Codeine

For other uses, see Codeine (disambiguation).

Codeine
Skeletal formula
Ball-and-stick model
Clinical data
Pronunciation/ˈkoʊdiːn/
Other names3-Methylmorphine
AHFS/Drugs.comMonograph
MedlinePlusa682065
License data
Pregnancy
category
Dependence
liability		High
Addiction
liability		High[2]
Routes of
administration		By mouth, rectal, subcutaneous, intramuscular
Drug classOpiate,
Antitussive
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~60% (by mouth)[3]
MetabolismLiver: CYP2D6 (to morphine), CYP3A4 (to norcodeine), UGT2B7 (to 3- and 6-glucuronides of codeine, norcodeine, and morphine)[5]
Metabolites• Morphine
• Norcodeine
• Others (e.g., conjugates)
Onset of action15–30 minutes[4]
Elimination half-life2.5–3 hours
Duration of action4–6 hours[4]
Identifiers
  • (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.882 Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO3
Molar mass299.370 g·mol−1
3D model (JSmol)
  • CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
  • 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 ☒N
  • Key:OROGSEYTTFOCAN-DNJOTXNNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[4][6] It is typically used to treat mild to moderate degrees of pain.[4][failed verification] Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen.[4] Evidence does not support its use for acute cough suppression in children.[7][8] In Europe, it is not recommended as a cough medicine in those under 12 years of age.[4] It is generally taken by mouth.[4] It typically starts working after half an hour, with maximum effect at two hours.[4] Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of addiction and overdose.[4]

Common side effects include vomiting, constipation, itchiness, lightheadedness, and drowsiness.[4] Serious side effects may include breathing difficulties and addiction.[4] Whether its use in pregnancy is safe is unclear.[4] Care should be used during breastfeeding, as it may result in opiate toxicity in the baby.[4] Its use as of 2016 is not recommended in children.[9] Codeine works following being broken down by the liver into morphine; how quickly this occurs depends on a person's genetics.[4]

Codeine was discovered in 1832 by Pierre Jean Robiquet.[10] 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.[11] It is on the World Health Organization's List of Essential Medicines.[12] Codeine occurs naturally and makes up about 2% of opium.[10]

  1. ^ "Codeine Use During Pregnancy". Drugs.com. 3 February 2020. Archived from the original on 30 December 2019. Retrieved 7 February 2020.
  2. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506. Archived from the original on 10 January 2023. Retrieved 20 August 2019.
  3. ^ Polsten GR, Wallace MS (21 June 2016). "Analgesic Agents in Rheumatic Disease". In Firestein GS, Budd R, Gabriel SE, McInnes IB, O'Dell JR (eds.). Kelley and Firestein's Textbook of Rheumatology. Elsevier Health Sciences. pp. 1081–. ISBN 978-0-323-41494-4.
  4. ^ a b c d e f g h i j k l m n "Codeine". The American Society of Health-System Pharmacists. Archived from the original on 18 January 2016. Retrieved 5 January 2016.
  5. ^ Shen H, He MM, Liu H, Wrighton SA, Wang L, Guo B, et al. (August 2007). "Comparative metabolic capabilities and inhibitory profiles of CYP2D6.1, CYP2D6.10, and CYP2D6.17". Drug Metabolism and Disposition. 35 (8): 1292–1300. doi:10.1124/dmd.107.015354. PMID 17470523. S2CID 2322678.
  6. ^ Prommer E (2010). "Role of codeine in palliative care". Journal of Opioid Management. 7 (5): 401–406. doi:10.5055/jom.2011.0081. PMID 22165039.
  7. ^ Paul IM (February 2012). "Therapeutic options for acute cough due to upper respiratory infections in children". Lung. 190 (1): 41–44. doi:10.1007/s00408-011-9319-y. PMID 21892785. S2CID 23865647.
  8. ^ Smith SM, Schroeder K, Fahey T (November 2014). "Over-the-counter (OTC) medications for acute cough in children and adults in community settings". The Cochrane Database of Systematic Reviews. 2014 (11): CD001831. doi:10.1002/14651858.CD001831.pub5. PMC 7061814. PMID 25420096.
  9. ^ Tobias JD, Green TP, Coté CJ (October 2016). "Codeine: Time to Say "No"". Pediatrics. 138 (4): e20162396. doi:10.1542/peds.2016-2396. PMID 27647717.
  10. ^ a b Newton D (2015). Prescription Drug Abuse: A Reference Handbook. ABC-CLIO. p. 20. ISBN 978-1-4408-3979-5. Archived from the original on 4 February 2017.
  11. ^ Narcotic Drugs 2014 (PDF). International Narcotics Control Board. 2015. p. 21. ISBN 9789210481571. Archived (PDF) from the original on 2 June 2015.
  12. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.


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