| Identification | More | [Name]
Flavoxate hydrochloride | [CAS]
3717-88-2 | [Synonyms]
3-METHYL-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-8-CARBOXYLIC ACID 2-(1-PIPERIDINYL)ETHYL ESTER HYDROCHLORIDE
3-METHYL-4-OXO-2-PHENYL-4H-BENZOPYRAN-8-CARBOXYLIC ACID 2-PIPERIDINYL ETHYL ESTER HYDROCHLORIDE
DW-61
FLAVOXATE HCL
FLAVOXATE HYDROCHLORIDE
REC-7-0040
1-piperidineethanol,3-methyl-4-oxo-2-phenyl-4h-1-benzopyran-8-carboxylate,h
2-piperidinoethyl-3-methyl-4-oxo-2-phenyl-4h-1-benzopyran-8-carboxylatehydro
3-methyl-4-oxo-2-phenyl-4h-1-benzopyran-8-carboxylicaci2-piperidinoethyl
bladderon
flaroxatehydrochloride
genurin
nsc-114649
piperidinoethyl-3-methylflavone-8-carboxylatehydrochloride
spasuret
FLAVOMYCINPREMIX
Urispas | [EINECS(EC#)]
223-066-4 | [Molecular Formula]
C24H26ClNO4 | [MDL Number]
MFCD00072099 | [Molecular Weight]
427.92 | [MOL File]
3717-88-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
232-234°C | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
H2O: ~6.6 mg/mL
| [form ]
solid
| [color ]
white
| [Usage]
Smooth muscle relaxant. Used as antispasmodic; in treatment of urinary incontinence | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [RTECS ]
DJ2450000
| [HS Code ]
29349990 | [Toxicity]
LD50 i.v. in rats: 27.4 mg/kg (Cazzulani) |
| Hazard Information | Back Directory | [Chemical Properties]
Flavoxate hydrochloride is Crystalline Solid
| [Originator]
Urispas,SKF,US,1971 | [Uses]
Antispasmodic;Phosphodiesterase inhibitor | [Uses]
Flavoxate hydrochloride is 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 | [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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