ChemSpider 2D Image | Diltiazem | C22H26N2O4S

Diltiazem

  • Molecular FormulaC22H26N2O4S
  • Average mass414.518 Da
  • Monoisotopic mass414.161316 Da
  • ChemSpider ID35850
  • defined stereocentres - 2 of 2 defined stereocentres


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(+)-cis-5-[2-(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one Acetate (Ester)
(+)-cis-Diltiazem
(+)-Diltiazem
(2S,3S)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
(2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate [ACD/IUPAC Name]
(2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-ylacetat
(2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl-acetat [German] [ACD/IUPAC Name]
(2S,3S)-5-[2-(dimethylamino)ethyl]-2-[4-(methyloxy)phenyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
(2S-cis)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS000583 [DBID]
AIDS-000583 [DBID]
Bio1_000371 [DBID]
Bio1_000860 [DBID]
Bio1_001349 [DBID]
BRN 3573079 [DBID]
C06958 [DBID]
CCRIS 4693 [DBID]
CRD-401 [DBID]
HSDB 6528 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      C05AE03 Wikidata Q422229
      C08DB01 Wikidata Q422229
    • Chemical Class:

      A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have <stereo>S</stereo> configuration. A calcium-channel blocker a nd vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension. ChEBI CHEBI:101278

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

Density: 1.3±0.1 g/cm3
Boiling Point: 594.4±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 88.6±3.0 kJ/mol
Flash Point: 313.3±30.1 °C
Index of Refraction: 1.621
Molar Refractivity: 115.2±0.4 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.63
ACD/LogD (pH 5.5): 0.55
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 2.34
ACD/LogD (pH 7.4): 2.06
ACD/BCF (pH 7.4): 10.08
ACD/KOC (pH 7.4): 74.19
Polar Surface Area: 84 Å2
Polarizability: 45.7±0.5 10-24cm3
Surface Tension: 56.2±5.0 dyne/cm
Molar Volume: 327.6±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) =  2.79
    Log Kow (Exper. database match) =  2.70
       Exper. Ref:  Hansch,C & Leo,A (1985)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  540.45  (Adapted Stein & Brown method)
    Melting Pt (deg C):  231.50  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.98E-011  (Modified Grain method)
    MP  (exp database):  207.5-212 deg C
    Subcooled liquid VP: 2.56E-009 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):  12.3
       log Kow used: 2.70 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  43.421 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.61E-017  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.321E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.70  (exp database)
  Log Kaw used:  -14.453  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.153
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8612
   Biowin2 (Non-Linear Model)     :   0.9805
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0562  (months      )
   Biowin4 (Primary Survey Model) :   3.4732  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2286
   Biowin6 (MITI Non-Linear Model):   0.0267
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.4140
 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):  3.41E-007 Pa (2.56E-009 mm Hg)
  Log Koa (Koawin est  ): 17.153
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  8.79 
       Octanol/air (Koa) model:  3.49E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.997 
       Mackay model           :  0.999 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 180.1769 E-12 cm3/molecule-sec
      Half-Life =     0.059 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.712 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.998 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  9502
      Log Koc:  3.978 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.805E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.829  years  
  Kb Half-Life at pH 7:      78.287  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.379 (BCF = 23.93)
       log Kow used: 2.70 (expkow database)

 Volatilization from Water:
    Henry LC:  8.61E-017 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.384E+013  hours   (5.769E+011 days)
    Half-Life from Model Lake :  1.51E+014  hours   (6.293E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               3.81  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.70  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       1.28e-007       1.42         1000       
   Water     12.6            1.44e+003    1000       
   Soil      87.2            2.88e+003    1000       
   Sediment  0.162           1.3e+004     0          
     Persistence Time: 2.52e+003 hr




                    

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