Bezitramide is an opioid

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

. Bezitramide itself is a prodrug which is readily

hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

in the

gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans a ...

to its

active metabolite An active metabolite is an active form of a drug after it has been processed by the body. Metabolites of drugs An active metabolite results when a drug is metabolized by the body into a modified form which continues to produce effects in the body ...

, despropionyl-bezitramide. Bezitramide was discovered at

Janssen Pharmaceutica Janssen Pharmaceuticals is a pharmaceutical company headquartered in Beerse, Belgium, and wholly-owned by Johnson & Johnson. It was founded in 1953 by Paul Janssen. In 1961, Janssen Pharmaceuticals was purchased by New Jersey-based America ...

in 1961. It is most commonly marketed under the trade name Burgodin. The drug was pulled from the shelves in the

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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 Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies ('' Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. Ther ...

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.Title 21 United States Code (USC) Controlled Substances Act
/ref> However, as of May 2021, it has never been marketed in the United States.

Synthesis

The Sn2 alkylation between 4-bromo-2,2-diphenylbutyronitrile 9186-58-8(1) and 4-(2-oxo-1-benzimidazolinyl)-piperidine

0662-53-7 66 may refer to: * 66 (number) * One of the years 66 BC, AD 66, 1966, 2066 * "66" (song), a song by Lil Yachty featuring Trippie Redd *66, a song by The Afghan Whigs, from the album 1965 * Sixty-Six (card game), a German card game * ''Sixty Six'' ( ...

(2) with affords depropionylbezitramide 3898-28-6(3). Acylation with

propanoic anhydride Propionic anhydride is an organic compound with the formula (CH3CH2CO)2O. This simple acid anhydride is a colourless liquid. It is a widely used reagent in organic synthesis as well as for producing specialty derivatives of cellulose. Synthesis I ...

then completed the synthesis of ' (4).

References

Synthetic opioids Prodrugs Benzimidazoles Piperidines Nitriles Ureas Propionamides Mu-opioid receptor agonists Janssen Pharmaceutica Belgian inventions {{analgesic-stub

Synthesis

See also

References