• Pefloxacin mesylate dihydrate packaged and labeled.

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SKU: P004

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Description

Pefloxacin Mesylate Dihydrate is a broad-spectrum, synthetic, third-generation fluoroquinolone antibiotic.  Perfloxacin, an analog of Norfloxacin, was discovered in 1979.  Pefloxacin, like other fluoroquinolones, inhibit bacterial DNA gyrase and Topoisomerase IV, which disrupts bacterial cell division.  Novel derivatives of Pefloxacin were found to have anti-cancer properties.  Pefloxacin mesylate dihydrate is freely soluble in aqueous solution.

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    CAS Number

    149676-40-4

    Molecular Formula

    C17H20FN3O3 · CH4O3S •2H2O

    Molecular Weight

    465.49

    Mechanism of Action

    Fluoroquinolone antibiotics like Pefloxacin target bacterial DNA gyrase, a type II topoisomerase enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited.  This enzyme is the primary target for Gram-negative bacteria.

    Pefloxacin inhibits topoisomerase IV, the primary target for Gram-positive bacteria.  Since this enzyme is required to separate replicated DNA, the inhibition results in strand breakage of the bacterial chromosome, which ultimately inhibits DNA replication and transcription.

    Storage Conditions

    2-8°C

    Tariff Code

    2933.59.3600

    Spectrum

    Pefloxacin is a broad spectrum antibiotic which targets a wide range of Gram-positive and Gram-negative organisms including a few Mycoplasma species such as M. bovis, M. tuberculosis, and M. africanum.

Applications

    Application

    Quinolone-topoisomerase biology is a useful model to understand host-parasite interactions and investigate manipulation of the bacterial chromosome by topoisomerases.

    Cancer Applications

    The in vitro effect of Pefloxacin on growth of normal hematopoietic progenitor stem cells and on leukemic cell lines was investigated.  It was found to have a dose-dependent inhibition of colony formation both from normal bone marrow cells and from the leukemic line K-562 cells and HL-60 cells when used at ≥ 25 µg/ml (Somekh et al, 1989).

     An evaluation of Pefloxacin derivatives and their biological activity was screened against human Pc-3 cancer cell lines and the compounds demonstrated anti-cancer properties (Allaka et al, 2016).

    Eukaryotic Cell Culture Applications

    Pefloxacin cytotoxicity in primary cultures of rat hepatocytes was evaluated and found to be hepatoxic at 400 mg/L (Nordmann et al, 1989).

    An investigation of Pefloxacin on human myelopoiesis in vitro was evaluated on cell cultures of mononuclear cells derived from human bone marrow samples and found it has no influence on the proliferation of human myeloid precursors at 0.5-50 ug/ml (Pallavicini et al, 1989).

    Microbiology Applications

    Pefloxacin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram- positive, Gram-negative, and Mycoplasma microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:

    • Helicobacter pylori 1 µg/mL - 8 µg/mL
    • Mycoplasma bovis 8 µg/mL
    • For a representative list of Pefloxacin MIC values, click here.

Specifications

    Form

    Powder

    Appearance

    Cream colored powder

    Source

    Synthetic

    Impurity Profile

    Impurity A| 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid (demethylated pefloxacin or norfloxacin)|70458-96-7|C16H18FN3O3|319.331| Impurity B| 6-chloro-1-ethyl-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (chlorinated homologue of pefloxacin)||C17H20ClN3O3|349.81| Impurity E| 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)quinoline-4(1H)-one (decarboxylated pefloxacin)||C16H20FN3O|389.35| Impurity D| 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-methylpiperazine 1-oxide (N-oxide of pefloxacin)|85145-21-7|C17H20FN3O4|349.36| Impurity C| 1-ethyl-6-fluoro-5-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (isopefloxacin)|70458-92-3|C17H20FN3O3|333.36| Impurity F| 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (N-ethyl acid) (norfloxacin impurity A)||C12H9ClFNO3|269.66| Impurity G| ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (N-ethyl ester)|||| Impurity H| 5-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (iso-N-ethyl acid)|

    pH

    3.5-4.5

    Melting Point

    271°C

    Assay

    ≥99.0%

    Loss on Drying

    ≤8.5%

References

    References

    Allaka T et al (2016)  Design, synthesis and biological activity evaluation of novel Pefloxacin derivatives as potential antibacterial agents. Med. Chem. Res. 25(5):977-993  PMID 3000292

    Drlica K and Zhao X (1997)  DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol. Molec. Biol. Rev. MMBR 6(3):377-392

    Nordmann P, Pechinot A and Kazmierczak A (1989)  Cytotoxicity and uptake of pefloxacin, ciprofloxacin, and ofloxacin in primary cultures of rat hepatocytes. J. Antimicrob. Chemother. 24(3):355-363  PMID 2808191

     Pallavicini F, ANtinori A, Federico G, Fantoni M and Nervo P (1989)  Influence of two quinolones, ofloxacin and pefloxacin, on human myelopoiesis in vitro. Antimicrob. Agents. Chemother. 33(1):122-123 PMID 2712545

    Somekh E, Shaked N and Rubinstein E (1989)  In vitro effects of Ciprofloxacin and Pefloxacin on growth of normal human hematopoietic progenitor cells and on leukemic cell lines. J. Pharmacol. and Exp. Ther. 248(1):415-418  PMID 2913285

    Wolfson, JS and David C. Hooper DC (1985)  The fluoroquinolones: Structures, mechanisms of action and resistance, and spectra of activity in vitro.  Antimicrob. Agents Chemother. 28(4):581-586

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