ChemSpider 2D Image | Dasatinib | C22H26ClN7O2S

Dasatinib

  • Molecular FormulaC22H26ClN7O2S
  • Average mass488.005 Da
  • Monoisotopic mass487.155731 Da
  • ChemSpider ID2323020

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Featured data source



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

302962-49-8 [RN]
5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]- [ACD/Index Name]
8712
dasatinib [Spanish] [INN]
dasatinib [French] [INN]
Dasatinib anhydrous
dasatinibum [Latin] [INN]
N-(2-Chlor-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl}amino)-1,3-thiazol-5-carboxamid [German] [ACD/IUPAC Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BMS354825 [DBID]
BMS 354825 [DBID]
BMS 35482513 [DBID]
BMS-354825 [DBID]
BR-47532 [DBID]
C488369 [DBID]
cid_3062316 [DBID]
D03658 [DBID]
Kinome_3650 [DBID]
Pharmakon1600-01502275 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1392
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1392
      IRRITANT Matrix Scientific 075512
      L01XE06 Wikidata Q419940
      no pictogram Axon Medchem 1392
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1392
      P261; P262 Biosynth Q-101345
      TBC SynQuest 8H48-5-73
      Toxic/Harmful/Teratogenic/Store at -20?C SynQuest 8H48-5-73
      Warning Axon Medchem 1392
    • Target Organs:

      Src inhibitor;Abl inhibitor;c-Kit inhibitor;EPHA antagonist TargetMol T1448
    • Chemical Class:

      An aminopyrimidine that is 2-methylpyrimidine which is substituted at position 4 by the primary amino group of 2-amino-1,3-thiazole-5-carboxylic acid and at position 6 by a 4-(2-hydroxyethyl)piperazin -1-yl group, and in which the carboxylic acid group has been formally condensed with 2-chloro-6-methylaniline to afford the corresponding amide. A multi-targeted kinase inhibitor, it is used, particul arly as the monohydrate, for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USA N) as well as to anhydrous dasatinib (INN). ChEBI CHEBI:49375
    • Bio Activity:

      Bcr-Abl MedChem Express HY-10181
      Bcr-Abl Src MedChem Express HY-10181
      Dasatinib(BMS-354825) is a potent and dual Abl/ Src inhibitor IC50 of ?1 nM/0.8 nM respectively; also inhibit c-Kit (WT)/c-Kit (D816V) with IC50 of 79 nM/37 nM.; IC50 value: ?1 nM/0.8 nM(Abl/ Src); 79 nM/37 nM (c-Kit WT/c-Kit D816V) [1] [2]; Target: Abl; Src; c-Kit; in vitro: Dasatinib is more effective than imatinib in inhibiting the proliferation of Ba/F3 cells expressing wild-type Bcr-Abl and Bcr-Abl mutants, with the exception of T315I. MedChem Express HY-10181
      Protein Tyrosine Kinase/RTK MedChem Express HY-10181
      Protein Tyrosine Kinase/RTK; MedChem Express HY-10181
      Src;Abl, Lck, Yes, Fyn;c-Kit; EPHA 2 TargetMol T1448
      Tyrosine Kinase/Adaptors TargetMol T1448

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

Density: 1.4±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.688
Molar Refractivity: 132.0±0.3 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 2.24
ACD/LogD (pH 5.5): -0.44
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 2.17
ACD/BCF (pH 7.4): 20.97
ACD/KOC (pH 7.4): 235.14
Polar Surface Area: 135 Å2
Polarizability: 52.3±0.5 10-24cm3
Surface Tension: 73.8±3.0 dyne/cm
Molar Volume: 346.4±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) =  1.10

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  696.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  304.61  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.76E-020  (Modified Grain method)
    Subcooled liquid VP: 1.18E-016 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):  98.38
       log Kow used: 1.10 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  15621 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.86E-029  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.718E-022 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.10  (KowWin est)
  Log Kaw used:  -27.119  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  28.219
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1667
   Biowin2 (Non-Linear Model)     :   0.0007
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.2256  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.4918  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4714
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -4.0776
 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):  1.57E-014 Pa (1.18E-016 mm Hg)
  Log Koa (Koawin est  ): 28.219
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.91E+008 
       Octanol/air (Koa) model:  4.06E+015 
   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 = 323.8530 E-12 cm3/molecule-sec
      Half-Life =     0.033 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.780 Min
   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    :  1.018E+004
      Log Koc:  4.008 

 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 = -0.504 (BCF = 0.3137)
       log Kow used: 1.10 (estimated)

 Volatilization from Water:
    Henry LC:  1.86E-029 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.954E+025  hours   (2.897E+024 days)
    Half-Life from Model Lake : 7.586E+026  hours   (3.161E+025 days)

 Removal In Wastewater Treatment:
    Total removal:               1.90  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       2.57e-012       0.793        1000       
   Water     45.7            4.32e+003    1000       
   Soil      54.2            8.64e+003    1000       
   Sediment  0.102           3.89e+004    0          
     Persistence Time: 1.74e+003 hr




                    

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