Record Information
Version1.0
Creation date2011-09-21 00:31:52 UTC
Update date2015-10-09 22:33:18 UTC
Primary IDFDB023577
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLoratadine
Descriptiondesloratadine is available off the shelf in Canada); Loratadine is a tricyclic antihistamine, which has a selective and peripheral H1-antagonist action. It has a long-lasting effect and does not normally cause drowsiness because it does not readily enter the central nervous system; An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic. Its active metabolite, desloratadine, is also on the market, though loratadine itself is the only drug of its class available over the counter (at least in the U.S. as of 2005. Loratadine is available off the shelf in the UK [HMDB]
CAS Number79794-75-5
Structure
Thumb
Synonyms
SynonymSource
ClaritinKegg
4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl esterMeSH
AlavertMeSH
ClariumMeSH
AmantadineHMDB
AnhissenHMDB
BonalergHMDB
ClaritineHMDB
ClaritynHMDB
ClarityneHMDB
CronopenHMDB
FlonidanHMDB
FristaminHMDB
HistaloranHMDB
KlaritinHMDB
LertamineHMDB
LisinoHMDB
LoracertHMDB
LoradexHMDB
LoranoxHMDB
LorastineHMDB
LoratidineHMDB
Loratadine wyeth brandMeSH, HMDB
Wyeth brand OF loratadineMeSH, HMDB
Loratadinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H23ClN2O2
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
InChI IdentifierInChI=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
Isomeric SMILESCCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2
Average Molecular Weight382.883
Monoisotopic Molecular Weight382.144805697
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLoratadine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6059000000-3d596b5ab5499c4089caSpectrum
Predicted GC-MSLoratadine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001r-0039000000-928ed9c6b46ba83ebe20Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-1279000000-1c522c39e53b6bbfb9aaSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-0039000000-928ed9c6b46ba83ebe20Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-067r-1292000000-3869907bd01f927b6f22Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-067i-0090000000-9bcbcadeda0bf07da702Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0frx-0090000000-2f8b7b5acca254e4cb20Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-067i-0090000000-b247e61957d933538341Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-dce8adc02434b224d589Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-7d2b8c3f5f87f99fcf7aSpectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0api-0090000000-8419cf3b0c888e52c95bSpectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-067r-0093000000-956a3618f6003ae45808Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-067i-0090000000-b62a29b4d6252b26f2bfSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001r-0009000000-d32917132c3359e65572Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0019-0019000000-1acbfc6c05c2d600a966Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-4558440f48e82bf6eefbSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0019-0009000000-ea1b61e9df959d6680c2Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-067i-0090000000-cf7d75b43a3c2c0f0d1eSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-066r-0090000000-c5d1377bb7159732d4dbSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-015i-0092000000-9bb7dcefe2f2f4f14bfdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-41dd9857a0206fa0f4e8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-1029000000-0c5a179194107a35af3eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-2091000000-fb50d1834a9a1d8d6c90Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1009000000-78af7865fc3439c125c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2009000000-df88de530c8ff41c69f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-7069000000-a5804bf835988dc83d2aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID3820
ChEMBL IDCHEMBL998
KEGG Compound IDC06818
Pubchem Compound ID3957
Pubchem Substance IDNot Available
ChEBI ID2618
Phenol-Explorer IDNot Available
DrugBank IDDB00455
HMDB IDHMDB05000
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 IDLoratadine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Histamine H1 receptorHRH1P35367
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference