8294. Rufloxacin

Nomenclature

CAS number: 101363-10-4
9-Fluoro-2,3-dihydro-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzothiazine-6-carboxylic acid; MF-934.
C17H18FN3O3S; mol wt 363.41.
C 56.18%, H 4.99%, F 5.23%, N 11.56%, O 13.21%, S 8.82%.

Description and references

Fluorinated quinolone; structurally similar to ofloxacin, q.v. Prepn: G. Mascellani et al., AU 85 39142; eidem, US 4684647 (1985, 1987 both to Mediolanum); V. Cecchetti et al., J. Med. Chem. 30, 465 (1987). In vitro activity: R. Wise et al., Antimicrob. Agents Chemother. 29, 649 (1992). Mechanism of action and resistance: L. J. V. Piddock et al., J. Antimicrob. Chemother. 31, 855 (1993). Pharmacokinetics and safety: J. C. Kisicki et al., ibid. 36, 1296 (1992). HPLC determn in biological fluids: F. Lombardi et al., J. Chromatogr. 576, 129 (1992). Clinical study in cystitis and urinary tract infections: R. Mattina et al., Infection 21, 106 (1993); in bronchitis: W. Klietmann et al., Antimicrob. Agents Chemother. 37, 2298 (1993).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 106017-08-7
ISF-09334; Qari (Mediolanum); Monos (SKB); Tebraxin (Bracco).
C17H18FN3O3S.HCl; mol wt 399.87.
C 51.06%, H 4.79%, F 4.75%, N 10.51%, O 12.00%, S 8.02%, Cl 8.87%.

Properties

Crystals from ethanol/water, mp 322-324° (Cecchetti). LD50 in rats, mice (mg/kg): 285, 224 i.v.; LD50 in rabbits, male, female rats (mg/kg): 660, 631, 501 orally (Cecchetti).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs