15301-69-6

Basic information

• Product Name: FLAVOXATE
• Synonyms: FLAVOXATE;2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate;2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate;4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-(1-piperidinyl)ethyl ester;3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-piperidinoethyl ester;Piperidinoethyl 3-methyl-2-phenyl-4-oxo-4H-1-benzopyran-8-carboxylate;2-(Piperidin-1-yl)ethyl 3-Methyl-4-oxo-2-phenyl-4H-chroMene-8-carboxylate;Flavoxate-d5
• CAS NO: 15301-69-6
• Molecular Formula: C₂₄H₂₅NO₄
• Molecular Weight: 391.46
• EINECS: 239-337-5
• Mol File: 15301-69-6.mol

Chemical Properties

• Melting Point: 87-88 °C
• Boiling Point: 564.1 °C at 760 mmHg
• Flash Point: 294.9 °C
• Appearance: /
• Density: 1.203 g/cm³
• Vapor Pressure: 9.56E-13mmHg at 25°C
• Refractive Index: 1.591
• PKA: 7.3(at 25℃)
• CAS DataBase Reference: FLAVOXATE(CAS DataBase Reference)
• NIST Chemistry Reference: FLAVOXATE(15301-69-6)
• EPA Substance Registry System: FLAVOXATE(15301-69-6)

Safety Data

• Hazardous Substances Data: 15301-69-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FLAVOXATE is used as a pharmaceutical active-containing film delivery device for oral transmucosal administration. This allows for a more convenient and efficient method of drug administration, enhancing patient compliance and overall treatment experience.
Used in Smooth Muscle Relaxation:
FLAVOXATE is also used as a relaxant for smooth muscles, which can be beneficial in treating various conditions related to muscle tension and spasms. Its muscle-relaxing properties make it a valuable asset in the management of such conditions.

Originator

Urispas,SKF,US,1971

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).

Therapeutic Function

Spasmolytic

InChI:InChI=1/C24H25NO4/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

Upstream product

• 91099-99-9 β-piperidinoethyl 3-propionylsalicylate 
• 98-88-4 benzoyl chloride 
• 3717-88-2 flavoxate hydrochloride 
• 91849-12-6 β-piperidinoethyl 6-bromo-3-methylflavone-8-carboxylate 
• 91830-40-9 β-piperidinoethyl 6-chloro-3-methylflavone-8-carboxylate 

Relevant articles and documents

Structural investigation, molecular structure and molecular docking of solifenacin succinate, flavoxate hydrochloride and tolterodine tartrate anti-cholinergic drugs: Correlation using thermal analysis and mass spectral fragmentation

In this work, solifenacin succinate (SOLS), flavoxate HCl (FLXHC) and tolterodine tartrate (TOLT) drugs were investigated using thermal analysis (TA) measurements in comparison with electron impact mass spectral fragmentation at 70?eV. Also chemical purity, melting point (using differential scanning calorimetry), activation energy and enthalpy in the process of characterizing medicines were important requirements evaluated in quality control of the pharmaceutical industry. The thermal decomposition of these drugs revealed a moderate stability up to 161, 215 and 195?°C for SOLS, FLXHC and TOLT drugs, respectively, before a complete decomposition in the temperature ranges of 161–800, 215–650 and 195–650?°C. The initial decomposition can be accounted for the loss of C7H12NO molecule, followed by loss of C20H20NO5 molecule for SOLS, loss of HCl, followed by loss of C24H25NO4 molecule for FLXHC, and loss of C23H30NO7 molecule followed by loss of C3H7 for TOLT drug. On the other hand, the molecular ion can easily fragmented by succinate, HCl and tartrate loss followed by loss of C2H5, C4H8 and C2H4 for SOLS, FLXHC and TOLT drugs, respectively. This is the best-selected pathway comparable with decomposition using TA. In addition, computational method including molecular docking was carried out to investigate the E. coli bacterial RNA (4p20) binding to the drug compounds under study. Molecular docking calculation indicated the existence of hydrogen bond and π-interaction between active sites of E. coli bacterial RNA (4p20) and O and or N and aromatic ring in all drug compounds which lead to their stabilization.

Halo-containing 3-methylflavone-8-carboxylic acid derivatives

This invention relates to derivatives of 3-methylflavone-8-carboxylic acid represented by the formula (1) STR1 wherein R represents a hydrogen atom, a lower alkyl group or a group STR2 (wherein R1 and R2 represent a lower alkyl group or R1 and R2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a halogen atom, which are useful as intermediates. This invention also relates to processes for preparing the same.

3-Propionylsalicylic acid derivatives and process for the preparation of the same

This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) STR1 wherein R represents a hydrogen atom, a lower alkyl group or a group STR2 (wherein R1 and R2 represent a lower alkyl group or R1 and R2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group STR3 when X is a hydrogen atom. This invention also relates to processes for preparing the same.