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Pradofloxacin
[CAS# 195532-12-8]

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Identification
Classification API >> Antibiotics
Name Pradofloxacin
Synonyms 7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
Molecular Structure CAS # 195532-12-8, Pradofloxacin, 7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
Molecular Formula C21H21FN4O3
Molecular Weight 396.41
CAS Registry Number 195532-12-8
EC Number 641-760-9
SMILES C1C[C@H]2CN(C[C@H]2NC1)C3=C(C=C4C(=C3C#N)N(C=C(C4=O)C(=O)O)C5CC5)F
Properties
Density 1.5±0.1 g/cm3 Calc.*
Boiling point 664.5±55.0 ºC 760 mmHg (Calc.)*
Flash point 355.7±31.5 ºC (Calc.)*
Index of refraction 1.691 (Calc.)*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol   GHS07;GHS08 Warning    Details
Hazard Statements H302-H341    Details
Precautionary Statements P203-P264-P270-P280-P301+P317-P318-P330-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Germ cell mutagenicityMuta.2H341
SDS Available
up Discovory and Applicatios
Pradofloxacin is a third-generation veterinary fluoroquinolone antibiotic developed specifically for use in companion animals such as dogs and cats. It belongs to the broader class of fluoroquinolones, which are synthetic chemotherapeutic agents known for their broad-spectrum antibacterial activity. Structurally, pradofloxacin is characterized by a tricyclic core that incorporates a fluoroquinolone scaffold, modified to enhance its potency and reduce the potential for resistance development. It contains a fluorine atom at the C-6 position and a cyano group at the C-8 position of the quinolone ring system, both of which contribute to its enhanced activity profile compared to earlier fluoroquinolones.

The discovery of pradofloxacin was part of a research effort aimed at improving the efficacy of fluoroquinolones against both Gram-positive and Gram-negative pathogens, particularly those causing skin, respiratory, and urinary tract infections in animals. In contrast to many human-use fluoroquinolones, pradofloxacin was tailored to target veterinary pathogens while addressing concerns about antimicrobial resistance. Its development included efforts to minimize off-target effects and limit its ability to select for resistant bacterial strains.

Mechanistically, pradofloxacin acts by inhibiting two essential bacterial enzymes involved in DNA replication and transcription: DNA gyrase (topoisomerase II) and topoisomerase IV. These enzymes play a vital role in supercoiling and segregating bacterial DNA. By simultaneously targeting both enzymes, pradofloxacin displays bactericidal activity and reduces the likelihood of bacteria developing resistance through single-point mutations. This dual targeting is especially important for pathogens such as *Staphylococcus pseudintermedius* and *Escherichia coli*, which are frequently encountered in veterinary infections.

One of the significant advances pradofloxacin offers over earlier fluoroquinolones is its increased activity against anaerobic bacteria and resistant strains of Gram-positive cocci. The presence of the cyano group at C-8 is believed to contribute to this anaerobic activity, a feature not commonly observed in other fluoroquinolones. This makes pradofloxacin particularly useful in treating mixed infections where anaerobes may be involved, such as periodontal diseases and infected wounds.

Pradofloxacin is well absorbed orally in animals, achieving therapeutic concentrations in serum and target tissues. It has favorable pharmacokinetics, with a long half-life that permits once-daily dosing, enhancing compliance in clinical settings. The drug is metabolized primarily in the liver and excreted in the urine and bile, allowing it to reach effective concentrations in both systemic and urinary tract infections.

In clinical veterinary practice, pradofloxacin is approved for the treatment of various bacterial infections, including skin infections (pyoderma), soft tissue infections, and lower urinary tract infections. It has also been used successfully to manage deep-seated infections, such as those involving the respiratory tract, due to its ability to penetrate tissues effectively.

Pradofloxacin's safety profile is generally favorable in dogs and cats when used at recommended dosages. However, like other fluoroquinolones, it may cause adverse effects such as gastrointestinal upset, and its use is contraindicated in growing animals due to the risk of cartilage damage. Care is also advised in animals with central nervous system disorders, as fluoroquinolones can lower the seizure threshold.

Importantly, pradofloxacin is not approved for use in food-producing animals, aligning with global efforts to preserve the efficacy of critical antibiotics by restricting their use in agriculture. This selective application helps mitigate the development of antimicrobial resistance in bacterial populations that may otherwise be transmitted to humans through the food chain.

Through rational design and targeted veterinary application, pradofloxacin represents an example of how fluoroquinolone antibiotics have been adapted for specific uses in animal health, contributing to effective infection control while addressing broader public health concerns surrounding antibiotic stewardship.

References

2007. Pradofloxacin in the treatment of canine deep pyoderma: a multicentred, blinded, randomized parallel trial. Veterinary Dermatology, 18(3).
DOI: 10.1111/j.1365-3164.2007.00584.x

2020. Bacterial Diseases. Feline Dermatology.
DOI: 10.1007/978-3-030-29836-4_11

2023. Polymorphism of Pradofloxacin: Crystal Structure Analysis, Stability Study, and Phase Transformation Behavior. Pharmaceutical Research, 40(4).
DOI: 10.1007/s11095-023-03509-w
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