4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one hydrochloride

• ChemBase ID: 72741
• Molecular Formular: C22H25Cl2N3O
• Molecular Mass: 418.3594
• Monoisotopic Mass: 417.1374678
• SMILES: c1ccc2c(c1)c(=O)n(nc2Cc1ccc(cc1)Cl)C1CCN(CCC1)C.Cl
• Canonical SMILES: CN1CCCC(CC1)n1nc(Cc2ccc(cc2)Cl)c2c(c1=O)cccc2.Cl
• 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
• InChIKey: YEJAJYAHJQIWNU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one hydrochloride
• IUPAC Traditional name: 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one hydrochloride; azelastine hydrochloride
• Synonyms: 4-[(4-Chlorophenyl)methyl]-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)-phthalazinone Hydrochloride; Afluon; Azeptin; Optilast; A-5610; E-0659; W-2979M; Azel; Lasticom; 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)phthalazin-1-one hydrochloride; Azelastine hydrochloride; Optivar; Azelastine hydrochloride; Azelastine hydrochloride; Allergodil; Rhinolast; Astelin; Optilas

Database IDs

• CAS Number: 79307-93-0
• MDL Number: MFCD00242783
• PubChem SID: 162037662
• PubChem CID: 54360

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.90765303
• LogD (pH = 7.4): 2.554609
• Log P: 4.0412636
• Molar Refractivity: 110.5154 cm^3
• Polarizability: 41.968857 Å^3
• Polar Surface Area: 35.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >10 mg/mL; Methanol; Water
• Apperance: White Solid; white to off-white powder
• Melting Point: 223-225°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Pharmacology Properties

• Target: histamine
• Mechanism of Action: Histamine H1-receptor antagonist and mediator release inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: HCl; hydrochloride
• Application(s): Used for the local treatment of allergic and vasomotor rhinitis and allergic conjunctivitis.
• Empirical Formula (Hill Notation): C22H24ClN3O · HCl

DETAILS

Selleck Chemicals - S2552

Biological Activity:
Azelastine hydrochloride (Astelin) is a potent, second-generation, selective, histamine antagonist. [1] Azelastine hydrochloride (Astelin) has a triple mode of action: Anti-histamine effect, mast-cell stabilizing effect and anti-inflammatory effect. Azelastine hydrochloride (Astelin) has a rapid onset of action: 15 minutes with the nasal spray and 3 minutes with the eye drops. The effect lasts for 12 hours. [2][3][4]

Sigma Aldrich - A7611

Biochem/physiol Actions
H1 histamine receptor antagonist; NF-kB activator.
Application
Azelastine hydrochloride is a H1 histamine receptor antagonist and NF-kB activator. Azelastine hydrochloride has been used in a study to investigate the potential of polymeric microspheres for treatment of allergic conjunctivitis.

Toronto Research Chemicals - A808250

Orally active H1-hystamine receptor antagonist. Antihistaminic.

REFERENCES

• 79307-93-0
• Tasaka, K., et al.: Arzneim.-Forsch., 29, 488 (1979)
• Chand, N., et al.: Int. J. Immunopharmacol., 7, 833 (1979)
• Tasaka, K. et al., Arzneim.-Forsch., 1979, 29, 488
• Zechel, H.J. et al., Arzneim.-Forsch., 1981, 31, 1184
• Hazama, H. et al., Eur. J. Pharmacol., 1994, 259, 143