ChemSpider 2D Image | Granisetron | C18H24N4O

Granisetron

  • Molecular FormulaC18H24N4O
  • Average mass312.409 Da
  • Monoisotopic mass312.195007 Da
  • ChemSpider ID10482033
  • defined stereocentres - 3 of 3 defined stereocentres


More details:






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

109889-09-0 [RN]
1H-Indazole-3-carboxamide, 1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]- [ACD/Index Name]
1-Methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazol-3-carboxamid [German] [ACD/IUPAC Name]
1-Methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide [ACD/IUPAC Name]
1-Méthyl-N-[(3-endo)-9-méthyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide [French] [ACD/IUPAC Name]
6230
BRL 43694A
endo-1-Methyl-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1H-indazole-3-carboxamide
Granisetron [Wiki]
granisetrón [Spanish] [INN]
More...

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

BRL 43694 [DBID]
C07023 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      P261; P262 Biosynth Q-101870
    • Chemical Class:

      A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1<element>H</element>-indazole-3-carboxylic acid with the primary amino group of (3-<stereo>endo</st ereo>)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT<smallsub>3</smallsub> receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting. ChEBI CHEBI:5537
    • Bio Activity:

      5-HT Receptor MedChem Express HY-B0071
      GPCR/G protein MedChem Express HY-B0071
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-B0071
      Granisetron is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemotherapy. MedChem Express
      Granisetron is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemotherapy.; IC50 Value: 17uM (GR reduced 5-HT-evoked contractions) [1]; Target: 5-HT3 receptor; in vitro: In rat forestomach GR reduced 5-HT-evoked contractions at IC50 17 /- 6 uM. MedChem Express HY-B0071
      Granisetron is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemotherapy.;IC50 Value: 17uM (GR reduced 5-HT-evoked contractions) [1];Target: 5-HT3 receptor;In vitro: In rat forestomach GR reduced 5-HT-evoked contractions at IC50 17 /- 6 uM. In isolated rabbit heart, GR 0.003-0.03 nM dose-dependently reduced s-HT tachycardia; at high levels GR reduced submaximal and maximal responses to 5-HT [1].;In vivo: Leukocyte accumulation was dose-dependently inhibited by granisetron both at 6 and 72 h after induction of inflammation. Granisetron increased PGE(2) level at a lower dose (50 microg/pouch) but higher doses (100 and 200 microg/pouch) inhibited the release. At the same time, TNFalpha production was decreased by the lower dose and increased by higher doses of granisetron in a reciprocal fashion [2]. The GTDS displayed non-inferiority to oral granisetron: complete control was achieved by 60% of patients in the GTDS group, and 65% MedChem Express HY-B0071

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

Density: 1.3±0.1 g/cm3
Boiling Point: 532.0±40.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 80.8±3.0 kJ/mol
Flash Point: 275.6±27.3 °C
Index of Refraction: 1.690
Molar Refractivity: 89.8±0.5 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.47
ACD/LogD (pH 5.5): -0.97
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.77
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 50 Å2
Polarizability: 35.6±0.5 10-24cm3
Surface Tension: 51.3±7.0 dyne/cm
Molar Volume: 234.8±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) =  3.00

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  494.74  (Adapted Stein & Brown method)
    Melting Pt (deg C):  210.14  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.03E-010  (Modified Grain method)
    Subcooled liquid VP: 3.73E-008 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):  28.42
       log Kow used: 3.00 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1806.1 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.66E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.829E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.00  (KowWin est)
  Log Kaw used:  -12.825  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.825
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6037
   Biowin2 (Non-Linear Model)     :   0.2770
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1998  (months      )
   Biowin4 (Primary Survey Model) :   3.3144  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0058
   Biowin6 (MITI Non-Linear Model):   0.0059
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.8292
 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):  4.97E-006 Pa (3.73E-008 mm Hg)
  Log Koa (Koawin est  ): 15.825
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.603 
       Octanol/air (Koa) model:  1.64E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.956 
       Mackay model           :  0.98 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 119.4084 E-12 cm3/molecule-sec
      Half-Life =     0.090 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.075 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.968 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  7589
      Log Koc:  3.880 

 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 = 1.611 (BCF = 40.8)
       log Kow used: 3.00 (estimated)

 Volatilization from Water:
    Henry LC:  3.66E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.827E+011  hours   (1.178E+010 days)
    Half-Life from Model Lake : 3.085E+012  hours   (1.285E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               5.69  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     5.57  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       6.32e-007       2.15         1000       
   Water     10.7            1.44e+003    1000       
   Soil      89              2.88e+003    1000       
   Sediment  0.268           1.3e+004     0          
     Persistence Time: 2.68e+003 hr




                    

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