Difluoxacin hydrochloride
[CAS# 91296-86-5]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Quinolone
• Name: Difluoxacin hydrochloride
• Synonyms: 6-Fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid hydrochloride
• Molecular Formula: C₂₁H₁₉F₂N₃O₃^.HCl
• Molecular Weight: 435.85
• CAS Registry Number: 91296-86-5
• EC Number: 688-928-8
• SMILES: CN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Difloxacin hydrochloride is a synthetic antibiotic that belongs to the fluoroquinolone class of drugs. It was developed to address the need for effective broad-spectrum antibiotics capable of treating a wide variety of bacterial infections in both humans and animals. Difloxacin hydrochloride stands out for its enhanced activity against certain bacterial strains that are resistant to other antibiotics, making it a valuable tool in the treatment of infections where other treatments have failed.

Difloxacin was first synthesized in the late 1980s as part of ongoing research to expand the fluoroquinolone family of antibiotics, which began in the 1960s with the discovery of nalidixic acid. The addition of a difluoro-substituted phenyl group to the quinolone structure resulted in difloxacin, which demonstrated improved antibacterial activity and a broader spectrum of effectiveness. Shortly after its development, difloxacin hydrochloride was introduced to the market for veterinary use, particularly for the treatment of infections in companion animals such as dogs.

The mechanism of action of difloxacin hydrochloride is similar to that of other fluoroquinolones. It targets bacterial DNA gyrase and topoisomerase IV, enzymes that are crucial for bacterial DNA replication, transcription, and repair. By inhibiting these enzymes, difloxacin disrupts the DNA processes necessary for bacterial growth and reproduction, leading to the death of the bacterial cells. This makes difloxacin hydrochloride effective against a wide range of Gram-negative and Gram-positive bacteria.

One of the primary applications of difloxacin hydrochloride is in veterinary medicine, where it is used to treat bacterial infections in dogs and other animals. It is particularly effective in treating skin and soft tissue infections, respiratory tract infections, and urinary tract infections caused by susceptible bacteria. The drug’s broad-spectrum activity also makes it a useful option for managing mixed bacterial infections, where more than one bacterial species is involved.

Difloxacin hydrochloride is usually administered orally in the form of tablets, making it convenient for use in a veterinary setting. The drug is well-absorbed from the gastrointestinal tract, ensuring effective levels in the bloodstream to combat infections. In some cases, difloxacin hydrochloride may also be used in combination with other antibiotics to enhance its effectiveness or to target a broader range of pathogens.

While difloxacin hydrochloride is generally well-tolerated, its use, like that of other fluoroquinolones, must be carefully managed to avoid the development of antibiotic resistance. Over time, bacteria can develop resistance to fluoroquinolones through mutations in the genes encoding their target enzymes or by increasing the activity of efflux pumps that remove the drug from bacterial cells. This has led to a growing awareness of the need for judicious use of difloxacin hydrochloride to preserve its effectiveness for future use.

In terms of side effects, difloxacin hydrochloride is associated with similar risks as other fluoroquinolones. In animals, potential side effects include gastrointestinal disturbances such as vomiting and diarrhea, as well as effects on the musculoskeletal system, including the risk of tendonitis and tendon rupture. These risks underscore the importance of using difloxacin hydrochloride under the guidance of a veterinarian, with careful attention to dosing and duration of treatment.

Although difloxacin hydrochloride is not as widely used as some other fluoroquinolones, its role in veterinary medicine remains significant, particularly in treating infections where other antibiotics may be less effective. Ongoing research and monitoring are essential to ensure that difloxacin hydrochloride continues to be a viable option for managing bacterial infections in animals, while also minimizing the risk of resistance development.

References

1986. In vitro evaluation of A-56619 (difloxacin) and A-56620: new aryl-fluoroquinolones. Antimicrobial Agents and Chemotherapy, 29(2).
DOI: 10.1128/aac.29.2.193

2020. Antibacterial Activity of Honey/Chitosan Nanofibers Loaded with Capsaicin and Gold Nanoparticles for Wound Dressing. Molecules (Basel, Switzerland), 25(20).
DOI: 10.3390/molecules25204770

2023. Pompon-like Bi2WO6 hierarchical nanostructures: preparation and their application in photodegradation of norfloxacin and difloxacin hydrochloride. Journal of Materials Science: Materials in Electronics, 34(7).
DOI: 10.1007/s10854-023-10144-z