AZELASTINE, (R)-

Possibly Marketed Outside US

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

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	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 Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316	Antagonist 2,849		8.9 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 104	Primary		Approved 8,583	ASTELIN

C_max

Value	Dose	Analyte	Population
0.26 ng/mL	0.28 mg 2 times / day multiple, nasal	AZELASTINE plasma	Homo sapiens
0.12 ng/mL	0.28 mg 2 times / day multiple, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
3.9 ng/mL	2.2 mg 2 times / day multiple, oral	AZELASTINE plasma	Homo sapiens
1.86 ng/mL	2.2 mg 2 times / day multiple, oral	DESMETHYLAZELASTINE plasma	Homo sapiens
200 pg/mL	548 μg single, nasal	AZELASTINE plasma	Homo sapiens
23 pg/mL	548 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
409 pg/mL	822 μg single, nasal	AZELASTINE plasma	Homo sapiens
38 pg/mL	822 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
235 pg/mL	548 μg single, nasal	AZELASTINE plasma	Homo sapiens
24 pg/mL	548 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
0.55 ng/mL	1 mg single, oral	AZELASTINE plasma	Homo sapiens
2.6 ng/mL	4 mg single, oral	AZELASTINE plasma	Homo sapiens
1.1 ng/mL	2 mg single, oral	AZELASTINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
5122 pg × h/mL	548 μg single, nasal	AZELASTINE plasma	Homo sapiens
2131 pg × h/mL	548 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
9312 pg × h/mL	822 μg single, nasal	AZELASTINE plasma	Homo sapiens
3824 pg × h/mL	822 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
6122 pg × h/mL	548 μg single, nasal	AZELASTINE plasma	Homo sapiens
2615 pg × h/mL	548 μg single, nasal	DESMETHYLAZELASTINE plasma	Homo sapiens
12.17 ng × h/mL	1 mg single, oral	AZELASTINE plasma	Homo sapiens
38.6 ng × h/mL	4 mg single, oral	AZELASTINE plasma	Homo sapiens
28.24 ng × h/mL	2 mg single, oral	AZELASTINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
20 h	2.2 mg 2 times / day multiple, oral	AZELASTINE plasma	Homo sapiens
45 h	2.2 mg 2 times / day multiple, oral	DESMETHYLAZELASTINE plasma	Homo sapiens
17.3 h	1 mg single, oral	AZELASTINE plasma	Homo sapiens
18.1 h	4 mg single, oral	AZELASTINE plasma	Homo sapiens
21.4 h	2 mg single, oral	AZELASTINE plasma	Homo sapiens

F_unbound

Value	Analyte	Population
5%	AZELASTINE plasma	Homo sapiens
16%	AZELASTINE plasma	Homo sapiens
12%	AZELASTINE plasma	Homo sapiens

PubMed

Show entries

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

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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
Record UNII	434T9969GH
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Code System

Code

Type

Description

CAS

143228-84-6

PRIMARY

PUBCHEM

12831280

PRIMARY

FDA UNII

434T9969GH

PRIMARY

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Related Record

Type

Details


					ZQI909440X

AZELASTINE

RACEMATE -> ENANTIOMER

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound