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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24ClN3O
Molecular Weight 381.898
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELASTINE, (S)-

SMILES

CN1CCC[C@@H](CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=C(C=CC=C4)C2=O

InChI

InChIKey=MBUVEWMHONZEQD-SFHVURJKSA-N
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/t18-/m0/s1

HIDE SMILES / InChI

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

Description

Azelastine (brand names AZEP, ASTEPRO, ASTELIN etc.) a phthalazine derivative, is an antihistamine and mast cell stabilizer available as a nasal spray for hay fever and as eye drops for allergic conjunctivitis. Azelastine is a potent antiallergic compound with histamine H1-receptor antagonist activity and a rapid onset and long duration of action. The major metabolite, desmethylazelastine, also exhibits H1- receptor antagonist activity. AZEP Nasal Spray is administered as a racemic mixture. The racemate, R- and S- enantiomers were equally potent at inhibiting eyelid histamine-induced oedema in rats, however the R-enantiomer was 2-fold less active at inhibiting eyeball histamine-induced oedema.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.9 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ASTELIN

PubMed

Sample Use Guides

In Vivo Use Guide
Adults and children aged 5 years and over:Each spray contains 125 ug of azelastine (as hydrochloride).One spray into each nostril twice daily as necessary (equivalent to a daily dose of 0.50 mg azelastine
Route of Administration: Nasal
In Vitro Use Guide
The greatest inhibition of mediator release was seen when cultured human mast cells (CHMCs) were pretreated with 24 uM of azelastine.
Substance Class Chemical
Record UNII
7Y9YE1DOYQ
Record Status Validated (UNII)
Record Version