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Bezitramide

From Wikipedia, the free encyclopedia
Opioid analgesic drug
Pharmaceutical compound
Bezitramide
Clinical data
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
  • 4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.035.744Edit this at Wikidata
Chemical and physical data
FormulaC31H32N4O2
Molar mass492.623 g·mol−1
3D model (JSmol)
  • O=C(N2c1ccccc1N(C2=O)C5CCN(CCC(C#N)(c3ccccc3)c4ccccc4)CC5)CC
  • InChI=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 checkY
  • Key:FLKWNFFCSSJANB-UHFFFAOYSA-N checkY
  (verify)

Bezitramide is an opioidanalgesic. Bezitramide itself is aprodrug which is readilyhydrolyzed in thegastrointestinal tract to itsactive metabolite, despropionyl-bezitramide.[2] Bezitramide was discovered atJanssen Pharmaceutica in 1961.[3][4][5] It is most commonly marketed under the trade nameBurgodin.

The drug was pulled from the shelves in theNetherlands 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.[6]

Bezitramide is regulated much the same asmorphine in all known jurisdictions and is aSchedule II substance under the United States' Controlled Substances Act of 1970, with an ACSCN of 9800 and zero annual manufacturing quota.[7] However, as of May 2021, it has never been marketed in the United States.

See also

[edit]

References

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  2. ^Meijer DK, Hovinga G, Versluis A, Bröring J, van Aken K, Moolenaar F, Wesseling H (1984). "Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain".European Journal of Clinical Pharmacology.27 (5):615–8.doi:10.1007/BF00556902.PMID 6519169.S2CID 23978449.
  3. ^US patent 3196157, Janssen PA, "Benzimidalinyl Piperidines", published 1963-06-11, issued 1965-07-20 
  4. ^Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, et al. (June 1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound".Arzneimittel-Forschung.21 (6):862–7.PMID 5109278.
  5. ^Knape H (April 1970)."Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)".British Journal of Anaesthesia.42 (4):325–8.doi:10.1093/bja/42.4.325.PMID 4913411.
  6. ^de Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ (August 1983). "[Death caused by one tablet of Burgodin]".Nederlands Tijdschrift voor Geneeskunde.127 (34):1552–3.PMID 6633692.
  7. ^"Title 21 United States Code (USC) Controlled Substances Act". Archived fromthe original on 2020-08-30. Retrieved2011-09-29.
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