2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde

• ChemBase ID: 4473
• Molecular Formular: C19H21N3O
• Molecular Mass: 307.38954
• Monoisotopic Mass: 307.16846231
• SMILES: CN1CCC(=C2c3ccccc3CCn3c2ncc3C=O)CC1
• Canonical SMILES: O=Cc1cnc2n1CCc1c(C2=C2CCN(CC2)C)cccc1
• InChI: InChI=1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3
• InChIKey: MWTBKTRZPHJQLH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde; 2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3,5,11,13-pentaene-6-carbaldehyde
• IUPAC Traditional name: alcaftadine
• Brand Name: Lastacaft
• Synonyms: Alcaftadine; 6,11-Dihydro-11-(1-methyl-4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde; R 89674

Database IDs

• CAS Number: 147084-10-4
• PubChem SID: 160967905; 99443288
• PubChem CID: 19371515

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.48679414
• LogD (pH = 7.4): 1.9729201
• Log P: 2.1713893
• Molar Refractivity: 102.8772 cm^3
• Polarizability: 34.95201 Å^3
• Polar Surface Area: 38.13 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -2.97
• Solubility (Water): 3.33e-01 g/l

DETAILS

DrugBank - DB06766

• Drug Groups: approved
• Description: Alcaftadine is a H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. This drug was approved in July 2010.
• Indication: For the prevention of itching associated with allergic conjunctivitis.
• Pharmacology: Following bilateral topical ocular administration of alcaftadine ophthalmic solution, 0.25%, the mean plasma Cmax of alcaftadine was approximately 60 pg/mL and the median Tmax occurred at 15 minutes. Plasma concentrations of alcaftadine were below the lower limit of quantification (10 pg/mL) by 3 hours after dosing. The mean Cmax of the active carboxylic acid metabolite was approximately 3 ng/mL and occurred at 1 hour after dosing. Plasma concentrations of the carboxylic acid metabolite were below the lower limit of quantification (100 pg/mL) by 12 hours after dosing.
• Biotransformation: The metabolism of alcaftadine is mediated by non-CYP450 cytosolic enzymes to the active carboxylic acid metabolite.
• Half Life: The elimination half-life of the carboxylic acid metabolite is approximately 2 hours following topical ocular administration.
• Protein Binding: The protein binding of alcaftadine and the active metabolite are 39.2% and 62.7% respectively.
• Elimination: Based on data following oral administration of alcaftadine, the carboxylic acid metabolite is primarily eliminated unchanged in the urine.
• External Links: RxList; Drugs.com

Toronto Research Chemicals - A514530

Alcaftadine is a H1 histamine receptor antagonist. Alcaftadine is used to prevent eye irritation and treat the signs and symptoms of allergic conjunctivitis.

REFERENCES

• Greiner, J.V. et al.: Clin. Ophthamol., 5, 87 (2011)
• Torkildsen, G. et al.: Curr. Med. Res. Opin., 27, 623 (2011)
• Bohets, H. et al.: J. Ocular Pharmcol. Therap., 27, 187 (2011)