1-{3-[bis(2H3)methylcarbamoyl]-3,3-diphenylpropyl}-4-(4-chlorophenyl)-4-hydroxypiperidin-1-ium-1-olate

• ChemBase ID: 172374
• Molecular Formular: C29H33ClN2O3
• Molecular Mass: 493.03692
• Monoisotopic Mass: 492.21797061
• SMILES: c1c(ccc(c1)C1(CC[N+](CC1)(CCC(c1ccccc1)(c1ccccc1)C(=O)N(C)C)[O-])O)Cl
• Canonical SMILES: Clc1ccc(cc1)C1(O)CC[N+](CC1)([O-])CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C29H33ClN2O3/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32(35)20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
• InChIKey: KXVSBTJVTUVNPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[bis(^2H₃)methylcarbamoyl]-3,3-diphenylpropyl}-4-(4-chlorophenyl)-4-hydroxypiperidin-1-ium-1-olate
• IUPAC Traditional name: 1-{3-[bis(^2H₃)methylcarbamoyl]-3,3-diphenylpropyl}-4-(4-chlorophenyl)-4-hydroxypiperidin-1-ium-1-olate
• Synonyms: trans-4-(4-Chlorophenyl)-4-hydroxy-N,N-(dimethyl-d6)-α,α-diphenyl-1-piperidinebutanamide 1-Oxide; Arestal-d6; Loperamide-d6 Oxide; R 58425-d6; Loperamide-d6 N-Oxide

Database IDs

• PubChem SID: 164228284
• PubChem CID: 71749831

CALCULATED PROPERTIES

• Acid pKa: 13.929086
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.6466148
• LogD (pH = 7.4): 3.646813
• Log P: 3.6468158
• Molar Refractivity: 141.3639 cm^3
• Polarizability: 54.379246 Å^3
• Polar Surface Area: 67.42 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L469462

Labelled Loperamide oxide (LOPOX). It is a prodrug of Loperamide (LOP). It is concluded that Loperamide oxide administered intraluminally is reduced to Loperamide and has the same antisecretory potency as Loperamide in jejunum and colon.

REFERENCES

• Lavrijsen, K., et al.: Drug Metab. Dispos., 23, 354 (1995)
• Hesselink, D., et al.: Clin. Pharmacol. Ther., 74, 245 (1995)
• Hooijberg, J., et al.: Biochem. Pharmacol., 67, 1541 (1995)