ChemSpider 2D Image | Escitalopram | C20H21FN2O

Escitalopram

  • Molecular FormulaC20H21FN2O
  • Average mass324.392 Da
  • Monoisotopic mass324.163788 Da
  • ChemSpider ID129277

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

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

Escitalopram [BAN] [INN] [JAN] [USAN] [Wiki]
(+)-Citalopram
(1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile [ACD/IUPAC Name]
(1S)-1-[3-(Diméthylamino)propyl]-1-(4-fluorophényl)-1,3-dihydro-2-benzofurane-5-carbonitrile [French] [ACD/IUPAC Name]
(1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorphenyl)-1,3-dihydro-2-benzofuran-5-carbonitril [German] [ACD/IUPAC Name]
(S)-citalopram
128196-01-0 [RN]
5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1S)- [ACD/Index Name]
Cipralex
Citalopram [Wiki]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:36791 [DBID]
4O4S742ANY [DBID]
EPA Pesticide Chemical Code 079011 [DBID]
KBio2_001881 [DBID]
KBio2_004449 [DBID]
KBio2_007017 [DBID]
KBio3_001864 [DBID]
KBioGR_001644 [DBID]
KBioSS_001881 [DBID]
Lopac-C-7861 [DBID]
More...
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Nitrile; Organofluoride; Ether; Drug; Food Toxin; Serotonin Uptake Inhibitor; Antidepressant, Second-Generation; Metabolite; Synthetic Compound; Antidepressive Agent, Second-Generation Toxin, Toxin-Target Database T3D3007

    • Safety:

      N06AB10 Wikidata Q423757

    • Target Organs:

      Serotonin uptake inhibitor;Noradrenaline uptake inhibitor;Histamine Receptor antagonist;Dopamine uptake inhibitor;AChR antagonist;Adrenergic Receptor agonist TargetMol T0185

    • Chemical Class:

      A 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has <stereo>S</stereo>-configuration at the chiral centre. It is the active enantiomer of citalopram. ChEBI CHEBI:36791
      A 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has S-configuration at the chiral centre. It is the active enantiomer of citalopram. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36791, CHEBI:36791

    • Bio Activity:

      Escitalopram is a selective serotonin reuptake inhibitor (SSRI) with Ki of 0.89 nM. MedChem Express
      Escitalopram is a selective serotonin reuptake inhibitor (SSRI) with Ki of 0.89 nM.;Target: SSRIsEscitalopram, the S-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD). Escitalopram has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of escitalopram is found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Escitalopram does not inhibit monoamine oxidase. MedChem Express HY-14258
      Neuronal Signaling; MedChem Express HY-14258
      Neuroscience;GPCR/G protein TargetMol T0185
      Sodium-dependent serotonin transporter;Sodium-dependent noradrenaline transporter;Histamine H1 receptor;Sodium-dependent dopamine transporter;Muscarinic AChR;??-adrenergic receptor TargetMol T0185
      SSRIs MedChem Express HY-14258

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 428.3±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Enthalpy of Vaporization: 68.3±3.0 kJ/mol
Flash Point: 212.8±28.7 °C
Index of Refraction: 1.591
Molar Refractivity: 92.1±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 2.51
ACD/LogD (pH 5.5): 0.34
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.47
ACD/LogD (pH 7.4): 1.27
ACD/BCF (pH 7.4): 1.68
ACD/KOC (pH 7.4): 12.59
Polar Surface Area: 36 Å2
Polarizability: 36.5±0.5 10-24cm3
Surface Tension: 49.9±5.0 dyne/cm
Molar Volume: 272.6±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) =  3.74

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  417.85  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.03  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.13E-007  (Modified Grain method)
    BP  (exp database):  178 @ 0.03 mm Hg deg C
    Subcooled liquid VP: 3.05E-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):  31.09
       log Kow used: 3.74 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  4.018 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.69E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.551E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.74  (KowWin est)
  Log Kaw used:  -8.959  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.699
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.6464
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5174  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.8768  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0288
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.5868
 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):  0.000407 Pa (3.05E-006 mm Hg)
  Log Koa (Koawin est  ): 12.699
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00738 
       Octanol/air (Koa) model:  1.23 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.21 
       Mackay model           :  0.371 
       Octanol/air (Koa) model:  0.99 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  92.1481 E-12 cm3/molecule-sec
      Half-Life =     0.116 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.393 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.291 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.537E+004
      Log Koc:  4.404 

 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 = 2.181 (BCF = 151.9)
       log Kow used: 3.74 (estimated)

 Volatilization from Water:
    Henry LC:  2.69E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:  3.92E+007  hours   (1.633E+006 days)
    Half-Life from Model Lake : 4.277E+008  hours   (1.782E+007 days)

 Removal In Wastewater Treatment:
    Total removal:              19.74  percent
    Total biodegradation:        0.24  percent
    Total sludge adsorption:    19.50  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       6.21e-005       2.79         1000       
   Water     4.37            4.32e+003    1000       
   Soil      94.7            8.64e+003    1000       
   Sediment  0.927           3.89e+004    0          
     Persistence Time: 7.86e+003 hr

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