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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Approved drug? Yes.
IUPAC Name Click here for help
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
International Nonproprietary Names Click here for help
INN number INN
850 diphenoxylate
Synonyms Click here for help
Co-phenotrope | diphenoxylate HCl | Lomotil®
Database Links Click here for help
CAS Registry No. 915-30-0
ChEMBL Ligand CHEMBL1201294
DrugBank Ligand DB01081
DrugCentral Ligand 918
GtoPdb PubChem SID 178103739
PubChem CID 13505
Search Google for chemical match using the InChIKey HYPPXZBJBPSRLK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HYPPXZBJBPSRLK
Search PubMed clinical trials diphenoxylate
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UniChem Compound Search for chemical match using the InChIKey HYPPXZBJBPSRLK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HYPPXZBJBPSRLK-UHFFFAOYSA-N
Wikipedia Diphenoxylate