2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene

• ChemBase ID: 600
• Molecular Formular: C20H22N2
• Molecular Mass: 290.40208
• Monoisotopic Mass: 290.17829871
• SMILES: N1(CCC(=C2c3c(CCc4c2nccc4)cccc3)CC1)C
• Canonical SMILES: CN1CCC(=C2c3ccccc3CCc3c2nccc3)CC1
• InChI: InChI=1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3
• InChIKey: SEBMTIQKRHYNIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene; 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene; 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,11,13-hexaene
• IUPAC Traditional name: 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaene; 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaene; azatadine
• Brand Name: Optimine
• Synonyms: Azatadina [INN-Spanish]; Azatadine Maleate; Azatadinum [INN-Latin]; Azatidine; Azatadine; 6,11-Dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (2Z)-2-Butenedioate; 5-(4'-N-Methylpiperidylidene)-4-azo-10:11-dihydrodibenzocycloheptene Dimaleate; Atoramin; Bonamid; Idulian; Optimine; Sch 10649; Trinalin; Zadine; Azatadine Dimaleate

Database IDs

• CAS Number: 3964-81-6
• PubChem SID: 46507958; 160964063
• PubChem CID: 19861
• CHEBI ID: 2946
• ATC CODE: R06AX09
• CHEMBL: 946
• Chemspider ID: 18709
• DrugBank ID: DB00719
• KEGG ID: D07482
• Unique Ingredient Identifier: 94Z39NID6C
• Wikipedia Title: Azatadine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3500031
• LogD (pH = 7.4): 3.1173546
• Log P: 3.7475412
• Molar Refractivity: 101.5287 cm^3
• Polarizability: 35.40821 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.67
• LOG S: -3.41
• Solubility (Water): 1.13e-01 g/l

PROPERTIES

Physical Property

• Solubility: Very soluble
• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB00719

• Drug Groups: approved
• Description: Antihistamines such as azatadine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release.
• Indication: For the relief of the symptoms of upper respiratory mucosal congestion in perennial and allergic rhinitis, and for the relief of nasal congestion and eustachian t.b. congestion.
• Pharmacology: Azatadine is an antihistamine, related to cyproheptadine, with anti-serotonin, anticholinergic (drying), and sedative effects. Azatadine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, azatadine is not used clinically as an anti-psychotic. Antihistamines antagonize the vasodilator effect of endogenously released histamine, especially in small vessels, and mitigate the effect of histamine which results in increased capillary permeability and edema formation. As consequences of these actions, antihistamines antagonize the physiological manifestations of histamine release in the nose following antigen-antibody interaction, such as congestion related to vascular engorgement, mucosal edema, and profuse, watery secretion, and irritation and sneezing resulting from histamine action on afferent nerve terminals.
• Toxicity: The oral LD₅₀ in mature rats and mice was greater than 1700 mg/kg and 600 mg/kg, respectively. Symptoms of overdose include clumsiness or unsteadiness, seizures, severe drowsiness, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath, shuffling walk, tic-like (jerky) movements of head and face, trembling and shaking of hands, and insomnia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Well absorbed after oral administration.
• References: Zhang D, Hansen EB Jr, Deck J, Heinze TM, Sutherland JB, Cerniglia CE: Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. Appl Environ Microbiol. 1996 Sep;62(9):3477-9. [Pubmed] ; Katelaris C: Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. Asian Pac J Allergy Immunol. 1990 Dec;8(2):103-7. [Pubmed] ; Small P, Barrett D, Biskin N: Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation. Ann Allergy. 1990 Feb;64(2 Pt 1):129-31. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A802950

Antihistaminic.

REFERENCES

• Zhang D, Hansen EB Jr, Deck J, Heinze TM, Sutherland JB, Cerniglia CE: Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. Appl Environ Microbiol. 1996 Sep;62(9):3477-9. Pubmed
• Katelaris C: Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. Asian Pac J Allergy Immunol. 1990 Dec;8(2):103-7. Pubmed
• Small P, Barrett D, Biskin N: Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation. Ann Allergy. 1990 Feb;64(2 Pt 1):129-31. Pubmed
• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2008)
• De Graw, A., et al.: J. Med. Chem., 53, 2464 (2008)
• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2008)