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Chemistry

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Also known as: Azelastine hcl, 79307-93-0, Optivar, Astelin, Allergodil, Rhinolast
Molecular Formula
C22H25Cl2N3O
Molecular Weight
418.4  g/mol
InChI Key
YEJAJYAHJQIWNU-UHFFFAOYSA-N
FDA UNII
0L591QR10I

Azelastine Hydrochloride
Azelastine Hydrochloride is the hydrochloride salt form of azelastine, a phthalazinone derivative with antihistaminergic activity. Azelastine hydrochloride competes with histamine for the H1 receptor, thereby diminishing the actions of histamine on effector cells and decreasing the histamine-mediated symptoms of allergic reaction, such as bronchoconstriction, vasodilation, increased capillary permeability and spasmodic contractions of gastrointestinal smooth muscle.
1 2D Structure

Azelastine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)phthalazin-1-one;hydrochloride
2.1.2 InChI
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
2.1.3 InChI Key
YEJAJYAHJQIWNU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1CCCC(CC1)N2C(=O)C3=CC=CC=C3C(=N2)CC4=CC=C(C=C4)Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
0L591QR10I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-((4-chlorophenyl)methyl)-2- (hexahydro-1-methyl-1h-azepin-4-yl)-1(2h)- Phthalazinone Hcl

2. 4-(p-chlorobenzyl)-2-(n-methylperhydroazepinyl-(4))-1-(2h)-phthalazinone

3. A 5610

4. A-5610

5. Afluon

6. Allergodil

7. Astelin

8. Azelastine

9. Azeptin

10. Corifina

11. Loxin

12. Optilast

13. Optivar

14. Rhinolast

15. Vividrin Akut Azelastin

2.3.2 Depositor-Supplied Synonyms

1. Azelastine Hcl

2. 79307-93-0

3. Optivar

4. Astelin

5. Allergodil

6. Rhinolast

7. Astepro

8. Azeptin

9. Azelastine (hydrochloride)

10. 37932-96-0

11. W-2979m

12. 4-(4-chlorobenzyl)-2-(1-methylazepan-4-yl)phthalazin-1(2h)-one Hydrochloride

13. A-5610

14. E-0659

15. Optilast

16. 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)phthalazin-1-one;hydrochloride

17. Chebi:2951

18. 0l591qr10i

19. 4-(p-chlorobenzyl)-2-(hexahydro-1-methyl-1h-azepin-4-yl)-1(2h)-phthalazinone Monohydrochloride

20. Ncgc00095173-01

21. Dsstox_cid_25945

22. Dsstox_rid_81243

23. Dsstox_gsid_45945

24. 1(2h)-phthalazinone, 4-((4-chlorophenyl)methyl)-2-(hexahydro-1-methyl-1h-azepin-4-yl)-, Monohydrochloride

25. 4-[(4-chlorophenyl)methyl]-2-(hexahydro-1-methyl-1h-azepin-4-yl)phthalazin-1(2h)-one Hydrochloride

26. Corifina

27. Optilas

28. (r)-azelastine Hcl

29. (s)-azelastine Hcl

30. 4-((4-chlorophenyl)methyl)-2-(hexahydro-1-methyl-1h-azepin-4-yl)phthalazin-1(2h)-one Hydrochloride

31. Smr000469183

32. Cas-79307-93-0

33. Radethazin

34. Zalastine

35. Azep

36. Sr-01000762975

37. A 5610

38. Astelin (tn)

39. Einecs 253-720-4

40. Azelastine Hydrochloride [usan:jan]

41. Mfcd00242783

42. Astepro Allergy

43. Cpd000469183

44. Schembl36770

45. Mls001401427

46. Mls006010756

47. Spectrum1505340

48. Unii-0l591qr10i

49. Azelastine Hydrochloride- Bio-x

50. Chembl1200809

51. Dtxsid2045945

52. Azelastine Hydrochloride (astelin)

53. Bcpp000358

54. Hms1922f04

55. Pharmakon1600-01505340

56. Bcp23404

57. Hy-b0462

58. Tox21_111469

59. Azelastine Hydrochloride [mi]

60. Ccg-40046

61. Nsc758971

62. Azelastine Hydrochloride (jp17/usp)

63. Azelastine Hydrochloride [jan]

64. Akos015895420

65. Tox21_111469_1

66. Ac-5498

67. Azelastine Hydrochloride [usan]

68. Bcp9000369

69. Ccg-100841

70. Nc00091

71. W- 979m

72. Azelastine Hydrochloride [mart.]

73. Azelastine Hydrochloride [vandf]

74. Azelastine Hydrochloride [usp-rs]

75. Azelastine Hydrochloride [who-dd]

76. Ncgc00095173-02

77. Ncgc00177979-05

78. Allergodil Pound>>azelastine Hydrochloride

79. As-14079

80. Ba164232

81. Azelastine Hydrochloride, >=98% (hplc)

82. Bcp0726000233

83. Ft-0662380

84. Ft-0662381

85. S2552

86. Sw197471-3

87. Azelastine Hydrochloride [orange Book]

88. Azelastine Hydrochloride [ep Monograph]

89. Azelastine Hydrochloride [usp Monograph]

90. C76537

91. D00659

92. Dymista Component Azelastine Hydrochloride

93. 307a930

94. Azelastine Hydrochloride Component Of Dymista

95. Sr-01000762975-4

96. Q27105897

97. Azelastine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

98. 4-(4-chlorobenzyl)-2-(1-methylazepan-4-yl)-1-phthalazinone Hydrochloride

99. Azelastine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

100. 4-(4-chlorobenzyl)-2-(1-methylazepan-4-yl)phthalazin-1(2h)-onehydrochloride

101. 4-[(4-chlorophenyl)methyl]-2-(1-methyl-4-azepanyl)phthalazin-1-one Hydrochloride

102. Azelastine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

103. Azelastine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 418.4 g/mol
Molecular Formula C22H25Cl2N3O
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass417.1374678 g/mol
Monoisotopic Mass417.1374678 g/mol
Topological Polar Surface Area35.9 Ų
Heavy Atom Count28
Formal Charge0
Complexity558
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameAstelin
PubMed HealthAzelastine (Into the nose)
Drug ClassesNasal Agent
Drug LabelAstelin (azelastine hydrochloride) Nasal Spray, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. Azelastine hydrochloride occurs as a white, almost odorless, crystalline powder with a b...
Active IngredientAzelastine hydrochloride
Dosage FormSpray, metered
RouteNasal
Strengtheq 0.125mg base/spray
Market StatusPrescription
CompanyMeda Pharms

2 of 8  
Drug NameAstepro
Drug LabelASTEPRO (azelastine hydrochloride) Nasal Spray 0.1%, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. ASTEPRO (azelastine hydrochloride) Nasal Spray 0.15%, 205.5 micrograms (mcg), is form...
Active IngredientAzelastine hydrochloride
Dosage FormSpray, metered
RouteNasal
Strengtheq 0.1876mg base/spray
Market StatusPrescription
CompanyMeda Pharms

3 of 8  
Drug NameAzelastine hydrochloride
Drug LabelASTEPRO (azelastine hydrochloride) Nasal Spray 0.1%, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. ASTEPRO (azelastine hydrochloride) Nasal Spray 0.15%, 205.5 micrograms (mcg), is form...
Active IngredientAzelastine hydrochloride
Dosage FormSolution/drops; Spray, metered
RouteNasal; Ophthalmic
Strength0.05%; eq 0.125mg base/spray; eq 0.1876mg base/spray
Market StatusPrescription
CompanyAlcon Pharma; Apotex; Sun Pharma Global; Perrigo Israel

4 of 8  
Drug NameOptivar
PubMed HealthAzelastine
Drug ClassesNasal Agent, Ophthalmologic Agent
Drug LabelOPTIVAR (azelastine hydrochloride ophthalmic solution), 0.05% is a sterile ophthalmic solution containing azelastine hydrochloride, a relatively selective H1-receptor antagonist for topical administration to the eyes. Azelastine hydrochloride is a...
Active IngredientAzelastine hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.05%
Market StatusPrescription
CompanyMeda Pharms

5 of 8  
Drug NameAstelin
PubMed HealthAzelastine (Into the nose)
Drug ClassesNasal Agent
Drug LabelAstelin (azelastine hydrochloride) Nasal Spray, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. Azelastine hydrochloride occurs as a white, almost odorless, crystalline powder with a b...
Active IngredientAzelastine hydrochloride
Dosage FormSpray, metered
RouteNasal
Strengtheq 0.125mg base/spray
Market StatusPrescription
CompanyMeda Pharms

6 of 8  
Drug NameAstepro
Drug LabelASTEPRO (azelastine hydrochloride) Nasal Spray 0.1%, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. ASTEPRO (azelastine hydrochloride) Nasal Spray 0.15%, 205.5 micrograms (mcg), is form...
Active IngredientAzelastine hydrochloride
Dosage FormSpray, metered
RouteNasal
Strengtheq 0.1876mg base/spray
Market StatusPrescription
CompanyMeda Pharms

7 of 8  
Drug NameAzelastine hydrochloride
Drug LabelASTEPRO (azelastine hydrochloride) Nasal Spray 0.1%, 137 micrograms (mcg), is an antihistamine formulated as a metered-spray solution for intranasal administration. ASTEPRO (azelastine hydrochloride) Nasal Spray 0.15%, 205.5 micrograms (mcg), is form...
Active IngredientAzelastine hydrochloride
Dosage FormSolution/drops; Spray, metered
RouteNasal; Ophthalmic
Strength0.05%; eq 0.125mg base/spray; eq 0.1876mg base/spray
Market StatusPrescription
CompanyAlcon Pharma; Apotex; Sun Pharma Global; Perrigo Israel

8 of 8  
Drug NameOptivar
PubMed HealthAzelastine
Drug ClassesNasal Agent, Ophthalmologic Agent
Drug LabelOPTIVAR (azelastine hydrochloride ophthalmic solution), 0.05% is a sterile ophthalmic solution containing azelastine hydrochloride, a relatively selective H1-receptor antagonist for topical administration to the eyes. Azelastine hydrochloride is a...
Active IngredientAzelastine hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.05%
Market StatusPrescription
CompanyMeda Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Histamine H1 Antagonists, Non-Sedating

A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)


Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


Lipoxygenase Inhibitors

Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Histamine-1 Receptor Antagonist [EPC]; Histamine H1 Receptor Antagonists [MoA]

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16-Jan-2021
23-Aug-2024
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DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY...DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20114

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DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY...DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY;0.05MG/SPRAY

USFDA APPLICATION NUMBER - 202236

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DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.05% **...DOSAGE - SOLUTION/DROPS;OPHTHALMIC - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21127

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DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY...DOSAGE - SPRAY, METERED;NASAL - 0.137MG/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22203

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