Flosequinan: Difference between revisions
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==Overview== | ==Overview== | ||
'''Flosequinan''' is a [[quinolone]] [[vasodilator]]. It has direct relaxing effects on peripheral arteries and veins. It is administered orally in cases of [[congestive heart failure]] in patients who are not responsive to [[digitalis]] or ACE inhibitors. It was sold under the trade name Manoplax. | '''Flosequinan''' is a [[quinolone]] [[vasodilator]]. It has direct relaxing effects on peripheral arteries and veins. It is administered orally in cases of [[congestive heart failure]] in patients who are not responsive to [[digitalis]] or ACE inhibitors. It was sold under the trade name Manoplax. | ||
It was withdrawn from the US market in October 1993 due to an increased risk of hospitalization or death.<ref>{{cite | It was withdrawn from the US market in October 1993 due to an increased risk of hospitalization or death.<ref>{{cite news |url=http://findarticles.com/p/articles/mi_m1370/is_n8_v27/ai_14584909 |title=Heart drug withdrawn - Boots Pharmaceuticals' Manoplax |format= |work= FDA Consumer|accessdate=2008-12-01 | year=1993}}</ref> | ||
==Synthesis== | |||
Both methods for forming the heterocyclic ring in quinolones involved cyclization into the carbocyclic ring. A closely related quinolone that displays cardiovascular rather than antibiotic activity is constructed by a condensation that closes the bond at the 2,3 position in the heterocyclic ring. | |||
[[File:Flosequinan Syn.png|center|700px {{US patent|5079264}} [[Nota bene|N.B.]]<ref>http://www.druglead.com/cds/flosequinan.html</ref>]] | |||
The starting material (2) is obtained by reaction of the aminoacetophenone derivative (1) with [[ethyl formate]]. Heating the product in [[EGME|ethylene glycol methyl ether]] leads to an aldol-like cyclization and the formation of a [[quinolone]] ring. The product, ''flosequinan'' (3), displays vasodilator and cardiotonic activities. | |||
==See also== | |||
*[[Mirisetron]] | |||
==References== | ==References== | ||
{{Reflist|2}} | {{Reflist|2}} | ||
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{{Vasodilators used in cardiac diseases}} | {{Vasodilators used in cardiac diseases}} | ||
[[Category:Withdrawn drugs]] | |||
[[Category:Vasodilators]] | [[Category:Vasodilators]] | ||
[[Category: | [[Category:Quinolines]] | ||
[[Category: | [[Category:Sulfoxides]] | ||
[[Category:Ketones]] | |||
[[Category:Organofluorides]] | |||
{{cardiovascular-drug-stub}} | |||
Latest revision as of 21:43, 14 April 2015
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| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
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| Formula | C11H10FNO2S |
| Molar mass | 239.267 g/mol |
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Flosequinan is a quinolone vasodilator. It has direct relaxing effects on peripheral arteries and veins. It is administered orally in cases of congestive heart failure in patients who are not responsive to digitalis or ACE inhibitors. It was sold under the trade name Manoplax.
It was withdrawn from the US market in October 1993 due to an increased risk of hospitalization or death.[1]
Synthesis
Both methods for forming the heterocyclic ring in quinolones involved cyclization into the carbocyclic ring. A closely related quinolone that displays cardiovascular rather than antibiotic activity is constructed by a condensation that closes the bond at the 2,3 position in the heterocyclic ring.
![700px U.S. Patent 5,079,264 N.B.[2]](/index.php/File:Flosequinan_Syn.png)
The starting material (2) is obtained by reaction of the aminoacetophenone derivative (1) with ethyl formate. Heating the product in ethylene glycol methyl ether leads to an aldol-like cyclization and the formation of a quinolone ring. The product, flosequinan (3), displays vasodilator and cardiotonic activities.
See also
References
- ↑ "Heart drug withdrawn - Boots Pharmaceuticals' Manoplax". FDA Consumer. 1993. Retrieved 2008-12-01.
- ↑ http://www.druglead.com/cds/flosequinan.html
- Pages with script errors
- Pages using duplicate arguments in template calls
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
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- Drugs with no legal status
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- Withdrawn drugs
- Vasodilators
- Quinolines
- Sulfoxides
- Ketones
- Organofluorides