Floctafenine

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{{Drugbox | drug_name = Floctafenine | IUPAC_name = 2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate | image = Floctafinine Wiki Str.png

| alt = | caption =

| tradename = | Drugs.com = International Drug Names | MedlinePlus = | pregnancy_AU = | pregnancy_US = | pregnancy_category= | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number = 23779-99-9 | ATCvet = | ATC_prefix = N02 | ATC_suffix = BG04 | PubChem = 3360 | DrugBank_Ref =  ☒N | DrugBank = DB08976 | ChemSpiderID = 3243


| C=20 | H=17 | F=3 | N=2 | O=4 | molecular_weight = 406.355 g/mol | smiles = FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO | InChI = 1/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) | InChIKey = APQPGQGAWABJLN-UHFFFAOYAH | 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 }}

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Floctafenine is a non-steroidal anti-inflammatory drug (NSAID).

Synthesis

700pxDE 1815467 ; eidem, U.S. Patent 3,644,368 Roussel Uclaf; [1]

The scheme involves first the conversion of ortho-trifluoromethyl aniline (1) to a quinolol. The compound is thus condensed with EMME (Ethoxy Methylene Malonic Diethyl Ester) 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. There is thus obtained the NSAID floctafenine.

See also

References


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