ChemSpider 2D Image | Zidovudine | C10H13N5O4

Zidovudine

  • Molecular FormulaC10H13N5O4
  • Average mass267.241 Da
  • Monoisotopic mass267.096741 Da
  • ChemSpider ID32555
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



Featured data source



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

1-(3-Azido-2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidin-2,4(1H,3H)-dion
1-[(2R,4S,5S)-4-azido-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-5-méthylpyrimidine-2,4(1H,3H)-dione
2,4(1H,3H)-pyrimidinedione, 1-(3-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-methyl-
30516-87-1 [RN]
3'-Azido-3'-deoxythymidine [ACD/IUPAC Name]
3'-Azido-3'-desoxythymidin [German] [ACD/IUPAC Name]
3'-Azido-3'-désoxythymidine [French] [ACD/IUPAC Name]
4B9XT59T7S
6118
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

DRG 0004 [DBID]
NSC602670 [DBID]
A2169_SIGMA [DBID]
C07210 [DBID]
CCRIS 105 [DBID]
D00413 [DBID]
DivK1c_000524 [DBID]
DRG-0004 [DBID]
HSDB 6515 [DBID]
MFCD00006536 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J05AF01 Wikidata Q198504
      P261; P262 Biosynth Q-201945
      Sold for research purposes under agreement from Viiv. Tocris Bioscience 4150
    • Target Organs:

      Reverse Transcriptase inhibitor TargetMol T1416
    • Chemical Class:

      A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase. ChEBI CHEBI:10110
    • Compound Source:

      synthetic Microsource [01502109]
    • Bio Activity:

      Anti-infection MedChem Express HY-17413
      Anti-infection; MedChem Express HY-17413
      Antiviral agent active exclusively against retroviruses, esp. AIDS virus and leukaemias; Drugs of choice for AIDS treatment Zerenex Molecular [ZBioX-0728]
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T1416
      Enzymes Tocris Bioscience 4150
      HIV MedChem Express HY-17413
      HIV NRTIs MedChem Express HY-17413
      Polymerases Tocris Bioscience 4150
      Reverse Transcriptase, Telomerase reverse transcriptase TargetMol T1416
      RNA/DNA Polymerase Tocris Bioscience 4150
      Selective reverse transcriptase inhibitor. Exhibits 100-fold selectivity for HIV reverse transcriptase over DNA polymerase ?. Suppresses HIV-1 replication and enhances cell viability in HIV-1 infected T cells. Attenuates growth of multiple myeloma (MM) cells in vitro and reduces growth of MM tumor xenografts in mice. Orally bioavailable and brain penetrant. Antiretroviral agent. Also decreases CRISPR-mediated homology directed repair (HDR) efficiency. Tocris Bioscience 4150
      Selective reverse transcriptase inhibitor. Exhibits 100-fold selectivity for HIV reverse transcriptase over DNA polymerase ?. Suppresses HIV-1 replication and enhances cell viability in HIV-1 infected T cells. Attenuates growth of multiple myeloma (MM) cells in vitro and reduces growth of MM tumor xenografts in mice. Orally bioavailable and brain penetrant. Antiretroviral agent. Also decreases CRI SPR-mediated homology directed repair (HDR) efficiency. Tocris Bioscience 4150
      Selective reverse transcriptase inhibitor. Exhibits 100-fold selectivity for HIV reverse transcriptase over DNA polymerase alpha. Suppresses HIV-1 replication and enhances cell viability in HIV-1 infected T cells. Attenuates growth of multiple myeloma (MM) cells in vitro and reduces growth of MM tumor xenografts in mice. Orally bioavailable and brain penetrant. Antiretroviral agent. Also decreases CRISPR-mediated homology directed repair (HDR) efficiency. Tocris Bioscience 4150
      Selective reverse transcriptase inhibitor; antiretroviral Tocris Bioscience 4150
      Zidovudine (Azidothymidine, AZT) is a nucleoside analog reverse-transcriptase inhibitor (NRTI), a type of antiretroviral drug used for the treatment of HIV/AIDS infection. MedChem Express
      Zidovudine (Azidothymidine, AZT) is a nucleoside analog reverse-transcriptase inhibitor (NRTI), a type of antiretroviral drug used for the treatment of HIV/AIDS infection.; IC50 value:; Target: NRTI; reverse-transcriptase; AZT is a thymidine analogue. MedChem Express HY-17413
      Zidovudine (Azidothymidine, AZT) is a nucleoside analog reverse-transcriptase inhibitor (NRTI), a type of antiretroviral drug used for the treatment of HIV/AIDS infection.;IC50 value:;Target: NRTI; reverse-transcriptaseAZT is a thymidine analogue. AZT works by selectively inhibiting HIV's reverse transcriptase, the enzyme that the virus uses to make a DNA copy of its RNA. Reverse transcription is necessary for production of HIV's double-stranded DNA, which would be subsequently integrated into the genetic material of the infected cell (where it is called a provirus). ;The azido group increases the lipophilic nature of AZT, allowing it to cross infected cell membranes easily by diffusion and thereby also to cross the blood?brain barrier. Cellular enzymes convert AZT into the effective 5'-triphosphate form. Studies have proven that the termination of HIV's forming DNA chains is the specific factor in the inhibitory effect. MedChem Express HY-17413

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

Density:
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction:
Molar Refractivity:
#H bond acceptors: 9
#H bond donors: 2
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: -0.53
ACD/LogD (pH 5.5): -0.09
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 21.22
ACD/LogD (pH 7.4): -0.09
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 21.07
Polar Surface Area: 91 Å2
Polarizability:
Surface Tension:
Molar Volume:

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -7.05

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  704.45  (Adapted Stein & Brown method)
    Melting Pt (deg C):  308.10  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.54E-020  (Modified Grain method)
    Subcooled liquid VP: 6.74E-017 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):  1e+006
       log Kow used: -7.05 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  20506 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.47E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.602E-026 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -7.05  (KowWin est)
  Log Kaw used:  -22.848  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.798
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4312
   Biowin2 (Non-Linear Model)     :   0.0426
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7577  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5804  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1805
   Biowin6 (MITI Non-Linear Model):   0.0232
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1451
 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):  8.99E-015 Pa (6.74E-017 mm Hg)
  Log Koa (Koawin est  ): 15.798
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.34E+008 
       Octanol/air (Koa) model:  1.54E+003 
   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 =  76.9815 E-12 cm3/molecule-sec
      Half-Life =     0.139 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.667 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 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: -7.05 (estimated)

 Volatilization from Water:
    Henry LC:  3.47E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.763E+021  hours   (1.151E+020 days)
    Half-Life from Model Lake : 3.015E+022  hours   (1.256E+021 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       2.57e-007       2.93         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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