Buflomedil: Difference between revisions

Page 1
Page 2
Content deleted Content added
added CSID, (Std)InChI & (Std)InChIKey
Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5
 
(26 intermediate revisions by 22 users not shown)
Line 1: Line 1:
{{Use dmy dates|date=February 2023}}
{{chembox
{{Chembox
| verifiedrevid = 462770158
| ImageFile=Buflomedil.svg
| ImageSize=
| PIN=4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one
| OtherNames=
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V7I71DQ432
| UNII = V7I71DQ432
| CASNo_Ref = {{cascite|correct|??}}
| verifiedrevid = 438975522
|ImageFile=Buflomedil.svg
|ImageSize=
|IUPACName=4-(pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one
|OtherNames=
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=55837-25-7
| CASNo=55837-25-7
| PubChem=2467
| PubChem=2467
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 188921
| ChEMBL = 188921
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2373
| ChemSpiderID = 2373
| SMILES = O=C(c1c(OC)cc(OC)cc1OC)CCCN2CCCC2
| SMILES = O=C(c1c(OC)cc(OC)cc1OC)CCCN2CCCC2
| 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
| 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
| InChIKey = OWYLAEYXIQKAOL-UHFFFAOYAG
| InChIKey = OWYLAEYXIQKAOL-UHFFFAOYAG
| StdInChI = 1S/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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OWYLAEYXIQKAOL-UHFFFAOYSA-N
| StdInChI = 1S/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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OWYLAEYXIQKAOL-UHFFFAOYSA-N
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>17</sub>H<sub>25</sub>NO<sub>4</sub>
| Formula=C<sub>17</sub>H<sub>25</sub>NO<sub>4</sub>
| MolarMass=307.38 g/mol
| MolarMass=307.38 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section6={{Chembox Pharmacology
| ATCCode_prefix = C04
| MainHazards=
| ATCCode_suffix = AX20
| FlashPt=
}}
| Autoignition=
|Section7={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
}}
}}
'''Buflomedil''', sold under the brand name '''Loftyl''', is a [[vasoactive]] drug used to treat [[claudication]] or the symptoms of [[peripheral arterial disease]]. It is currently not approved by the [[Food and Drug Administration]] (FDA) for use in the United States.


==Toxicity==
'''Buflomedil''' is a vasoactive drug used to treat [[claudication]] or the symptoms of peripheral arterial disease. It is currently not approved by the FDA for use in the United States.
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>
Currently available as trade name tablet Loftyl


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>
== Toxicity ==


==Synthesis==
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".
[[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]]]


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]].
Various adverse effects have been reported to the FDA.<ref>http://www.drugcite.com/?q=BUFLOMEDIL&s=&a=</ref>


== References ==
==References==
{{reflist}}
{{Reflist}}


{{Peripheral vasodilators}}
{{Peripheral vasodilators}}
{{Adrenergic receptor modulators}}


[[Category:Alpha-1 blockers]]
[[Category:Alpha-2 blockers]]
[[Category:Piceol ethers]]
[[Category:1-Pyrrolidinyl compounds]]
[[Category:Resorcinol ethers]]
[[Category:Vasodilators]]
[[Category:Vasodilators]]
[[Category:Pyrrolidines]]
[[Category:Ketones]]
[[Category:Phenol ethers]]



{{cardiovascular-drug-stub}}


{{Cardiovascular-drug-stub}}
[[ar:بفلوميديل]]
[[de:Buflomedil]]
[[fr:Buflomédil]]
[[pl:Buflomedyl]]
[[pt:Buflomedil]]