ChemSpider 2D Image | mercaptopurine | C5H4N4S

mercaptopurine

  • Molecular FormulaC5H4N4S
  • Average mass152.177 Da
  • Monoisotopic mass152.015671 Da
  • ChemSpider ID580869

More details:



Featured data source



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

1,7-Dihydro-6H-purin-6-thion [German] [ACD/IUPAC Name]
1,7-Dihydro-6H-purine-6-thione [ACD/IUPAC Name]
1,7-Dihydro-6H-purine-6-thione [French] [ACD/IUPAC Name]
1,9-DIHYDRO-6H-PURINE-6-THIONE
200-037-4 [EINECS]
50-44-2 [RN]
587
6H-purine-6-thione, 1,9-dihydro-
6-Mercapto-1H-purine
6-Mercaptopurine
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

U 4748 [DBID]
63810_FLUKA [DBID]
AG-670/31547064 [DBID]
AIDS007317 [DBID]
AIDS-007317 [DBID]
C01756 [DBID]
C02380 [DBID]
CCRIS 2761 [DBID]
CHEBI:2208 [DBID]
DivK1c_000493 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      YELLOW POWDER NIH Clinical Collection [SMR000544948]
    • Safety:

      L01BB02 Wikidata Q418529
    • Target Organs:

      Dehydrogenase inhibitor; DNA/RNA Synthesis TargetMol T0010
    • Chemical Class:

      A member of the class of purines that is 6,7-dihydro-1<element>H</element>-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis. ChEBI CHEBI:2208, CHEBI:50667
      A thiol that is the tautomer of mercaptopurine. ChEBI CHEBI:2208, CHEBI:50667
    • Compound Source:

      synthetic Microsource [01500387]
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13677
      Cell Cycle/DNA Damage; MedChem Express HY-13677
      DNA Damage/DNA Repair; Metabolism TargetMol T0010
      IMPDH;HPRT TargetMol T0010
      Mercaptopurine (6-mercaptopurine; 6-MP) is an immunosuppressive drug; is a thiopurine. MedChem Express
      Mercaptopurine (6-mercaptopurine; 6-MP) is an immunosuppressive drug; is a thiopurine.; IC50 Value: 149.5?124.9 nM (PBMC blastogenesis) [1]; Target: Nucleoside antimetabolite; in vitro: Both AZ and 6-MP dose-dependently suppressed PBMC blastogenesis. MedChem Express HY-13677
      Mercaptopurine (6-mercaptopurine; 6-MP) is an immunosuppressive drug; is a thiopurine.;IC50 Value: 149.5?124.9 nM (PBMC blastogenesis) [1];Target: Nucleoside antimetabolite;In vitro: Both AZ and 6-MP dose-dependently suppressed PBMC blastogenesis. Mean +/- s.d. IC50 (concentration of drug that gave 50% inhibition) values for AZ and 6-MP were 230.4 +/- 231.3 and 149.5 +/- 124.9 nM, respectively [1]. After incubation of PBMCs with 100 microM AZ for 4 days, 35.3-92.5 microM 6-MP was liberated into the culture medium. ;In vivo: The conversion of 6-mercaptopurine to 6-thiouric acid was prevented when allopurinol or oxypurinol were added to the lumen. At a luminal drug concentration of 1 mmol/l, allopurinol increased the rate at which 6-mercaptopurine appeared in the serosal secretions by 90% compared with an increase of only 50% with oxypurinol [2]. Combined treatment with 150 R X-rays and 150 mg/kg 6-mercaptopurine gave an additive effect and demonstrated conclusively that the peak MedChem Express HY-13677
      Nucleoside antimetabolite/analog MedChem Express HY-13677
  • Gas Chromatography

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

Density: 1.6±0.1 g/cm3
Boiling Point: 490.6±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization: 72.8±3.0 kJ/mol
Flash Point: 250.5±23.2 °C
Index of Refraction: 1.820
Molar Refractivity: 41.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: -0.18
ACD/LogD (pH 5.5): -2.31
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -2.70
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 93 Å2
Polarizability: 16.2±0.5 10-24cm3
Surface Tension: 105.4±3.0 dyne/cm
Molar Volume: 94.2±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) =  0.60

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  484.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  202.65  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.97E-010  (Modified Grain method)
    Subcooled liquid VP: 6.76E-008 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):  2.29e+004
       log Kow used: 0.60 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  73646 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.51E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.843E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.60  (KowWin est)
  Log Kaw used:  -8.734  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.334
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4413
   Biowin2 (Non-Linear Model)     :   0.2575
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7279  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5198  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1224
   Biowin6 (MITI Non-Linear Model):   0.0430
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5023
 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):  9.01E-006 Pa (6.76E-008 mm Hg)
  Log Koa (Koawin est  ): 9.334
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.333 
       Octanol/air (Koa) model:  0.00053 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.923 
       Mackay model           :  0.964 
       Octanol/air (Koa) model:  0.0407 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  88.7979 E-12 cm3/molecule-sec
      Half-Life =     0.120 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.445 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.944 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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: 0.60 (estimated)

 Volatilization from Water:
    Henry LC:  4.51E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.601E+007  hours   (6.673E+005 days)
    Half-Life from Model Lake : 1.747E+008  hours   (7.279E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.0107          2.89         1000       
   Water     44.2            900          1000       
   Soil      55.7            1.8e+003     1000       
   Sediment  0.0883          8.1e+003     0          
     Persistence Time: 976 hr




                    

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