(3S )-8-amino-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H -Pyrido[1,2,3-de ]-1,4-benzoxazine-6-carboxylic acid
[CAS# 135325-15-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: (3S )-8-amino-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H -Pyrido[1,2,3-de ]-1,4-benzoxazine-6-carboxylic acid
• Synonyms: (2S)-8-amino-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Molecular Formula: C₁₃H₁₀F₂N₂O₄
• Molecular Weight: 296.23
• CAS Registry Number: 135325-15-4
• SMILES: C[C@H]1COC2=C3N1C=C(C(=O)C3=C(C(=C2F)F)N)C(=O)O

Properties

• Solubility: Insoluble (4.0E^-3 g/L) (25 ºC), Calc.^*
• Density: 1.67±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 536.2±50.0 ºC (760 Torr), Calc.^*
• Flash point: 278.1±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2021 ACD/Labs)

Discovory and Applicatios

(3S)-8-Amino-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid is a quinolone derivative that emerged from the quest to develop new broad-spectrum antibacterial agents. The compound was identified through structure-activity relationship (SAR) studies aimed at enhancing the efficacy and spectrum of fluoroquinolones. Its discovery involved modifying the core structure of existing quinolones by introducing fluorine atoms and specific functional groups to increase antibacterial potency and overcome resistance mechanisms. The stereochemical configuration (3S) was found to be critical for optimal interaction with bacterial targets. This compound represents a significant advancement in the development of antibiotics, particularly for treating resistant bacterial infections.

The compound serves as a broad-spectrum antibiotic effective against a wide range of Gram-positive and Gram-negative bacteria. Its mode of action typically involves inhibiting bacterial DNA gyrase and topoisomerase IV, enzymes crucial for DNA replication and cell division, leading to bacterial cell death. Due to its fluorinated structure and unique functional groups, it is particularly effective against bacterial strains that have developed resistance to other antibiotics, including multidrug-resistant (MDR) and extensively drug-resistant (XDR) strains. This makes it a valuable tool in combating infections where conventional antibiotics fail. The compound is often used in the treatment of respiratory tract infections, including pneumonia and bronchitis, as well as urinary tract infections (UTIs). Its efficacy in these conditions stems from its ability to achieve high concentrations in tissues and fluids where infections commonly occur.

The compound is a key active ingredient in the formulation of new antibacterial drugs. Its properties allow for the development of oral and intravenous formulations, providing flexibility in treatment options based on the severity of infections and patient needs. It can be used in combination with other antibiotics or adjuvants to enhance antibacterial efficacy and prevent the development of resistance. Combination therapy can broaden the spectrum of activity and reduce the likelihood of bacterial survival through different mechanisms of action.

Ongoing clinical trials evaluate the safety and efficacy of this compound in various infections, including skin infections, intra-abdominal infections, and complicated UTIs. These trials aim to establish optimal dosing regimens, identify potential side effects, and expand its therapeutic indications. Research focuses on understanding how this compound interacts with bacterial targets and mechanisms of resistance. This knowledge aids in the design of next-generation antibiotics and strategies to overcome emerging resistance.

The compound plays a significant role in treating both hospital-acquired infections (HAIs) and community-acquired infections (CAIs). Its broad-spectrum activity and effectiveness against resistant strains make it a critical option in managing severe infections in clinical settings. In certain high-risk patients or surgical procedures, the compound may be used prophylactically to prevent bacterial infections. Its ability to cover a broad range of pathogens makes it suitable for such preventative applications.

Similar to its use in humans, the compound is employed in veterinary medicine to treat bacterial infections in animals. Its broad-spectrum antibacterial properties make it effective against common veterinary pathogens, ensuring the health and productivity of livestock and companion animals.