Bezitramide: Difference between revisions

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{{Drugbox|
{{Drugbox
|IUPAC_name = ''4-[4-(2-oxo-3-propanoyl-benzoimidazol-1-yl)-1-piperidyl]-2,2-diphenyl-butanenitrile''
| verifiedrevid = 447617484
| image=Bezitramide.png
| IUPAC_name = 4-[4-(2-oxo-3-propanoyl-2,3-dihydro-1''H''-benzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
| CAS_number=15301-48-1
| image = Bezitramide.png
| ATC_prefix=
 
| ATC_suffix=
<!--Clinical data-->
| ATC_supplemental=
| tradename =
| PubChem=61791
| pregnancy_category =
| DrugBank=
| legal_AU =
| C=31 | H=32 | N=4 | O=2
| legal_US = Schedule II
| molecular_weight = 492.612 g/mol
| legal_status =
| bioavailability=  
| routes_of_administration = Oral
| metabolism =  
 
| elimination_half-life=
<!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| excretion =   
| excretion =   
| pregnancy_category =  
 
| legal_status =  
<!--Identifiers-->
| legal_AU =  
| CASNo_Ref = {{cascite|??|??}}
| routes_of_administration= Oral
| CAS_number = 15301-48-1
| ATC_prefix = N02
| ATC_suffix = AC05
| PubChem = 61791
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01459
| ChEMBL = 2104149
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 55675
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3KXW0Y310I
 
<!--Chemical data-->
| C=31 | H=32 | N=4 | O=2
| molecular_weight = 492.611 g/mol
| smiles = O=C(N2c1ccccc1N(C2=O)C5CCN(CCC(C#N)(c3ccccc3)c4ccccc4)CC5)CC
| InChI = 1/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
| InChIKey = FLKWNFFCSSJANB-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FLKWNFFCSSJANB-UHFFFAOYSA-N
}}
}}
'''Bezitramide''' is a narcotic [[analgesic]]. Bezitramide itself is a [[prodrug]] which is readily [[Hydrolysis|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<sup>®</sup>. 
__NOTOC__


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.
{{SI}}


Bezitramide is regulated much the same as morphine in all known jurisdictions and is, surprisingly, a Schedule II rather than Schedule I narcotic under the United States' Controlled Substances Act of 1970. However, it has to this point never been marketed in the United States.
{{CMG}}


Other drugs which are legal for medical use in the US but not marketed up to this point in time include [[phenazocine]], [[metopon]], [[alphaprodine]] (formerly marketed as Nisentil) , [[anileridine]] (formerly marketed as Leritine), [[ethylmorphine]] (regulated like codeine and therefore preparations with other active ingredients can be Schedule III or Schedule V), [[isomethadone]], [[levomethorphan]], [[metazocine]], [[piminodine]] (formerly marketed as Alvodine), [[racemethorphan]], [[moramide intermediate]] (the most common moramide, the Schedule I [[dextromoramide]] was once marketed in the US as Dimorlin<sup>®</sup> for a short time in the 1950s), and [[racemorphan]]. <!--The previous paragraph has almost nothing to do with Bezitramide. It doesn't belong on this page-->
==Overview==
'''Bezitramide''' is an opioid [[analgesic]]. Bezitramide itself is a [[prodrug]] which is readily [[Hydrolysis|hydrolyzed]] in the [[gastrointestinal tract]] to its main [[metabolite]], [[despropionyl-bezitramide]]. Bezitramide was discovered at [[Janssen Pharmaceutica]] in 1961.<ref>{{ cite patent | country = US | number = 3196157 | status = patent | title = BENZIMIDAZOLINYL PIPERIDINES | pubdate = 1963-06-11 | gdate = 1965-07-20 | inventor = Paul A. J. Janssen.}}</ref><ref>{{cite pmid|5109278}}</ref><ref>{{cite pmid|4913411}}</ref> 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.<ref>{{cite pmid|6633692}}</ref>
 
Bezitramide is regulated much the same as [[morphine]] in all known jurisdictions and is a [[Controlled Substances Act|Schedule II]] substance under the United States' Controlled Substances Act of 1970, with an ACSCN of 9800 and zero annual manufacturing quota.<ref>[http://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm Title 21 United States Code (USC) Controlled Substances Act]</ref> However, it has to this point never been marketed in the United States.


==References==
==References==
* Knape H., Bezitramide, an orally active analgesic. An investigation on pain following operations for lumbar disc protrusion (preliminary report), Br J Anaesth. 1970 Apr;42(4):325-8.
{{Reflist|2}}
* Janssen PA, Niemegeers CJ, Schellekens KH, Marsboom RH, Herin VV, Amery WK, Admiraal PV, Bosker JT, Crul JF, Pearce C, Zegveld C., Bezitramide (R 4845), a new potent and orally long-acting analgesic compound, Arzneimittelforschung. 1971 Jun;21(6):862-7.
* de Vos JC, Rohof OJ, Bernsen PJ, Conemans JM, van Unnik AJ. Death caused by one tablet of Burgodin. (Dutch). Nederlands Tijdschrift voor Geneeskunde. 1983 Aug 20;127(34):1552-3.
 
{{opioids}}


{{Analgesics}}
{{Opioidergics}}


[[Category:Drugs]]
[[Category:Synthetic opioids]]
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[[Category:Prodrugs]]
{{WikiDoc Sources}}
[[Category:Benzimidazoles]]
[[Category:Piperidines]]
[[Category:Nitriles]]
[[Category:Ureas]]
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[[Category:Mu-opioid agonists]]
[[Category:Janssen Pharmaceutica]]
[[Category:Belgian inventions]]
[[Category:Drug]]

Revision as of 20:39, 10 April 2015

Bezitramide
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC31H32N4O2
Molar mass492.611 g/mol
3D model (JSmol)
  (verify)


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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.[1][2][3] 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.[4]

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.[5] However, it has to this point never been marketed in the United States.

References

  1. ↑ US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20 
  2. ↑ PMID 5109278 (PMID 5109278)
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  3. ↑ PMID 4913411 (PMID 4913411)
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  4. ↑ PMID 6633692 (PMID 6633692)
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  5. ↑ Title 21 United States Code (USC) Controlled Substances Act
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