2314. Ciprofloxacin

Nomenclature

CAS number: 85721-33-1
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid; Bay q 3939.
C17H18FN3O3; mol wt 331.34.
C 61.62%, H 5.48%, F 5.73%, N 12.68%, O 14.49%.

Description and references

Fluorinated quinolone antibacterial. Prepn: K. Grohe et al., DE 3142854; eidem, US 4670444 (1983, 1987 both to Bayer AG); K. Grohe, H. Heitzer, Ann. 1987, 29. Antibacterial spectrum in vitro: B. Watt, F. V. Brown, J. Antimicrob. Chemother. 17, 605 (1986); C. M. Bassey et al., ibid. 623. HPLC determn in biological fluids: W. Gau et al., J. Liq. Chromatogr. 8, 485 (1985). Pharmacokinetics: G. Hoffken et al., Antimicrob. Agents Chemother. 27, 375 (1985); of extended release formulation: C. B. Washington et al., J. Clin. Pharmacol. 45, 1236 (2005). Clinical trials: C. A. Ramirez et al., ibid. 28, 128 (1985); B. E. Scully et al., Lancet 1, 819 (1986). Symposia on antibacterial spectrum and clinical use: Am. J. Med. 82, Suppl. 4A, 1-404 (1987); J. Antimicrob. Chemother. 26, Suppl. F, 3-193 (1990). Review of clinical safety and efficacy in children: R. Kubin, Infection 21, 413-421 (1993); of US FDA approval in postexposure inhalational anthrax: A. Myerhoff et al., Clin. Infect. Dis. 29, 303-308 (2004); of clinical experience in urinary tract infections: A. D. Hickerson, C. C. Carson, Expert Opin. Invest. Drugs 15, 519-532 (2006); of therapeutic potential in a broad spectrum of infections: H. Koch et al., Clin. Drug Invest. 26, 645-654 (2006).

Chemical structure

Properties

Faintly yellowish to light yellow crystalline powder. Dec 255-257°. Sol in dilute (0.1N) HCl. Practically insol in water and ethanol.

Derivative

Monohydrochloride monohydrate.

Nomenclature

CAS number: 86393-32-0
Bay o 9867; Ciflox (Bayer); Ciloxan (Alcon); Cipro (Bayer); Ciprobay (Bayer); Ciproxan (Bayer); Ciproxin (Bayer); Flociprin (IBI); Septicide (Virbac); Uniflox (Bayer).
C17H18FN3O3.HCl.H2O; mol wt 385.82.
C 52.92%, H 5.49%, F 4.92%, N 10.89%, O 16.59%, Cl 9.19%.

Properties

Light yellow crystalline powder. mp 318-320°. Slightly sol in water.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Quinolones and Analogs