ChemSpider 2D Image | Ribavirin | C8H12N4O5

Ribavirin

  • Molecular FormulaC8H12N4O5
  • Average mass244.205 Da
  • Monoisotopic mass244.080765 Da
  • ChemSpider ID34439
  • defined stereocentres - 4 of 4 defined stereocentres


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

1-(b-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
1-(β-D-Ribofuranosyl)-1H-1,2,4-triazol-3-carboxamid [German] [ACD/IUPAC Name]
1-(β-D-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide [ACD/IUPAC Name]
1-(β-D-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide [French] [ACD/IUPAC Name]
1,2,4-Triazole-3-carboxamide, 1-β-D-ribofuranosyl-
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-1,2,4-triazol-3-carboxamid [German]
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-1,2,4-triazole-3-carboxamide
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-1H-1,2,4-triazole-3-carboxamide [French]
1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide
1H-1,2,4-triazole-3-carboxamide, 1-b-D-ribofuranosyl-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

49717AWG6K [DBID]
CHEBI:63580 [DBID]
ICN 1229 [DBID]
UNII-49717AWG6K [DBID]
AIDS000053 [DBID]
AIDS-000053 [DBID]
BRN 0892462 [DBID]
D00423 [DBID]
DivK1c_000782 [DBID]
DRG-0028 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      Danger Biosynth Q-201670
      GHS08 Biosynth Q-201670
      H360 Biosynth Q-201670
      Harmful/Teratogenic SynQuest 4H48-1-NQ
      IRRITANT Matrix Scientific 075767
      J05AB04 Wikidata Q421862
      P201; P308+P313 Biosynth Q-201670
    • Target Organs:

      RNA synthesis inhibitor;ADK activator;DH inhibitor TargetMol T0684
    • Chemical Class:

      A 1-ribosyltriazole that is the 1-ribofuranosyl derivative of 1,2,4-triazole-3-carboxamide. An inhibitor of HCV polymerase. ChEBI CHEBI:63580
    • Compound Source:

      synthetic Microsource [01503938]
    • Bio Activity:

      Anti-infection MedChem Express HY-B0434
      Anti-infection; MedChem Express HY-B0434
      Antiviral agent; Zerenex Molecular [ZBioX-0082]
      Antiviral guanosine analog; blocks eIF4E activity Tocris Bioscience 4501
      Antiviral guanosine ribonucleoside analog; misincorporated into mRNA by viral-dependent RNA polymerases. Binds to and redistributes mammalian eIF4E from the nucleus to the cytoplasm (Ki ~ 0.3 ?M for t he active metabolite, ribavirin triphosphate). Represses colony formation of primary AML-M5 progenitor cells (IC50 ~ 1 ?M); reduces disease severity in acute myeloid leukemia (AML). Orally available. Tocris Bioscience 4501
      Antiviral guanosine ribonucleoside analog; misincorporated into mRNA by viral-dependent RNA polymerases. Binds to and redistributes mammalian eIF4E from the nucleus to the cytoplasm (Ki ~ 0.3 ?M for the active metabolite, ribavirin triphosphate). Represses colony formation of primary AML-M5 progenitor cells (IC50 ~ 1 ?M); reduces disease severity in acute myeloid leukemia (AML). Orally available. Tocris Bioscience 4501
      Antiviral guanosine ribonucleoside analog; misincorporated into mRNA by viral-dependent RNA polymerases. Binds to and redistributes mammalian eIF4E from the nucleus to the cytoplasm (Ki ~ 0.3 muM for the active metabolite, ribavirin triphosphate). Represses colony formation of primary AML-M5 progenitor cells (IC50 ~ 1 muM); reduces disease severity in acute myeloid leukemia (AML). Orally available. Tocris Bioscience 4501
      Cell Biology Tocris Bioscience 4501
      Cell Metabolism Tocris Bioscience 4501
      DNA Damage/DNA Repair TargetMol T0684
      DNA, RNA and Protein Synthesis Tocris Bioscience 4501
      HCV MedChem Express HY-B0434
      HCV RSV MedChem Express HY-B0434
      Ribavirin is a nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. MedChem Express
      Ribavirin is a nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses.; Target: HCV; RSV; Ribavirin is a guanosine (ribonucleic) analog used to stop viral RNA synthesis and viral mRNA capping, thus, it is a nucleoside inhibitor. MedChem Express HY-B0434
      Ribavirin is a nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses.;Target: HCV; RSVRibavirin is a guanosine (ribonucleic) analog used to stop viral RNA synthesis and viral mRNA capping, thus, it is a nucleoside inhibitor. Ribavirin is an anti-viral drug used off-label for severe RSV infection (individually), hepatitis C infection (can be used in conjunction with peginterferon alfa-2b or peginterferon alfa-2a), and some other viral infections. Ribavirin is a prodrug, which when metabolized resembles purine RNA nucleotides. In this form it interferes with RNA metabolism required for viral replication. How it exactly affects viral replication is unknown; Multiple mechanisms may be responsible for its actions [1]. MedChem Express HY-B0434
      RNA polymerase;ADK;IMPDH1 TargetMol T0684

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

Density: 2.1±0.1 g/cm3
Boiling Point: 639.8±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.0 mmHg at 25°C
Enthalpy of Vaporization: 99.3±3.0 kJ/mol
Flash Point: 340.7±34.3 °C
Index of Refraction: 1.823
Molar Refractivity: 51.1±0.5 cm3
#H bond acceptors: 9
#H bond donors: 5
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 1
ACD/LogP: -2.26
ACD/LogD (pH 5.5): -2.07
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.78
ACD/LogD (pH 7.4): -2.07
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.78
Polar Surface Area: 144 Å2
Polarizability: 20.3±0.5 10-24cm3
Surface Tension: 106.8±7.0 dyne/cm
Molar Volume: 117.1±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) =  -2.03
    Log Kow (Exper. database match) =  -1.85
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  489.15  (Adapted Stein & Brown method)
    Melting Pt (deg C):  207.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.1E-013  (Modified Grain method)
    Subcooled liquid VP: 4.39E-011 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):  4.74e+004
       log Kow used: -1.85 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.96E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.457E-018 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.85  (exp database)
  Log Kaw used:  -19.390  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.540
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.9703
   Biowin2 (Non-Linear Model)     :   0.8963
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.0765  (weeks       )
   Biowin4 (Primary Survey Model) :   4.0794  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7045
   Biowin6 (MITI Non-Linear Model):   0.3315
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.4976
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.85E-009 Pa (4.39E-011 mm Hg)
  Log Koa (Koawin est  ): 17.540
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  513 
       Octanol/air (Koa) model:  8.51E+004 
   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 =  40.4550 E-12 cm3/molecule-sec
      Half-Life =     0.264 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.173 Hrs
   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    :  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: -1.85 (expkow database)

 Volatilization from Water:
    Henry LC:  9.96E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 9.186E+017  hours   (3.828E+016 days)
    Half-Life from Model Lake : 1.002E+019  hours   (4.176E+017 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       6.49e-010       6.35         1000       
   Water     39              360          1000       
   Soil      60.9            720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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