Bezitramide
{{Short description|Opioid analgesic drug}}
{{Drugbox
| verifiedrevid = 447617484
| IUPAC_name = 4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
| image = Bezitramide.svg
| image_class = skin-invert-image
| tradename =
| pregnancy_category =
| legal_AU =
| legal_BR = A1
| legal_BR_comment = {{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=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
| legal_CA = Schedule I
| legal_US = Schedule II
| legal_DE = Anlage I
| routes_of_administration = Oral
| bioavailability =
| metabolism =
| excretion =
| CAS_number = 15301-48-1
| ATC_prefix = N02
| ATC_suffix = AC05
| PubChem = 61791
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01459
| KEGG = D07289
| ChEMBL = 2104149
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 55675
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3KXW0Y310I
| C=31 | H=32
| N=4 | O=2
| smiles = O=C(N2c1ccccc1N(C2=O)C5CCN(CCC(C#N)(c3ccccc3)c4ccccc4)CC5)CC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FLKWNFFCSSJANB-UHFFFAOYSA-N
}}
Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active metabolite, despropionyl-bezitramide.{{cite journal | vauthors = Meijer DK, Hovinga G, Versluis A, Bröring J, van Aken K, Moolenaar F, Wesseling H | title = Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain | journal = European Journal of Clinical Pharmacology | volume = 27 | issue = 5 | pages = 615–8 | year = 1984 | pmid = 6519169 | doi = 10.1007/BF00556902 | s2cid = 23978449 }} Bezitramide was discovered at Janssen Pharmaceutica in 1961.{{ cite patent | country = US | number = 3196157 | status = patent | title = Benzimidalinyl Piperidines | pubdate = 1963-06-11 | gdate = 1965-07-20 | inventor = Janssen PA }}{{cite journal | vauthors = Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, Admiraal PV, Bosker JT, Crul JF, Pearce C, Zegveld C | display-authors = 6 | title = Bezitramide (R 4845), a new potent and orally long-acting analgesic compound | journal = Arzneimittel-Forschung | volume = 21 | issue = 6 | pages = 862–7 | date = June 1971 | pmid = 5109278 }}{{cite journal | vauthors = Knape H | title = Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report) | journal = British Journal of Anaesthesia | volume = 42 | issue = 4 | pages = 325–8 | date = April 1970 | pmid = 4913411 | doi = 10.1093/bja/42.4.325 | doi-access = free }} It is most commonly marketed under the trade name Burgodin.
The drug was pulled from the shelves in the Netherlands in 2004 after fatal overdose cases, including one where a five-year-old child took one tablet from his mother's purse, ate it, and promptly died.{{cite journal | vauthors = de Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ | title = [Death caused by one tablet of Burgodin] | journal = Nederlands Tijdschrift voor Geneeskunde | volume = 127 | issue = 34 | pages = 1552–3 | date = August 1983 | pmid = 6633692 }}
Bezitramide is regulated much the same as morphine in all known jurisdictions and is a Schedule II substance under the United States' Controlled Substances Act of 1970, with an ACSCN of 9800 and zero annual manufacturing quota.{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm |title=Title 21 United States Code (USC) Controlled Substances Act |access-date=2011-09-29 |archive-date=2020-08-30 |archive-url=https://web.archive.org/web/20200830032541/https://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm |url-status=dead }} However, as of May 2021, it has never been marketed in the United States.