4-{2-[4-({1-[(4-fluorophenyl)methyl]-1H-1,3-benzodiazol-2-yl}amino)piperidin-1-yl]ethyl}phenol

• ChemBase ID: 166385
• Molecular Formular: C27H29FN4O
• Molecular Mass: 444.5437632
• Monoisotopic Mass: 444.23253979
• SMILES: c1ccc2c(c1)n(c(n2)NC1CCN(CC1)CCc1ccc(cc1)O)Cc1ccc(cc1)F
• Canonical SMILES: Oc1ccc(cc1)CCN1CCC(CC1)Nc1nc2c(n1Cc1ccc(cc1)F)cccc2
• InChI: InChI=1S/C27H29FN4O/c28-22-9-5-21(6-10-22)19-32-26-4-2-1-3-25(26)30-27(32)29-23-14-17-31(18-15-23)16-13-20-7-11-24(33)12-8-20/h1-12,23,33H,13-19H2,(H,29,30)
• InChIKey: LAGYWHSFHIMTPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[4-({1-[(4-fluorophenyl)methyl]-1H-1,3-benzodiazol-2-yl}amino)piperidin-1-yl]ethyl}phenol
• IUPAC Traditional name: 4-{2-[4-({1-[(4-fluorophenyl)methyl]-1,3-benzodiazol-2-yl}amino)piperidin-1-yl]ethyl}phenol
• Synonyms: 4-[2-[4-[[1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]phenol; Desmethylastemizole; O-Demethylastemizole; R 44271; O-Desmethyl Astemizole

Database IDs

• CAS Number: 73736-50-2
• PubChem SID: 162260518
• PubChem CID: 155805

CALCULATED PROPERTIES

• Acid pKa: 10.270207
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2972403
• LogD (pH = 7.4): 3.8180094
• Log P: 5.024252
• Molar Refractivity: 131.1609 cm^3
• Polarizability: 50.605396 Å^3
• Polar Surface Area: 53.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 92-94°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D290750

A metabolite of Astemizole.

REFERENCES

• Nagata, K., et al.: J. Biol. Chem., 268, 24720 (1993)
• Benton, R., et al.: Clin. Pharmacol. Ther., 59, 383 (1993)
• Hashizume, T., et al.: Drug Metab. Dispos., 26, 566 (1993)
• Scarborough, P., et al.: Drug Metab. Rev., 31, 205 (1993)