Flavoxate hydrochloride CAS 3717-88-2
Introduction：Basic information about Flavoxate hydrochloride CAS 3717-88-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Flavoxate hydrochloride Basic information
| Product Name: | Flavoxate hydrochloride |
| Synonyms: | FLAVOMYCINPREMIX;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;Urispas;Flavoxate hydrochloride,3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-(1-piperidinyl)ethyl ester hydrochloride, DW-61, Rec-7-0040;Flavoxate Hydrochloride (200 mg) |
| CAS: | 3717-88-2 |
| MF: | C24H26ClNO4 |
| MW: | 427.92 |
| EINECS: | 223-066-4 |
| Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;ACTIVE PHARMACEUTICAL INGREDIENTS;API |
| Mol File: | 3717-88-2.mol |
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 |
| Major Application | pharmaceutical (small molecule) |
| 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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral STOT SE 3 |
| Toxicity | LD50 i.v. in rats: 27.4 mg/kg (Cazzulani) |
| Chemical Properties | Flavoxate hydrochloride is Crystalline Solid |
| Originator | Urispas,SKF,US,1971 |
| Uses | Smooth muscle relaxant. Used as antispasmodic; in treatment of urinary incontinence. |
| Pharmaceutical Applications | 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 ofcarbon 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 bydistillation and the mixture is heated at 150° to 160°C for 4 hours. The cooledreaction mixture is treated with ice and hydrochloric acid and the product, 2-hydroxy-3-carboxypropiophenone, is obtained from the oily residue bydistillation in vacuo. A mixture of 1.9 grams of 2-hydroxy-3-carboxypropiophenone, 5.0 grams ofsodium benzoate and 20.0 grams of benzoic anhydride is heated at 180° to190°C for 6 hours. A solution of 15.0 grams of potassium hydroxide in 50 mlof ethanol and 20 ml of water is added and refluxed for 1 hour. The mixture isevaporated 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 mlof anhydrous benzene is added 10.0 grams of thionyl chloride. The mixture isrefluxed for 2 hours during which the suspended solid goes into solution. Thesolvent is completely removed by distillation, the residue extracted withbenzene and the extract evaporated to dryness. The product, 3-methylflavone-8-carboxylic acid chloride, is recrystallized from ligroin to givecrystals melting at 155° to 156°C. To 11.0 grams of 3-methylflavone-8-carboxylic acid chloride dissolved in 150ml of anhydrous benzene is added at room temperature 4.8 grams ofpiperidinoethanol and the mixture refluxed for 2 to 3 hours. The separatedsolid is filtered, washed with benzene and dried. The product, piperidinoethyl3-methylflavone-8-carboxylate hydrochloride is obtained as a colorlesscrystalline solid, MP 232° to 234°C, (from US Patent 2,921,070). |
| Brand name | Urispas (Ortho-McNeil). |
| Therapeutic Function | Spasmolytic |
| Biological Activity | L-type Ca2+ (Cav1.2) channel inhibitor |
| 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. |
Flavoxate hydrochloride Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->2-Piperidinoethanol-->Aluminum chloride-->Propionyl chloride-->Salicylic acid-->Benzoic anhydride |
