Lomefloxacin
Title: Lomefloxacin
CAS Registry Number: 98079-51-7
CAS Name: 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
Molecular Formula: C17H19F2N3O3
Molecular Weight: 351.35
Percent Composition: C 58.11%, H 5.45%, F 10.81%, N 11.96%, O 13.66%
Literature References: Fluorinated quinolone antibacterial. DNA gyrase antagonist. Prepn: Y. Itoh et al., DE 3433924; eidem, US 4528287 (both 1985 to Hokuriku Pharm.). In vitro and in vivo activity: T. Hirose et al., Antimicrob. Agents Chemother. 31, 854 (1987). Comparative antibacterial spectrum in vitro: R. Wise et al., ibid. 32, 617 (1988). HPLC determn in urine and bile and preliminary pharmacokinetics in rats: A. Saito et al., ibid. 156. Photochemistry study: E. Fasani et al., Eur. J. Org. Chem.2004, 5075. Supplement on antibacterial spectrum, pharmacokinetics and clinical efficacy: Chemotherapy (Tokyo) 36, Suppl. 2, 1-1418 (1988). Comprehensive description: Y. D. Sanzgiri et al., Anal. Profiles Drug Subs. Excip. 23, 321-369 (1994).
Properties: Colorless needles from ethanol, mp 239-240.5°. Soly at 25° (mg/ml): 1.03 at ionic strength 0.15 M NaCl. uv max (0.15 M acetate buffer, pH 5): 226, 288, 320 nm (aM ´ 10-3 15.5, 36.7, 13.5); uv max (0.05 M phosphate buffer, pH 7): 282, 326 nm (aM ´ 10-3 31.5, 13.3); uv max (0.15 M borate buffer, m = 0.15 M with NaCl, pH 9): 282, 328 nm (aM ´ 10-3 29.3, 13.2). LD50 in mice (mg/kg): 245.6 i.v.; >4000 orally (Itoh).
Melting point: mp 239-240.5°
Absorption maximum: uv max (0.15 M acetate buffer, pH 5): 226, 288, 320 nm (aM ´ 10-3 15.5, 36.7, 13.5); uv max (0.05 M phosphate buffer, pH 7): 282, 326 nm (aM ´ 10-3 31.5, 13.3); uv max (0.15 M borate buffer, m = 0.15 M with NaCl, pH 9): 282, 328 nm (aM ´ 10-3 29.3, 13.2)
Toxicity data: LD50 in mice (mg/kg): 245.6 i.v.; >4000 orally (Itoh)
 
Derivative Type: Monohydrochloride
CAS Registry Number: 98079-52-8
Manufacturers' Codes: NY-198; SC-47111
Trademarks: Bareon (Hokuriku); Chimono (Lusofarmaco); Lomebact (Shionogi); Maxaquin (Pharmacia); Okacin (Novartis); Okacyn (Novartis)
Molecular Formula: C17H19F2N3O3.HCl
Molecular Weight: 387.81
Percent Composition: C 52.65%, H 5.20%, F 9.80%, N 10.84%, O 12.38%, Cl 9.14%
Properties: Colorless needles from water, mp 290-300° (dec).
Melting point: mp 290-300° (dec)
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Quinolones and Analogs.

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