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Routes of administration | Oral |
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ECHA InfoCard | 100.035.744 ![]() |
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Formula | C31H32N4O2 |
Molar mass | 492.623 g·mol−1 |
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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.
The Sn2 alkylation between 4-bromo-2,2-diphenylbutyronitrile [39186-58-8] (1) and 4-(2-oxo-1-benzimidazolinyl)-piperidine [20662-53-7] (2) with affords depropionylbezitramide [83898-28-6] (3). Acylation with propanoic anhydride then completed the synthesis of Bezitramide (4).
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