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;
PubChemCID	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	492.623g·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)

Bezitramideis an opioidanalgesic.Bezitramide itself is aprodrugwhich is readilyhydrolyzedin thegastrointestinal tractto itsactive metabolite,despropionyl-bezitramide.^[2]Bezitramide was discovered atJanssen Pharmaceuticain 1961.^[3]^[4]^[5]It is most commonly marketed under the trade nameBurgodin.

The drug was pulled from the shelves in theNetherlandsin 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 asmorphinein all known jurisdictions and is aSchedule IIsubstance 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.

References[edit]

^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.
^Meijer DK, 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): 615–8.doi:10.1007/BF00556902.PMID 6519169.S2CID 23978449.
^US patent 3196157,Janssen PA, "Benzimidalinyl Piperidines", published 1963-06-11, issued 1965-07-20
^Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, et al. (June 1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound".Arzneimittel-Forschung.21(6): 862–7.PMID 5109278.
^Knape H (April 1970)."Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)".British Journal of Anaesthesia.42(4): 325–8.doi:10.1093/bja/42.4.325.PMID 4913411.
^de Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ (August 1983). "[Death caused by one tablet of Burgodin]".Nederlands Tijdschrift voor Geneeskunde.127(34): 1552–3.PMID 6633692.
^"Title 21 United States Code (USC) Controlled Substances Act".Archived fromthe originalon 2020-08-30.Retrieved2011-09-29.

[1] Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.

[2] Meijer DK, 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): 615–8.doi:10.1007/BF00556902.PMID 6519169.S2CID 23978449.

[3] US patent 3196157,Janssen PA, "Benzimidalinyl Piperidines", published 1963-06-11, issued 1965-07-20

[4] Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, et al. (June 1971). "Bezitramide (R 4845), a new potent and orally long-acting analgesic compound".Arzneimittel-Forschung.21(6): 862–7.PMID 5109278.

[5] Knape H (April 1970)."Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report)".British Journal of Anaesthesia.42(4): 325–8.doi:10.1093/bja/42.4.325.PMID 4913411.

[6] Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ (August 1983). "[Death caused by one tablet of Burgodin]".Nederlands Tijdschrift voor Geneeskunde.127(34): 1552–3.PMID 6633692.

[7] "Title 21 United States Code (USC) Controlled Substances Act".Archived fromthe originalon 2020-08-30.Retrieved2011-09-29.

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