ChemSpider 2D Image | nepicastat | C14H15F2N3S

nepicastat

  • Molecular FormulaC14H15F2N3S
  • Average mass295.351 Da
  • Monoisotopic mass295.095459 Da
  • ChemSpider ID7971947
  • defined stereocentres - 1 of 1 defined stereocentres


More details:






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

173997-05-2 [RN]
177645-08-8 [RN]
2H-Imidazole-2-thione, 5-(aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl]-1,3-dihydro- [ACD/Index Name]
5-(Aminomethyl)-1-((2S)-5,7-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)-1,3-dihydro-2H-imidazole-2-thione
5-(Aminomethyl)-1-[(2S)-5,7-difluor-1,2,3,4-tetrahydro-2-naphthalinyl]-1,3-dihydro-2H-imidazol-2-thion [German] [ACD/IUPAC Name]
5-(Aminométhyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tétrahydro-2-naphtalényl]-1,3-dihydro-2H-imidazole-2-thione [French] [ACD/IUPAC Name]
5-(Aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl]-1,3-dihydro-2H-imidazole-2-thione [ACD/IUPAC Name]
7691
nepicastat [INN]
nepicastat [Spanish] [INN]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      IRRITANT Matrix Scientific 093133
    • Chemical Class:

      A member of the class of 1,3-dihydroimidazole-2-thiones that is 1,3-dihydro-2<element>H</element>-imidazole-2-thione in which one of the nitrogens is substituted by a 5,7-difluoro-1,2,3,4-tetrahydrona phthalen-2-yl group while the carbon adjacent to it is substituted by an aminomethyl group (the <stereo>S</stereo> enantiomer). It is a potent and selective inhibitor of both bovine and human dopamine <locant>beta</locant>-hydroxylase, an enzyme that catalyzes the conversion of dopamine to norepinephrine. ChEBI CHEBI:139334
      A member of the class of 1,3-dihydroimidazole-2-thiones that is 1,3-dihydro-2H-imidazole-2-thione in which one of the nitrogens is substituted by a 5,7-difluoro-1,2,3,4-tetrahydrona; phthalen-2-yl gro up while the carbon adjacent to it is substituted by an aminomethyl group (the S enantiomer). It is a potent and selective inhibitor of both bovine and human dopamine; beta-hydroxylase, an enzyme tha t catalyzes the conversion of dopamine to norepinephrine. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:139334
    • Bio Activity:

      Dopamine ?-hydroxylase MedChem Express HY-13289
      Metabolism/Protease MedChem Express HY-13289
      Metabolism/Protease; MedChem Express HY-13289
      Nepicastat (SYN117; RS-25560-197) is a dopamine beta-hydroxylase inhibitor with IC50 of 8.5 ? 0.8 and 9.0 ? 0.8 nM for bovine and human, respectively. MedChem Express HY-13289
      Nepicastat (SYN117; RS-25560-197) is a dopamine beta-hydroxylase inhibitor with IC50 of 8.5 ? 0.8 and 9.0 ? 0.8 nM for bovine and human, respectively. ;IC50 value: 8.5/9.0 nM(bovine/human dopamine beta-hydroxylase)Dopamine beta-hydroxylase is an enzyme that catalyzes the conversion of dopamine to norepinephrine. Nepicastat (SYN117; RS-25560-197) has been studied as a possible treatment for congestive heart failure, and appears to be well tolerated as such. MedChem Express HY-13289
      Nepicastat (SYN117; RS-25560-197) is a dopamine beta-hydroxylase inhibitor with IC50 of 8.5 ± 0.8 and 9.0 ± 0.8 nM for bovine and human, respectively. MedChem Express http://www.medchemexpress.com/nepicastat.html

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

Density: 1.4±0.1 g/cm3
Boiling Point: 401.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.3±3.0 kJ/mol
Flash Point: 196.8±31.5 °C
Index of Refraction: 1.665
Molar Refractivity: 77.9±0.4 cm3
#H bond acceptors: 3
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 2.31
ACD/LogD (pH 5.5): -1.36
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -0.46
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.38
Polar Surface Area: 73 Å2
Polarizability: 30.9±0.5 10-24cm3
Surface Tension: 63.2±5.0 dyne/cm
Molar Volume: 209.5±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) =  2.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  432.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  181.24  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.08E-008  (Modified Grain method)
    Subcooled liquid VP: 1.3E-006 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):  2439
       log Kow used: 2.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  163.56 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.09E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.908E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.03  (KowWin est)
  Log Kaw used:  -8.898  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.928
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.5397
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5531  (recalcitrant)
   Biowin4 (Primary Survey Model) :   3.5602  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0210
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1170
 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):  0.000173 Pa (1.3E-006 mm Hg)
  Log Koa (Koawin est  ): 10.928
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0173 
       Octanol/air (Koa) model:  0.0208 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.385 
       Mackay model           :  0.581 
       Octanol/air (Koa) model:  0.625 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 230.2385 E-12 cm3/molecule-sec
      Half-Life =     0.046 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.557 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.483 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.346E+004
      Log Koc:  4.129 

 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 = 0.866 (BCF = 7.348)
       log Kow used: 2.03 (estimated)

 Volatilization from Water:
    Henry LC:  3.09E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.256E+007  hours   (1.357E+006 days)
    Half-Life from Model Lake : 3.552E+008  hours   (1.48E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               2.27  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.18  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       0.000248        1.07         1000       
   Water     22.6            4.32e+003    1000       
   Soil      77.3            8.64e+003    1000       
   Sediment  0.0951          3.89e+004    0          
     Persistence Time: 3.07e+003 hr




                    

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