ChemSpider 2D Image | Efavirenz | C14H9ClF3NO2

Efavirenz

  • Molecular FormulaC14H9ClF3NO2
  • Average mass315.675 Da
  • Monoisotopic mass315.027405 Da
  • ChemSpider ID57715
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

(4S)-6-Chlor-4-(cyclopropylethinyl)-4-(trifluormethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-on [German] [ACD/IUPAC Name]
(4S)-6-Chlor-4-(cyclopropylethinyl)-4-(trifluormethyl)-4H-3,1-benzoxazin-2-ol [German] [ACD/IUPAC Name]
(4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one [ACD/IUPAC Name]
(4S)-6-Chloro-4-(cyclopropyléthynyl)-4-(trifluorométhyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one [French] [ACD/IUPAC Name]
(4S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-4H-3,1-benzoxazin-2-ol [ACD/IUPAC Name]
(4S)-6-Chloro-4-(cyclopropyléthynyl)-4-(trifluorométhyl)-4H-3,1-benzoxazin-2-ol [French] [ACD/IUPAC Name]
154598-52-4 [RN]
2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)- [ACD/Index Name]
4H-3,1-Benzoxazin-2-ol, 6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-, (4S)- [ACD/Index Name]
efavirenz [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS032934 [DBID]
AIDS-032934 [DBID]
AIDS106821 [DBID]
AIDS-106821 [DBID]
C08088 [DBID]
D00896 [DBID]
DMP 266 [DBID]
DMP-266 [DBID]
HSDB 7163 [DBID]
L 743726 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J05AG03 Wikidata Q422645
    • Target Organs:

      AntiVirus TargetMol T2393
    • Chemical Class:

      1,4-Dihydro-2<element>H</element>-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (<stereo>S</stereo> configuration) and at the 6 position by chlori ne. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection. ChEBI CHEBI:119486
    • Drug Status:

      Approved BIONET-Key Organics KS-5380
    • Bio Activity:

      Anti-infection; MedChem Express HY-10572
      Efavirenz is a non-nucleoside reverse transcriptase inhibitor (NNRTI).;IC50 Value: 60 nM [1];Target: NNRTIs; HIV;In vitro: Efavirenz is a potent inhibitor of the wild-type HIV-1 RT (Ki = 2.93 nM) and exhibited a 95% inhibitory concentration of 1.5 nM for the inhibition of HIV-1 replicative spread in cell culture [2]. Efavirenz inhibited synthesis using an RNA PPT-primed substrate with an IC50 of 17 nM. In contrast to L-697661 and nevirapine, efavirenz also inhibited synthesis with the DNA PPT-primed substrate. However, with an IC50 of 345 nM, the activity of efavirenz was more than 20-fold less potent as an inhibitor of DNA PPT-primed synthesis compared with reactions in which an RNA PPT primer was used [3]. ;In vivo: Efavirenz occasions drug-lever responding in rats discriminating LSD from saline, and this effect is abolished by selective blockade of the 5-HT(2A) receptor. Similar to LSD, efavirenz induces head-twitch responses in wild-type, but not in 5-HT(2A)-knockout, mice [4] MedChem Express HY-10572
      HIV NNRTIs MedChem Express HY-10572
      Microbiology & Virology TargetMol T2393
      NNRTIs; HIV TargetMol T2393

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

Density: 1.5±0.1 g/cm3
Boiling Point: 340.6±42.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 58.4±3.0 kJ/mol
Flash Point: 159.8±27.9 °C
Index of Refraction: 1.581
Molar Refractivity: 68.4±0.4 cm3
#H bond acceptors: 3
#H bond donors: 1
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 4.84
ACD/LogD (pH 5.5): 4.38
ACD/BCF (pH 5.5): 1260.15
ACD/KOC (pH 5.5): 5766.04
ACD/LogD (pH 7.4): 4.38
ACD/BCF (pH 7.4): 1258.37
ACD/KOC (pH 7.4): 5757.93
Polar Surface Area: 38 Å2
Polarizability: 27.1±0.5 10-24cm3
Surface Tension: 51.3±5.0 dyne/cm
Molar Volume: 205.3±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) =  4.15

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  390.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  161.51  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.56E-007  (Modified Grain method)
    Subcooled liquid VP: 1.4E-005 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):  2.816
       log Kow used: 4.15 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.4789 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Halides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.39E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  8.201E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.15  (KowWin est)
  Log Kaw used:  -5.657  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  9.807
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.1389
   Biowin2 (Non-Linear Model)     :   0.0001
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5566  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.0575  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0792
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0660
 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):  0.00187 Pa (1.4E-005 mm Hg)
  Log Koa (Koawin est  ): 9.807
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00161 
       Octanol/air (Koa) model:  0.00157 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0549 
       Mackay model           :  0.114 
       Octanol/air (Koa) model:  0.112 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 103.6280 E-12 cm3/molecule-sec
      Half-Life =     0.103 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.239 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.293830 E-17 cm3/molecule-sec
      Half-Life =     3.900 Days (at 7E11 mol/cm3)
      Half-Life =     93.605 Hrs
   Fraction sorbed to airborne particulates (phi): 0.0844 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.998E+004
      Log Koc:  4.477 

 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 = 2.499 (BCF = 315.1)
       log Kow used: 4.15 (estimated)

 Volatilization from Water:
    Henry LC:  5.39E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.93E+004  hours   (804.2 days)
    Half-Life from Model Lake : 2.107E+005  hours   (8780 days)

 Removal In Wastewater Treatment:
    Total removal:              37.35  percent
    Total biodegradation:        0.38  percent
    Total sludge adsorption:    36.97  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       0.0193          2.41         1000       
   Water     5.82            4.32e+003    1000       
   Soil      90.5            8.64e+003    1000       
   Sediment  3.7             3.89e+004    0          
     Persistence Time: 5.02e+003 hr




                    

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