Azelastine

Base Information

• Chemical Name: Azelastine
• CAS No.: 58581-89-8
• Deprecated CAS: 153483-42-2
• Molecular Formula: C22H24ClN3O
• Molecular Weight: 381.905
• Hs Code.: 2933990090
• European Community (EC) Number: 611-699-2
• UNII: ZQI909440X
• DSSTox Substance ID: DTXSID6022638
• Nikkaji Number: J13.831B
• Wikipedia: Azelastine
• Wikidata: Q419820
• NCI Thesaurus Code: C61643
• RXCUI: 18603
• Pharos Ligand ID: VKY49BVV56A6
• Metabolomics Workbench ID: 145700
• ChEMBL ID: CHEMBL639
• Mol file: 58581-89-8.mol

Synonyms:4-((4-chlorophenyl)methyl)-2- (hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)- phthalazinone HCl;4-(p-chlorobenzyl)-2-(N-methylperhydroazepinyl-(4))-1-(2H)-phthalazinone;A 5610;A-5610;Afluon;Allergodil;Astelin;azelastine;azelastine hydrochloride;Azeptin;Corifina;Loxin;Optilast;Optivar;Rhinolast;Vividrin akut Azelastin

Chemical Property of Azelastine

Chemical Property:

• Appearance/Colour: white crystal powder
• Refractive Index: 1.5790 (estimate)
• Boiling Point: 533.9 °C at 760 mmHg
• PKA: pKa 9.82(H2O t=25 I=0.025) (Uncertain)
• Flash Point: 276.7 °C
• PSA: 38.13000
• Density: 1.25 g/cm³
• LogP: 4.23540
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 381.1607901
• Heavy Atom Count: 27
• Complexity: 558

Purity/Quality:

98%,99%, ^*data from raw suppliers

Azelastine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,T
• Hazard Codes: N,T

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCCC(CC1)N2C(=O)C3=CC=CC=C3C(=N2)CC4=CC=C(C=C4)Cl
• Recent ClinicalTrials: Prospective, Randomized, Multinational, Multicenter, Double-blind, Placebo and Active Controlled Trial in 4 Parallel-groups of Patients Suffering From Seasonal Allergic Rhinitis
• Recent EU Clinical Trials: A multicenter, randomized, double-blind, placebo and active controlled parallel-group trial to assess the efficacy and safety of the fixed combination medicinal product Mometasone furoate + Azelastine hydrochloride nasal spray (50 + 140 mcg) in the treatment of seasonal allergic rhinitis
• Uses: anesthetic, anticonvulsant
• Clinical Use: Azelastine, although not a close structural analogue to the benzimidazoles, has some structural similarities to them. It is used as a nasal spray for allergic rhinitis and as eye drops for allergic conjunctivitis.Like olopatadine, azelastine also stabilizes mast cells, preventing degranulation and subsequent release of histamine, leukotrienes, and PGD2. It is available in Europe for systemic use in the treatment of asthma and seasonal allergies. Besides antihistaminic effects, it also may block release of histamine and other inflammatory mediators from mast cells. When administered orally, the N-dealkylated metabolite appears to contribute significantly to its pharmacological effects.

Technology Process of Azelastine

There total 15 articles about Azelastine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

azelastine hydrochloride (79307-93-0,153408-27-6) → azelastine (58581-89-8,143228-85-7)

Guidance literature:

With sodium hydroxide; In water; pH=10; Inert atmosphere;

DOI:10.1021/jacs.6b09690

Reference yield:

1H-azepine, 4-hydrazinohexahydro-1-methyl, dihydrochloride + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8,143228-85-7)

Guidance literature:

1H-azepine, 4-hydrazinohexahydro-1-methyl, dihydrochloride; 2‐(4-chlorophenylacetyl)benzoic acid; With sodium hydroxide; In methanol; water; for 4h; Heating / reflux;

With hydrogenchloride; In methanol; 2,8-dimethylnonan-5-one; water;

Reference yield:

C14H23N3O(2+)*C4H2O4(2-) + 2‐(4-chlorophenylacetyl)benzoic acid (53242-76-5) → azelastine (58581-89-8,143228-85-7)

Guidance literature:

C₁₄H₂₃N₃O⁽²⁺⁾*C₄H₂O₄^(2-); With hydrogenchloride; at 20 ℃; for 2h; Reflux;

2‐(4-chlorophenylacetyl)benzoic acid; for 2h; Reflux;

upstream raw materials:

4-[(4-chlorophenyl)methyl]-1(2H)-phthalazinone

2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride

2‐(4-chlorophenylacetyl)benzoic acid

2-Benzoyl-1-(hexahydro-1-methyl-1H-azepin-4-yl)hydrazin-hydrochlorid

Downstream raw materials:

2-(1-benzylazepan-4-yl)-4-(4-chlorobenzyl)phthalazin-1(2H)-one

(R)-azelastine

(S)-azelastine

azelastine hydrochloride