ChemSpider 2D Image | Raltegravir | C20H21FN6O5

Raltegravir

  • Molecular FormulaC20H21FN6O5
  • Average mass444.416 Da
  • Monoisotopic mass444.155731 Da
  • ChemSpider ID16445111

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4-Pyrimidinecarboxamide, N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-2-[1-methyl-1-[[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino]ethyl]-6-oxo- [ACD/Index Name]
518048-05-0 [RN]
8842
N-(4-Fluorbenzyl)-5-hydroxy-1-methyl-2-(2-{[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}-2-propanyl)-6-oxo-1,6-dihydro-4-pyrimidincarboxamid [German] [ACD/IUPAC Name]
N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-2-(2-{[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}-2-propanyl)-6-oxo-1,6-dihydro-4-pyrimidinecarboxamide [ACD/IUPAC Name]
N-(4-Fluorobenzyl)-5-hydroxy-1-méthyl-2-(2-{[(5-méthyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}-2-propanyl)-6-oxo-1,6-dihydro-4-pyrimidinecarboxamide [French] [ACD/IUPAC Name]
N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-2-(2-{[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}propan-2-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamide
raltegravir [Spanish] [INN]
raltégravir [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

22VKV8053U [DBID]
UNII:22VKV8053U [DBID]
UNII-22VKV8053U [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      H302+H312+H332 W&J PharmaChem, Inc. [203059]
      J05AX08 Wikidata Q421552
      P302+P352+P304+P312+P503+P351+P338+P403+P235+P280+P260 W&J PharmaChem, Inc. [203059]
    • Bio Activity:

      Anti-infection MedChem Express HY-10353
      Anti-infection; Metabolism/Protease; MedChem Express HY-10353
      HIV MedChem Express HY-10353
      HIV HIV Integrase MedChem Express HY-10353
      Raltegravir(MK0518) is a potent integrase (IN) inhibitor, used to treat HIV infection. MedChem Express
      Raltegravir(MK0518) is a potent integrase (IN) inhibitor, used to treat HIV infection.; Target: Integrase (IN); HIV; Raltegravir (MK-0518) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN with IC50 of 90 nM and 40 nM, respectively. MedChem Express HY-10353
      Raltegravir(MK0518) is a potent integrase (IN) inhibitor, used to treat HIV infection.;Target: Integrase (IN); HIVRaltegravir (MK-0518) is a potent integrase (IN) inhibitor for WT and S217Q PFV IN with IC50 of 90 nM and 40 nM, respectively. PFV IN carrying the S217H substitution is 10-fold less susceptible to Raltegravir with IC50 of 900 nM. PFV IN displays 10% of WT activity and is inhibited by Raltegravir with an IC50 of 200 nM, indicating a ~twofold decrease in susceptibility to the IN strand transfer inhibitor (INSTI) compared with WT IN. S217Q PFV IN is as sensitive to Raltegravir as the WT enzyme [1]. Raltegravir induces viro-immunological improvement of nonhuman primates with progressing SIVmac251 infection. One non-human primate shows an undetectable viral load following Raltegravir monotherapy. In acutely infected human lymphoid CD4+ T-cell lines MT-4 and CEMx174, SIVmac251 replication is efficiently inhibited by Raltegravir, which shows an EC90 in the low nanomolar range MedChem Express HY-10353

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

Density: 1.5±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.651
Molar Refractivity: 110.8±0.5 cm3
#H bond acceptors: 11
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: -0.68
ACD/LogD (pH 5.5): -1.56
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.13
ACD/LogD (pH 7.4): -3.32
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 150 Å2
Polarizability: 43.9±0.5 10-24cm3
Surface Tension: 53.8±7.0 dyne/cm
Molar Volume: 303.5±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) =  0.40

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  756.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  332.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.54E-022  (Modified Grain method)
    Subcooled liquid VP: 1.38E-018 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):  728.8
       log Kow used: 0.40 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  53943 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Acrylamides
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.11E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.643E-025 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.40  (KowWin est)
  Log Kaw used:  -20.429  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.829
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3859
   Biowin2 (Non-Linear Model)     :   0.0031
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5205  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.7438  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0359
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.0686
 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):  1.84E-016 Pa (1.38E-018 mm Hg)
  Log Koa (Koawin est  ): 20.829
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.63E+010 
       Octanol/air (Koa) model:  1.66E+008 
   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 =  46.0582 E-12 cm3/molecule-sec
      Half-Life =     0.232 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.787 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): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  617.7
      Log Koc:  2.791 

 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: 0.40 (estimated)

 Volatilization from Water:
    Henry LC:  9.11E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.355E+019  hours   (5.645E+017 days)
    Half-Life from Model Lake : 1.478E+020  hours   (6.158E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  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       0.00143         5.38         1000       
   Water     52.1            4.32e+003    1000       
   Soil      47.8            8.64e+003    1000       
   Sediment  0.105           3.89e+004    0          
     Persistence Time: 1.55e+003 hr




                    

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