicotinate [ACD/IUPAC Name]
ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate
Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AGN 190168 [DBID]
AGN-190168 [DBID]
C12531 [DBID]
CCRIS 4693 [DBID]
D01132 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Not Available Novochemy [NC-28840]
    • Safety:

      20/21/22 Novochemy [NC-28840]
      20/21/36/37/39 Novochemy [NC-28840]
      D05AX05 Wikidata Q3981685
      GHS07; GHS09 Novochemy [NC-28840]
      H332; H403 Novochemy [NC-28840]
      IRRITANT Matrix Scientific 090221
      P261; P262 Biosynth Q-102516
      P301+P310; P337+P313 Novochemy [NC-28840]
      Warning Novochemy [NC-28840]
      Xn Novochemy [NC-28840]
    • Chemical Class:

      The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin. ChEBI CHEBI:32184
    • Drug Status:

      approved BIONET-Key Organics BS-1012
    • Bio Activity:

      Nuclear Receptors Tocris Bioscience 3997
      RAR/RXR MedChem Express HY-15388
      Receptor-selective acetylenic retinoid; binds at retinoid acid receptors (RAR) -? and -?. Topically used for the treatment of skin disorders, particularly psoriasis and acne. Implicated in the treatme nt of basal cell carcinomas; induces upregulation of Bax in vivo. Exhibits antiproliferative and proapoptotic activity. Upregulates TIGs (Tazarotene-induced genes), including the cell adhesion molecul e TIG1 and the tumor-suppressor TIG3. Tocris Bioscience 3997
      Receptor-selective acetylenic retinoid; binds at retinoid acid receptors (RAR) -? and -?. Topically used for the treatment of skin disorders, particularly psoriasis and acne. Implicated in the treatment of basal cell carcinomas; induces upregulation of Bax in vivo. Exhibits antiproliferative and proapoptotic activity. Upregulates TIGs (Tazarotene-induced genes), including the cell adhesion molecule TIG1 and the tumor-suppressor TIG3. Tocris Bioscience 3997
      Receptor-selective acetylenic retinoid; binds at retinoid acid receptors (RAR) -beta and -gamma. Topically used for the treatment of skin disorders, particularly psoriasis and acne. Implicated in the treatment of basal cell carcinomas; induces upregulation of Bax in vivo. Exhibits antiproliferative and proapoptotic activity. Upregulates TIGs (Tazarotene-induced genes), including the cell adhesion molecule TIG1 and the tumor-suppressor TIG3. Tocris Bioscience 3997
      Receptor-selective retinoid; binds RAR-? and -? Tocris Bioscience 3997
      Receptor-selective retinoid; binds RAR-beta and -gamma Tocris Bioscience 3997
      Retinoic Acid Receptors Tocris Bioscience 3997

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

Density: 1.2±0.1 g/cm3
Boiling Point: 499.8±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 76.8±3.0 kJ/mol
Flash Point: 256.1±28.7 °C
Index of Refraction: 1.625
Molar Refractivity: 101.4±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 1
ACD/LogP: 6.22
ACD/LogD (pH 5.5): 5.67
ACD/BCF (pH 5.5): 12019.32
ACD/KOC (pH 5.5): 28971.20
ACD/LogD (pH 7.4): 5.67
ACD/BCF (pH 7.4): 12019.36
ACD/KOC (pH 7.4): 28971.30
Polar Surface Area: 64 Å2
Polarizability: 40.2±0.5 10-24cm3
Surface Tension: 57.5±5.0 dyne/cm
Molar Volume: 287.0±5.0 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) =  5.56

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  455.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  191.86  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.34E-009  (Modified Grain method)
    Subcooled liquid VP: 3.57E-007 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):  0.1085
       log Kow used: 5.56 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.94759 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.17E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.702E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  5.56  (KowWin est)
  Log Kaw used:  -9.052  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.612
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4159
   Biowin2 (Non-Linear Model)     :   0.2203
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1364  (months      )
   Biowin4 (Primary Survey Model) :   3.3974  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1838
   Biowin6 (MITI Non-Linear Model):   0.0278
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2894
 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):  4.76E-005 Pa (3.57E-007 mm Hg)
  Log Koa (Koawin est  ): 14.612
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.063 
       Octanol/air (Koa) model:  100 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.695 
       Mackay model           :  0.834 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  47.3179 E-12 cm3/molecule-sec
      Half-Life =     0.226 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.713 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.432000 E-17 cm3/molecule-sec
      Half-Life =     2.653 Days (at 7E11 mol/cm3)
      Half-Life =     63.667 Hrs
   Fraction sorbed to airborne particulates (phi): 0.765 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4.909E+005
      Log Koc:  5.691 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  3.776E-002  L/mol-sec
  Kb Half-Life at pH 8:     212.462  days   
  Kb Half-Life at pH 7:       5.817  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 3.581 (BCF = 3809)
       log Kow used: 5.56 (estimated)

 Volatilization from Water:
    Henry LC:  2.17E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.058E+007  hours   (2.108E+006 days)
    Half-Life from Model Lake : 5.518E+008  hours   (2.299E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              88.99  percent
    Total biodegradation:        0.75  percent
    Total sludge adsorption:    88.24  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       0.000279        5            1000       
   Water     3.81            1.44e+003    1000       
   Soil      59.6            2.88e+003    1000       
   Sediment  36.6            1.3e+004     0          
     Persistence Time: 4.4e+003 hr




                    

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