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Showing Compound Escitalopram (FDB023596)

Record Information
Version1.0
Creation date2011-09-21 00:32:09 UTC
Update date2015-07-21 06:57:47 UTC
Primary IDFDB023596
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEscitalopram
DescriptionA furancarbonitrile that is one of the Serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Escitalopram (Cipralex) is a medication developed by the Danish pharmaceutical company Lundbeck, that acts as a selective serotonin reuptake inhibitor (SSRI). It is typically used as an antidepressant to treat depression associated with mood disorders, although it also may be used in the treatment of body dysmorphic disorder and anxiety, including OCD. In the United States, the drug is marketed under the name Lexapro by Forest Laboratories, Inc; Escitalopram is a medication that acts as a selective serotonin reuptake inhibitor (SSRI). It is typically used as an antidepressant to treat depression associated with mood disorders, although it also may be used in the treatment of body dysmorphic disorder and anxiety, including OCD; Discontinuation from antidepressants, especially abruptly, has been known to cause certain withdrawal symptoms. One possible discontinuation symptom from Escitalopram is a type of spontaneous nerve pulse known as paresthesia or 'electric shock sensations', described by some patients as a feeling of small electric shocks, which may be accompanied by dizziness. These pulses may be short in duration, only milliseconds long, may affect any region of the body, and recur up to several times a minute, throughout all waking hours. They can be increased by physical activity, but are not solely linked to muscular activity. Other discontinuation symptoms include extreme sensitivity to loud sounds and bright lights, chills, hot flushes, cold sweats, reddening of the face, abdominal pain, weight gain and extreme mental fatigue. [HMDB]
CAS Number128196-01-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability35.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H21FN2O
IUPAC name(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
InChI IdentifierInChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
InChI KeyWSEQXVZVJXJVFP-FQEVSTJZSA-N
Isomeric SMILESCN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
Average Molecular Weight324.3919
Monoisotopic Molecular Weight324.163791509
Classification
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl halide
  • Aryl fluoride
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Carbonitrile
  • Nitrile
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791 )
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEscitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-6190000000-9c092c583199a2a486efSpectrum
Predicted GC-MSEscitalopram, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-1497000000-a840cd3176ff240d74f62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0bt9-0692000000-dbd03d31621a5efaba542021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-84c6ddc8fad411d8541f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1029000000-d4716f92fec4a098ef2c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-5290000000-45334fd57d41c1fadf1a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-23521c8b9dc4834c93282021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0091000000-bdb51930294423bb33152021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1590000000-b821092ee64991ad43902021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1029000000-b0f10b0f7897ca083ed52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-2294000000-5935fccdd160458bb8362016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9740000000-7a3a98de78c385feae562016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-5baf9d241e4712801e872021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3079000000-3efd9cf0f4fddbeed2c92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1950000000-69ba9b80f8bec9cbe8742021-09-24View Spectrum
NMRNot Available
ChemSpider ID129277
ChEMBL IDCHEMBL1508
KEGG Compound IDNot Available
Pubchem Compound ID146570
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01175
HMDB IDHMDB05028
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEscitalopram
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference