Codeine

Codeine
Clinical data
Pronunciation	/ˈkoʊdiːn/
Other names	3-Methylmorphine
AHFS/Drugs.com	Monograph
MedlinePlus	a682065
Pregnancy; category	AU: A;
Dependence; liability	High
Addiction; liability	High
Routes of; administration	By mouth, rectal, subcutaneous injection, intramuscular injection
Drug class	Opioid; Antitussives
ATC code	R05DA04 (WHO) ; Combinations: N02AA59 (WHO), N02AA79 (WHO), N02AJ08 (WHO), N02AJ06 (WHO), N02AJ07 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug) / S4 (Prescription only); BR: Class A2 (Narcotic drugs) / Class C1; CA: Schedule I; DE: Anlage III (Special prescription form required); NZ: Class C; UK: Class B / Pharmacy medicine; US: Schedule II / Schedule III–V; UN: Narcotic Schedule II / Narcotic Schedule III;
Pharmacokinetic data
Bioavailability	Oral: ~90%
Metabolism	Liver: CYP2D6 (to morphine), CYP3A4 (to norcodeine), UGT2B7 (to 3- and 6-glucuronides of codeine, norcodeine, and morphine)
Metabolites	• Morphine; • Norcodeine; • Others (e.g., conjugates)
Onset of action	15–30 minutes
Elimination half-life	2.5–3 hours
Duration of action	4–6 hours
Identifiers
	IUPAC name (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol;
CAS Number	76-57-3 ;
PubChem CID	5284371;
IUPHAR/BPS	1673;
DrugBank	DB00318 ;
ChemSpider	4447447 ;
UNII	UX6OWY2V7J;
KEGG	C06174 ;
ChEBI	CHEBI:16714 ;
ChEMBL	ChEMBL485 ;
CompTox Dashboard (EPA)	DTXSID2020341 ;
ECHA InfoCard	100.000.882
Chemical and physical data
Formula	C18H21NO3
Molar mass	299.370 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O;
	InChI InChI=1S/C18H21NO3/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,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1 ; Key:OROGSEYTTFOCAN-DNJOTXNNSA-N ;
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Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of habituation and overdose.

Common side effects include vomiting, constipation, itchiness, lightheadedness, and drowsiness. Serious side effects may include breathing difficulties and addiction. Whether its use in pregnancy is safe is unclear. Care should be used during breastfeeding, as it may result in opiate toxicity in the baby. Its use as of 2016 is not recommended in children. Codeine works following being broken down by the liver into morphine; how quickly this occurs depends on a person's genetics.

Codeine was discovered in 1832 by Pierre Jean Robiquet. In 2013, about 361,000 kg (795,000 lb) of codeine were produced while 249,000 kg (549,000 lb) were used, which made it the most commonly taken opiate. It is on the World Health Organization's List of Essential Medicines. Codeine occurs naturally and makes up about 2% of opium.

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