Bezitramide

Bezitramide
Clinical data
Routes of; administration	Oral
ATC code	N02AC05 (WHO) ;
Legal status
Legal status	BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); 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 ;
ChemSpider	55675 ;
UNII	3KXW0Y310I;
KEGG	D07289;
ChEMBL	ChEMBL2104149;
CompTox Dashboard (EPA)	DTXSID90165197 ;
ECHA InfoCard	100.035.744
Chemical and physical data
Formula	C31H32N4O2
Molar mass	492.623 g·mol−1
3D model (JSmol)	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 ; Key:FLKWNFFCSSJANB-UHFFFAOYSA-N ;
	(verify)

Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active metabolite, despropionyl-bezitramide.^[2] Bezitramide was discovered at Janssen Pharmaceutica in 1961.^[3]^[4]^[5] It is most commonly marketed under the trade name Burgodin.

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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.^[6]

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.^[7] However, as of May 2021, it has never been marketed in the United States.

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Bezitramide

See also

References

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