Chemistry:Bezitramide

From HandWiki
Short description: Opioid analgesic drug
Bezitramide
Bezitramide.svg
Clinical data
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC31H32N4O2
Molar mass492.623 g·mol−1
3D model (JSmol)
  (verify)

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.

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, as of May 2021, it has never been marketed in the United States.

See also

References

  1. "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. 1984. doi:10.1007/BF00556902. PMID 6519169. 
  2. Janssen PA, "Benzimidalinyl Piperidines", US patent 3196157, published 1963-06-11, issued 1965-07-20
  3. "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound". Arzneimittel-Forschung 21 (6): 862–7. June 1971. PMID 5109278. 
  4. "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. April 1970. doi:10.1093/bja/42.4.325. PMID 4913411. 
  5. "[Death caused by one tablet of Burgodin]". Nederlands Tijdschrift voor Geneeskunde 127 (34): 1552–3. August 1983. PMID 6633692. 
  6. "Title 21 United States Code (USC) Controlled Substances Act". http://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm.