Bezitramide

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Bezitramide
Bezitramide.svg
Clinical data
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.035.744
Chemical and physical data
Formula C31H32N4O2
Molar mass 492.611 g/mol
3D model (JSmol)
  (verify)

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.

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[edit]

  1. ^ . doi:10.1007/BF00556902.  Missing or empty |title= (help)
  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. PMID 4913411. doi:10.1093/bja/42.4.325. 
  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