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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:27 UTC
HMDB IDHMDB0015107
Secondary Accession Numbers
  • HMDB15107
Metabolite Identification
Common NameAzelastine
DescriptionAzelastine is only found in individuals that have used or taken this drug. It is a phthalazine derivative, and is an antihistamine and mast cell stabilizer available as a nasal spray for hay fever and as eye drops for allergic conjunctivitis.Azelastine competes with histamine for the H1-receptor sites on effector cells and acts as an antagonist by inhibiting the release of histamine and other mediators involved in the allergic response.
Structure
Thumb
Synonyms
ValueSource
4-(P-Chlorobenzyl)-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1-(2H)-phthalazinoneChEBI
AzelastinaChEBI
AzelastinumChEBI
4-(P-Chlorobenzyl)-2-(N-methylperhydroazepinyl-(4))-1-(2H)-phthalazinoneMeSH
AfluonMeSH
AstelinMeSH
Dagra brand OF azelastine hydrochlorideMeSH
muro Brand OF azelastineMeSH
OptilastMeSH
Orion brand OF azelastine hydrochlorideMeSH
Viatris brand OF azelastine hydrochlorideMeSH
Wallace brand OF azelastine hydrochlorideMeSH
4-((4-Chlorophenyl)methyl)-2- (hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)- phthalazinone HCLMeSH
ASTA medica brand OF azelastine hydrochlorideMeSH
CorifinaMeSH
LoxinMeSH
OptivarMeSH
RhinolastMeSH
Vividrin akut azelastinMeSH
AzeptinMeSH
Bayer brand OF azelastine hydrochlorideMeSH
Sanfer brand OF azelastine hydrochlorideMeSH
AllergodilMeSH
Mann brand OF azelastine hydrochlorideMeSH
Azelastine hydrochlorideMeSH
Chemical FormulaC22H24ClN3O
Average Molecular Weight381.898
Monoisotopic Molecular Weight381.160790112
IUPAC Name4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one
Traditional Nameazelastine
CAS Registry Number58581-89-8
SMILES
CN1CCCC(CC1)N1N=C(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C22H24ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18H,4-5,12-15H2,1H3
InChI KeyMBUVEWMHONZEQD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phthalazinones. These are compounds containing a phthalazine bearing a ketone group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazanaphthalenes
Direct ParentPhthalazinones
Alternative Parents
Substituents
  • Phthalazinone
  • Azepane
  • Chlorobenzene
  • Halobenzene
  • Pyridazinone
  • Monocyclic benzene moiety
  • Aryl chloride
  • Pyridazine
  • Aryl halide
  • Benzenoid
  • Heteroaromatic compound
  • Lactam
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.0092 g/LNot Available
LogP4.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0092 g/LALOGPS
logP3.81ALOGPS
logP4.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity110.52 m³·mol⁻¹ChemAxon
Polarizability41.54 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, Positivesplash10-03di-9886000000-488eee761663db10fdf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0219000000-689aed0dccf673820d4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-2908000000-3d19ebb91515adce237bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-3cb870845555c5786c73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0369000000-b74e000f63bb368b99b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l0-9410000000-7199ebf04c51eb076d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9890b690027006b28ee1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1159000000-752e6f7ffd2b5aeeca78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1190000000-e1fac913b1bac2247139View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Azelastine H1-Antihistamine ActionPw061691Pw061691 greyscalePw061691 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00972 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00972 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00972
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2180
KEGG Compound IDC07768
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzelastine
METLIN IDNot Available
PubChem Compound2267
PDB IDNot Available
ChEBI ID2950
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Horak F: Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. Ther Clin Risk Manag. 2008 Oct;4(5):1009-22. [PubMed:19209282 ]
  2. Bernstein JA: Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. Curr Med Res Opin. 2007 Oct;23(10):2441-52. [PubMed:17723160 ]