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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:59 UTC
HMDB IDHMDB0015107
Secondary Accession Numbers
  • HMDB15107
Metabolite Identification
Common NameAzelastine
DescriptionAzelastine, also known as optivar or afluon, belongs to the class of organic compounds known as phthalazinones. Phthalazinones are compounds containing a phthalazine bearing a ketone group. Following allergen exposure in sensitized individuals, IgE-receptor cross-linking on mast cells results in the release of histamine, which binds to H1-receptors and contributes to typical allergic symptoms such as itching, sneezing, and congestion. Azelastine is a very strong basic compound (based on its pKa). In humans, azelastine is involved in azelastine h1-antihistamine action. Azelastine antagonizes the actions of histamine, resulting in the relief of histamine-mediated allergy symptoms. Azelastine is a potentially toxic compound. Histamine H1-receptors are G-protein-coupled receptors with 7 transmembrane spanning domains that are found on nerve endings, smooth muscle cells, and glandular cells. Azelastine is also available as a combination product of Azelastine and fluticasone propionate called Dymista®. Elimination half-life of the active metabolite, desmethylazelastine, is 54 hours (after oral administration of azelastine).
Structure
Data?1582753259
Synonyms
ValueSource
4-(p-Chlorobenzyl)-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1-(2H)-phthalazinoneChEBI
AzelastinaChEBI
AzelastinumChEBI
OptivarKegg
4-(p-Chlorobenzyl)-2-(N-methylperhydroazepinyl-(4))-1-(2H)-phthalazinoneHMDB
AfluonHMDB
AstelinHMDB
Dagra brand OF azelastine hydrochlorideHMDB
Muro brand OF azelastineHMDB
OptilastHMDB
Orion brand OF azelastine hydrochlorideHMDB
Viatris brand OF azelastine hydrochlorideHMDB
Wallace brand OF azelastine hydrochlorideHMDB
4-((4-Chlorophenyl)methyl)-2- (hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)- phthalazinone HCLHMDB
ASTA medica brand OF azelastine hydrochlorideHMDB
CorifinaHMDB
LoxinHMDB
RhinolastHMDB
Vividrin akut azelastinHMDB
AzeptinHMDB
Bayer brand OF azelastine hydrochlorideHMDB
Sanfer brand OF azelastine hydrochlorideHMDB
AllergodilHMDB
Mann brand OF azelastine hydrochlorideHMDB
Azelastine hydrochlorideHMDB
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
Description belongs to the class of organic compounds known as phthalazinones. Phthalazinones are compounds containing a phthalazine bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
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
Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9886000000-488eee761663db10fdf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0219000000-689aed0dccf673820d4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-2908000000-3d19ebb91515adce237bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-3cb870845555c5786c73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0369000000-b74e000f63bb368b99b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03l0-9410000000-7199ebf04c51eb076d6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-9890b690027006b28ee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1159000000-752e6f7ffd2b5aeeca78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1190000000-e1fac913b1bac2247139Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00972
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]