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

Details

Stereochemistry RACEMIC
Molecular Formula C22H24ClN3O
Molecular Weight 381.8992
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELASTINE

SMILES

CN1CCCC(CC1)n2c(=O)c3ccccc3c(Cc4ccc(cc4)Cl)n2

InChI

InChIKey=MBUVEWMHONZEQD-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula C22H24ClN3O
Molecular Weight 381.8992
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including: http://www.rxlist.com/astelin-drug.htm | https://www.drugs.com/pro/azelastine.html

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ASTELIN

Approved Use

Azelastine hydrochloride ophthalmic solution is indicated for the treatment of itching of the eye associated with allergic conjunctivitis.

Launch Date

8.4680638E11
Palliative
ASTELIN

Approved Use

Azelastine hydrochloride ophthalmic solution is indicated for the treatment of itching of the eye associated with allergic conjunctivitis.

Launch Date

8.4680638E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
61.59 pg/mL
0.28 mg single, nasal
dose: 0.28 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1526.8 pg × h/mL
0.28 mg single, nasal
dose: 0.28 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22 h
unknown, unknown
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
unknown, unknown
AZELASTINE HYDROCHLORIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 mg 1 times / day multiple, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 38.5 years (range: 18-64 years)
n = 16
Health Status: unhealthy
Condition: Chronic Idiopathic Urticaria
Age Group: 38.5 years (range: 18-64 years)
Sex: M+F
Population Size: 16
Sources:
Disc. AE: Taste perversion, Gastritis...
AEs leading to
discontinuation/dose reduction:
Taste perversion (2 patients)
Gastritis (1 patient)
Somnolence (1 patient)
Sources:
0.015 mg 2 times / day multiple, ophthalmic
Dose: 0.015 mg, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.015 mg, 2 times / day
Sources:
unhealthy, 4-12 years
n = 51
Health Status: unhealthy
Condition: seasonal allergic conjunctiviti
Age Group: 4-12 years
Sex: M+F
Population Size: 51
Sources:
Disc. AE: Burning sensation, Taste bitter...
AEs leading to
discontinuation/dose reduction:
Burning sensation (1 patient)
Taste bitter (1 patient)
Sources:
274 ug 2 times / day multiple, intranasal
Recommended
Dose: 274 ug, 2 times / day
Route: intranasal
Route: multiple
Dose: 274 ug, 2 times / day
Sources: Page: p. 44
unhealthy, > 12 years
n = 216
Health Status: unhealthy
Condition: seasonal allergic rhinitis.
Age Group: > 12 years
Population Size: 216
Sources: Page: p. 44
Disc. AE: Somnolence, Back pain...
AEs leading to
discontinuation/dose reduction:
Somnolence (2 patients)
Back pain (1 patient)
Taste perversion (1 patient)
Sinusitis (1 patient)
Sources: Page: p. 44
AEs

AEs

AESignificanceDosePopulation
Gastritis 1 patient
Disc. AE
4 mg 1 times / day multiple, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 38.5 years (range: 18-64 years)
n = 16
Health Status: unhealthy
Condition: Chronic Idiopathic Urticaria
Age Group: 38.5 years (range: 18-64 years)
Sex: M+F
Population Size: 16
Sources:
Somnolence 1 patient
Disc. AE
4 mg 1 times / day multiple, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 38.5 years (range: 18-64 years)
n = 16
Health Status: unhealthy
Condition: Chronic Idiopathic Urticaria
Age Group: 38.5 years (range: 18-64 years)
Sex: M+F
Population Size: 16
Sources:
Taste perversion 2 patients
Disc. AE
4 mg 1 times / day multiple, oral
Dose: 4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 4 mg, 1 times / day
Sources:
unhealthy, 38.5 years (range: 18-64 years)
n = 16
Health Status: unhealthy
Condition: Chronic Idiopathic Urticaria
Age Group: 38.5 years (range: 18-64 years)
Sex: M+F
Population Size: 16
Sources:
Burning sensation 1 patient
Disc. AE
0.015 mg 2 times / day multiple, ophthalmic
Dose: 0.015 mg, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.015 mg, 2 times / day
Sources:
unhealthy, 4-12 years
n = 51
Health Status: unhealthy
Condition: seasonal allergic conjunctiviti
Age Group: 4-12 years
Sex: M+F
Population Size: 51
Sources:
Taste bitter 1 patient
Disc. AE
0.015 mg 2 times / day multiple, ophthalmic
Dose: 0.015 mg, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.015 mg, 2 times / day
Sources:
unhealthy, 4-12 years
n = 51
Health Status: unhealthy
Condition: seasonal allergic conjunctiviti
Age Group: 4-12 years
Sex: M+F
Population Size: 51
Sources:
Back pain 1 patient
Disc. AE
274 ug 2 times / day multiple, intranasal
Recommended
Dose: 274 ug, 2 times / day
Route: intranasal
Route: multiple
Dose: 274 ug, 2 times / day
Sources: Page: p. 44
unhealthy, > 12 years
n = 216
Health Status: unhealthy
Condition: seasonal allergic rhinitis.
Age Group: > 12 years
Population Size: 216
Sources: Page: p. 44
Sinusitis 1 patient
Disc. AE
274 ug 2 times / day multiple, intranasal
Recommended
Dose: 274 ug, 2 times / day
Route: intranasal
Route: multiple
Dose: 274 ug, 2 times / day
Sources: Page: p. 44
unhealthy, > 12 years
n = 216
Health Status: unhealthy
Condition: seasonal allergic rhinitis.
Age Group: > 12 years
Population Size: 216
Sources: Page: p. 44
Taste perversion 1 patient
Disc. AE
274 ug 2 times / day multiple, intranasal
Recommended
Dose: 274 ug, 2 times / day
Route: intranasal
Route: multiple
Dose: 274 ug, 2 times / day
Sources: Page: p. 44
unhealthy, > 12 years
n = 216
Health Status: unhealthy
Condition: seasonal allergic rhinitis.
Age Group: > 12 years
Population Size: 216
Sources: Page: p. 44
Somnolence 2 patients
Disc. AE
274 ug 2 times / day multiple, intranasal
Recommended
Dose: 274 ug, 2 times / day
Route: intranasal
Route: multiple
Dose: 274 ug, 2 times / day
Sources: Page: p. 44
unhealthy, > 12 years
n = 216
Health Status: unhealthy
Condition: seasonal allergic rhinitis.
Age Group: > 12 years
Population Size: 216
Sources: Page: p. 44
PubMed

PubMed

TitleDatePubMed
Evaluation of the efficacy of olopatadine hydrochloride 0.1% ophthalmic solution and azelastine hydrochloride 0.05% ophthalmic solution in the conjunctival allergen challenge model.
2001 Aug
[Influence of peplomycin on pulmonary function (PaO2, %DLco) in patients with oral carcinoma].
2001 Sep
Mechanism of the antitussive effect of azelastine in guinea pigs.
2002
Azelastine is more potent than olopatadine n inhibiting interleukin-6 and tryptase release from human umbilical cord blood-derived cultured mast cells.
2002 May
A study of intranasal distribution of azelastine hydrochloride aqueous nasal spray with different spray techniques.
2002 Oct
Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity.
2003 Sep
Pharmacokinetic interactions between Japanese traditional medicine (kampo) and modern medicine (III). Effect of Sho-seiryu-to on the pharmacokinetics of azelastine hydrochloride in rats.
2004 May
Review of the pharmacology, clinical efficacy, and safety of azelastine hydrochloride.
2005 Jul
[Azelastine hydrochloride in the treatment of allergic rhinitis].
2005 Sep
Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells.
2006 Oct 10
Onset of action of azelastine nasal spray compared with mometasone nasal spray and placebo in subjects with seasonal allergic rhinitis evaluated in an environmental exposure chamber.
2007 Jul-Aug
Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability.
2007 Oct
Comparison of the conjunctival toxicity of topical ocular antiallergic agents.
2008 Dec
Combination therapy with azelastine hydrochloride nasal spray and fluticasone propionate nasal spray in the treatment of patients with seasonal allergic rhinitis.
2008 Jan
Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis.
2008 Oct
Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops.
2008 Sep
Contact allergic dermatitis and periocular depigmentation after using olapatidine eye drops.
2008 Sep-Oct
Management of allergic conjunctivitis: an evaluation of the perceived comfort and therapeutic efficacy of olopatadine 0.2% and azelastine 0.05% from two prospective studies.
2009
Influence of epinastine hydrochloride, an H1-receptor antagonist, on the function of mite allergen-pulsed murine bone marrow-derived dendritic cells in vitro and in vivo.
2009
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Effects of olopatadine hydrochloride nasal spray 0.6% in the treatment of seasonal allergic rhinitis: a phase III, multicenter, randomized, double-blind, active- and placebo-controlled study in adolescents and adults.
2009 Jan
Allergen-induced airway inflammation and its therapeutic intervention.
2009 Oct
Advanced taste sensors based on artificial lipids with global selectivity to basic taste qualities and high correlation to sensory scores.
2010
Double-blind, placebo-controlled study of azelastine and fluticasone in a single nasal spray delivery device.
2010 Aug
Prevention and management of antineoplastic therapy induced oral mucositis.
2010 Jul
Rhinitis in the geriatric population.
2010 May 13
Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis.
2010 Sep 7
The discovery of phthalazinone-based human H1 and H3 single-ligand antagonists suitable for intranasal administration for the treatment of allergic rhinitis.
2011 Apr 14
Patents

Sample Use Guides

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
Created
by admin
on Fri Jun 25 22:00:16 UTC 2021
Edited
by admin
on Fri Jun 25 22:00:16 UTC 2021
Record UNII
ZQI909440X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZELASTINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
AZELASTINE [VANDF]
Common Name English
AZELASTINE [WHO-DD]
Common Name English
AZELASTINE [INN]
Common Name English
1(2H)-PHTHALAZINONE, 4-((4-CHLOROPHENYL)METHYL)-2-(HEXAHYDRO-1-METHYL-1H-AZEPIN-4-YL)-
Systematic Name English
NSC-758971
Code English
4-(4-CHLOROBENZYL)-2-(1-METHYLAZEPAN-4-YL)PHTHALAZIN-1(2H)-ONE
Systematic Name English
AZELASTINE [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-VATC QS01GX07
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-ATC S01GX07
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-ATC R06AX19
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-VATC QR06AX19
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-ATC R01AC03
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
WHO-VATC QR01AC03
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
NDF-RT N0000175519
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
NDF-RT N0000175587
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
Code System Code Type Description
MESH
C020976
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
INN
4074
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
IUPHAR
7121
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
NCI_THESAURUS
C61643
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
HSDB
7991
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
RXCUI
18603
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY RxNorm
PUBCHEM
2267
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
MERCK INDEX
M2169
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
271
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
DRUG BANK
DB00972
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
EPA CompTox
58581-89-8
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
WIKIPEDIA
AZELASTINE
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
LACTMED
Azelastine
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL639
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
EVMPD
SUB05649MIG
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
CAS
58581-89-8
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
FDA UNII
ZQI909440X
Created by admin on Fri Jun 25 22:00:16 UTC 2021 , Edited by admin on Fri Jun 25 22:00:16 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Desmethylazelastine, by the cytochrome P450 enzyme system. The specific P450 isoforms responsible for the biotransformation of azelastine have not been identified
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC SINGLE DOSE

INTRANASAL ADMINISTRATION