Levofloxacin hydrochloride Produkt Beschreibung

Levofloxacin hydrochloride Struktur
100986-85-4
  • CAS-Nr.100986-85-4
  • Bezeichnung:Levofloxacin hydrochloride
  • Englisch Name:Levofloxacin hydrochloride
  • Synonyma:
    LVFX;evofL;HR 355;Cravit;Crarit;dr3355;Tavanic;Levaquin;RWJ 25213;Ophthalmic
  • CBNumber:CB4122906
  • Summenformel:C18H20FN3O4
  • Molgewicht:361.37
  • MOL-Datei:100986-85-4.mol
Levofloxacin hydrochloride physikalisch-chemischer Eigenschaften
Sicherheit

Levofloxacin hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R22:Gesundheitsschädlich beim Verschlucken.
    R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
    R68:Irreversibler Schaden möglich.
    R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
  • S-Sätze Betriebsanweisung: S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
    S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
    S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  • Beschreibung Levofloxacin, the optically active S-isomer of the fluoroquinolone antibiotic ofloxacin, is two to four times more potent than ofloxacin with reportedly less side effects in treating infections of the lower respiratory and urinary tract, prostate infections and sexually transmitted diseases. It has broad and potent antibacterial activity over common Grampositive and -negative aerobic pathogens and obligate anaerobes. Different from the cephem antibiotics, levofloxacin is unique in its marked selectivity against members of the family Enterobacteriaceae and its negligible effect on predominant anaerobes. Levofloxacin also exhibits satisfactory antimicrobial effects in surgical infections and it may be used for treatment of gastrointestinal infections such as traveler’s diarrhea associated with the pathogenic Enterobacteriaceae.
  • Chemische Eigenschaften Slight yellow powder
  • Originator Daiichi (Japan)
  • Verwenden Antibacterial.
  • Manufacturing Process ()-3-Acetoxymethyl-7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine (m.p. 73- 74°C) was synthesized by hydrogenation of a compound prepared from 2,3- difluoro-6-nitrophenol, 1-acetoxy-3-chloro-2-propane and potassium iodide. The hydrogenation was carried out on Raney nickel. The resulting compound was dissolved in THF, and 3,5-dinitrobenzoyl chloride and pyridine were added thereto, followed by heating at 60°C for 3 hours. The mixture was concentrated, and the concentrate was dissolved in ethyl acetate, washed successively with diluted hydrochloric acid, an aqueous solution of sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated. Addition of n-hexane to the concentrate caused precipitation of yellow crystals of a racemate. The yield of 3,5-dinitrobenzoyl derivative of the ()-3- acetoxymethyl-7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine 3.93 g.
    To 2.0 ml of Amberlite XAD 7 was added 2.0 ml of a 0.05 M phosphoric acid buffer (pH 7.0) having dissolved therein 20 mg of lipoprotein lipase, and the system was allowed to stand at room temperature for 18 hours to thereby adsorb the enzyme onto the resin. The resin was filtered. A solution of 250 mg of 3,5-dinitrobenzoyl derivative of ()-3-acetoxymethyl-7,8-difluoro-2,3- dihydro-4H-[1,4]benzoxazine as a substrate in 25 ml of a mixed solvent of benzene and n-hexane (4:1 by volume) was added to the resin, followed byallowing to react at 37°C for 4 hours. It was obtained 117 mg of a 3,5- dinitrobenzoyl derivative of the (-)-3-acetoxymethyl-7,8-difluoro-2,3-dihydro- 4H-[1,4]benzoxazine and 65 mg of a derivative of the (-)-3-acetoxymethyl- 7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine.
    In 135 ml THF was dissolved 3.03 g of a 3,5-dinitrobenzoyl derivative of (-)- 3-acetoxymethyl-7,8-difluoro-2,3-dihydro-4H-[1,4]benzoxazine, and 135 ml of ethanol and 30 ml of 1.0 N potassium hydroxide were added to the solution. After 30 min 3 ml of acetic acid was added thereto for neutralization. The mixture was concentrated. The solid was subjected to column chromatography using 40 g of silica gel and eluted with chloroform/methanol to obtain 1.17 g of (-)-7,8-difluoro-2,3-dihydro-3-hydroxymethyl-4H-[1,4]benzoxazine; [α]D22 = -14.1° (c = 1.80, CHCl3).
    To 1.17 g of (-)-7,8-difluoro-2,3-dihydro-3-hydroxymethyl-4H-[1,4] benzoxazine was added 2.77 g of thionyl chloride in pyridine. The reaction mixture was concentrated and the concentrate was subjected to column chromatography using 40 g of silica gel and eluted with chloroform to obtain 1.18 g of the reaction product as a colorless oily product. This product was dissolved in 30 ml of dimethyl sulfoxide, and 0.41 g of sodium borohydride was added thereto, followed by heating at 80-90°C for 1 hour. The reaction mixture was dissolved in 500 ml of benzene, washed with water to remove the dimethyl sulfoxide, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography using 40 g of silica gel and eluted with benzene to obtain 0.80 g of (-)-7,8-difluoro-2,3-dihydro-3-methyl-4H-[1,4]benzoxazine as a colorless oily product; [α]D25 = -9.6° (c = 2.17, CHCl3). Optical Purity: >99% e.e.
    To 1.13 g of (-)-7,8-difluoro-2,3-dihydro-3-methyl-4H-[1,4]benzoxazine was added 1.58 g of diethyl ethoxymethylenemalonate, and the mixture was stirred at 130-140°C for 70 min. The reaction mixture was subjected to column chromatography using 50 g of silica gel and eluted with chloroform to obtain 2.47 g of diethyl [(-)-7,8-difluoro-3-methyl-2,3-dihydro-4H-[1,4] benzoxazin-4-yl]methylenemalonate. This product was dissolved in 5 ml of acetic anhydride, and 10 ml of a mixture of acetic anhydride and concentrated sulfuric acid (2/1 by volume) with stirring under ice-cooling, followed by stirring at 50-60°C for 40 min. To the reaction mixture were added ice and an aqueous solution of sodium bicarbonate, and the product was extracted three times with 150 ml portions of chloroform. Th
  • Trademarks Iquix (Sanofi Winthrop); Levaquin (Ortho-McNeil); Quixin (Sanofi Winthrop);Cravit.
  • Therapeutic Function Antibacterial
  • Antimicrobial activity Levofloxacin is the active component of ofloxacin; d-ofloxacin is without significant antibacterial activity. It exhibits good activity in vitro against Gram-positive cocci (including Str. pneumoniae), Enterobacteriaceae, some fastidious Gram-negative bacilli and Ps. aeruginosa as well as chlamydiae, Mycoplasma pneumoniae, L. pneumophila and M. tuberculosis. MICs for Acinetobacter spp. and Sten. maltophilia are 0.06–0.25 and 0.5–2.0 mg/L, respectively. Activity against anaerobes is moderate to low.
  • Pharmazeutische Anwendungen For molecular weight and structure, see ofloxacin . Levofloxacin is the l-isomer of ofloxacin.
  • Pharmakokinetik Oral absorption: >95%
    Cmax 500 mg oral: c. 5 mg/L after 1.5–2 h
    750 mg oral: c. 8 mg/L after 1.5–2 h
    500 mg intravenous (90-min infusion): c. 6 mg/L end infusion
    750 mg intravenous (90-min infusion) :c. 12 mg/L end infusion
    Plasma half-life :6–8 h
    Volume of distribution:0.6–0.8 L/kg
    Plasma protein binding: <25%
    Co-administration with antacids, calcium, sucralfate and heavy metals decreases bioavailability and AUC. No interactions with warfarin or theophylline have been observed. Co-administration of a non-steroidal anti-inflammatory drug may increase the risk of convulsions. It undergoes limited metabolism and is primarily eliminated unchanged in urine by both glomerular filtration and tubular secretion. The free AUC:MIC ratio for Str. pneumoniae increases from about 55 to 70 when the daily dosage is raised from 500 mg to 750 mg.
    It is stable in plasma and does not revert to d-ofloxacin. It undergoes limited metabolism and is primarily eliminated unchanged in the urine. Renal clearance in excess of the glomerular filtration rate suggests that tubular secretion also occurs. Concomitant administration of either cimetidine or probenecid reduces renal clearance by approximately onethird. Clearance is reduced and half-life is prolonged in patients with impaired renal function (creatinine clearance <50 mL/min) requiring dosage adjustment in such patients.
  • Clinical Use Acute bacterial sinusitis
    Acute bacterial exacerbations of chronic bronchitis, community-acquired pneumonia
    Uncomplicated and complicated skin and skin structure infections
    Uncomplicated and complicated urinary infections including acute pyelonephritis
    Chronic bacterial prostatitis
  • Nebenwirkungen Side effects have been reported in 6–7% of patients and include fever, rash and other events common to the group. Elderly patients are at increased risk of developing severe tendon disorders including rupture, a risk increased by concomitant corticosteroid therapy.
Levofloxacin hydrochloride Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Levofloxacin hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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100986-85-4, Levofloxacin hydrochloride Verwandte Suche:
  • (s)-ofloxacin
  • 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (S)-
  • Cravit
  • HR 355
  • Levaquin
  • RWJ 25213-097
  • Tavanic
  • (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazin-yl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid
  • Levofloxacin
  • L-Ofloxacin
  • LVFX
  • Ophthalmic
  • RWJ 25213
  • Crarit
  • S-(-)-9-Fluom-2,3-dihydrcr3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid hemihydrate
  • [3S,(-)]-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
  • Levofloxacin (350 mg)
  • Levofloxacin HeMihidrated
  • Levofloxacin(Levaquin)
  • Levofloxacin hemyhydrate
  • Erlotinib-d13 HCl
  • Lelofloxacin
  • Mesylate Levofloxacin
  • LEVOFLOXACIN 99%
  • 7h-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylicacid,2,3-dihydro-9-fluoro-3-m
  • dr3355
  • hemihydrate,(s)-ethyl-10-(4-methyl-1-piperazinyl)-7-oxo
  • LEVOFLOXACIN HCL
  • (3s)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7h-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid monohydrochloride
  • Levofloxacin base
  • (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hemihydrate
  • 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (3S)- (9CI)
  • Levofloxacin heMihydrate API
  • acid Monohydrochloride
  • (S)-9-fluoro-3-Methyl-10-(4-Methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
  • Levofloxacin, HeMihydrate, USP
  • (S)-9, 10-DIFLUORO-3-METHYL-7-OXO-7H-PYRIDO(1,2,3-DE)-1,4-BENZOXAZINE-6-CARBOXYLIC ACID
  • (S)-Ofloxacin,99%e.e.
  • Levofloxacin solution
  • Pharmaceutical Intermediates Levofloxacin base CAS 100986-85-4
  • Levofloxcin
  • Levofloxacin&gt
  • Levofloxacin Levofloxacin
  • Levofloxacin,>98%
  • evofL
  • 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (3S)-
  • RiMantadin
  • levoflaxacin
  • Levofloxacin hydrochloride USP/EP/BP
  • (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-1 0-oxo-4-oxa-1-azatricyclo[7.3.1.0,5,13]trideca-5(13 ),6,8,11-tetraene-11-carboxylic acid
  • 100986-85-4
  • 1381997-71-0
  • 138199-17-0
  • C18H2OFN3O412H2O
  • C18H20FN3O4HCl
  • C18H20FN3O4ClH
  • 2C18H20FN3O4H2O
  • Antibiotics G-M