SKU: L001  / 
    CAS Number: 138199-71-0

    Levofloxacin

    ¥11,827.46 - ¥72,879.70
    Levofloxacin
    • Detailed Description

      CAS Number: 138199-71-0

      Molecular Formula: C18H20FN3O4 • 0.5H2O

      Molecular Weight: 370.38

      Mechanism of Action:

      Fluoroquinolone antibiotics target bacterial DNA gyrase (a type IIA topoisomerase) an enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited.  It has also been shown to inhibit topoisomerase IV, which is another type IIA topoisomerase.  Topoisomerase IV is needed to separate DNA that has been replicated prior to bacterial cell division.  If DNA remains unseparated, the process stops and the bacterial cell division ceases.

      Authors found anti-cancer activity was due to inhibition of mitochondrial electron transport chain complex I and III, leading to mitochondrial respiration inhibition, and reduction of ATP production.  Additionally, it increased levels of reactive oxygen species (ROS), mitochondria superoxide and hydrogen peroxide in vitro.

      Storage Conditions: 2-8°C

      Tariff Code: 2933.59.3600

    • Applications

      Spectrum:

      Levofloxacin is a broad-spectrum antibiotic targeting most aerobic Gram-positive and Gram-negative bacteria.  It is moderately active against anaerobes.  It can also be used against Mycoplasmas.   It is effective against pathogens causing pneumonia such as  Streptococcus pneumoniae, and Haemophilus influenzae.

      Resistance to fluoroquinolones is common in Staphylococcus and Pseudomonas.  Resistance can occur in multiple ways, one of which involves an alteration in topoisomerase IV enzyme.

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

      • Haemophilus influenzae 0.00625 µg/mL – 1 µg/mL
      • Streptococcus pneumoniae 0.05 µg/mL - 4 µg/mL
      • For a representative list of Levofloxacin MIC values, click here.

      Resistance to fluoroquinolones is common in Staphyloccus and Pseudomonas.  Resistance occurs in multiple ways, one way is via alteration in topoisomerase IV enzyme.  

      Cancer Applications:

      Levofloxacin was active against a panel of lung cancer cell lines via inhibition of proliferation and inducing apoptosis, in vitro.  This is novel research to show that it was active against multiple lung cancer cell lines, and attributed to its ability to induce mitochondrial dysfunctions and oxidative stress (Song et al, 2016).

      Levofloxacin was active against breast cancer cell lines in vitro, acting synergistically with 5-Fluorouracil in breast cancer.  It acts via mitochondrial biogenesis inhibition, and authors showed the effects were reversed by acetyl-L-carnitine (ALCAR, a mitochondrial fuel) confirmation that its action is via inhibition of mitochondrial biogenesis.  Breast cancer cells have increased mitocondrial biogenesis compared to normal cells, and thus targeting mitochondrial biogenesis has been a potential anti-cancer strategy.  

    • Specifications

      Form: Powder

      Appearance: Light yellow crystalline powder

      Source: Synthetic

      Assay: Purity: Not less than 98.5%

      Residue On Ignition: Not more than 0.2%

      Heavy Metals: Not more than 20 ppm

      Loss on Drying: Not more than 3.0%

      Melting Point: 218-227 °C

      Optical Rotation: -95° to -103°

      Identification: Positive

    • Technical Data

      Solubility: Chloroform: Soluble
      Glacial acetic acid: Soluble
      Water: Insoluble

      Impurity Profile: Impurity A| (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid; N-Desmethyl Levofloxacin|117707-40-1|C17H18FN3O4|347.34| Impurity B| 8,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid; Levofloxacin Difluoro Carboxylic Acid|100986-89-8|C13H9F2NO4|281.21| Impurity C| Ethyl (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-carboxylate ; Levofloxacin Ethyl Ester|177472-30-9|C20H24FN3O4|389.42| Impurity D||||| Impurity UN1| LEVOFLOXACIN N-OXIDE ; (-)-(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 N-oxide||C18H20FN3O5|377.37| Levofloxacin R-Isomer| (+)-(R)-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; (R)-(+)-Ofloxacin; D-Ofloxacin; D-Levofloxacin|100986-86-5|C18H20FN3O4|361.37| Levofloxacin Desethylene Impurity| N,N＊-Desethylene Levofloxacin Hydrochloride; (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-[(2-methylamino)ethylamino]-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine||C16H19ClFN3O4|371.79| Levofloxacin Descarboxy Impurity| (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine|178964-53-9|C17H20FN3O2|317.36| Levofloxacin Desethylene Diformyl Impurity| Desethylene Diformyl Levofloxacin; N,N＊-Desethylene-N,N＊-diformyl Levofloxacin; (S)-9-Fluoro-10-[formyl[2-(formylmethylamino)ethyl]amino]-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid|151377-74-1|C18H18FN3O6|391.35| Levofloxacin Desfluoro Impurity| (-)-(S)-2,3-Dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid|117620-85-6|C18H21N3O4|343.38|

    • References

      References:

      Bebear CM, Renaudin H, Bryskier A, Bebear C (2000) Comparative activities of telithromycin (HMR 3647), levofloxacin, and other Antimicrobial Agents against human Mycoplasmas . Antimicrob. Agents and Chemother.  44 (7) 1980-1982  PMID  10858366

      Davis R and Bryson HM (1994)  Levofloxacin. A review of its antibacterial activity, pharmacokinetics and therapeutic efficacy. Drugs. 47(4):677-700  PMID 7516863

      Song et al (2016)  Antibiotic drug Levofloxacin inhibits proliferation and induces apoptosis of lung cancer cells through inducing mitochondrial dysfunction and oxidative damager.  Biomed. Pharmacother. 84:1137-1143

      Staff (2009)  New FDA requirements for post-marketing studies and clinical trials: Patent Strategy .  memoANDA.  Fish and Richardson pVIII.  Archived from the original on 27Aug 2025.  US 5053407. 

      Wolfson JS and Hooper DC (1985)  The fluoroquinolones: Structures, mechanisms of action and resistance, and spectra of activity in vitro. Antimicrob. Agents Chemother.  28(4):581-586  PMID  3000292

      Yu M, Li R and Zhang J (2016)  Repositioning of antibiotic Levofloxacin as a mitochondrial biogenesis inhibitor to target breast cancer.  Biochem. Biophys. Res. Comm. 471(4):639-645

    Levofloxacin is a broad-spectrum third-generation fluoroquinolone and one of the isomers of ofloxacin, specifically the optical S-(-) isomer.  It is a DNA gyrase inhibitor shown to inhibit topoisomerase IV.  Levofloxacin was synthesized by scientists at Daiichi Pharmaceutical Co. Ltd (Tokyo, Japan) and is one of the later generation fluoroquinolones referred to as 'respiratory quinolones' to distinguish them from earlier fluoroquinolones which had modest activity towards Streptococcus pneumoniae. It acts as a bactericide.  Levofloxacin is called a chiral switch (a chiral compound that has been approved as a racemate but has been re-developed as a single enantiomer. It can be used ot study antibiotic resistance.

    Levofloxacin is soluble in glacial acetic acid and chloroform.  It is insoluble in water.

    CAS Number: 138199-71-0

    Molecular Formula: C18H20FN3O4 • 0.5H2O

    Molecular Weight: 370.38

    Mechanism of Action:

    Fluoroquinolone antibiotics target bacterial DNA gyrase (a type IIA topoisomerase) an enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited.  It has also been shown to inhibit topoisomerase IV, which is another type IIA topoisomerase.  Topoisomerase IV is needed to separate DNA that has been replicated prior to bacterial cell division.  If DNA remains unseparated, the process stops and the bacterial cell division ceases.

    Authors found anti-cancer activity was due to inhibition of mitochondrial electron transport chain complex I and III, leading to mitochondrial respiration inhibition, and reduction of ATP production.  Additionally, it increased levels of reactive oxygen species (ROS), mitochondria superoxide and hydrogen peroxide in vitro.

    Storage Conditions: 2-8°C

    Tariff Code: 2933.59.3600

    Spectrum:

    Levofloxacin is a broad-spectrum antibiotic targeting most aerobic Gram-positive and Gram-negative bacteria.  It is moderately active against anaerobes.  It can also be used against Mycoplasmas.   It is effective against pathogens causing pneumonia such as  Streptococcus pneumoniae, and Haemophilus influenzae.

    Resistance to fluoroquinolones is common in Staphylococcus and Pseudomonas.  Resistance can occur in multiple ways, one of which involves an alteration in topoisomerase IV enzyme.

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

    • Haemophilus influenzae 0.00625 µg/mL – 1 µg/mL
    • Streptococcus pneumoniae 0.05 µg/mL - 4 µg/mL
    • For a representative list of Levofloxacin MIC values, click here.

    Resistance to fluoroquinolones is common in Staphyloccus and Pseudomonas.  Resistance occurs in multiple ways, one way is via alteration in topoisomerase IV enzyme.  

    Cancer Applications:

    Levofloxacin was active against a panel of lung cancer cell lines via inhibition of proliferation and inducing apoptosis, in vitro.  This is novel research to show that it was active against multiple lung cancer cell lines, and attributed to its ability to induce mitochondrial dysfunctions and oxidative stress (Song et al, 2016).

    Levofloxacin was active against breast cancer cell lines in vitro, acting synergistically with 5-Fluorouracil in breast cancer.  It acts via mitochondrial biogenesis inhibition, and authors showed the effects were reversed by acetyl-L-carnitine (ALCAR, a mitochondrial fuel) confirmation that its action is via inhibition of mitochondrial biogenesis.  Breast cancer cells have increased mitocondrial biogenesis compared to normal cells, and thus targeting mitochondrial biogenesis has been a potential anti-cancer strategy.  

    Form: Powder

    Appearance: Light yellow crystalline powder

    Source: Synthetic

    Assay: Purity: Not less than 98.5%

    Residue On Ignition: Not more than 0.2%

    Heavy Metals: Not more than 20 ppm

    Loss on Drying: Not more than 3.0%

    Melting Point: 218-227 °C

    Optical Rotation: -95° to -103°

    Identification: Positive

    Solubility: Chloroform: Soluble
    Glacial acetic acid: Soluble
    Water: Insoluble

    Impurity Profile: Impurity A| (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid; N-Desmethyl Levofloxacin|117707-40-1|C17H18FN3O4|347.34| Impurity B| 8,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid; Levofloxacin Difluoro Carboxylic Acid|100986-89-8|C13H9F2NO4|281.21| Impurity C| Ethyl (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-carboxylate ; Levofloxacin Ethyl Ester|177472-30-9|C20H24FN3O4|389.42| Impurity D||||| Impurity UN1| LEVOFLOXACIN N-OXIDE ; (-)-(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 N-oxide||C18H20FN3O5|377.37| Levofloxacin R-Isomer| (+)-(R)-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; (R)-(+)-Ofloxacin; D-Ofloxacin; D-Levofloxacin|100986-86-5|C18H20FN3O4|361.37| Levofloxacin Desethylene Impurity| N,N＊-Desethylene Levofloxacin Hydrochloride; (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-[(2-methylamino)ethylamino]-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine||C16H19ClFN3O4|371.79| Levofloxacin Descarboxy Impurity| (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine|178964-53-9|C17H20FN3O2|317.36| Levofloxacin Desethylene Diformyl Impurity| Desethylene Diformyl Levofloxacin; N,N＊-Desethylene-N,N＊-diformyl Levofloxacin; (S)-9-Fluoro-10-[formyl[2-(formylmethylamino)ethyl]amino]-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid|151377-74-1|C18H18FN3O6|391.35| Levofloxacin Desfluoro Impurity| (-)-(S)-2,3-Dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid|117620-85-6|C18H21N3O4|343.38|

    References:

    Bebear CM, Renaudin H, Bryskier A, Bebear C (2000) Comparative activities of telithromycin (HMR 3647), levofloxacin, and other Antimicrobial Agents against human Mycoplasmas . Antimicrob. Agents and Chemother.  44 (7) 1980-1982  PMID  10858366

    Davis R and Bryson HM (1994)  Levofloxacin. A review of its antibacterial activity, pharmacokinetics and therapeutic efficacy. Drugs. 47(4):677-700  PMID 7516863

    Song et al (2016)  Antibiotic drug Levofloxacin inhibits proliferation and induces apoptosis of lung cancer cells through inducing mitochondrial dysfunction and oxidative damager.  Biomed. Pharmacother. 84:1137-1143

    Staff (2009)  New FDA requirements for post-marketing studies and clinical trials: Patent Strategy .  memoANDA.  Fish and Richardson pVIII.  Archived from the original on 27Aug 2025.  US 5053407. 

    Wolfson JS and Hooper DC (1985)  The fluoroquinolones: Structures, mechanisms of action and resistance, and spectra of activity in vitro. Antimicrob. Agents Chemother.  28(4):581-586  PMID  3000292

    Yu M, Li R and Zhang J (2016)  Repositioning of antibiotic Levofloxacin as a mitochondrial biogenesis inhibitor to target breast cancer.  Biochem. Biophys. Res. Comm. 471(4):639-645