difenoxin   Click here for help

GtoPdb Ligand ID: 7592

Synonyms: difenoxin hydrochloride | MCN-JR-15,403-11 | Motofen® | R-15403
Approved drug
difenoxin is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Difenoxin is an active metabolite of diphenoxylate.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 64.33
Molecular weight 424.22
XLogP 5.55
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES N#CC(c1ccccc1)(c1ccccc1)CCN1CCC(CC1)(C(=O)O)c1ccccc1
Isomeric 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)
InChI Key UFIVBRCCIRTJTN-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Approved for the treatment of acute and chronic diarrhea. The 1978 FDA approval was for a a brand mixture containing difenoxin hydrochloride and atropine sulphate (Motofen). The atropine is added to decrease deliberate opioid misuse.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Although difenoxin is capable of crossing the blood brain barrier and produces weak sedative and analgesic effects, its most significant and clinically useful effects are via activation of peripheral opioid receptors in the intestine. Activation of intestinal opioid receptors inhibits peristalsis, therby increasing intestinal transit time.