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Details

Stereochemistry RACEMIC
Molecular Formula C22H24ClN3O.ClH
Molecular Weight 418.359
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELASTINE HYDROCHLORIDE

SMILES

Cl.CN1CCCC(CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=CC=CC=C4C2=O

InChI

InChIKey=YEJAJYAHJQIWNU-UHFFFAOYSA-N
InChI=1S/C22H24ClN3O.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H24ClN3O
Molecular Weight 381.898
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Azelastine, a phthalazine derivative, is an antihistamine and mast cell stabilizer. Azelastine is oxidatively metabolized to the principal active metabolite, desmethylazelastine, by the cytochrome P450 enzyme system. It is indicated for the relief of the symptoms of seasonal allergic rhinitis and perennial allergic rhinitis. The most common adverse reactions are: pyrexia, dysgeusia, nasal discomfort, epistaxis, headache, sneezing, fatigue, somnolence, upper respiratory infection, cough, rhinalgia, vomiting, otitis media, contact dermatitis, and oropharyngeal pain. Concurrent use of Azelastine with alcohol or other central nervous system depressants should be avoided because reductions in alertness and impairment of central nervous system performance may occur.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
872.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ASTELIN
Palliative
ASTELIN

Cmax

ValueDoseCo-administeredAnalytePopulation
61.59 pg/mL
0.28 mg single, nasal
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1526.8 pg × h/mL
0.28 mg single, nasal
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
22 h
unknown, unknown
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
unknown, unknown
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
0.1% or 0.15% azelastine hydrochloride: 1 or 2 sprays per nostril once or twice daily.
Route of Administration: Nasal
In Vitro Use Guide
In a rat mast RBL-2H3 cell line, azelastine inhibited Ag- and ionomycin-induced TNF-alpha release with IC50 values of 25.7 +/- 3.4 uM and 1.66 +/- 0.45 uM, respectively.
Substance Class Chemical
Record UNII
0L591QR10I
Record Status Validated (UNII)
Record Version