Codeine

Codeine is an opiate drug. In the human body, it is made into morphine by the liver (a prodrug). It is the morphine that gives codeine its effects. It is mainly…

Codeine
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 class
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityc. 60% (by mouth)[3]
MetabolismLiver: CYP2D6 (to morphine), CYP3A4 (to norcodeine), UGT2B7 (to 3- and 6-glucuronides of codeine, norcodeine, and morphine)[5]
Metabolites
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 mass299.37 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 drug. In the human body, it is made into morphine by the liver (a prodrug). It is the morphine that gives codeine its effects. It is mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found in the sap of the opium poppy, Papaver somniferum.[4][6]

It is usually used to treat lower amounts of pain than morphine is used for.[4][not in the source given] It might work better if mixed with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen.[4] It should not be used for coughs in children.[7][8] It is usually taken by mouth.[4] It typically starts working after half an hour, working best two hours after taking.[4] It lasts for about four to six hours overall. Codeine can be addictive and too much can cause overdose.[4]

Common side effects are nausea, vomiting, constipation, itchiness, lightheadedness, and sleepiness.[4] Codeine was first found in 1832 by Pierre Jean Robiquet.[9] It is on the World Health Organization's List of Essential Medicines.[10] Codeine makes up about 2% of opium.[9]

References

  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. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 "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, Li C (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. ↑ 9.0 9.1 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.
  10. ↑ 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.

Notes

  1. ↑ S4 only if in drug combinations; see #Legal status.
  2. ↑ Class C1 only for low doses; see exemptions on Portaria SVS/MS 344/98.
  3. ↑ Pharmacy medicine if purchased in a low dose from a licensed pharmacy or in low dose drug combination; see #Legal status.
  4. ↑ Schedule III-V only if in drug combination; see #Legal status.
  5. ↑ Schedule III only if in drug combination; see #Legal status.



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