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
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
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 organ (biology), organs of the digestive syste ...
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 American c ...
in 1961. It is most commonly marketed under the trade name Burgodin.
The drug was pulled from the shelves in the
Netherlands
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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 analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make ...
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(2) with affords depropionylbezitramide 3898-28-6(3). Acylation with propanoic anhydride then completed the synthesis of ' (4).
See also
* Benperidol
Benperidol, sold under the trade name Anquil among others, is a typical antipsychotic primarily used to treat hypersexuality syndromes and can be used to treat schizophrenia. It is a highly potent butyrophenone derivative and is the most potent n ...
* Brorphine
Brorphine is a piperidine-based opioid analgesic compound. Brorphine was originally discovered in a 2018 paper investigating functionally biased opioid compounds, with the intention of finding safer analgesics that produce less respiratory depre ...
* J-113,397
J-113,397 is an opioid drug which was the first compound found to be a highly selective antagonist for the nociceptin receptor, also known as the ORL-1 receptor. It is several hundred times selective for the ORL-1 receptor over other opioid rece ...
References
Synthetic opioids
Prodrugs
Benzimidazoles
Piperidines
Nitriles
Ureas
Propionamides
Mu-opioid receptor agonists
Janssen Pharmaceutica
Belgian inventions
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