4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide

• ChemBase ID: 167245
• Molecular Formular: C27H29ClN2O2
• Molecular Mass: 448.98436
• Monoisotopic Mass: 448.19175586
• SMILES: c1c(ccc(c1)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C(=O)N)O)Cl
• Canonical SMILES: Clc1ccc(cc1)C1(O)CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C(=O)N
• InChI: InChI=1S/C27H29ClN2O2/c28-24-13-11-21(12-14-24)26(32)15-18-30(19-16-26)20-17-27(25(29)31,22-7-3-1-4-8-22)23-9-5-2-6-10-23/h1-14,32H,15-20H2,(H2,29,31)
• InChIKey: PXJHDOGGBLQFRX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide
• IUPAC Traditional name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanamide
• Synonyms: 4-(4-Chlorophenyl)-4-hydroxy-α,α-diphenyl-1-piperidinebutanamide; R 21345; N-Didesmethyl Loperamide

Database IDs

• CAS Number: 66164-06-5
• PubChem SID: 162261378
• PubChem CID: 25129795

CALCULATED PROPERTIES

• Acid pKa: 13.961757
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.95497715
• LogD (pH = 7.4): 2.2863026
• Log P: 4.3238387
• Molar Refractivity: 129.5256 cm^3
• Polarizability: 50.57477 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 210-212°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D441135

A metabolite of Loperamide; a new and improved PET radiotracer for imaging P-gp function.

REFERENCES

• Rahman, A., et al.: Cancer Res., 54, 5543 (1994)
• Sai, Y., et al.: Xenobiotica, 30, 327 (1994)
• Eneroth, A., et al.: Eur. J. Pharm. Sci., 12, 205 (1994)
• Kim, K., et al.: Drug Metab. Dispos., 31, 1090 (1994)