Bezitramide

Bezitramide
Clinical data
Routes of; administration	Oral
ATC code	N02AC05 (WHO) ;
Legal status
Legal status	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;
ChEMBL	ChEMBL2104149;
CompTox Dashboard (EPA)	DTXSID90165197 ;
ECHA InfoCard	100.035.744
Chemical and physical data
Formula	C31H32N4O2
Molar mass	492.611 g/mol 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 main 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, it has to this point never been marketed in the United States.

References

^ Meijer, D. K. F; Hovinga, G; Versluis, A; Bröring, J; Van Aken, K; Moolenaar, F; Wesseling, H (1984). "Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain". European Journal of Clinical Pharmacology. 27 (5): 615. doi:10.1007/BF00556902. PMID 6519169.
^ US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20
^ Janssen, P. A.; Niemegeers, C. J.; Schellekens, K. H.; Marsboom, R. H.; Herin, V. V.; Amery, W. K.; Admiraal, P. V.; Bosker, J. T.; Crul, J. F.; Pearce, C.; Zegveld, C. (1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound". Arzneimittel-Forschung. 21 (6): 862–867. PMID 5109278.
^ Knape, H. (1970). "Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)". British Journal of Anaesthesia. 42 (4): 325–328. doi:10.1093/bja/42.4.325. PMID 4913411.
^ De Vos, J. C.; Rohof, O. J.; Bernsen, P. J.; Conemans, J. M.; Van Unnik, A. J. (1983). "Death caused by one tablet of Burgodin". Nederlands tijdschrift voor geneeskunde. 127 (34): 1552–1553. PMID 6633692.
^ Title 21 United States Code (USC) Controlled Substances Act

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

[1] Meijer, D. K. F; Hovinga, G; Versluis, A; Bröring, J; Van Aken, K; Moolenaar, F; Wesseling, H (1984). "Pharmacokinetics of the oral narcotic analgesic bezitramide and preliminary observations on its effect on experimentally induced pain". European Journal of Clinical Pharmacology. 27 (5): 615. doi:10.1007/BF00556902. PMID 6519169.

[2] US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20

[3] Janssen, P. A.; Niemegeers, C. J.; Schellekens, K. H.; Marsboom, R. H.; Herin, V. V.; Amery, W. K.; Admiraal, P. V.; Bosker, J. T.; Crul, J. F.; Pearce, C.; Zegveld, C. (1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound". Arzneimittel-Forschung. 21 (6): 862–867. PMID 5109278.

[4] Knape, H. (1970). "Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)". British Journal of Anaesthesia. 42 (4): 325–328. doi:10.1093/bja/42.4.325. PMID 4913411.

[5] De Vos, J. C.; Rohof, O. J.; Bernsen, P. J.; Conemans, J. M.; Van Unnik, A. J. (1983). "Death caused by one tablet of Burgodin". Nederlands tijdschrift voor geneeskunde. 127 (34): 1552–1553. PMID 6633692.

[6] Title 21 United States Code (USC) Controlled Substances Act

[1]

[2]

[3]

[4]

[5]

[6]