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| | Flavoxate hydrochloride Basic information |
| | Flavoxate hydrochloride Chemical Properties |
| Melting point | 232-234°C | | storage temp. | Inert atmosphere,Room Temperature | | solubility | H2O: ~6.6 mg/mL | | form | solid | | color | white | | CAS DataBase Reference | 3717-88-2(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | RTECS | DJ2450000 | | HS Code | 29349990 | | Toxicity | LD50 i.v. in rats: 27.4 mg/kg (Cazzulani) |
| | Flavoxate hydrochloride Usage And Synthesis |
| Chemical Properties | Flavoxate hydrochloride is Crystalline Solid
| | Originator | Urispas,SKF,US,1971 | | Uses | Flavoxate hydrochloride is used as antispasmodic; in treatment of urinary incontinence
| | Uses | Antispasmodic;Phosphodiesterase inhibitor | | Uses | Smooth muscle relaxant. Used as antispasmodic; in treatment of urinary incontinence. | | Definition | ChEBI: The hydrochloride salt of flavoxate. | | 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 | | Veterinary Drugs and Treatments | Flovoxate may be considered for treating dogs with detrusor hyperspasticity
(hyperactive bladder, urge incontinence). |
| | Flavoxate hydrochloride Preparation Products And Raw materials |
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