Buflomedil: Difference between revisions
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{{Use dmy dates|date=February 2023}} |
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{{chembox |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = V7I71DQ432 |
| UNII = V7I71DQ432 |
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| CASNo=55837-25-7 |
| CASNo=55837-25-7 |
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| PubChem=2467 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 188921 |
| ChEMBL = 188921 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2373 |
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| SMILES = O=C(c1c(OC)cc(OC)cc1OC)CCCN2CCCC2 |
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| InChI = 1/C17H25NO4/c1-20-13-11-15(21-2)17(16(12-13)22-3)14(19)7-6-10-18-8-4-5-9-18/h11-12H,4-10H2,1-3H3 |
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| InChIKey = OWYLAEYXIQKAOL-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula=C<sub>17</sub>H<sub>25</sub>NO<sub>4</sub> |
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| MolarMass=307.38 g/mol |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = C04 |
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| ATCCode_suffix = AX20 |
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| Autoignition= |
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| AutoignitionPt = |
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This drug has been suspended from marketing in the European Union, because of concerns about severe [[neurotoxicity|neurological]] and [[cardiac toxicity]].<ref>{{cite web |url=http://www.medscape.com/viewarticle/753768 |title=Buflomedil-Containing Drugs May Be Suspended in EU|publisher=Medscape|access-date=20 February 2023}}</ref><ref>[http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/public_health_alerts/2011/11/human_pha_detail_000045.jsp&mid=WC0b01ac058001d126 Archived copy] EMA {{Webarchive|url=https://web.archive.org/web/20120123172802/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fmedicines%2Fhuman%2Fpublic_health_alerts%2F2011%2F11%2Fhuman_pha_detail_000045.jsp&mid=WC0b01ac058001d126 |date=23 January 2012}}</ref> In its press release dated 17 November 2011 EMA suggested that doctors "should stop using buflomedil and consider alternative treatment options". The European Commission advised all member states to revoke marketing authorisation.<ref>{{cite web |url=https://www.bfarm.de/SharedDocs/Downloads/DE/Arzneimittel/Pharmakovigilanz/Risikoinformationen/RisikoBewVerf/a-f/buflomedil_durchf_beschluss.pdf?__blob=publicationFile&v=3|title=Buflomedil durchf beschluss|language=de|date=February 2012|website=bfarm.de|access-date=20 February 2023}}</ref> |
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Currently available as trade name tablet Loftyl |
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Various [[adverse effect]]s have been reported to the FDA.<ref>{{Cite web |url=http://www.drugcite.com/?q=BUFLOMEDIL&s=&a= |title=Drug cite |access-date=18 November 2011 |archive-date=4 March 2016 |archive-url=https://web.archive.org/web/20160304091514/http://www.drugcite.com/?q=BUFLOMEDIL&s=&a= |url-status=dead }}</ref> |
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==Synthesis== |
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This drug might be suspended from marketing in the European Union, because of concerns about severe neurological and cardiac toxicity.<ref>Medscape: http://www.medscape.com/viewarticle/753768</ref><ref>EMA: http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/public_health_alerts/2011/11/human_pha_detail_000045.jsp&mid=WC0b01ac058001d126</ref> In its press release dated 17 November 2011 EMA suggested that doctors "should stop using buflomedil and consider alternative treatment options". |
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[[File:Buflomedil synthesis.svg|thumb|center|500px|Patent:<ref>DE2122144 idem Louis Lafon, {{US patent|3895030}} (1975 to Orsymonde); </ref> [http://en.cnki.com.cn/Article_en/CJFDTOTAL-AHHG201203008.htm China1] [http://en.cnki.com.cn/Article_en/CJFDTotal-ZJTY200609000.htm China2]]] |
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Acylation between 1,3,5-trimethoxybenzene [621-23-8] ('''1''') and 4-pyrrolidinobutyronitrile [35543-25-0] ('''2''') occurs in chlorobenzene solvent in the presence of gaseous hydrochloric acid to give ''Bufomedil'' ('''3'''). This is a demonstration of the [[Hoesch reaction]]. |
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Various adverse effects have been reported to the FDA.<ref>http://www.drugcite.com/?q=BUFLOMEDIL&s=&a=</ref> |
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== |
==References== |
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{{ |
{{Reflist}} |
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{{Peripheral vasodilators}} |
{{Peripheral vasodilators}} |
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{{Adrenergic receptor modulators}} |
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[[Category:1-Pyrrolidinyl compounds]] |
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[[Category:Resorcinol ethers]] |
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[[Category:Vasodilators]] |
[[Category:Vasodilators]] |
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[[ar:بفلوميديل]] |
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[[de:Buflomedil]] |
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[[fr:Buflomédil]] |
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[[pl:Buflomedyl]] |
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[[pt:Buflomedil]] |