Bezitramide

Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its main metabolite, despropionyl-bezitramide.[1] Bezitramide was discovered at Janssen Pharmaceutica in 1961.[2][3][4] It is most commonly marketed under the trade name Burgodin.

Bezitramide
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule II
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.744
Chemical and physical data
FormulaC31H32N4O2
Molar mass492.611 g/mol g·mol−1
3D model (JSmol)
  (verify)

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.[5]

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.[6] However, it has to this point never been marketed in the United States.

References
  1. Meijer, D. K. F; 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. doi:10.1007/BF00556902. PMID 6519169.
  2. US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20
  3. Janssen, P. A.; Niemegeers, C. J.; Schellekens, K. H.; Marsboom, R. H.; Herin, V. V.; Amery, W. K.; Admiraal, P. V.; Bosker, J. T.; Crul, J. F.; Pearce, C.; Zegveld, C. (1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound". Arzneimittel-Forschung. 21 (6): 862–867. PMID 5109278.
  4. Knape, H. (1970). "Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)". British Journal of Anaesthesia. 42 (4): 325–328. doi:10.1093/bja/42.4.325. PMID 4913411.
  5. De Vos, J. C.; Rohof, O. J.; Bernsen, P. J.; Conemans, J. M.; Van Unnik, A. J. (1983). "Death caused by one tablet of Burgodin". Nederlands tijdschrift voor geneeskunde. 127 (34): 1552–1553. PMID 6633692.
  6. Title 21 United States Code (USC) Controlled Substances Act


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.