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| | FLAVOXATE Basic information |
| Product Name: | FLAVOXATE | | Synonyms: | FLAVOXATE;2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate;2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate;4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-(1-piperidinyl)ethyl ester;3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-piperidinoethyl ester;Piperidinoethyl 3-methyl-2-phenyl-4-oxo-4H-1-benzopyran-8-carboxylate;2-(Piperidin-1-yl)ethyl 3-Methyl-4-oxo-2-phenyl-4H-chroMene-8-carboxylate;Flavoxate-d5 | | CAS: | 15301-69-6 | | MF: | C24H25NO4 | | MW: | 391.46 | | EINECS: | 239-337-5 | | Product Categories: | | | Mol File: | 15301-69-6.mol |  |
| | FLAVOXATE Chemical Properties |
| Melting point | 87-88 °C | | Boiling point | 564.1±50.0 °C(Predicted) | | density | 1.203±0.06 g/cm3(Predicted) | | form | Off-white solid. | | pka | 7.3(at 25℃) | | CAS DataBase Reference | 15301-69-6(CAS DataBase Reference) |
| Toxicity | LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975) |
| | FLAVOXATE Usage And Synthesis |
| Originator | Urispas,SKF,US,1971 | | Uses | Flavoxate is a pharmaceutical active-containing film delivery device for oral transmucosal administration. | | Uses | Relaxant (smooth muscle). | | Definition | ChEBI: A carboxylic ester resulting from the formal condensation of 3-methylflavone-8-carboxylic acid with 2-(1-piperidinyl)ethanol. | | Manufacturing Process | A mixture of 13.3 grams of anhydrous aluminum chloride and 100 ml of
carbon disulfide is added to 19.4 grams of 2-propionyloxybenzoic acid
(prepared from the reaction of propionyl chloride and 2-hydroxybenzoic acid).
After an initial evolution of hydrogen chloride, the solvent is removed by
distillation and the mixture is heated at 150° to 160°C for 4 hours. The cooled
reaction mixture is treated with ice and hydrochloric acid and the product, 2-
hydroxy-3-carboxypropiophenone, is obtained from the oily residue by
distillation in vacuo.
A mixture of 1.9 grams of 2-hydroxy-3-carboxypropiophenone, 5.0 grams of
sodium benzoate and 20.0 grams of benzoic anhydride is heated at 180° to
190°C for 6 hours. A solution of 15.0 grams of potassium hydroxide in 50 ml
of ethanol and 20 ml of water is added and refluxed for 1 hour. The mixture is
evaporated and the residue after addition of water yields 3-methylflavone-8-
carboxylic acid.
To a suspension of 12.0 grams of 3-methylflavone-8-carboxylic acid in 200 ml
of anhydrous benzene is added 10.0 grams of thionyl chloride. The mixture is
refluxed for 2 hours during which the suspended solid goes into solution. The
solvent is completely removed by distillation, the residue extracted with
benzene and the extract evaporated to dryness. The product, 3-
methylflavone-8-carboxylic acid chloride, is recrystallized from ligroin to give
crystals melting at 155° to 156°C.
To 11.0 grams of 3-methylflavone-8-carboxylic acid chloride dissolved in 150
ml of anhydrous benzene is added at room temperature 4.8 grams of
piperidinoethanol and the mixture refluxed for 2 to 3 hours. The separated
solid is filtered, washed with benzene and dried. The product, piperidinoethyl
3-methylflavone-8-carboxylate hydrochloride is obtained as a colorless
crystalline solid, MP 232° to 234°C, (from US Patent 2,921,070). | | Brand name | Urispas (Ortho-McNeil). | | Therapeutic Function | Spasmolytic |
| | FLAVOXATE Preparation Products And Raw materials |
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