Floctafenine
{{Short description|Chemical compound}}
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{{Drugbox
| drug_name =
| IUPAC_name = 2,3-Dihydroxypropyl 2-
| image = Floctafenine.svg
| image_class = skin-invert-image
| alt =
| caption =
| tradename =
| Drugs.com = {{Drugs.com|international|floctafenine}}
| MedlinePlus =
| pregnancy_AU =
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| routes_of_administration =
| ATC_prefix = N02
| ATC_suffix = BG04
| legal_AU =
| legal_CA = Rx-only
| legal_CA_comment = {{cite web | title=Product monograph brand safety updates | website=Health Canada | date=6 June 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=8 June 2024}}
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| bioavailability =
| protein_bound =
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| CAS_number = 23779-99-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O04HVX6A9Q
| PubChem = 3360
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB08976
| ChemSpiderID = 3243
| C=20 | H=17 | F=3 | N=2 | O=4
| smiles = FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO
| StdInChI = 1S/C20H17F3N2O4/c21-20(22,23)15-6-3-5-13-17(8-9-24-18(13)15)25-16-7-2-1-4-14(16)19(28)29-11-12(27)10-26/h1-9,12,26-27H,10-11H2,(H,24,25)
| StdInChIKey = APQPGQGAWABJLN-UHFFFAOYSA-N
}}
Floctafenine is a nonsteroidal anti-inflammatory drug (NSAID).
Synthesis
Floctafenine can be synthesized beginning with the conversion of ortho-trifluoromethyl aniline (1) to a quinolol.{{Cite patent|country=DE|number=1815467A1|pubdate=1969-07-24|title=Neue Chinolidinderivate und Verfahren zu ihrer Herstellung [Novel quinolidine derivatives and processes for their preparation]|assign=Roussel-Uclaf|inventor1-last=Allais|inventor1-first=André|inventor2-last=Meier|inventor2-first=Jean}}{{US patent|3644368}} Roussel Uclaf{{Cite journal | doi = 10.1055/s-1980-28923| title = A New, Convenient Synthesis of Glafenine and Floctafenine| journal = Synthesis| volume = 1980| pages = 54–55| year = 1980| vauthors = Mouzin G, Cousse H, Autin JM | s2cid = 97164628}} The compound is then condensed with ethoxy methylene malonic diethyl ester (EMME) and cyclized thermally (2). That intermediate is then saponified; the resulting acid is decarboxylated and finally converted to the 4-chloroquinoline (3) by reaction with phosphorus oxychloride. The displacement of chlorine with methyl anthranilate (4) then affords the coupled intermediate (5). An ester interchange of that product with glycerol leads to the glyceryl ester, floctafenine (6).
References
{{reflist}}
{{Anti-inflammatory products}}
{{Prostanoidergics}}
Category:Nonsteroidal anti-inflammatory drugs
Category:Trifluoromethyl compounds
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