Showing metabocard for Loratadine (BMDB0005000)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:30 UTC
Update Date2020-05-11 19:58:21 UTC
BMDB IDBMDB0005000
Secondary Accession Numbers
  • BMDB05000
Metabolite Identification
Common NameLoratadine
DescriptionLoratadine, also known as claritin or alavert, belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle. Based on a literature review a significant number of articles have been published on Loratadine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl esterChEBI
AerotinaChEBI
AlarinChEBI
AlavertChEBI
AlerprivChEBI
AllerclearChEBI
CiveranChEBI
ClaratyneChEBI
ClaritinChEBI
LoracertChEBI
LoradamedChEBI
LoradexChEBI
LorastineChEBI
LoratadinaChEBI
LoratadinumChEBI
LoratyneChEBI
Wal-itinChEBI
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate ethyl esterGenerator
4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl esterMeSH
ClariumMeSH
AmantadineHMDB
AnhissenHMDB
BonalergHMDB
ClaritineHMDB
ClaritynHMDB
ClarityneHMDB
CronopenHMDB
FlonidanHMDB
FristaminHMDB
HistaloranHMDB
KlaritinHMDB
LertamineHMDB
LisinoHMDB
LoranoxHMDB
LoratidineHMDB
Loratadine wyeth brandMeSH, HMDB
Wyeth brand OF loratadineMeSH, HMDB
Chemical FormulaC22H23ClN2O2
Average Molecular Weight382.883
Monoisotopic Molecular Weight382.144805697
IUPAC Nameethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
Traditional Nameethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
CAS Registry Number79794-75-5
SMILES
CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2
InChI Identifier
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
InChI KeyJCCNYMKQOSZNPW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzocycloheptapyridines
Sub ClassNot Available
Direct ParentBenzocycloheptapyridines
Alternative Parents
Substituents
  • Benzocycloheptapyridine
  • Piperidinecarboxylic acid
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Carbamic acid ester
  • Carbonic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP5.2SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP4.8ALOGPS
logP4.55ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)4.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity116.98 m³·mol⁻¹ChemAxon
Polarizability41.68 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-004i-6059000000-3d596b5ab5499c4089caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001r-0039000000-928ed9c6b46ba83ebe20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-1279000000-1c522c39e53b6bbfb9aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-0039000000-928ed9c6b46ba83ebe20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-067r-1292000000-3869907bd01f927b6f22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-067i-0090000000-9bcbcadeda0bf07da702View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0frx-0090000000-2f8b7b5acca254e4cb20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-067i-0090000000-b247e61957d933538341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-dce8adc02434b224d589View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-7d2b8c3f5f87f99fcf7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0api-0090000000-8419cf3b0c888e52c95bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-067r-0093000000-956a3618f6003ae45808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-067i-0090000000-b62a29b4d6252b26f2bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001r-0009000000-d32917132c3359e65572View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0019-0019000000-1acbfc6c05c2d600a966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-4558440f48e82bf6eefbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0019-0009000000-ea1b61e9df959d6680c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-067i-0090000000-cf7d75b43a3c2c0f0d1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-066r-0090000000-c5d1377bb7159732d4dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-015i-0092000000-9bb7dcefe2f2f4f14bfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-41dd9857a0206fa0f4e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-1029000000-0c5a179194107a35af3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-2091000000-fb50d1834a9a1d8d6c90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1009000000-78af7865fc3439c125c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2009000000-df88de530c8ff41c69f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-7069000000-a5804bf835988dc83d2aView 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, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Brain
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005000
DrugBank IDDB00455
Phenol Explorer Compound IDNot Available
FooDB IDFDB023577
KNApSAcK IDNot Available
Chemspider ID3820
KEGG Compound IDC06818
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLoratadine
METLIN ID1021
PubChem Compound3957
PDB IDNot Available
ChEBI ID6538
References
Synthesis ReferenceVilani, Frank J. Antihistaminic 11-(4-piperidylidene)-5H-benzo-(5,6)-cyclohepta-[1,2-b]-pyridines. U.S. (1981), 4 pp. CODEN: USXXAM US 4282233 19810804 CAN 95:203761 AN 1981:603761
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available