ChemSpider 2D Image | Stavudine | C10H12N2O4

Stavudine

  • Molecular FormulaC10H12N2O4
  • Average mass224.213 Da
  • Monoisotopic mass224.079712 Da
  • ChemSpider ID17270
  • defined stereocentres - 2 of 2 defined stereocentres


More details:



Featured data source



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

1-(2,3-Dideoxy-b-glycero-pent-2-enofuranosyl)thymine
1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidindion [German] [ACD/IUPAC Name]
1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione [ACD/IUPAC Name]
1-[(2R,5S)-5-(Hydroxyméthyl)-2,5-dihydro-2-furanyl]-5-méthyl-2,4(1H,3H)-pyrimidinedione [French] [ACD/IUPAC Name]
1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidin-2,4(1H,3H)-dion
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
1-[(2R,5S)-5-(hydroxyméthyl)-2,5-dihydrofuran-2-yl]-5-méthylpyrimidine-2,4(1H,3H)-dione
2(1H)-Pyrimidinone, 1-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-4-hydroxy-5-methyl- [ACD/Index Name]
2,4(1H,3H)-Pyrimidinedione, 1-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl- [ACD/Index Name]
3056-17-5 [RN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63581 [DBID]
DRG 0043 [DBID]
AIDS000005 [DBID]
AIDS-000005 [DBID]
AIDS000884 [DBID]
AIDS-000884 [DBID]
BMY 27857 [DBID]
BMY-27857 [DBID]
BRN 0618327 [DBID]
C07312 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE CRYSTALLINE POWDER NIH Clinical Collection [SMR000058350] , [SMR000673569]
      white powder Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Combustible. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      Danger Biosynth Q-201743
      EUH014; H314 Biosynth Q-201743
      GHS05 Biosynth Q-201743
      IRRITANT Matrix Scientific 069591
      Minimize exposure. Oxford University Chemical Safety Data (No longer updated) More details
      P280; P305+P351+P338; P310 Biosynth Q-201743
    • Target Organs:

      Antiviral;Reverse Transcriptase inhibitor TargetMol T1404
    • Drug Status:

      approved BIONET-Key Organics KS-1115
    • Bio Activity:

      Anti-infection MedChem Express HY-B0116
      Anti-infection; MedChem Express HY-B0116
      Antivirals Tocris Bioscience 4990
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T1404
      HIV MedChem Express HY-B0116
      HIV NRTIs MedChem Express HY-B0116
      Nucleoside analog; antiviral Tocris Bioscience 4990
      Nucleoside analog; antiviral that inhibits HIV replication in vitro. Orally bioavailable. Tocris Bioscience 4990
      Other Pharmacology Tocris Bioscience 4990
      Reverse Transcriptase TargetMol T1404
      Stavudine is a nucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. MedChem Express
      Stavudine is a nucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.; Target: HIV RT; NRTIs; Stavudine is a dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. MedChem Express HY-B0116
      Stavudine is a nucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.;Target: HIV RT; NRTIsStavudine is a dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. Stavudine is an analog of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it [1]. Mice were treated for 2 weeks with stavudine d4T (500 mg/kg/day), L-carnitine (200 mg/kg/day) or both drugs concomitantly. Body fatness was assessed by dual energy X-ray absorptiometry, and investigations were performed in plasma, liver, muscle and WAT. D4T reduced the gain of body adiposity, WAT leptin, whole body FAO and plasma ketone bodies, and increased liver triglycerides and plasma aminotransferases with mild ultrastructural abnormalities MedChem Express HY-B0116

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: 1.575
Molar Refractivity: 53.9±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.86
ACD/LogD (pH 5.5): -0.67
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 10.29
ACD/LogD (pH 7.4): -0.67
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 10.20
Polar Surface Area: 79 Å2
Polarizability: 21.4±0.5 10-24cm3
Surface Tension: 53.5±3.0 dyne/cm
Molar Volume: 163.1±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) =  -0.79
    Log Kow (Exper. database match) =  -0.72
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  495.19  (Adapted Stein & Brown method)
    Melting Pt (deg C):  210.35  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.82E-012  (Modified Grain method)
    Subcooled liquid VP: 2.62E-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):  6595
       log Kow used: -0.72 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  42587 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.31E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.262E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.72  (exp database)
  Log Kaw used:  -13.025  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.305
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4522
   Biowin2 (Non-Linear Model)     :   0.0768
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8550  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6440  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3010
   Biowin6 (MITI Non-Linear Model):   0.0587
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5163
 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):  3.49E-008 Pa (2.62E-010 mm Hg)
  Log Koa (Koawin est  ): 12.305
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  85.9 
       Octanol/air (Koa) model:  0.495 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.975 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 121.3140 E-12 cm3/molecule-sec
      Half-Life =     0.088 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.058 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    21.137501 E-17 cm3/molecule-sec
      Half-Life =     0.054 Days (at 7E11 mol/cm3)
      Half-Life =      1.301 Hrs
   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: -0.72 (expkow database)

 Volatilization from Water:
    Henry LC:  2.31E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.795E+011  hours   (1.581E+010 days)
    Half-Life from Model Lake :  4.14E+012  hours   (1.725E+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       0.000254        0.806        1000       
   Water     38.9            360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr




                    

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