3587. Enoxacin

Nomenclature

CAS number: 74011-58-8
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid; AT-2266; CI-919; PD-107779; Comprecin (Parke-Davis); Flumark (Dainippon).
C15H17FN4O3; mol wt 320.32.
C 56.24%, H 5.35%, F 5.93%, N 17.49%, O 14.98%.

Description and references

Fluorinated quinolone antibacterial; nalidixic acid analog. Prepn and antibacterial activity: J. Matsumoto et al., EP 9425; eidem, US 4352803; eidem, US 4359578 (1980, 1982, 1982 all to Dainippon and Roger Bellon); J. Matsumoto et al., J. Med. Chem. 27, 292 (1984). HPLC determn in plasma, urine: T. B. Vree et al., J. Chromatogr. 343, 449 (1985). In vitro comparison with other quinolones and azaquinolones: S. Selwyn, M. Bakhtiar, Drugs Exp. Clin. Res. 10, 653 (1984). Pharmacokinetics, therapeutic efficacy: K. G. Naber et al., Infection 13, 219 (1985). Efficacy in treatment of urinary tract infections: R. R. Bailey, B. A. Peddie, N. Z. Med. J. 98, 286 (1985). Toxicology studies: H. Senda et al., Chemotherapy (Tokyo) 32, Suppl. 3, 192 (1984). Series of articles on activity, pharmacology, metabolism, early clinical studies: ibid. 1-1093; J. Antimicrob. Chemother. 14, Suppl. C, 1-96 (1984); on activity, pharmacokinetics, clinical safety and efficacy: Infection 14, Suppl. 3, S183-S220 (1986).

Chemical structure

Properties

Crystals from ethanol/methylene chloride, mp 220-224°. LD50 in male, female mice, male, female rats (mg/kg): 327, 391, 236, 294 i.v.; 1237, 1320, >2000, >2000 s.c.; all >5000 orally (Senda).

Derivative

Sesquihydrate.

Nomenclature

CAS number: 84294-96-2
Bactidan (Fabre); Enoxen (Dainippon); Enoxor (Fabre); Gyramid (Warner-Lambert).
C15H17FN4O3.1 1/2 H2O; mol wt 329.33.
C 54.71%, H 5.51%, F 5.77%, N 17.01%, O 17.00%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs