ChemSpider 2D Image | Delavirdine | C22H28N6O3S

Delavirdine

  • Molecular FormulaC22H28N6O3S
  • Average mass456.561 Da
  • Monoisotopic mass456.194366 Da
  • ChemSpider ID5423

More details:



Featured data source



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

1-(5-Methanesulfonamido-1H-indol-2-ylcarbonyl)-4-[3-(1-methylethylamino)pyridinyl]piperazine
1-[3-(Isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine
1-[3-[(1-Methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]-1H-indol-2-yl]carbonyl]piperazine
136817-59-9 [RN]
Delavirdine [INN] [Wiki]
delavirdine [INN_en]
Methanesulfonamide, N-[2-[[4-[3-[(1-methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1H-indol-5-yl]- [ACD/Index Name]
N-[2-({4-[3-(Isopropylamino)-2-pyridinyl]-1-piperazinyl}carbonyl)-1H-indol-5-yl]methanesulfonamide [ACD/IUPAC Name]
N-[2-({4-[3-(Isopropylamino)-2-pyridinyl]-1-pipérazinyl}carbonyl)-1H-indol-5-yl]méthanesulfonamide [French] [ACD/IUPAC Name]
N-[2-({4-[3-(Isopropylamino)-2-pyridinyl]-1-piperazinyl}carbonyl)-1H-indol-5-yl]methansulfonamid [German] [ACD/IUPAC Name]
More...

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

AIDS005059 [DBID]
AIDS-005059 [DBID]
AIDS086776 [DBID]
AIDS-086776 [DBID]
C06941 [DBID]
PubChem Substance ID 329831176 [DBID]
U 90152 [DBID]
U-90152 [DBID]
  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1815
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1815
      J05AG02 Wikidata Q370244
      no pictogram Axon Medchem 1815
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1815
      Warning Axon Medchem 1815
    • Chemical Class:

      The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1<element>H</element>-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavird ine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfon ic acid salt) with other antiretrovirals for combination therapy of HIV infection. ChEBI CHEBI:119573
    • Bio Activity:

      Anti-infection MedChem Express HY-10571
      Anti-infection; MedChem Express HY-10571
      Delavirdine(U 90152) is a potent non-nucleoside reverse transcriptase inhibitor (NNRTI). MedChem Express
      Delavirdine(U 90152) is a potent non-nucleoside reverse transcriptase inhibitor (NNRTI).; IC50 Value: 0.26 uM (Recombinant HIV-1 RT) [1]; Target: HIV-1 reverse transcriptase; NNRTI; in vitro: U-90152 [1-(5-methanesulfonamido-1H-indol-2-yl-carbonyl)-4-[3-(1-methyl eth yl-amino)pyridinyl]piperazine], which inhibited recombinant HIV-1 RT at a 50% inhibitory concentration (IC50) of 0.26 microM (compared with IC50s of > 440 microM for DNA polymerases alpha and delta). MedChem Express HY-10571
      Delavirdine(U 90152) is a potent non-nucleoside reverse transcriptase inhibitor (NNRTI).;IC50 Value: 0.26 uM (Recombinant HIV-1 RT) [1];Target: HIV-1 reverse transcriptase; NNRTI;In vitro: U-90152 [1-(5-methanesulfonamido-1H-indol-2-yl-carbonyl)-4-[3-(1-methyl eth yl-amino)pyridinyl]piperazine], which inhibited recombinant HIV-1 RT at a 50% inhibitory concentration (IC50) of 0.26 microM (compared with IC50s of > 440 microM for DNA polymerases alpha and delta). U-90152 blocked the replication in peripheral blood lymphocytes of 25 primary HIV-1 isolates, including variants that were highly resistant to 3'-azido-2',3'-dideoxythymidine (AZT) or 2',3'-dideoxyinosine, with a mean 50% effective dose of 0.066 +/- 0.137 microM. U-90152 had low cellular cytotoxicity, causing less than 8% reduction in peripheral blood lymphocyte viability at 100 microM. In experiments assessing inhibition of the spread of HIV-1IIIB in cell cultures, U-90152 was much more effective than AZT. When approximately MedChem Express HY-10571
      HIV MedChem Express HY-10571
      HIV NNRTIs MedChem Express HY-10571

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

Density: 1.4±0.1 g/cm3
Boiling Point: 732.0±70.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.4 mmHg at 25°C
Enthalpy of Vaporization: 106.8±3.0 kJ/mol
Flash Point: 396.5±35.7 °C
Index of Refraction: 1.681
Molar Refractivity: 124.3±0.4 cm3
#H bond acceptors: 9
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: -1.21
ACD/LogD (pH 5.5): -0.58
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.78
ACD/BCF (pH 7.4): 1.28
ACD/KOC (pH 7.4): 20.51
Polar Surface Area: 119 Å2
Polarizability: 49.3±0.5 10-24cm3
Surface Tension: 72.3±3.0 dyne/cm
Molar Volume: 328.8±3.0 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) =  2.34

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  658.65  (Adapted Stein & Brown method)
    Melting Pt (deg C):  286.71  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.65E-015  (Modified Grain method)
    Subcooled liquid VP: 2.11E-012 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):  13.66
       log Kow used: 2.34 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  826.02 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.63E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.165E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.34  (KowWin est)
  Log Kaw used:  -22.723  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  25.063
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1468
   Biowin2 (Non-Linear Model)     :   0.0014
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5321  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.9793  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.7085
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.9960
 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):  2.81E-010 Pa (2.11E-012 mm Hg)
  Log Koa (Koawin est  ): 25.063
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.07E+004 
       Octanol/air (Koa) model:  2.84E+012 
   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 = 310.7874 E-12 cm3/molecule-sec
      Half-Life =     0.034 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.779 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  1.598E+005
      Log Koc:  5.203 

 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 = 1.100 (BCF = 12.59)
       log Kow used: 2.34 (estimated)

 Volatilization from Water:
    Henry LC:  4.63E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.702E+021  hours   (1.126E+020 days)
    Half-Life from Model Lake : 2.948E+022  hours   (1.228E+021 days)

 Removal In Wastewater Treatment:
    Total removal:               2.71  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.62  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       1.35e-012       0.826        1000       
   Water     15.2            4.32e+003    1000       
   Soil      84.7            8.64e+003    1000       
   Sediment  0.102           3.89e+004    0          
     Persistence Time: 4.1e+003 hr




                    

Click to predict properties on the Chemicalize site






Advertisement