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Bezitramide
Systematic (IUPAC) name
4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
Identifiers
CAS number 15301-48-1
ATC code N02AC05
PubChem 61791
ChemSpider 55675
Chemical data
Formula C 31H32N4O2  
Mol. mass 492.611 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Oral
 Yes check.svgY(what is this?)  (verify)

Bezitramide is a narcotic 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. 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.

Bezitramide is regulated much the same as morphine in all known jurisdictions and is, surprisingly, a Schedule II rather than Schedule I narcotic under the United States' Controlled Substances Act of 1970. However, it has to this point never been marketed in the United States.

Other drugs which are legal for medical use in the US but not marketed up to this point in time include phenazocine, metopon, alphaprodine (formerly marketed as Nisentil) , anileridine (formerly marketed as Leritine), ethylmorphine (regulated like codeine and therefore preparations with other active ingredients can be Schedule III or Schedule V), isomethadone, levomethorphan, metazocine, piminodine (formerly marketed as Alvodine), racemethorphan, moramide intermediate (the most common moramide, the Schedule I dextromoramide was once marketed in the US as Dimorlin for a short time in the 1950s), and racemorphan.

References

  • Knape H., Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report), Br J Anaesth. 1970 Apr;42(4):325-8.
  • Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, Admiraal PV, Bosker JT, Crul JF, Pearce C, Zegveld C., Bezitramide (R 4845), a new potent and orally long-acting analgesic compound, Arzneimittelforschung. 1971 Jun;21(6):862-7.
  • de Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ. Death caused by one tablet of Burgodin. (Dutch). Nederlands Tijdschrift voor Geneeskunde. 1983 Aug 20;127(34):1552-3. PMID: 6633692
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