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

InChI

InChI=1S/C24H25NO4.ClH/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25;/h2,4-5,8-12H,3,6-7,13-16H2,1H3;1H

InChIKey

XOEVKNFZUQEERE-UHFFFAOYSA-N

SMILES

C12OC(=C(C)C(=O)C=1C=CC=C2C(=O)OCCN1CCCCC1)C1C=CC=CC=1.Cl

CAS DataBase Reference

3717-88-2(CAS DataBase Reference)

Safety Information

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)

MSDS

• Language:English Provider:SigmaAldrich

Flavoxate hydrochloride Usage And Synthesis

Chemical Properties

Flavoxate hydrochloride is Crystalline Solid

Originator

Urispas,SKF,US,1971

Uses

Smooth muscle relaxant. Used as antispasmodic; in treatment of urinary incontinence.

Uses

Antispasmodic;Phosphodiesterase inhibitor

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

Side effects

The following adverse reactions have been observed, but there are not enough data to support an estimate of their frequency.
Gastrointestinal: Nausea, vomiting, dry mouth.
CNS: Vertigo, headache, mental confusion, especially in the elderly, drowsiness, nervousness.
Hematologic: Leukopenia (one case which was reversible upon discontinuation of the drug).
Cardiovascular: Tachycardia and palpitation.
Allergic: Urticaria and other dermatoses, eosinophilia and hyperpyrexia.
Ophthalmic: Increased ocular tension, blurred vision, disturbance in eye accommodation.
Renal: Dysuria.

Veterinary Drugs and Treatments

Flovoxate may be considered for treating dogs with detrusor hyperspasticity (hyperactive bladder, urge incontinence).

Pharmacology

Flavoxate hydrochloride counteracts smooth muscle spasm of the urinary tract and exerts its effect directly on the muscle. In a single study of 11 normal male subjects, the time to onset of action was 55 minutes. The peak effect was observed at 112 minutes. 57% of the flavoxate hydrochloride was excreted in the urine within 24 hours.

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