High Purity Gatifloxacin Powder CAS 112811-59-3 Effective Against Gram-Positive and Gram-Negative Bacterial Infections

Gatifloxacin More Info

Gatifloxacin , identified by the Chemical Abstracts Service Registry Number 112811-59-3, is a synthetic broad-spectrum antibiotic belonging to the fourth-generation fluoroquinolone family. This class of antimicrobials is characterized by a fluorinated quinolone ring structure that is essential for their potent antibacterial activity. The molecular formula of gatifloxacin is C₁₉H₂₂FN₃O₄, and it possesses a molecular weight of approximately 375.39 grams per mole. Its formal IUPAC name is 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, a designation that precisely describes the arrangement of functional groups responsible for its pharmacological properties. In pharmaceutical development, it has also been referred to by the research codes AM-1155 and PD135432. As a substance, it appears as a microcrystalline to crystalline powder and exhibits a defined melting point between one hundred eighty-two and one hundred eighty-five degrees Celsius.

The mechanism by which gatifloxacin exerts its antibacterial effects involves the inhibition of two critical bacterial enzymes: DNA gyrase and topoisomerase IV. These enzymes are essential for the processes of bacterial DNA replication, transcription, and repair, and their disruption leads to the death of the bacterial cell. This dual-targeting mechanism is a hallmark of advanced fluoroquinolones and contributes to their potency and ability to reduce the likelihood of resistance development. The structural features of gatifloxacin, particularly the methoxy group at the C-8 position and the 3-methylpiperazinyl moiety at the C-7 position, enhance its activity against a broad spectrum of pathogens. This includes important gram-positive organisms such as Staphylococcus aureus and Streptococcus pneumoniae, gram-negative bacteria including Haemophilus influenzae, Escherichia coli, and Klebsiella pneumoniae, as well as atypical pathogens like Chlamydia pneumoniae and Mycoplasma pneumoniae.

The regulatory history of gatifloxacin presents a notable dichotomy based on its route of administration. Initially developed by Bristol-Myers Squibb and approved in 1999 under the brand name Tequin, the oral and intravenous formulations were widely used for the treatment of community-acquired pneumonia, bronchitis, and sinusitis. However, post-marketing surveillance and subsequent clinical studies revealed a significant safety concern linked to systemic use: dysglycemia. Patients receiving oral or injectable gatifloxacin exhibited an elevated risk of both hypoglycemia and hyperglycemia, sometimes severe enough to require hospitalization. This distinct toxicity profile, which was more pronounced than with other fluoroquinolones, ultimately led to the withdrawal of these systemic formulations from the market in the United States and many other countries around 2006.

Despite the withdrawal of its systemic forms, the ophthalmic formulation of gatifloxacin was deemed safe and remains an important therapeutic option. When administered as eye drops, under brand names such as Zymar and Zymaxid, the systemic absorption of the drug is negligible, thereby circumventing the risk of blood glucose disturbances that plagued the oral and intravenous versions. In this topical application, gatifloxacin is indicated for the treatment of bacterial conjunctivitis caused by susceptible strains of bacteria. The typical dosing regimen involves frequent instillation in the affected eye during the first day of treatment, followed by a reduced frequency for approximately one week. This localized therapy allows for high concentrations of the antibiotic at the site of infection while maintaining a favorable systemic safety profile.

The adverse effect profile of ophthalmic gatifloxacin is generally mild and confined to the ocular region. Patients may experience temporary eye irritation, burning, stinging, blurred vision, or a transient alteration in taste following administration. As with all antibiotic preparations, there is a potential risk of hypersensitivity reactions in sensitive individuals, and prolonged use may occasionally lead to an overgrowth of non-susceptible organisms, including fungi. The compound's physical and chemical properties, including its stability and solubility, have been thoroughly characterized to ensure the efficacy and safety of the final pharmaceutical product. In the broader context of antimicrobial therapy, the case of gatifloxacin serves as an instructive example of how a single drug can have divergent fates depending on its formulation, with its utility successfully preserved in a localized application while its systemic use was curtailed due to an unacceptable risk of metabolic toxicity.

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