Bezitramide

Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active 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 mass492.623 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 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.
  2. US patent 3196157, Janssen PA, "Benzimidalinyl Piperidines", published 1963-06-11, issued 1965-07-20
  3. 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.
  4. 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.
  5. 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.
  6. Title 21 United States Code (USC) Controlled Substances Act
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