ChemSpider 2D Image | Rilpivirine | C22H18N6

Rilpivirine

  • Molecular FormulaC22H18N6
  • Average mass366.418 Da
  • Monoisotopic mass366.159302 Da
  • ChemSpider ID4953643

  • Double-bond stereo - Double-bond stereo

More details:

Featured data source
The Merck Index Online

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

4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
4-{[4-({4-[(E)-2-Cyanovinyl]-2,6-dimethylphenyl}amino)-2-pyrimidinyl]amino}benzonitrile [ACD/IUPAC Name]
4-{[4-({4-[(E)-2-Cyanovinyl]-2,6-diméthylphényl}amino)-2-pyrimidinyl]amino}benzonitrile [French] [ACD/IUPAC Name]
4-{[4-({4-[(E)-2-Cyanvinyl]-2,6-dimethylphenyl}amino)-2-pyrimidinyl]amino}benzonitril [German] [ACD/IUPAC Name]
500287-72-9 [RN]
Benzonitrile, 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]- [ACD/Index Name]
Edurant [Trade name]
Rilpivirine [INN] [USAN] [Wiki]
(E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
(E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

R 278474 [DBID]
TMC-278 [DBID]
AIDS169030 [DBID]
AIDS-169030 [DBID]
R278474 [DBID]
R-278474 [DBID]
TMC 278 [DBID]
TMC278 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      J05AG05 Wikidata Q421547

    • Target Organs:

      Reverse Transcriptase inhibitor TargetMol T2330

    • Chemical Class:

      An aminopyrimidine that is pyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 4-cyanophenyl and 4-[(<stereo>E</stereo>)-2-cyanovinyl]-2,6-dimethylphenyl groups re spectively. Used for treatment of HIV. ChEBI CHEBI:68606
      An aminopyrimidine that is pyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 4-cyanophenyl and 4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl groups respectively. Used for treatment of HIV. ChEBI CHEBI:68606

    • Bio Activity:

      Anti-infection; MedChem Express HY-10574
      DNA Damage/DNA Repair;Microbiology & Virology TargetMol T2330
      HIV NNRTIs MedChem Express HY-10574
      Reverse Transcriptase TargetMol T2330
      Rilpivirine(R 278474, TMC 278) is a type of anti-HIV medicine called a non-nucleoside reverse transcriptase inhibitor (NNRTI). MedChem Express http://www.medchemexpress.com/pd-169316.html
      Rilpivirine(R 278474, TMC 278) is a type of anti-HIV medicine called a non-nucleoside reverse transcriptase inhibitor (NNRTI). ;IC50 Value: ;Target: NNRTIsRilpivirine(TMC278) is a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1. NNRTIs work by binding to and blocking HIV reverse transcriptase, an HIV enzyme. This prevents HIV from replicating and lowers the amount of HIV in the blood.Rilpivirine does not cure HIV/AIDS. It is not known if rilpivirine reduces the risk of passing HIV to other people. MedChem Express HY-10574

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 634.1±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.9 mmHg at 25°C
Enthalpy of Vaporization: 93.7±3.0 kJ/mol
Flash Point: 337.3±34.3 °C
Index of Refraction: 1.665
Molar Refractivity: 106.6±0.4 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.63
ACD/LogD (pH 5.5): 3.44
ACD/BCF (pH 5.5): 218.02
ACD/KOC (pH 5.5): 1449.40
ACD/LogD (pH 7.4): 3.63
ACD/BCF (pH 7.4): 336.18
ACD/KOC (pH 7.4): 2234.95
Polar Surface Area: 97 Å2
Polarizability: 42.3±0.5 10-24cm3
Surface Tension: 72.3±5.0 dyne/cm
Molar Volume: 287.0±5.0 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) =  3.93

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  563.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.49  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.81E-012  (Modified Grain method)
    Subcooled liquid VP: 6.35E-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):  1.176
       log Kow used: 3.93 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.59548 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.30E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.152E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.93  (KowWin est)
  Log Kaw used:  -12.664  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.594
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8289
   Biowin2 (Non-Linear Model)     :   0.9883
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8051  (months      )
   Biowin4 (Primary Survey Model) :   2.8349  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3890
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3736
 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):  8.47E-008 Pa (6.35E-010 mm Hg)
  Log Koa (Koawin est  ): 16.594
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  35.4 
       Octanol/air (Koa) model:  9.64E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 209.2960 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 210.5120 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    0.613 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    0.610 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.052500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     0.105000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    21.829 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =    10.914 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.41E+005
      Log Koc:  5.382 

 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 = 2.327 (BCF = 212.2)
       log Kow used: 3.93 (estimated)

 Volatilization from Water:
    Henry LC:  5.3E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.115E+011  hours   (8.811E+009 days)
    Half-Life from Model Lake : 2.307E+012  hours   (9.612E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              26.97  percent
    Total biodegradation:        0.30  percent
    Total sludge adsorption:    26.68  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       5.61e-005       1.22         1000       
   Water     8.59            1.44e+003    1000       
   Soil      89.2            2.88e+003    1000       
   Sediment  2.17            1.3e+004     0          
     Persistence Time: 2.91e+003 hr

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