Flavoxate hydrochloride

Chemical Name 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-piperidino-ethyl ester hydrochloride 

Common Name 2-piperidinoethyl 3-methylflavone-8-carboxylate Structural Formula  

Trade Name Manufacturer Country Year Introduced 

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 pro-pionyl 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. 

Urispas Protea Raw Materials Salicylic acid Aluminum chloride Thionyl chloride Australia Propioriyl chloride 8enzoic anhydride Piperidinoethanol  

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Smooth muscle relaxants flavoxate hydrochloride oxybutynin chloride tolterodine L-tartrate... 

Tertiary amines used for their antispasmodic properties are dicyclomine hydrochloride (Ben-tyl, others), oxyphencyclimine hydrochloride (daricon), flavoxate hydrochloride (Uripas), and oxyburynin chloride (Ditropan). The latter two are indicated specifically for urological disorders. These agents appear to exert some nonspecific direct relaxant effect on smooth muscle. In therapeutic doses they decrease spasm of the gastrointestinal tract, biliary tract, ureter, and uterus characteristic atropine-like effects on the salivary glands and the eye also are seen with oxybutynin. 

Using oxidation conditions of ra-chloroperbenzoic acid, the API dibucaine can be easily oxidized to its N-oxide analog (Fig. 37) (58). An additional example includes the API flavoxate hydrochloride, which degrades to the corresponding N-oxide in 3% aqueous hydrogen peroxide (59). 

Calcium Aminosalicylate Phenindamine Tartrate 427.9 Flavoxate Hydrochloride... 

Enomoto U, Ohnishi Y, Kimura M, Kawada A, Ishibashi A. Drug eruption due to flavoxate hydrochloride. Contact Dermatitis 1999 40(6) 337-8. 

Fontani F and Setnikar I, Chemical and physical properties of flavoxate, Pharmazeutische Industrie, 36, 802-805 (1974). Cited in Goldberg Y, Flavoxate hydrochloride, APDS, 28, 82 (2001). 

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