ChemSpider 2D Image | Azathioprine | C9H7N7O2S

Azathioprine

  • Molecular FormulaC9H7N7O2S
  • Average mass277.263 Da
  • Monoisotopic mass277.038177 Da
  • ChemSpider ID2178

More details:



Featured data source



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

1291
1H-Purine, 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-
207-175-4 [EINECS]
446-86-6 [RN]
6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purin [German] [ACD/IUPAC Name]
6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purine [ACD/IUPAC Name]
6-[(1-Méthyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-1H-purine [French] [ACD/IUPAC Name]
6-[(1-Methyl-4-nitroimidazol-5-yl)thio]purine
7H-Purine, 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]- [ACD/Index Name]
Azamun [Trade name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

A2593_SIAL [DBID]
A4638_SIAL [DBID]
AI3-50290 [DBID]
AI-981/34845012 [DBID]
AIDS047879 [DBID]
AIDS-047879 [DBID]
BW 57322 [DBID]
CBDivE_013132 [DBID]
CCRIS 62 [DBID]
CHEBI:2948 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      YELLOW POWDER NIH Clinical Collection [SMR000427366]
    • Safety:

      45-22-36/37/38-20/21/22 LKT Labs [A9803]
      Carc., Xn, Xi LKT Labs [A9803]
      H350, H302, H319, H335, H315, H332, H312, H302 LKT Labs [A9803]
      IRRITANT Matrix Scientific 047900
      L04AX01 Wikidata Q18939
    • Target Organs:

      Rac1 inhibitor;DNA sythesis inhibitor TargetMol T1237
    • Chemical Class:

      A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, presc ribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS. ChEBI CHEBI:2948
    • Drug Status:

      approved BIONET-Key Organics KS-1146
    • Compound Source:

      synthetic Microsource [01500133]
    • Bio Activity:

      Azathioprine(Azasan, Imuran; BW 57-322) is a drug that suppresses the immune system and is used in organ transplantation and autoimmune disease. MedChem Express HY-B0256, http://www.medchemexpress.com/dydrogesterone.html
      Azathioprine(Azasan, Imuran; BW 57-322) is a drug that suppresses the immune system and is used in organ transplantation and autoimmune disease. ;Target: Azathioprine is an immunosuppressive antimetabolite pro-drug. It is an imidazolyl derivative of 6-mercaptopurine and many of its biological effects are similar to those of the parent compound. Azathioprine is converted into 6-mercaptopurine in the body where it blocks purine metabolism and DNA synthesis. Thus it most strongly affects proliferating cells, such as the T cells and B cells of the immune system. The main adverse effect of azathioprine is bone marrow suppression, which can be life-threatening, especially in people with a genetic deficiency of the enzyme thiopurine S-methyltransferase. It is also listed by the International Agency for Research on Cancer as a Group 1 carcinogen (carcinogenic to humans) [1-3]. MedChem Express HY-B0256
      Cell Biology Tocris Bioscience 4099
      Cell Metabolism Tocris Bioscience 4099
      DNA Damage/DNA Repair TargetMol T1237
      DNA, RNA and Protein Synthesis Tocris Bioscience 4099
      Others MedChem Express HY-B0256
      Purine analog. Blocks DNA replication and the de novo pathway of purine synthesis. Immunosuppressive and anti-inflammatory drug; induces apoptosis in human T-lymphocytes. Prodrug of 6-mercaptopurine ( Cat. No. 4103). Tocris Bioscience 4099
      Purine analog. Blocks DNA replication and the de novo pathway of purine synthesis. Immunosuppressive and anti-inflammatory drug; induces apoptosis in human T-lymphocytes. Prodrug of 6-mercaptopurine (Cat. No. 4103). Tocris Bioscience 4099
      Purine analog; prodrug of 6-mercaptopurine (Cat. No. 4103) Tocris Bioscience 4099
      Rac1;HGPRT TargetMol T1237
  • Gas Chromatography

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

Density: 1.9±0.1 g/cm3
Boiling Point: 685.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 96.9±3.0 kJ/mol
Flash Point: 368.5±31.5 °C
Index of Refraction: 1.924
Molar Refractivity: 68.9±0.5 cm3
#H bond acceptors: 9
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 0.67
ACD/LogD (pH 5.5): 0.01
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 24.17
ACD/LogD (pH 7.4): -0.04
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 21.47
Polar Surface Area: 143 Å2
Polarizability: 27.3±0.5 10-24cm3
Surface Tension: 98.4±7.0 dyne/cm
Molar Volume: 145.4±7.0 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) =  -0.09
    Log Kow (Exper. database match) =  0.10
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  566.08  (Adapted Stein & Brown method)
    Melting Pt (deg C):  243.47  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.41E-012  (Modified Grain method)
    MP  (exp database):  243.5 deg C
    Subcooled liquid VP: 5.61E-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):  272.3
       log Kow used: 0.10 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.6532e+005 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.64E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.229E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.10  (exp database)
  Log Kaw used:  -12.967  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.067
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3105
   Biowin2 (Non-Linear Model)     :   0.0312
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4169  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3393  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2752
   Biowin6 (MITI Non-Linear Model):   0.0006
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2562
 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):  7.48E-008 Pa (5.61E-010 mm Hg)
  Log Koa (Koawin est  ): 13.067
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  40.1 
       Octanol/air (Koa) model:  2.86 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 202.8993 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.633 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  93.28
      Log Koc:  1.970 

 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: 0.10 (expkow database)

 Volatilization from Water:
    Henry LC:  2.64E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.693E+011  hours   (1.539E+010 days)
    Half-Life from Model Lake : 4.028E+012  hours   (1.679E+011 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       9.44e-005       1.27         1000       
   Water     45.6            900          1000       
   Soil      54.3            1.8e+003     1000       
   Sediment  0.0886          8.1e+003     0          
     Persistence Time: 983 hr




                    

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