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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
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| verifiedrevid = 444453345
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status =
| routes_of_administration =
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 76568-02-0
| CAS_number = 76568-02-0
| ATC_prefix = C01
| ATC_prefix = C01
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04195
| KEGG = D04195
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 3672315
| ChemSpiderID = 3672315
| smiles = CN1C=C(C(=O)C2=C1C=C(C=C2)F)S(=O)C
| smiles = CN1C=C(C(=O)C2=C1C=C(C=C2)F)S(=O)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI = 1/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3
| InChIKey = UYGONJYYUKVHDD-UHFFFAOYAJ
| StdInChI = 1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3
| StdInChI = 1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3
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| StdInChIKey = UYGONJYYUKVHDD-UHFFFAOYSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=11 | H=10 | F=1 | N=1 | O=2 | S=1
| C=11 | H=10 | F=1 | N=1 | O=2 | S=1
| molecular_weight = 239.267 g/mol
}}
}}
'''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]] that was discovered and developed by [[Boots UK]] and was sold for about a year under the trade name Manoplax. It had been approved in 1992 in the US and UK to treat people with [[heart failure]] who could not tolerate ACE inhibitors or digitalis.<ref name=Independent>{{cite news|last1=Hosking|first1=Patrick | name-list-style = vanc |title=Manoplax: from heart to heartbreak: With millions lost on its 'wonder|url=https://www.independent.co.uk/news/business/manoplax-from-heart-to-heartbreak-with-millions-lost-on-its-wonder-drug-patrick-hosking-asks-whether-1487095.html|work=The Independent|date=25 July 1993}}</ref>
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>


Boots initiated a clinical trial called PROFILE to see if the drug could be useful in a wider population. The study was terminated early in 1993 due to increased mortality in the drug arm of the trial; preliminary results were published in a conference abstract by the PI [[Milton Packer]] and others, which promised data and analysis would be forthcoming in a future paper,<ref>{{cite journal | vauthors = van Veldhuisen DJ, Poole-Wilson PA | title = The underreporting of results and possible mechanisms of 'negative' drug trials in patients with chronic heart failure | journal = International Journal of Cardiology | volume = 80 | issue = 1 | pages = 19–27 | date = August 2001 | pmid = 11532543 | doi = 10.1016/s0167-5273(01)00447-8 }}</ref> which was finally published in 2017.<ref>{{cite journal | vauthors = Packer M, Pitt B, Rouleau JL, Swedberg K, DeMets DL, Fisher L | title = Long-Term Effects of Flosequinan on the Morbidity and Mortality of Patients With Severe Chronic Heart Failure: Primary Results of the PROFILE Trial After 24 Years | journal = JACC. Heart Failure | volume = 5 | issue = 6 | pages = 399–407 | date = June 2017 | pmid = 28501522 | doi = 10.1016/j.jchf.2017.03.003 | doi-access = free }}</ref>
⚫
==References==

Boots withdrew it from the market in July 1993.<ref name=Independent/><ref>{{cite news|last1=Associated Press|title=Heart Failure Drug Manoplax Taken Off Market|url=https://apnews.com/41d97c60a47c8e296bb592d042586dc2|work=AP News Archive|date=July 19, 1993}}</ref>

⚫
== References ==
{{Reflist}}
{{Reflist}}


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[[Category:Withdrawn drugs]]
[[Category:Withdrawn drugs]]
[[Category:Vasodilators]]
[[Category:Vasodilators]]
[[Category:Quinolines]]
[[Category:4-Quinolones]]
[[Category:Sulfoxides]]
[[Category:Sulfoxides]]
[[Category:Ketones]]
[[Category:Fluoroarenes]]
[[Category:Organofluorides]]



{{cardiovascular-drug-stub}}
{{cardiovascular-drug-stub}}

Latest revision as of 13:25, 16 January 2023

Flosequinan
Clinical data
ATC code
Identifiers
  • (RS)-7-fluoro-3-methanesulfinyl-1-methyl-1,4-dihydroquinolin-4-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H10FNO2S
Molar mass239.26 g·mol−1
3D model (JSmol)
  • CN1C=C(C(=O)C2=C1C=C(C=C2)F)S(=O)C
  • InChI=1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3 ☒N
  • Key:UYGONJYYUKVHDD-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Flosequinan is a quinolone vasodilator that was discovered and developed by Boots UK and was sold for about a year under the trade name Manoplax. It had been approved in 1992 in the US and UK to treat people with heart failure who could not tolerate ACE inhibitors or digitalis.[1]

Boots initiated a clinical trial called PROFILE to see if the drug could be useful in a wider population. The study was terminated early in 1993 due to increased mortality in the drug arm of the trial; preliminary results were published in a conference abstract by the PI Milton Packer and others, which promised data and analysis would be forthcoming in a future paper,[2] which was finally published in 2017.[3]

Boots withdrew it from the market in July 1993.[1][4]

References

[edit]
  1. ^ a b Hosking P (25 July 1993). "Manoplax: from heart to heartbreak: With millions lost on its 'wonder". The Independent.
  2. ^ van Veldhuisen DJ, Poole-Wilson PA (August 2001). "The underreporting of results and possible mechanisms of 'negative' drug trials in patients with chronic heart failure". International Journal of Cardiology. 80 (1): 19–27. doi:10.1016/s0167-5273(01)00447-8. PMID 11532543.
  3. ^ Packer M, Pitt B, Rouleau JL, Swedberg K, DeMets DL, Fisher L (June 2017). "Long-Term Effects of Flosequinan on the Morbidity and Mortality of Patients With Severe Chronic Heart Failure: Primary Results of the PROFILE Trial After 24 Years". JACC. Heart Failure. 5 (6): 399–407. doi:10.1016/j.jchf.2017.03.003. PMID 28501522.
  4. ^ Associated Press (July 19, 1993). "Heart Failure Drug Manoplax Taken Off Market". AP News Archive.
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