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QuickView for Codeine (compound)

Summary
General Info

PubChem

PubChem Compound 11066604

PubChem Compound 11066604

Name:	Codeine
PubChem Compound ID:	11066604
Description:	An opioid analgesic related to MORPHINE but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough.
Molecular formula:	C₁₈H₂₁NO₃
Molecular weight:	302.383 g/mol

DrugBank

Identification

Name:	Codeine
Name (isomeric):	DB00318
Drug Type:	small molecule
Description:	An opioid analgesic related to MORPHINE but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough.
Synonyms:	Norcodeine, N-Methyl; L-Codeine; Codeine anhydrous; Norcodine, N-Methyl; Methylmorphine; Morphine monomethyl ether
Brand:	Coducept, Codicept
Brand name mixture:	Co-codamol(codeine + acetaminophen)
Category:	Narcotics, Analgesics, Antitussive Agents, Antitussives, Opiate Agonists, Analgesics, Opioid
CAS number:	76-57-3

Pharmacology

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.
Mechanism of Action:	Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface ... show more » Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability. show less «
Absorption:	Well absorbed following oral administration with a bioavailability of approximately 90%.
Protein binding:	7-25%
Biotransformation:	Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6.
Half Life:	2-4 hours
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

Interactions

Food interaction:

Avoid alcohol.

Take with food, food reduces irritation.

To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).

Drug interaction:

Dihydroquinidine barbiturate	Quinidine decreases the analgesic effect of codeine
Terbinafine	Terbinafine may decrease the efficacy of Codeine by inhibiting active metabolite production. Consider an alternate analgesic or monitor for effectiveness of Codeine.
Quinidine	Quinidine decreases the analgesic effect of codeine
Cimetidine	Cimetidine may decrease the therapeutic effect of codeine by decreasing its metabolism to its active metabolite, morphine. Monitor for changes in the therapeutic effect of codeine if cimetidine is initiated, discontinued or dose changed.
Triprolidine	The CNS depressants, Triprolidine and Codeine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.

Targets

Mu-type opioid receptor

Kappa-type opioid receptor

Delta-type opioid receptor

Enzymes

Cytochrome P450 2D6

Cytochrome P450 3A4

Cytochrome P450 3A5

Cytochrome P450 3A7