Showing metabocard for Citalopram (BMDB0005038)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:56 UTC
Update Date2020-05-11 20:45:56 UTC
BMDB IDBMDB0005038
Secondary Accession Numbers
  • BMDB05038
Metabolite Identification
Common NameCitalopram
DescriptionCitalopram, also known as citadur or bonitrile, 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. Citalopram is a drug which is used for the treatment of depression, as indicated by the fda label [fda label]. off-label indications include but are not limited to: treatment of sexual dysfunction, post-stroke behavioural changes, ethanol abuse, obsessive-compulsive disorder (ocd) in children, and diabetic neuropathy [fda label], [a321], [a322], [a323], [a324], [a174406], [a174409], [a174412]. Citalopram exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Citalopram.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CitadurKegg
BonitrileHMDB
CelexaHMDB
Citalopram hydrobromideHMDB
NitalapramHMDB
EscitalopramHMDB
CytalopramHMDB
LexaproHMDB
Escitalopram oxalateHMDB
SeropramHMDB
Chemical FormulaC20H21FN2O
Average Molecular Weight324.3919
Monoisotopic Molecular Weight324.163791509
IUPAC Name1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional Namerecital
CAS Registry Number59729-33-8
SMILES
CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier
InChI=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
InChI KeyWSEQXVZVJXJVFP-UHFFFAOYSA-N
Chemical Taxonomy
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
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability35.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-6190000000-9c092c583199a2a486efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0009000000-589e7ae88aee7da0e0bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0029000000-8fd40dc922da5ab2c8b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0291000000-c60cbea4e4e6acbb4599View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00l2-0290000000-f2131534473e56b3c8a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00mk-0390000000-e6cd61150feeca1d2867View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0291000000-ff658bd6b54adccbaf03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0009000000-67fa40aabd862948aaf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0129000000-60abdaff2f5d8f72e271View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bt9-0981000000-1eba423765a46f1dd6b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-514f2e0bb73903b25b90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-f27f46e3a573498d9f9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-5ba355c707bc5008c067View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0009000000-a115136f2084cc2a6a47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0129000000-474ae50db9e74e5a31beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bt9-0981000000-011dbb85d8e791486397View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-99aedc452f996b9c9113View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-c8734dde2a469350af7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-cff11d70160f94e8fc2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0391000000-e7862ea10a18e5771adcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0980000000-d24616414bd7fc5e1182View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0970000000-1c68a33d62afa4612071View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0394000000-f3c86fb3bf5bc7669307View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0390000000-5c227e85878c48f06a42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0239000000-900cc91bba3c1f9f3674View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03di-0291000000-50d4588c6e576ed9479bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9110000000-5b1fde1b7a58929c7f2dView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Liver
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005038
DrugBank IDDB00215
Phenol Explorer Compound IDNot Available
FooDB IDFDB023605
KNApSAcK IDNot Available
Chemspider ID2669
KEGG Compound IDC07572
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitalopram
METLIN ID1781
PubChem Compound2771
PDB IDNot Available
ChEBI ID77397
References
Synthesis ReferencePetersen, Hans; Bogeso, Klaus Peter; Bech Sommer, Michael. Lundbeck A/S, Method for the preparation of citalopram. PCT Int. Appl. (1998), 16 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available