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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-16 11:45:18 UTC
Update Date2017-10-23 19:04:14 UTC
HMDB IDHMDB0005000
Secondary Accession Numbers
  • HMDB05000
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
ClaritinKegg
AlavertHMDB
AmantadineHMDB
AnhissenHMDB
BonalergHMDB
ClaritineHMDB
ClaritynHMDB
ClarityneHMDB
CronopenHMDB
FlonidanHMDB
FristaminHMDB
HistaloranHMDB
KlaritinHMDB
LertamineHMDB
LisinoHMDB
LoracertHMDB
LoradexHMDB
LoranoxHMDB
LorastineHMDB
LoratidineHMDB
ClariumMeSH
Loratadine wyeth brandMeSH
Wyeth brand OF loratadineMeSH
4-(8-chloro-5,6-dihydro-11H-benzo(5,6)Cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl esterMeSH
Chemical FormulaC22H23ClN2O2
Average Molecular Weight382.883
Monoisotopic Molecular Weight382.144805697
IUPAC Nameethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate
Traditional Nameloratadine
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
DescriptionThis compound 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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Nervous system disorders:

    Renal and urinary disorders:

    Eye disorders:

    Gastrointestinal disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP5.20SANGSTER (1994)
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
Polarizability41.67 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
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
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
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 SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Brain
  • Central Nervous System
  • Skin
Pathways
NameSMPDB/PathwhizKEGG
Loratadine H1-Antihistamine ActionPw061144Pw061144 greyscalePw061144 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.02 +/- 0.33 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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 ID210803
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)Download (PDF)
General References
  1. Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
  2. Green LB, Hornyak JE, Hurvitz EA: Amantadine in pediatric patients with traumatic brain injury: a retrospective, case-controlled study. Am J Phys Med Rehabil. 2004 Dec;83(12):893-7. [PubMed:15624567 ]
  3. Purohit A, Melac M, Pauli G, Frossard N: Comparative activity of cetirizine and desloratadine on histamine-induced wheal-and-flare responses during 24 hours. Ann Allergy Asthma Immunol. 2004 Jun;92(6):635-40. [PubMed:15237765 ]
  4. Kornhuber J, Quack G, Danysz W, Jellinger K, Danielczyk W, Gsell W, Riederer P: Therapeutic brain concentration of the NMDA receptor antagonist amantadine. Neuropharmacology. 1995 Jul;34(7):713-21. [PubMed:8532138 ]
  5. Deep P, Dagher A, Sadikot A, Gjedde A, Cumming P: Stimulation of dopa decarboxylase activity in striatum of healthy human brain secondary to NMDA receptor antagonism with a low dose of amantadine. Synapse. 1999 Dec 15;34(4):313-8. [PubMed:10529725 ]
  6. Strong DK, Eisenstat DD, Bryson SM, Sitar DS, Arbus GS: Amantadine neurotoxicity in a pediatric patient with renal insufficiency. DICP. 1991 Nov;25(11):1175-7. [PubMed:1763530 ]
  7. Ramboer I, Bumtbacea R, Lazarescu D, Radu JR: Cetirizine and loratadine: a comparison using the ED50 in skin reactions. J Int Med Res. 2000 Mar-Apr;28(2):69-77. [PubMed:10898119 ]
  8. Shiller AD, Burke DT, Kim HJ, Calvanio R, Dechman KG, Santini C: Treatment with amantadine potentiated motor learning in a patient with traumatic brain injury of 15 years' duration. Brain Inj. 1999 Sep;13(9):715-21. [PubMed:10507453 ]
  9. Wilkinson R, Meythaler JM, Guin-Renfroe S: Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury. Brain Inj. 1999 Dec;13(12):1025-31. [PubMed:10628507 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6