View source for Codeine

{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 456481929
| image = Codeine Structure.svg
| image_class = skin-invert-image
| width = 175px
| alt = Skeletal formula
| image2 = Codeine molecule ball.png
| width2 = 
| alt2 = Ball-and-stick model
| caption = <!-- Clinical data -->
| pronounce = {{IPAc-en|ˈ|k|oʊ|d|iː|n}}
| tradename = 
| Drugs.com = {{drugs.com|monograph|codeine}}
| MedlinePlus = a682065
| DailyMedID = Codeine
| pregnancy_AU = A
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Codeine Use During Pregnancy | website=Drugs.com | date=3 February 2020 | url=https://www.drugs.com/pregnancy/codeine.html | access-date=7 February 2020 | archive-date=30 December 2019 | archive-url=https://web.archive.org/web/20191230164005/https://www.drugs.com/pregnancy/codeine.html | url-status=live }}</ref>
| pregnancy_category = 
| dependency_liability = High
| addiction_liability = High<ref>{{cite book |vauthors=Bonewit-West K, Hunt SA, Applegate E |title=Today's Medical Assistant: Clinical and Administrative Procedures |date=2012 |page=571 |publisher=Elsevier Health Sciences |isbn=9781455701506 |url=https://books.google.com/books?id=YalYPI1KqTQC&pg=PA571 |access-date=20 August 2019 |archive-date=10 January 2023 |archive-url=https://web.archive.org/web/20230110030031/https://books.google.com/books?id=YalYPI1KqTQC&pg=PA571 |url-status=live }}</ref>
| routes_of_administration = [[Oral administration|By mouth]], [[rectal administration|rectal]], [[subcutaneous injection|subcutaneous]], [[intramuscular injection|intramuscular]]
| class = {{ubli|[[Opiate]];|[[Antitussive]]}}
| ATC_prefix = R05
| ATC_suffix = DA04
| ATC_supplemental = Combinations: {{ATC|N02|AA59}}, {{ATC|N02|AA79}}, {{ATC|N02|AJ08}}, {{ATC|N02|AJ06}}, {{ATC|N02|AJ07}}
        
<!-- Legal status -->| legal_AU = S8
| legal_AU_comment = / S4 (Prescription only){{efn|S4 only if in drug combinations; see [[#Legal status]].}}
| legal_BR = A2
| legal_BR_comment = / [[Brazilian Controlled Drugs and Substances Act|Class C1]]{{efn|Class C1 only for low doses; see exemptions on [[Brazilian Controlled Drugs and Substances Act|Portaria SVS/MS 344/98]].}}
| legal_CA = Schedule I
| legal_CA_comment = 
| legal_DE = Anlage III
| legal_DE_comment = 
| legal_NZ = Class C
| legal_NZ_comment = 
| legal_UK = Class B
| legal_UK_comment = / [[Pharmacy medicine]]{{efn|Pharmacy medicine if purchased in a low dose from a licensed pharmacy or in low dose drug combination; see [[#Legal status]].}}
| legal_US = Schedule II
| legal_US_comment = / Schedule III–V{{efn|Schedule III-V only if in drug combination; see [[#Legal status]].}}
| legal_UN = N II
| legal_UN_comment = / Narcotic Schedule III{{efn|Schedule III only if in drug combination; see [[#Legal status]].}}
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->| bioavailability = c. 60% (by mouth)<ref name="FiresteinBudd2016">{{cite book| vauthors= Polsten GR, Wallace MS | chapter = Analgesic Agents in Rheumatic Disease | veditors = Firestein GS, Budd R, Gabriel SE, McInnes IB, O'Dell JR |title=Kelley and Firestein's Textbook of Rheumatology | chapter-url = https://books.google.com/books?id=kBZ6DAAAQBAJ&pg=PA1081 |date=21 June 2016|publisher=Elsevier Health Sciences|isbn=978-0-323-41494-4|pages=1081–}}</ref>
| protein_bound = 
| metabolism = [[Liver]]: [[CYP2D6]] (to [[morphine]]), [[CYP3A4]] (to [[norcodeine]]), [[UGT2B7]] (to 3- and 6-[[glucuronide]]s of codeine, norcodeine, and morphine)<ref name="pmid17470523">{{cite journal | vauthors = Shen H, He MM, Liu H, Wrighton SA, Wang L, Guo B, Li C | title = Comparative metabolic capabilities and inhibitory profiles of CYP2D6.1, CYP2D6.10, and CYP2D6.17 | journal = Drug Metabolism and Disposition | volume = 35 | issue = 8 | pages = 1292–1300 | date = August 2007 | pmid = 17470523 | doi = 10.1124/dmd.107.015354 | s2cid = 2322678 }}</ref>
| metabolites = *[[Morphine]]
* [[Norcodeine]]
* Others (e.g., [[conjugation (biochemistry)|conjugate]]s)
| onset = 15–30 minutes<ref name=AHFS2016 />
| elimination_half-life = 2.5–3 hours
| duration_of_action = 4–6 hours<ref name=AHFS2016 />
| excretion = <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 76-57-3
| CAS_supplemental = 
| PubChem = 5284371
| IUPHAR_ligand = 1673
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00318
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447447
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = UX6OWY2V7J
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06174
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = 
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16714
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 485
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 3-Methylmorphine

<!-- Chemical and physical data -->| IUPAC_name = (5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
| C = 18
| H = 21
| N = 1
| O = 3
| SMILES = CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OROGSEYTTFOCAN-DNJOTXNNSA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}
'''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]], [[cough|coughing]], and [[diarrhea]]. It is also commonly used as a [[recreational drug]]. It is found in the [[sap]] of the [[opium poppy]], ''Papaver somniferum''.<ref name=AHFS2016>{{cite web|title=Codeine |url=https://www.drugs.com/monograph/codeine.html |publisher=The American Society of Health-System Pharmacists |access-date=5 January 2016|url-status=live|archive-url=https://web.archive.org/web/20160118164241/http://www.drugs.com/monograph/codeine.html|archive-date=18 January 2016}}</ref><ref>{{cite journal | vauthors = Prommer E | title = Role of codeine in palliative care | journal = Journal of Opioid Management | volume = 7 | issue = 5 | pages = 401–406 | date = 2010 | pmid = 22165039 | doi = 10.5055/jom.2011.0081 }}</ref>

It is usually used to treat lower amounts of pain than [[morphine]] is used for.<ref name=AHFS2016 />{{Failed verification |date=March 2024 |reason=Recommended for that use in one country, nothing said about typical usage.}} It might work better if mixed with [[paracetamol]] (acetaminophen) as [[codeine/paracetamol]] or a [[nonsteroidal anti-inflammatory drug]] (NSAID) such as [[aspirin]] or [[ibuprofen]].<ref name=AHFS2016 /> It should not be used for coughs in children.<ref name="paul-im-2012">{{cite journal | vauthors = Paul IM | title = Therapeutic options for acute cough due to upper respiratory infections in children | journal = Lung | volume = 190 | issue = 1 | pages = 41–44 | date = February 2012 | pmid = 21892785 | doi = 10.1007/s00408-011-9319-y | s2cid = 23865647 }}</ref><ref>{{cite journal |vauthors=Smith SM, Schroeder K, Fahey T |date=November 2014 |title=Over-the-counter (OTC) medications for acute cough in children and adults in community settings |journal=The Cochrane Database of Systematic Reviews |volume=2014 |issue= 11|pages= CD001831|doi=10.1002/14651858.CD001831.pub5 |pmid=25420096|pmc=7061814 }}</ref> It is usually taken by mouth.<ref name=AHFS2016 /> It typically starts working after half an hour, working best two hours after taking.<ref name=AHFS2016 /> It lasts for about four to six hours overall. Codeine can be [[addiction|addictive]] and too much can cause [[overdose]].<ref name=AHFS2016 /> 

Common [[side effect]]s are [[nausea]], [[vomiting]], [[constipation]], [[pruritis|itchiness]], [[lightheadedness]], and sleepiness.<ref name=AHFS2016 /> Codeine was first found in 1832 by [[Pierre Jean Robiquet]].<ref name=New2015>{{cite book| vauthors = Newton D |title= Prescription Drug Abuse: A Reference Handbook |date=2015 |publisher=ABC-CLIO |isbn=978-1-4408-3979-5 |page=20 |url=https://books.google.com/books?id=mcAnCwAAQBAJ&pg=PA20|url-status=live|archive-url= https://web.archive.org/web/20170204073214/https://books.google.com/books?id=mcAnCwAAQBAJ&pg=PA20 |archive-date=4 February 2017}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> Codeine makes up about 2% of [[opium]].<ref name=New2015 />

== Codeine Media ==
<gallery widths='160px' heights='100%' mode='traditional' caption=''>
File:Coughsyrup-promethcode.jpg|The recreational drug [[Lean_(drug)|lean]] can be created with codeine syrup (pictured).
</gallery>
== References ==
{{reflist}}
== Notes ==
{{notelist}}


{{Medical-stub}}

{{Cough and cold preparations}}
{{Alkaloids}}
{{Antidiarrheals, intestinal anti-inflammatory and anti-infective agents}}
{{Opioid receptor modulators}}

[[Category:Opioids]]
[[Category:Analgesics]]
[[Category:4,5-Epoxymorphinans]]
[[Category:Alcohols]]