Editing Dihydrocodeine (section)

{{Short description|Opioid}}
{{distinguish|hydrocodone|codeine}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Cleanup|reason=significant portions of unreferenced, vague or incorrect information. Additionally, the areas that are cited are highly inappropriate citations.|date=August 2014}}
{{Drugbox
| Verifiedfields     = changed
| Watchedfields      = changed
| verifiedrevid      = 464367349
| IUPAC_name         = 4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol
| image              = Dihydrocodeine skeletal.svg
| image_class        = skin-invert-image
| image2             = Dihydrocodeine3DanJ.gif

<!--Clinical data-->| tradename          = 
| Drugs.com          = {{drugs.com|international|dihydrocodeine}}
| pregnancy_US       = 
| legal_AU           = S3
| legal_AU_comment   = {{longitem|(S3) (S4) (S8) depending on dose and other constituents}}
| legal_BR           = A2
| legal_BR_comment   = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 – Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-03 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA           = Schedule I
| legal_DE           = Rx-only/Anlage III
| legal_UK           = Class B
| legal_US           = Schedule II
| legal_US_comment   = (Schedule III in drug combination)
| legal_status       = 
| routes_of_administration = {{hlist |[[Oral administration|oral]] |[[Subcutaneous administration|subcutaneous]] |[[Intramuscular injection|intramuscular]] |[[Suppository|rectal]] |possibly&nbsp;[[Sublingual administration|sublingual]]{{\}}[[Buccal administration|buccal]]}}
<!--Pharmacokinetic data-->| bioavailability    = By mouth: 21% (range 12–34%)<ref name="EurJClinPharmacol1983-Rowell">{{cite journal | vauthors = Rowell FJ, Seymour RA, Rawlins MD | title = Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites | journal = European Journal of Clinical Pharmacology | volume = 25 | issue = 3 | pages = 419–424 | year = 1983 | pmid = 6628531 | doi = 10.1007/BF01037958 | s2cid = 29370394 }}</ref>
| metabolism         = {{longitem|Mainly [[liver|hepatic]], through [[CYP3A4]] and [[CYP2D6]]}}
| metabolites        = • [[Dihydromorphine]]<br />• [[Nordihydrocodeine]]<br />• Others (e.g., [[conjugation (biochemistry)|conjugate]]s)
| elimination_half-life = 4 hours<ref name="EurJClinPharmacol1983-Rowell"/>
| excretion          = <!--Identifiers-->
| IUPHAR_ligand      = 7594
| CAS_number_Ref     = {{cascite|changed|??}}
| CAS_number         = 125-28-0
| ATC_prefix         = N02
| ATC_suffix         = AA08
| PubChem            = 5284543
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB01551
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 4447600
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = N9I9HDB855
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D07831
| ChEMBL_Ref         = {{ebicite|changed|EBI}}
| ChEMBL             = 1595
<!--Chemical data-->| C                  = 18
| H                  = 23
| N                  = 1
| O                  = 3
| smiles             = O[C@@H]1[C@@H]2OC3=C(OC)C=CC4=C3[C@@]2([C@H]5CC1)CCN(C)[C@@H]5C4
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C18H23NO3/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,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = RBOXVHNMENFORY-DNJOTXNNSA-N
| synonyms           = 6α-Hydrocodol<ref name="FFFLM2007">{{cite book| vauthors = Karch SB |title=Pharmacokinetics and Pharmacodynamics of Abused Drugs|url=https://books.google.com/books?id=9fwUQvF4r-cC&pg=PA56|date=9 October 2007|publisher=CRC Press|isbn=978-1-4200-5460-6|pages=56–}}</ref>
| dependency_liability = High
| addiction_liability = High
}}

'''Dihydrocodeine''' is a semi-[[Chemical synthesis|synthetic]] opioid [[analgesic]] prescribed for pain or severe [[dyspnea]], or as an [[antitussive]], either alone or compounded with [[paracetamol]] (acetaminophen) (as in [[co-dydramol]]) or [[aspirin]]. It was developed in Germany in 1908 and first marketed in 1911.<ref>{{Cite book|url=https://books.google.com/books?id=qoyYobgX0uwC|title=Encyclopedia of Psychopharmacology| vauthors = Stolerman I |date= 31 July 2010 |publisher=Springer Science & Business Media|isbn=9783540686989|language=en}}</ref>

Commonly available as tablets, solutions, elixirs, and other oral forms, dihydrocodeine is also available in some countries as an injectable solution for deep subcutaneous and intra-muscular administration. As with [[codeine]], intravenous administration should be avoided, as it could result in [[anaphylaxis]] and life-threatening [[pulmonary edema]]. In the past, dihydrocodeine suppositories were used. Dihydrocodeine is available in suppository form on prescription. Dihydrocodeine is used as an alternative to codeine and similarly belongs to step 2 of the [[Pain ladder|WHO analgesic ladder]].<ref name=":2">{{cite journal | vauthors = Leppert W, Mikołajczak P, Kamińska E, Szulc M | title = Analgesia and serum assays of controlled-release dihydrocodeine and metabolites in cancer patients with pain | journal = Pharmacological Reports | date = 2012 | volume = 64 | issue = 1 | pages = 84–93 | doi = 10.1016/s1734-1140(12)70734-x | pmid = 22580524 | url = http://if-pan.krakow.pl/pjp/pdf/2012/1_84.pdf }}</ref>

<!-- Society and culture -->
It was first described in 1911 and approved for medical use in 1948.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=52X |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA52X |language=en}}</ref> Dihydrocodeine was developed during the search for more effective cough medication, especially to help reduce the spread of tuberculosis, pertussis, and pneumonia in the years from c.a. 1895 to 1915. It is similar in chemical structure to codeine.