dihydrocodeine   Click here for help

GtoPdb Ligand ID: 7594

Synonyms: DF-118 | Dicogesic® | dihydrocodeine bitartrate | Drocode | Paracodeine®
Approved drug
dihydrocodeine is an approved drug (FDA (1958, as bitartrate with aspirin and caffeine))
Compound class: Synthetic organic
Comment: Dihydrocodeine is a semi-synthetic opioid analgesic.
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View more information in the IUPHAR Pharmacology Education Project: dihydrocodeine

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 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 41.93
Molecular weight 301.17
XLogP 1.06
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
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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 COc1ccc2c3c1OC1C43CCN(C(C2)C4CCC1O)C
Isomeric SMILES COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CC[C@@H]1O)C
InChI InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChI Key RBOXVHNMENFORY-DNJOTXNNSA-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 pain or severe dyspnea (shortness of breath), or as an antitussive, either alone or as a brand mixture with paracetamol e.g. co-dydramol, or aspirin. There is no information of the US FDA website regarding approval of a single agent formulation containing dihydrocodeine. Individual national approval agencies may have granted marketing authorisation for this drug (e.g. UK 1986).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Dihydrocodeine 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.