Bezitramide (4-[4-(2-oxo-3-propanoyl-benzoimidazol-1-yl)-1-piperidyl]-2,2-diphenyl-butanenitrile MW: 492.612 g/mol, MF: C₃₁H₃₂N₄O₂) 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 a five year old child took one tablet from his mother's purse, ate it, and promptly died. An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain and to achieve analgesia. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ... The gastrointestinal tract or digestive tract, also referred to as the GI tract or the alimentary canal, (nourishment canal) or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and expels the remaining waste. ... A metabolite is the product of metabolism. ... Johnson & Johnson NYSE: JNJ is an international pharmaceutical, medical devices and consumer packaged goods manufacturer founded in 1885. ... 1961 (MCMLXI) was a common year starting on Sunday (the link is to a full 1961 calendar). ...

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 narketed 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. Anileridine (Leritine®) is a synthetic opioid and strong analgesic medication. ... Ethylmorphine is a drug in the class of both opiates (representing a minor synthetic change from morphine) and opioids (being effective in the CNSs opioid reception system) . Its effects in humans mainly stem from its metabolic conversion to morphine. ... Levomethorphan is an optical isomer of dextromethorphan. ... Dextromoramide is the right-handed isomer of the moramide molecule. ...

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.