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Codeine

Catalog No. DB00318 Name DrugBank
CAS Number 76-57-3 Website http://www.ualberta.ca/
M. F. C18H21NO3 Telephone (780) 492-3111
M. W. 299.36424 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 203

SYNONYMS

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
IUPAC Traditional name
codeine
Brand Name
Codicept
Coducept
Synonyms
Norcodeine, N-Methyl
Methylmorphine
Norcodine, N-Methyl
Codeine anhydrous
L-Codeine
Morphine monomethyl ether

DATABASE IDS

PubChem CID 5284371
PubChem SID 46507764
CAS Number 76-57-3

PROPERTIES

Hydrophobicity(logP) 1.19 [AVDEEF,A ET AL. (1996)]
Solubility 9 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DETAILS

Description (English)
Item Information
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
Wikipedia
RxList
Drugs.com

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