4096. Flavoxate

Nomenclature

CAS number: 15301-69-6
3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-(1-piperidinyl)ethyl ester; 3-methylflavone-8-carboxylic acid β-piperidinoethyl ester; 2-piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate; 2-piperidinoethyl 3-methylflavone-8-carboxylate.
C24H25NO4; mol wt 391.46.
C 73.64%, H 6.44%, N 3.58%, O 16.35%.

Description and references

Smooth muscle relaxant. Prepn of the hydrochloride: P. Da Re et al., J. Med. Pharm. Chem. 2, 263 (1960); P. Da Re, US 2921070 and US 3350411 (1960 to Recordati and 1967 to Seceph). Pharmacological studies: I. Setnikar et al., J. Pharmacol. Exp. Ther. 130, 356 (1960). Mechanism of action: P. Cazzulani et al., Arch. Int. Pharmacodyn. 274, 189 (1985). Pharmacokinetics in rats: I. Setnikar et al., Arzneim.-Forsch. 25, 1916 (1975); in man: M. Bertoli et al., Pharmacol. Res. Commun. 8, 417 (1976). In vivo activity: C. Pietra, P. Cazzulani, Farmaco Ed. Prat. 41, 267 (1986). Determn in tissues: A. Cova, I. Setnikar, Arzneim.-Forsch. 25, 1707 (1975). Clinical evaluations: D. V. Bradley, R. J. Cazort, J. Clin. Pharmacol. 10, 65 (1970); A. Zanollo, F. Catanzaro, Urol. Int. 35, 176 (1980). Clinical comparison with phenazopyridine: S. Gould, Urology 5, 612 (1975). Short review: R. Ruffmann, A. Sartini, Drugs Exp. Clin. Res. 13, 57 (1987).

Chemical structure

Properties

Crystals, pK 7.3. Soly in water at 37°: 0.001% (w/v). Sol in ethanol and chloroform. LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975).

Derivative

Hydrochloride.

Nomenclature

CAS number: 3717-88-2
DW-61; Rec-7-0040; Bladderon (Nippon Shinyaku); Genurin (Recordati); Patricin (Kaken); Spasuret (Asche); Urispas (SKB).
C24H25NO4.HCl; mol wt 427.92.
C 67.36%, H 6.12%, N 3.27%, O 14.96%, Cl 8.28%.

Properties

Crystals from ethanol + ether, mp 232-234°. LD50 i.v. in rats: 27.4 mg/kg (Cazzulani).

Derivative

Succinate.

Nomenclature

CAS number: 28782-19-6
C24H25NO4.C4H6O4; mol wt 509.55.
C 66.00%, H 6.13%, N 2.75%, O 25.12%.

Properties

Soly in water at 37°: 33.7% (w/v).

Therapeutic Category

Antispasmodic; in treatment of urinary incontinence.

Keywords

Antispasmodic; Antimuscarinic