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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 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
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

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.0092 g/LNot Available
LogP4.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available192.697http://allccs.zhulab.cn/database/detail?ID=AllCCS00001063
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.75730932474
DeepCCS[M-H]-185.36830932474
DeepCCS[M-2H]-219.63230932474
DeepCCS[M+Na]+195.84430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AzelastineCN1CCCC(CC1)N1N=C(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2C1=O4240.4Standard polar33892256
AzelastineCN1CCCC(CC1)N1N=C(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2C1=O3133.9Standard non polar33892256
AzelastineCN1CCCC(CC1)N1N=C(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2C1=O3320.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Azelastine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9886000000-488eee761663db10fdf72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azelastine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azelastine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine , positive-QTOFsplash10-001i-0219000000-689aed0dccf673820d4e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine LC-ESI-QFT , positive-QTOFsplash10-03e9-2908000000-3d19ebb91515adce237b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 35V, Positive-QTOFsplash10-03e9-1908000000-95d1d10eb0ad7e0a5caa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 40V, Positive-QTOFsplash10-00di-0593000000-58523cbdb28285c913e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 50V, Positive-QTOFsplash10-05i0-0940000000-8644fd48c2a4a3af1ceb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 50V, Positive-QTOFsplash10-05i0-0950000000-344a725e5180781636512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 20V, Positive-QTOFsplash10-001i-0009000000-47ec9bd1fd4efec1a3932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 35V, Positive-QTOFsplash10-001i-1349000000-8e49a62427e3060b124f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 10V, Positive-QTOFsplash10-001i-0009000000-66d30432d2e83b7bef0b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azelastine 30V, Positive-QTOFsplash10-001i-0129000000-f11386dc3536cefda9782021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 10V, Positive-QTOFsplash10-001i-0019000000-3cb870845555c5786c732016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 20V, Positive-QTOFsplash10-053r-0369000000-b74e000f63bb368b99b12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 40V, Positive-QTOFsplash10-03l0-9410000000-7199ebf04c51eb076d6c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 10V, Negative-QTOFsplash10-001i-0019000000-9890b690027006b28ee12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 20V, Negative-QTOFsplash10-001i-1159000000-752e6f7ffd2b5aeeca782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 40V, Negative-QTOFsplash10-014i-1190000000-e1fac913b1bac22471392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 10V, Positive-QTOFsplash10-001i-0009000000-65debeb41831c291eceb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 20V, Positive-QTOFsplash10-001i-0209000000-d6632dfc2bb4c411543c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 40V, Positive-QTOFsplash10-03fr-3942000000-125e45b36545578394a02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 10V, Negative-QTOFsplash10-001i-0009000000-e093c6464a3534f2d4482021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 20V, Negative-QTOFsplash10-001i-0019000000-d58a8236055ebf7fd0e32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azelastine 40V, Negative-QTOFsplash10-05o0-6963000000-f9e3f6b0ea6656234db42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00972 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]