103995-33-1

Basic information

• Product Name: Levofloxacin Tetrafluoro Impurity 2
• Synonyms: Levofloxacin Tetrafluoro Impurity 2;ethyl (Z)-3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylate;Levofloxacin Impurity 15
• CAS NO: 103995-33-1
• Molecular Formula: C₁₄H₁₂F₄O₄
• Molecular Weight: 320.24
• Mol File: 103995-33-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 400.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.333±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Levofloxacin Tetrafluoro Impurity 2(CAS DataBase Reference)
• NIST Chemistry Reference: Levofloxacin Tetrafluoro Impurity 2(103995-33-1)
• EPA Substance Registry System: Levofloxacin Tetrafluoro Impurity 2(103995-33-1)

Safety Data

• Hazardous Substances Data: 103995-33-1(Hazardous Substances Data)

Usage

General Description

Levofloxacin Tetrafluoro Impurity 2 is a chemical impurity that may be present in levofloxacin, a broad-spectrum antibiotic used to treat a variety of bacterial infections. This impurity is a derivative of levofloxacin that contains four fluorine atoms, making it fluorinated. While the specific effects of this impurity are not well-documented, it is important to monitor and control its presence in the final product to ensure the safety and effectiveness of levofloxacin for patient use. Close attention to the level of impurities, including Levofloxacin Tetrafluoro Impurity 2, is essential in the pharmaceutical industry to maintain product quality and regulatory compliance.

Upstream product

• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 109-94-4 formic acid ethyl ester 
• 1020966-22-6 ethyl 2,3,4,5-tetrafluorobenzoyl acetate 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 448210-36-4 3-[N'-(pyridine-4-carbonyl)-hydrazino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester 
• 476005-99-9 6,7,8-trifluoro-1-[(4-methoxy-benzimidoyl)-amino]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 371249-10-4 7-tetrafluorophenyl-6-ethoxycarbonyl-1,2,4-triazolo[1,5-a]pyrimidine 
• 371249-03-5 7-tetrafluorophenyl-6-ethoxycarbonylpyrazolo[1,5-a]pyrimidine 
• 1041438-68-9 ethyl 1-(4-cyano-2,3,5,6-tetrafluorophenyl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 103994-84-9 ethyl 6,7,8-trifluoro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 79660-46-1 ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 100986-86-5 (R)-ofloxacin 
• 110548-03-3 (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate 
• 110548-06-6 (+)-ethyl 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate 
• 100986-89-8 levofloxacin Q-acid 
• 110548-07-7 (+)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid 

Relevant articles and documents

Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation

Thirty novel 9-fluoro-2,3-dihydro-8,10-(mono/di-sub)-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acids were synthesized from 2,3,4,5-tetrafluoro benzoic acid and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from mycobacteria. Among the synthesized compounds, 10-[2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active compound in vitro with MIC99 of 0.19 μM and 0.09 μM against MTB and MTR-TB, respectively. In the in vivo animal model also the same compound decreased the bacterial load in lung and spleen tissues with 1.91 and 2.91 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 10-[(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active in the inhibition of the supercoiling activity of DNA gyrase with an IC50 of 10.0 μg/mL. The results demonstrate the potential and importance of developing new oxazino quinolone derivatives against mycobacterial infections.

AN IMPROVED PROCESS FOR THE PREPARATION OF LEVOFLOXACIN HEMIHYDRATE

The present invention relates to an improved process for preparation of Levofloxacin hemihydrate having single individual impurity not more than 0.1% and free from particulate matter and from the other enantiomer (R-form) which comprises dissolving levofloxacin technical grade in aqueous alkaline solution, treating the resulting solution with activated carbon at room temperature, removing the undissolved particulate matter filtration, bringing the pH of the aqueous alkaline levofloxacin solution to neutral using dilute mineral acid, removing the precipitated particulate matter by filtration, acidifying the resulting solution, treating the acidified solution with activated carbon at room temperature, filtering the undissolved particulate matter by filtration, neutralizing the acidic solution, filtering again to remove any particulate matter present and, extracting the resulting product with chlorinated solvent and concentrating under vacuum using aqueous tetrahydrofuran or in admixture with other organic solvents to get highly pure levofloxacin hemihydrate having single individual impurity is less than 0.1% and fee from particulate matter and from the other enantiomer (R-form).

Antibacterial 1,7-diamino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

Antibacterially effective 1,7-diamino-1,4-dihydro-4-oxo-3-(aza)quinolinecarboxylic acids of the formula STR1 in which A is nitrogen or C--R1, R1 is nitro or halogen, R2 and R3 each independently is C1