ChemSpider 2D Image | Ziprasidone | C21H21ClN4OS

Ziprasidone

  • Molecular FormulaC21H21ClN4OS
  • Average mass412.936 Da
  • Monoisotopic mass412.112457 Da
  • ChemSpider ID54841

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146939-27-7 [RN]
2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro- [ACD/Index Name]
2H-indol-2-one, 5-2-4-(1,2-benzisothiazol-3-yl)-1-piperazinylethyl-6-chloro-1,3-dihydro-
5-{2-[4-(1,2-Benzisothiazol-3-yl)piperazin-1-yl]ethyl}-6-chlor-1,3-dihydro-2H-indol-2-on
5-{2-[4-(1,2-Benzisothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
5-{2-[4-(1,2-Benzothiazol-3-yl)-1-piperazinyl]ethyl}-6-chlor-1,3-dihydro-2H-indol-2-on [German] [ACD/IUPAC Name]
5-{2-[4-(1,2-Benzothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one [ACD/IUPAC Name]
5-{2-[4-(1,2-Benzothiazol-3-yl)-1-pipérazinyl]éthyl}-6-chloro-1,3-dihydro-2H-indol-2-one [French] [ACD/IUPAC Name]
5-{2-[4-(1,2-Benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
5-{2-4-(1,2-benzothiazol-3-yl)piperazin-1-ylethyl}-6-chloro-1,3-dihydro-2H-indol-2-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:10119 [DBID]
C07568 [DBID]
CP 88059 [DBID]
CP-88059 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N05AE04 Wikidata Q205517
    • Chemical Class:

      A piperazine compound having 1,2-benzothiazol-3-yl- and 2-(6-chloro-1,3-dihydro-2-oxindol-5-yl)ethyl substituents attached to the nitrogen atoms. ChEBI CHEBI:10119
    • Bio Activity:

      5-HT Receptor MedChem Express HY-14542
      5-HT Receptor Dopamine Receptor MedChem Express HY-14542
      GPCR/G protein MedChem Express HY-14542
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-14542
      Ziprasidone(CP88059) is a combined 5-HT (serotonin) and dopamine receptor antagonist which exhibits potent effects of antipsychotic activity. MedChem Express
      Ziprasidone(CP88059) is a combined 5-HT (serotonin) and dopamine receptor antagonist which exhibits potent effects of antipsychotic activity.; IC50 value:; Target: 5-HT receptor; Dopamine receptor; Ziprasidone possesses an in vitro 5-HT2A/dopamine D2 receptor affinity ratio higher than any clinically available antipsychotic agent. MedChem Express HY-14542
      Ziprasidone(CP88059) is a combined 5-HT (serotonin) and dopamine receptor antagonist which exhibits potent effects of antipsychotic activity.;IC50 value:;Target: 5-HT receptor; Dopamine receptorZiprasidone possesses an in vitro 5-HT2A/dopamine D2 receptor affinity ratio higher than any clinically available antipsychotic agent. In vivo, ziprasidone antagonizes 5-HT2A receptor-induced head twitch with 6-fold higher potency than for blockade of d-amphetamine-induced hyperactivity, a measure of central dopamine D2 receptor antagonism. Ziprasidone also has high affinity for the 5-HT1A, 5-HT1D and 5-HT2C receptor subtypes, which may further enhance its therapeutic potential [1]. Ziprasidone sulfoxide and sulfone were the major metabolites in human serum. The affinities of the sulfoxide and sulfone metabolites for 5-HT2 and D2 receptors are low with respect to ziprasidone, and are thus unlikely to contribute to its antipsychotic effects [2]. Ziprasidone was associated with significant di MedChem Express HY-14542

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

Density: 1.4±0.1 g/cm3
Boiling Point: 554.8±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 83.6±3.0 kJ/mol
Flash Point: 289.3±30.1 °C
Index of Refraction: 1.681
Molar Refractivity: 114.1±0.3 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 4.00
ACD/LogD (pH 5.5): 1.27
ACD/BCF (pH 5.5): 1.14
ACD/KOC (pH 5.5): 6.06
ACD/LogD (pH 7.4): 3.40
ACD/BCF (pH 7.4): 155.36
ACD/KOC (pH 7.4): 825.65
Polar Surface Area: 77 Å2
Polarizability: 45.2±0.5 10-24cm3
Surface Tension: 61.5±3.0 dyne/cm
Molar Volume: 301.4±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) =  3.60

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  609.40  (Adapted Stein & Brown method)
    Melting Pt (deg C):  263.70  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.02E-013  (Modified Grain method)
    Subcooled liquid VP: 4.19E-011 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):  2.133
       log Kow used: 3.60 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.8198 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.43E-019  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.598E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.60  (KowWin est)
  Log Kaw used:  -16.580  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.180
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.2775
   Biowin2 (Non-Linear Model)     :   0.0042
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.3665  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5790  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4870
   Biowin6 (MITI Non-Linear Model):   0.0002
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -3.5540
 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):  5.59E-009 Pa (4.19E-011 mm Hg)
  Log Koa (Koawin est  ): 20.180
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  537 
       Octanol/air (Koa) model:  3.72E+007 
   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 = 333.9819 E-12 cm3/molecule-sec
      Half-Life =     0.032 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    23.058 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    :  4.816E+005
      Log Koc:  5.683 

 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 = 2.074 (BCF = 118.6)
       log Kow used: 3.60 (estimated)

 Volatilization from Water:
    Henry LC:  6.43E-019 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  1.85E+015  hours   (7.71E+013 days)
    Half-Life from Model Lake : 2.019E+016  hours   (8.411E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              15.51  percent
    Total biodegradation:        0.20  percent
    Total sludge adsorption:    15.31  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       4.37e-008       0.769        1000       
   Water     4.6             4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  0.661           3.89e+004    0          
     Persistence Time: 7.72e+003 hr




                    

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