ChemSpider 2D Image | (-)-Lamivudine | C8H11N3O3S

(-)-Lamivudine

  • Molecular FormulaC8H11N3O3S
  • Average mass229.256 Da
  • Monoisotopic mass229.052109 Da
  • ChemSpider ID54812
  • defined stereocentres - 2 of 2 defined stereocentres


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(-)-Lamivudine
(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cystosine
134678-17-4 [RN]
2(1H)-Pyrimidinone, 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]- [ACD/Index Name]
2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl], (-)(2R,5S)
2T8Q726O95
4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinon [German] [ACD/IUPAC Name]
4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone [ACD/IUPAC Name]
4-Amino-1-[(2R,5S)-2-(hydroxyméthyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone [French] [ACD/IUPAC Name]
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63577 [DBID]
AIDS000388 [DBID]
AIDS-000388 [DBID]
AIDS005663 [DBID]
AIDS-005663 [DBID]
AIDS072582 [DBID]
AIDS-072582 [DBID]
AIDS184196 [DBID]
AIDS-184196 [DBID]
AIDS224016 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE TO CREAM COLORED POWDER NIH Clinical Collection [SMR000466319]
    • Safety:

      GHS07 Biosynth Q-201275
      H315; H319; H335 Biosynth Q-201275
      J05AF05 Wikidata Q422631
      P261; P280; P302+P352; P304+P340; P305+P351+P338; P312 Biosynth Q-201275
      Warning Biosynth Q-201275
    • Target Organs:

      Antiviral;Reverse Transcriptase inhibitor TargetMol T0682
    • Chemical Class:

      A monothioacetal that consists of cytosine having a (2<stereo>R</stereo>,5<stereo>S</stereo>)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcr iptase, it is used as an antiviral in the treatment of AIDS and hepatitis B. ChEBI CHEBI:63577
    • Drug Status:

      approved BIONET-Key Organics KS-1073
    • Bio Activity:

      Anti-infection MedChem Express HY-B0250
      Anti-infection; MedChem Express HY-B0250
      HIV MedChem Express HY-B0250
      HIV NRTIs MedChem Express HY-B0250
      Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor with an IC50 of 2.7 mM. MedChem Express
      Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor with an IC50 of 2.7 mM.; Target: NRTIs; HIV; Lamivudine is a reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. MedChem Express HY-B0250
      Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor with an IC50 of 2.7 mM.;Target: NRTIs; HIVLamivudine is a reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine can inhibit virus replication rapidly and improveliver function, prevent exacerbation in patients with advanced schistosomiasis with chronic B hepatitis [1]. IC50 value of lamivudine on B. adolescentis was 200 microg x mL(-1), and the IC50 values of lamivudine on S. dysenteriae and E. coli were higher than 3 000 microg x mL(-1) and 6 000 microg x mL(1), respectively. Therefore, lamivudine made different inhibitory effects on the three bacteria, in which the B. adolescentis was most susceptible to lamivudine. This work showed that taking lamivudine chronically is likely to affect the balance of good flora in the intestinal tract, and migh MedChem Express HY-B0250
      Microbiology & Virology TargetMol T0682
      Potent antiviral agent; Zerenex Molecular [ZBioX-0524]
      Reverse Transcriptase TargetMol T0682

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

Density: 1.7±0.1 g/cm3
Boiling Point: 475.4±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.7 mmHg at 25°C
Enthalpy of Vaporization: 85.2±6.0 kJ/mol
Flash Point: 241.3±31.5 °C
Index of Refraction: 1.755
Molar Refractivity: 54.1±0.5 cm3
#H bond acceptors: 6
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.71
ACD/LogD (pH 5.5): -1.00
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.64
ACD/LogD (pH 7.4): -0.98
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 6.94
Polar Surface Area: 113 Å2
Polarizability: 21.5±0.5 10-24cm3
Surface Tension: 79.3±7.0 dyne/cm
Molar Volume: 132.2±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) =  -2.62
    Log Kow (Exper. database match) =  -0.93
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  397.16  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.53  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.23E-009  (Modified Grain method)
    Subcooled liquid VP: 2.24E-007 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):  9366
       log Kow used: -0.93 (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 :   5.63E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.651E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.93  (exp database)
  Log Kaw used:  -15.638  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.708
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4498
   Biowin2 (Non-Linear Model)     :   0.0719
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8438  (weeks       )
   Biowin4 (Primary Survey Model) :   3.6367  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2991
   Biowin6 (MITI Non-Linear Model):   0.0611
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5494
 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):  2.99E-005 Pa (2.24E-007 mm Hg)
  Log Koa (Koawin est  ): 14.708
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.1 
       Octanol/air (Koa) model:  125 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.784 
       Mackay model           :  0.889 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 178.2929 E-12 cm3/molecule-sec
      Half-Life =     0.060 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.720 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec
      Half-Life =     6.549 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.837 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  19.82
      Log Koc:  1.297 

 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: -0.93 (expkow database)

 Volatilization from Water:
    Henry LC:  5.63E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.575E+014  hours   (6.561E+012 days)
    Half-Life from Model Lake : 1.718E+015  hours   (7.157E+013 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       7.37e-010       1.43         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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