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ChemSpider 2D Image | Pyrimethamine | C12H13ClN4

Pyrimethamine

  • Molecular FormulaC12H13ClN4
  • Average mass248.711 Da
  • Monoisotopic mass248.082870 Da
  • ChemSpider ID4819

More details:

Featured data source
The Merck Index Online

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

Pyrimethamine [BAN] [INN] [JAN] [USAN] [USP] [Wiki]
2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl- [ACD/Index Name]
200-364-2 [EINECS]
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine [ACD/IUPAC Name]
5-(4-Chlorophényl)-6-éthyl-2,4-pyrimidinediamine [French] [ACD/IUPAC Name]
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
5-(4-chlorophényl)-6-éthylpyrimidine-2,4-diamine
5-(4-Chlorphenyl)-6-ethyl-2,4-pyrimidindiamin [German] [ACD/IUPAC Name]
5-(4-Chlorphenyl)-6-ethylpyrimidin-2,4-diamin
58-14-0 [RN]
More...

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

219864 [DBID]
2215 [DBID]
UV8140000 [DBID]
Z3614QOX8W [DBID]
46706_RIEDEL [DBID]
4753 R.P. [DBID]
76021-83-5 [DBID] [RN]
AI3-25005 [DBID]
AIDS006885 [DBID]
AIDS-006885 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      white powder OU Chemical Safety Data (No longer updated) More details

    • Stability:

      Stable, but light sensitive. Combustible. Incompatiblewith strong oxidizing agents. OU Chemical Safety Data (No longer updated) More details

    • Toxicity:

      Organic Compound; Organochloride; Amine; Drug; Antimalarial; Folic Acid Antagonist; Metabolite; Antiprotozoal Agent; Synthetic Compound Toxin, Toxin-Target Database T3D4779
      ORL-MUS LD50 92 mg kg-1, IPR-MUS LD50 74 mg kg-1 OU Chemical Safety Data (No longer updated) More details

    • Safety:

      P01BD01 Wikidata Q421072
      Safety glasses, gloves, good ventilation. OU Chemical Safety Data (No longer updated) More details

    • Target Organs:

      DHFR inhibitor TargetMol T0849

    • Chemical Class:

      An aminopyrimidine that is pyrimidine-2,4-diamine which is substituted at position 5 by a <ital>p</ital>-chlorophenyl group and at position 6 by an ethyl group. It is a folic acid antagonist used as a n antimalarial or with a sulfonamide to treat toxoplasmosis. ChEBI CHEBI:8673
      An aminopyrimidine that is pyrimidine-2,4-diamine which is substituted at position 5 by a p-chlorophenyl group and at position 6 by an ethyl group. It is a folic acid antagonist used as an antimalaria l or with a sulfonamide to treat toxoplasmosis. ChEBI CHEBI:8673

    • Bio Activity:

      Antifolate Antiparasitic MedChem Express HY-18062
      Anti-infection MedChem Express HY-18062
      Anti-infection; Cell Cycle/DNA Damage; MedChem Express HY-18062
      Antiparasitic MedChem Express HY-18062
      DHFR TargetMol T0849
      Metabolism TargetMol T0849
      Multidrug Transporters Tocris Bioscience 3918
      Potent inhibitor of multi-drug and toxin extrusion (MATE) transporters (Ki values are 46 and 77 nM for human MATE2-K-HEK293 and MATE1-HEK293 cells respectively). Also inhibits dihydrofolate reductase (DHFR). Tocris Bioscience 3918
      Potent inhibitor of multidrug and toxin extrusion (MATE) transporters (Ki values are 46 and 77 nM for human MATE2-K-HEK293 and MATE1-HEK293 cells respectively). Also inhibits dihydrofolate reductase (DHFR) and STAT3. Decreases proliferation of human autosomal dominant polycystic kidney disease cells. Tocris Bioscience 3918
      Potent inhibitor of multi-drug and toxin extrusion (MATE) transporters (Ki values are 46 and 77 nM for human MATE2-K-HEK293 and MATE1-HEK293 cells respectively). Also inhibits dihydrofolate reductase (DHFR). Tocris Bioscience 3918
      Potent inhibitor of multidrug and toxin extrusion (MATE) transporters; also DHFR and STAT3 inhibitor Tocris Bioscience 3918
      Potent inhibitor of multi-drug and toxin extrusion (MATE) transporters; also inhibits DHFR Tocris Bioscience 3918
      Pyrimethamine(RP4753) is a medication used for protozoal infections; interferes with tetrahydrofolic acid synthesis from folic acid by inhibiting the enzyme dihydrofolate reductase (DHFR). MedChem Express
      Pyrimethamine(RP4753) is a medication used for protozoal infections; interferes with tetrahydrofolic acid synthesis from folic acid by inhibiting the enzyme dihydrofolate reductase (DHFR).; IC50 Value: 15.4 nM (Plasmodium falciparum) [1]; Target: DHFR; antifolate; in vitro: Three susceptibility levels (susceptible, intermediate, and resistant) were observed in the response of culture-adapted clones and strains to pyrimethamine (50% inhibitory concentration [IC50]) < 100, 100-2,000, and > 2,000 nM) and cycloguanil (IC50 < 50, 50-500, and > 500 nM). MedChem Express HY-18062
      Pyrimethamine(RP4753) is a medication used for protozoal infections; interferes with tetrahydrofolic acid synthesis from folic acid by inhibiting the enzyme dihydrofolate reductase (DHFR).;IC50 Value: 15.4 nM (Plasmodium falciparum) [1];Target: DHFR; antifolate;In vitro: Three susceptibility levels (susceptible, intermediate, and resistant) were observed in the response of culture-adapted clones and strains to pyrimethamine (50% inhibitory concentration [IC50]) < 100, 100-2,000, and > 2,000 nM) and cycloguanil (IC50 < 50, 50-500, and > 500 nM). Based on these susceptibility levels, 73 and 68 of 96 fresh clinical isolates were susceptible to pyrimethamine (mean IC50 15.4 nM) and cycloguanil (mean IC50 11.1 nM), respectively [1]. We tested pyrimethamine(previously reported to suppress SOD1 expression), several compounds currently in trials in human and murine ALS, and a set of 1040 FDA-approved compounds. In a PC12 cell-based assay, no compounds reduced SOD1 promoter activity without MedChem Express HY-18062
      Transporters Tocris Bioscience 3918
  • Gas Chromatography

    • Retention Index (Kovats):

      2371 (estimated with error: 89) NIST Spectra mainlib_290938, replib_12048, replib_246424, replib_248011

    • Retention Index (Normal Alkane):

      2138 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 58140; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

    • Retention Index (Linear):

      2140 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 58140; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 368.4±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 61.5±3.0 kJ/mol
Flash Point: 176.6±30.7 °C
Index of Refraction: 1.667
Molar Refractivity: 67.1±0.5 cm3
#H bond acceptors: 4
#H bond donors: 4
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.03
ACD/LogD (pH 5.5): -0.23
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.18
ACD/LogD (pH 7.4): 0.19
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.72
Polar Surface Area: 74 Å2
Polarizability: 26.6±0.5 10-24cm3
Surface Tension: 51.7±7.0 dyne/cm
Molar Volume: 180.2±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) =  2.41
    Log Kow (Exper. database match) =  2.69
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  422.65  (Adapted Stein & Brown method)
    Melting Pt (deg C):  176.47  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.32E-008  (Modified Grain method)
    MP  (exp database):  233.5 deg C
    Subcooled liquid VP: 2.33E-006 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):  121.3
       log Kow used: 2.69 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  85.306 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Anilines (amino-meta)

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.08E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.561E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.69  (exp database)
  Log Kaw used:  -8.355  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.045
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.0339
   Biowin2 (Non-Linear Model)     :   0.0031
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0982  (months      )
   Biowin4 (Primary Survey Model) :   3.0383  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3594
   Biowin6 (MITI Non-Linear Model):   0.0010
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.7049
 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):  0.000311 Pa (2.33E-006 mm Hg)
  Log Koa (Koawin est  ): 11.045
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00966 
       Octanol/air (Koa) model:  0.0272 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.259 
       Mackay model           :  0.436 
       Octanol/air (Koa) model:  0.685 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 201.1013 E-12 cm3/molecule-sec
      Half-Life =     0.053 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.638 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.347 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1569
      Log Koc:  3.195 

 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 = 1.371 (BCF = 23.51)
       log Kow used: 2.69 (expkow database)

 Volatilization from Water:
    Henry LC:  1.08E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  8.55E+006  hours   (3.562E+005 days)
    Half-Life from Model Lake : 9.327E+007  hours   (3.886E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               3.77  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.66  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       0.00178         1.28         1000       
   Water     13              1.44e+003    1000       
   Soil      86.9            2.88e+003    1000       
   Sediment  0.162           1.3e+004     0          
     Persistence Time: 2.43e+003 hr

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