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))
Comment: Dihydrocodeine is a semi-synthetic opioid analgesic.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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.