Bezitramide: Difference between revisions
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{{Drugbox| | {{Drugbox | ||
|IUPAC_name = | | 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 | ||
| image = Bezitramide.png | |||
| | |||
| | <!--Clinical data--> | ||
| | | tradename = | ||
| | | pregnancy_category = | ||
| | | legal_AU = | ||
| | | legal_US = Schedule II | ||
| legal_status = | |||
| bioavailability= | | routes_of_administration = Oral | ||
| metabolism = | |||
<!--Pharmacokinetic data--> | |||
| bioavailability = | |||
| metabolism = | |||
| excretion = | | excretion = | ||
| | |||
| | <!--Identifiers--> | ||
| | | CASNo_Ref = {{cascite|??|??}} | ||
| | | 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 | |||
}} | }} | ||
__NOTOC__ | |||
{{SI}} | |||
{{CMG}} | |||
==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== | ||
{{Reflist|2}} | |||
{{ | |||
{{Analgesics}} | |||
{{Opioidergics}} | |||
[[Category: | [[Category:Synthetic opioids]] | ||
[[Category:Prodrugs]] | |||
[[Category:Benzimidazoles]] | |||
[[Category:Piperidines]] | |||
[[Category:Nitriles]] | |||
[[Category:Ureas]] | |||
[[Category:Propionamides]] | |||
[[Category:Mu-opioid agonists]] | |||
[[Category:Janssen Pharmaceutica]] | |||
[[Category:Belgian inventions]] | |||
[[Category:Drug]] |
Revision as of 20:39, 10 April 2015
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Clinical data | |
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Routes of administration | Oral |
ATC code | |
Legal status | |
Legal status |
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Identifiers | |
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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 | |
Formula | C31H32N4O2 |
Molar mass | 492.611 g/mol |
3D model (JSmol) | |
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(verify) |
WikiDoc Resources for Bezitramide |
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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
- ↑ US patent 3196157, Paul A. J. Janssen., "BENZIMIDAZOLINYL PIPERIDINES", published 1963-06-11, issued 1965-07-20
- ↑ PMID 5109278 (PMID 5109278)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ PMID 4913411 (PMID 4913411)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ PMID 6633692 (PMID 6633692)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand - ↑ Title 21 United States Code (USC) Controlled Substances Act
- Pages with script errors
- Pages with incomplete PMID references
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Chemical articles with unknown parameter in Infobox drug
- Articles without KEGG source
- Synthetic opioids
- Prodrugs
- Benzimidazoles
- Piperidines
- Nitriles
- Ureas
- Propionamides
- Mu-opioid agonists
- Janssen Pharmaceutica
- Belgian inventions
- Drug