AZELASTINE

First approved in 1996

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H24ClN3O
Molecular Weight	381.898
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	381.898
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022203s010s011lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022203s010s011lbl.pdf	Antagonist 2778	872.0 nM [Kd]
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10421623	Substrate 661
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10421623	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022203s010s011lbl.pdf	Palliative		Approved 8429	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
Perennial allergic rhinitis 47 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022203s010s011lbl.pdf	Palliative		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
61.59 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23681835	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

Value	Dose	Co-administered	Analyte	Population
1526.8 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23681835	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
22 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020114s028lbl.pdf	unknown, unknown		AZELASTINE HYDROCHLORIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
12% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020114s028lbl.pdf	unknown, unknown		AZELASTINE HYDROCHLORIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/11316966/	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: https://pubmed.ncbi.nlm.nih.gov/11316966/	Disc. AE: Taste perversion, Gastritis... AEs leading to discontinuation/dose reduction: Taste perversion (2 patients) Gastritis (1 patient) Somnolence (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/11316966/
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: https://pubmed.ncbi.nlm.nih.gov/9787982/	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: https://pubmed.ncbi.nlm.nih.gov/9787982/	Disc. AE: Burning sensation, Taste bitter... AEs leading to discontinuation/dose reduction: Burning sensation (1 patient) Taste bitter (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/9787982/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44	unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/11316966/	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: https://pubmed.ncbi.nlm.nih.gov/11316966/
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: https://pubmed.ncbi.nlm.nih.gov/11316966/	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: https://pubmed.ncbi.nlm.nih.gov/11316966/
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: https://pubmed.ncbi.nlm.nih.gov/11316966/	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: https://pubmed.ncbi.nlm.nih.gov/11316966/
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: https://pubmed.ncbi.nlm.nih.gov/9787982/	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: https://pubmed.ncbi.nlm.nih.gov/9787982/
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: https://pubmed.ncbi.nlm.nih.gov/9787982/	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: https://pubmed.ncbi.nlm.nih.gov/9787982/
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44	unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44	unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44	unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44	unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20114S006_Astelin%20Nasal%20Spray_medr_P2.pdf Page: p. 44

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2950	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2950
ChemicalBook	CB6256007	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6256007
MolPort	MolPort-006-167-674	https://www.molport.com/shop/molecule-link/MolPort-006-167-674

PubMed

Title	Date	PubMed
Review of the pharmacology, clinical efficacy, and safety of azelastine hydrochloride.	2005 Jul	20476933
[Azelastine hydrochloride in the treatment of allergic rhinitis].	2005 Sep	16335418
Combination therapy with azelastine hydrochloride nasal spray and fluticasone propionate nasal spray in the treatment of patients with seasonal allergic rhinitis.	2008 Jan	18254486
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	19381339
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.	2009 Aug 31	21437146
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	19243710

Patents

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 Created by `admin` on `Fri Dec 15 18:58:21 UTC 2023` Edited by `admin` on `Fri Dec 15 18:58:21 UTC 2023`
Record UNII	ZQI909440X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AZELASTINE

Official Name

English

AZELASTINE [VANDF]

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 [WHO-DD]

Common Name

English

AZELASTINE [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000190