dextropropoxyphene   Click here for help

GtoPdb Ligand ID: 7593

Synonyms: (+)-alpha-propoxyphene | Darvon® | propoxyphene
Approved drug
dextropropoxyphene is an approved drug
Compound class: Synthetic organic
Comment: Dextropropoxyphene is principally an opioid analgesic. Chemically it is an optical isomer of levopropoxyphene (the (2R,3S) optical isomer with PubChem CID 200742); dextropropoxyphene being the (2S,3R) enantiomer. Marketing in Europe and the US has been discontinued due to concerns of fatal overdoses and heart arrhythmias.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 29.54
Molecular weight 339.22
XLogP 4.37
No. Lipinski's rules broken 0

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
Click here for help

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/)

✖
Canonical SMILES CCC(=O)OC(c1ccccc1)(C(CN(C)C)C)Cc1ccccc1
Isomeric SMILES CCC(=O)O[C@](c1ccccc1)([C@@H](CN(C)C)C)Cc1ccccc1
InChI InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
InChI Key XLMALTXPSGQGBX-GCJKJVERSA-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 mild pain. Although withdrawn from the US and European markets, other individual national approval agencies may still grant marketing authorisation for this drug. The majority of international brand names contain this drug in combination with paracetamol, some contain dextropropoxyphene and metamizole.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Dextropropoxyphene is a μ opioid receptor agonist. Activation of this receptor on central nervous system neurons inhibits intracellular adenylate cyclase. Downstream this leads to reduced calcium influx via membrane calcium channels, and increased potassium permeability by opening membrane potassium channels. This ultimately leads to hyperpolarization of the cell membrane potential and suppression of action potential transmission of ascending pain pathways. Experimental evidence also suggests that dextropropoxyphene can behave as a potent, noncompetitive α3β4 neuronal nicotinic acetylcholine receptor antagonist [1], and as a weak serotonin reuptake inhibitor.