FLAVOXATE Chemical Properties

Melting point:

87-88 °C

Boiling point:

564.1±50.0 °C(Predicted)

Density 

1.203±0.06 g/cm3(Predicted)

pka

7.3(at 25℃)

form 

Off-white solid.

CAS DataBase Reference

15301-69-6(CAS DataBase Reference)

Safety Information

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(15301-69-6)Related Product Information

• Vincamine
• SAFFLOWER YELLOW
• L-Glutamine
• Pentoxifylline
• Aristoforin
• Tizanidine
• FLAVOXATE HYDROCHLORIDE (FAD)
• Flavoxate impurity B
• Flavoxate impurity A
• FLAVOXATE HCL,FLAVOXATE HYDROCHLORIDE
• Terflavoxate
• FLAVOXATE
• 3-Quinuclidinyl 3-methylflavone-8-carboxylate hydrochloride
• 4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-(1-pipe ridinyl)cyclohexyl ester, hydrochloride, trans-(+-)-