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Bezitramide

 

Bezitramide

Bezitramide
Systematic (IUPAC) name
4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
Clinical data
Legal status
Routes of
administration
Oral
Identifiers
CAS Registry Number
ATC code N02
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
ChEMBL
Chemical data
Formula C31H32N4O2
Molecular mass 492.611 g/mol
 Y   

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

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

References

  1. ^ US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20 
  2. ^ 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.  
  3. ^ 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.  
  4. ^ 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.  
  5. ^ Title 21 United States Code (USC) Controlled Substances Act



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