AZELASTINE, (R)-

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 Search

SMILES

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

InChI

InChIKey=MBUVEWMHONZEQD-GOSISDBHSA-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-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H24ClN3O
Molecular Weight	381.898
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.meda.com.au/fileadmin/user_upload/AU/Product_manager/Current_Azep_PI_v5.pdf | https://www.drugbank.ca/drugs/DB00972 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020114s023lbl.pdf

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 Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: http://www.meda.com.au/fileadmin/user_upload/AU/Product_manager/Current_Azep_PI_v5.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/21381763 \| https://www.ncbi.nlm.nih.gov/pubmed/22985961	Antagonist 2849		8.9 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 104 Sources: http://www.meda.com.au/fileadmin/user_upload/AU/Product_manager/Current_Azep_PI_v5.pdf	Primary		Approved 8583	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 1996

C_max

Value	Dose	Analyte	Population
0.26 ng/mL OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	0.28 mg 2 times / day multiple, nasal dose: 0.28 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	AZELASTINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.12 ng/mL OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	0.28 mg 2 times / day multiple, nasal dose: 0.28 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
3.9 ng/mL OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	2.2 mg 2 times / day multiple, oral dose: 2.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AZELASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.86 ng/mL OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	2.2 mg 2 times / day multiple, oral dose: 2.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
200 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
409 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	822 μg single, nasal dose: 822 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
38 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	822 μg single, nasal dose: 822 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
235 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
24 pg/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.55 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=18	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23675185/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
5122 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2131 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9312 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	822 μg single, nasal dose: 822 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3824 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	822 μg single, nasal dose: 822 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6122 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2615 pg × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/e1797a8f2c2b38487c21ccb8946319d339761af5#page=23	548 μg single, nasal dose: 548 μg route of administration: Nasal experiment type: SINGLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.17 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=18	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
38.6 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
28.24 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23675185/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
20 h OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	2.2 mg 2 times / day multiple, oral dose: 2.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AZELASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
45 h OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	2.2 mg 2 times / day multiple, oral dose: 2.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DESMETHYLAZELASTINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
17.3 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=18	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
18.1 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_4490004F1080_1_006_1F.pdf#page=19	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
21.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23675185/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	AZELASTINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Analyte	Population
5% OTHER https://www.medicines.org.uk/emc/product/1623/smpc#PHARMACOKINETIC_PROPS	AZELASTINE plasma	Homo sapiens
16% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/170033_4490004F1021_1_010_1F.pdf#page=22	AZELASTINE plasma	Homo sapiens
12% OTHER https://www.pdr.net/drug-summary/Astepro-azelastine-hydrochloride-994#15	AZELASTINE plasma	Homo sapiens

PubMed

Title	Date	PubMed
Simultaneous enantioselective separation of azelastine and three of its metabolites for the investigation of the enantiomeric metabolism in rats. I. Liquid chromatography-ionspray tandem mass spectrometry and electrokinetic capillary chromatography.	2003 Aug 15	12906914

Patents

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 Created by `admin` on `Mon Mar 31 22:26:28 GMT 2025` Edited by `admin` on `Mon Mar 31 22:26:28 GMT 2025`
Record UNII	434T9969GH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

1(2H)-PHTHALAZINONE, 4-((4-CHLOROPHENYL)METHYL)-2-((4R)-HEXAHYDRO-1-METHYL-1H-AZEPIN-4-YL)-

Preferred Name

English

AZELASTINE, (R)-

Common Name

English

Code System Code Type Description

CAS

143228-84-6

Created by admin on Mon Mar 31 22:26:28 GMT 2025 , Edited by admin on Mon Mar 31 22:26:28 GMT 2025

PRIMARY

PUBCHEM

12831280

Created by admin on Mon Mar 31 22:26:28 GMT 2025 , Edited by admin on Mon Mar 31 22:26:28 GMT 2025

PRIMARY

FDA UNII

434T9969GH

Created by admin on Mon Mar 31 22:26:28 GMT 2025 , Edited by admin on Mon Mar 31 22:26:28 GMT 2025

PRIMARY

Related Record Type Details


					ZQI909440X

AZELASTINE

RACEMATE -> ENANTIOMER

Details

SMILES

InChI

DescriptionSources: http://www.meda.com.au/fileadmin/user_upload/AU/Product_manager/Current_Azep_PI_v5.pdf | https://www.drugbank.ca/drugs/DB00972 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020114s023lbl.pdf

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.meda.com.au/fileadmin/user_upload/AU/Product_manager/Current_Azep_PI_v5.pdf | https://www.drugbank.ca/drugs/DB00972 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020114s023lbl.pdf

C_max

T_1/2

F_unbound