Lomefloxacin hydrochloride

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Lomefloxacin hydrochloride
Category Antibiotics
Catalog number BBF-03971
CAS 98079-52-8
Molecular Weight 387.81
Molecular Formula C17H20ClF2N3O3
Purity >98%

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Description

Lomefloxacin hydrochloride is a fluoroquinolone antibiotic used to treat bacterial infections including bronchitis and urinary tract infections.

Specification

Related CAS 98079-51-7 (free base)
Synonyms Lomefloxacin hydrochloride; Maxaquin; Ny-198; Bareon; SC 4711; SC-4711; SC4711
Storage Store at -20°C
IUPAC Name 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;hydrochloride
Canonical SMILES CCN1C=C(C(=O)C2=CC(=C(C(=C21)F)N3CCNC(C3)C)F)C(=O)O.Cl
InChI InChI=1S/C17H19F2N3O3.ClH/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22;/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25);1H
InChI Key KXEBLAPZMOQCKO-UHFFFAOYSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 542.7°C at 760 mmHg
Melting Point 290-300°C
Solubility Soluble in DMSO (19 mg/mL), DMF (20 mg/ml), Ethanol (20 mg/ml)

Reference Reading

1.A study of the phototoxic potential of trovafloxacin in BALB/c mice.
Mayne JT;Johnson NJ;Kluwe WM;Lencoski DL;Polzer RJ J Antimicrob Chemother. 1997 Jun;39 Suppl B:67-73.
Trovafloxacin, a broad-spectrum naphthyridone antimicrobial agent, was evaluated for potential phototoxicity in a standardized in-vivo test system that has been used previously to assess quinolone antibiotics. Fasted BALB/c mice were given a single oral dose of either trovafloxacin mesylate (10, 30, 90 or 250 mg/kg) or the positive control lomefloxacin hydrochloride (71 mg/kg) and immediately exposed to long-wave ultraviolet (UVA) light. Animals were irradiated for 4 h, equal to a total UV light irradiation of approximately 18 J/cm2. Before dosing, at the end of the irradiation period and at approximately 24, 48, 72 and 96 h after dosing, both ears of each mouse were evaluated for changes indicative of a positive response: erythema, oedema or a measurable increase in ear thickness. Under the conditions of this study, trovafloxacin produced a mild response (erythema and a slight increase in ear thickness) in mice given a dose of 90 or 250 mg/kg; no significant response was observed in mice given either lower doses (10 or 30 mg/kg) or the vehicle. In contrast, 71 mg/kg of lomefloxacin produced a strong and persistent phototoxic response. The results of this study demonstrate that the phototoxic potential of trovafloxacin is considerably less than that of lomefloxacin and, when compared with similar studies with related compounds, suggest that trovafloxacin is among the least phototoxic of the fluoroquinolone class.
2.In vitro activities of lomefloxacin and temafloxacin against pathogens causing diarrhea.
Segreti J;Nelson JA;Goodman LJ;Kaplan RL;Trenholme GM Antimicrob Agents Chemother. 1989 Aug;33(8):1385-7.
The in vitro activities of temafloxacin (A63004) and lomefloxacin (SC-47111; NY-198) were compared with those of seven other antibiotics against 146 isolates of bacterial enteric pathogens, including Campylobacter jejuni and Campylobacter coli. Ciprofloxacin was the most active drug against the Salmonella, Shigella, Yersinia, and Vibrio spp. tested. Lomefloxacin, temafloxacin, and difloxacin were the most active drugs tested against Campylobacter spp. (MIC for 90% of strains, 0.125 to 0.25 micrograms/ml).
3.Analysis of sepsis in allogeneic bone marrow transplant recipients: a single-center study.
Mitsui H;Karasuno T;Santo T;Fukushima K;Matsunaga H;Nakamura H;Hiraoka A J Infect Chemother. 2003 Sep;9(3):238-42.
We reviewed the records of 235 consecutive recipients of allogeneic bone marrow transplantation (allo-BMT) at our center between February 1983 and October 2000. Sepsis occurred in 25 patients (10.6%) at a median of 10 days (range, 1-280 days) after BMT. Five of the 25 patients (20%) died of sepsis. Pathogens isolated from blood culture were gram-positive cocci in 19 patients, gram-negative rods in 7, fungi in 2, and others in 1 patient. Two pathogens were detected concomitantly in 4 patients. Univariate analysis revealed that risk factors for sepsis were selective gut decontamination using lomefloxacin hydrochloride and nystatin, an unrelated donor, HLA mismatched BMT, and stomatitis. Multivariate logistic regression analysis revealed that an unrelated donor was the only significant independent risk factor, with a relative risk of 5.432. In 12 of 25 patients with sepsis, the pathogens of sepsis were sensitive to antibiotics used for gut decontamination. Selective gut decontamination significantly increased the incidence of sepsis, especially that with gram-positive cocci, but not the mortality rate of sepsis, compared with total gut decontamination using vancomycin. We also found a significant relationship between pathogens isolated from blood culture and those isolated from surveillance cultures of stool, urine, and gargled water in the period before sepsis occurred.

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