Substance
ID:203
Names and Identifiers
IUPAC Traditional name
codeine
Synonyms
Codeine anhydrousL-CodeineMorphine monomethyl etherMethylmorphineNorcodeine, N-MethylCodeineNorcodine, N-Methyl
Brand Name
CodiceptCoducept
IUPAC name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
Properties
Physical Property
Hydrophobicity(logP)
1.19 [AVDEEF,A ET AL. (1996)]
Solubility
9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Molecule Details
Drug Groups
illicit; approved
Description
An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. [PubChem]
Indication
For treatment and management of pain (Systemic), also used as an Antidiarrheal and as a cough suppressant.
Pharmacology
Codeine, an opiate agonist in the CNS, is similar to other phenanthrene derivatives such as morphine. Codeine, in combination with guaifenesin or iodinated glycerol, is used as a cough suppressant and, as a single agent or in combination with acetaminophen or other products, is used for pain control and as an antidiarrheal agent.
Toxicity
Respiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue.
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6.
Absorption
Well absorbed following oral administration with a bioavailability of approximately 90%.
Half Life
2-4 hours
Protein Binding
7-25%
References
•
Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831.
[Pubmed]
•
Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8.
[Pubmed]
•
Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. Pubmed
• Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. Pubmed
• Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. Pubmed