U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24ClN3O.ClH
Molecular Weight 418.3601
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELASTINE HYDROCHLORIDE, (R)-

SMILES

CN1CCC[C@]([H])(CC1)n2c(=O)c3ccccc3c(Cc4ccc(cc4)Cl)n2.Cl

InChI

InChIKey=YEJAJYAHJQIWNU-GMUIIQOCSA-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/t18-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H24ClN3O
Molecular Weight 381.8992
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment:: Azelastine is systemically absorbed and can cross the blood–brain barrier. In mice, azelastine showed a definite central action. In rats, a high dose of 100 mg/kg azelastine produced a slight suppression of the paradoxical sleep.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ASTELIN

Approved Use

Astelin Nasal Spray is indicated for the treatment of the symptoms of seasonal allergic rhinitis such as rhinorrhea, sneezing, and nasal pruritus in adults and children 5 years and older, and for the treatment of the symptoms of vasomotor rhinitis, such as rhinorrhea, nasal congestion and postnasal drip in adults and children 12 years and older.

Launch Date

8.4680638E11
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: To male Wistar rats one single dose of 50 mg/kg AZELASTINE, (R)- was applied orally (by oral gavage): https://www.ncbi.nlm.nih.gov/pubmed/12906914
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
Curator's Comment:: Sensitized cultured human mast cells (CHMCs) were pretreated with various concentrations of azelastine or olopatadine for 5 minutes. Then, CHMCs were challenged with anti-immunoglobulin E (IgE) and the released mediators were quantitated.
The greatest inhibition of mediator release was seen when cultured human mast cells (CHMCs) were pretreated with 24 uM of azelastine.
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:37:35 UTC 2021
Edited
by admin
on Fri Jun 25 23:37:35 UTC 2021
Record UNII
A33K416J2W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZELASTINE HYDROCHLORIDE, (R)-
Common Name English
1(2H)-PHTHALAZINONE, 4-((4-CHLOROPHENYL)METHYL)-2-(HEXAHYDRO-1-METHYL-1H-AZEPIN-4-YL)-, MONOHYDROCHLORIDE, (R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
71313551
Created by admin on Fri Jun 25 23:37:35 UTC 2021 , Edited by admin on Fri Jun 25 23:37:35 UTC 2021
PRIMARY
FDA UNII
A33K416J2W
Created by admin on Fri Jun 25 23:37:35 UTC 2021 , Edited by admin on Fri Jun 25 23:37:35 UTC 2021
PRIMARY
CAS
153408-28-7
Created by admin on Fri Jun 25 23:37:35 UTC 2021 , Edited by admin on Fri Jun 25 23:37:35 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER