1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid

• ChemBase ID: 1296
• Molecular Formular: C28H28N2O2
• Molecular Mass: 424.53412
• Monoisotopic Mass: 424.21507815
• SMILES: OC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
• Canonical SMILES: N#CC(c1ccccc1)(c1ccccc1)CCN1CCC(CC1)(C(=O)O)c1ccccc1
• InChI: InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)
• InChIKey: UFIVBRCCIRTJTN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid
• IUPAC Traditional name: difenoxin
• Synonyms: Difenoxin; Difenoxin; Motofen; 1-(3-Cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic Acid; 1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotic Acid; Difenoxilic Acid; Difenoxine; Difenoxylic Acid; Diphenoxylic Acid; Lyspafen; McN-JR 15403-11

Database IDs

• CAS Number: 35607-36-4; 28782-42-5
• PubChem SID: 46508854; 160964756
• PubChem CID: 34328
• CHEBI ID: 4534
• ATC CODE: A07DA04
• CHEMBL: 1201321
• Chemspider ID: 31620
• DrugBank ID: DB01501
• KEGG ID: D03809
• Unique Ingredient Identifier: 3ZZ5BJ9F2Q
• Wikipedia Title: Difenoxin

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3836012
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.6480064
• LogD (pH = 7.4): 2.647184
• Log P: 2.6497838
• Molar Refractivity: 137.2442 cm^3
• Polarizability: 49.10158 Å^3
• Polar Surface Area: 64.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.39
• LOG S: -5.31
• Solubility (Water): 2.08e-03 g/l

PROPERTIES

Pharmacology Properties

• Legal Status: Schedule I (by itself); Schedule IV (with atropine) (US)

DETAILS

DrugBank - DB01501

• Drug Groups: illicit; experimental
• Elimination: Difenoxin is metabolized to an inactive hydroxylated metabolite.; Both the drug and its metabolites are excreted, mainly as conjugates, in urine and feces.

Toronto Research Chemicals - D445400

The active metabolite of Diphenoxylate. Antiperistaltic; antidiarrheal. This is a controlled substance (opiate).

REFERENCES

• Soudijin, W., et al.: Arzneim.-Forsch., 22, 513 (1972)
• Megens, A.A., et al.: Eur. J. Pharma.,178, 357 (1972)