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	492.623 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.^[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 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

[1] 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.

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

[3] 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.

[4] 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.

[5] 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.

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

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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	492.623 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
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Bezitramide

See also

References