diphenoxylate   Click here for help

GtoPdb Ligand ID: 7164

Synonyms: Co-phenotrope | diphenoxylate HCl | Lomotil®
Approved drug
diphenoxylate is an approved drug
Compound class: Synthetic organic
Comment: Diphenoxylate is a phenylpiperidine series, centrally-active opioid antidiarrheal drug. Diphenoxylate is metabolised in vivo to form difenoxin. Both diphenoxylate and difenoxin can be prescribed in fixed-dose combination with atropine to act as an abuse deterrent. Atropine causes severe weakness and nausea if standard doses are exceeded.
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View more information in the IUPHAR Pharmacology Education Project: 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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 0
Rotatable bonds 9
Topological polar surface area 53.33
Molecular weight 452.25
XLogP 6.29
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
Isomeric SMILES CCOC(=O)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C#N)c1ccccc1
InChI InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
InChI Key HYPPXZBJBPSRLK-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to treat diarrhea. The US FDA website only has records for this compound as an active component in formulations also containing atropine. Such formulations appear to have been approved since at least 1960. Neither the EMA or eMC list any drugs containing diphenoxylate.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Diphenoxylate is a chemical relative of pethidine, an opioid analgesic. CHEMBL list the drug target as the μ opioid receptor (OPRM1). This drug is believed to increase intestinal transit time by slowing peristalsis. This allows the gut to re-absorb more water, producing firmer stools. See the DrugBank link for further details.