Bezitramide

Bezitramide

Clinical data
Routes of administration	Oral
ATC code	N02AC05 (WHO)
Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) US: Schedule II
Identifiers
IUPAC name 4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
CAS Number	15301-48-1
PubChem CID	61791
DrugBank	DB01459 Y
ChemSpider	55675 Y
UNII	3KXW0Y310I
ChEMBL	CHEMBL2104149
ECHA InfoCard	100.035.744
Chemical and physical data
Formula	C31H32N4O2
Molar mass	492.611 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N2c1ccccc1N(C2=O)C5CCN(CCC(C#N)(c3ccccc3)c4ccccc4)CC5)CC
InChI InChI=1S/C31H32N4O2/c1-2-29(36)35-28-16-10-9-15-27(28)34(30(35)37)26-17-20-33(21-18-26)22-19-31(23-32,24-11-5-3-6-12-24)25-13-7-4-8-14-25/h3-16,26H,2,17-22H2,1H3 Y Key:FLKWNFFCSSJANB-UHFFFAOYSA-N Y

Bezitramide is an opioid 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 a Schedule II substance under the United States' Controlled Substances Act of 1970, with an ACSCN of 9800 and zero annual manufacturing quota. However, it has to this point never been marketed in the United States.