Moxifloxacin
Catalog Number: BT-253447
CAS Number: 151096-09-2
Molecular Formula: C21H24FN3O4
Molecular Weight: 401.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Moxifloxacin is a fluoroquinolone antibiotic that is used to treat a wide range of bacterial infections. It was first approved by the FDA in 1999 and has since become a popular choice for treating respiratory, skin, and urinary tract infections. Moxifloxacin is known for its broad-spectrum activity against both gram-positive and gram-negative bacteria, making it a versatile drug in the fight against bacterial infections.
Properties
CAS Number
151096-09-2
Product Name
Moxifloxacin
IUPAC Name
7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
Molecular Formula
C21H24FN3O4
Molecular Weight
401.4 g/mol
InChI
InChI=1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
InChI Key
FABPRXSRWADJSP-MEDUHNTESA-N
SMILES
COC1=C2C(=CC(=C1N3CC4CCCNC4C3)F)C(=O)C(=CN2C5CC5)C(=O)O
Solubility
In water, 1146 mg/L at 25 °C (est)
1.68e-01 g/L
1.68e-01 g/L
Synonyms
1-cyclopropyl--7-(2,8-diazabicyclo(4.3.0)non-8-yl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Actira
Avalox
Avelox
BAY 12 8039
BAY 12-8039
BAY 128039
BAY-12-8039
BAY-128039
BAY128039
Izilox
moxifloxacin
moxifloxacin hydrochloride
Octegra
Proflox
Actira
Avalox
Avelox
BAY 12 8039
BAY 12-8039
BAY 128039
BAY-12-8039
BAY-128039
BAY128039
Izilox
moxifloxacin
moxifloxacin hydrochloride
Octegra
Proflox
Canonical SMILES
COC1=C2C(=CC(=C1N3CC4CCCNC4C3)F)C(=O)C(=CN2C5CC5)C(=O)O
Isomeric SMILES
COC1=C2C(=CC(=C1N3C[C@@H]4CCCN[C@@H]4C3)F)C(=O)C(=CN2C5CC5)C(=O)O
Method of Synthesis or Extraction
Moxifloxacin is synthesized through a multi-step process that involves the reaction of various chemical compounds. The most commonly used method of synthesis involves the reaction of 7-amino-8-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid with ethyl cyanoacetate in the presence of a base. This reaction produces the intermediate compound, which is then further reacted with various reagents to produce the final product.
The efficiency and yield of the synthesis process depend on several factors, including the purity of the starting materials, the reaction conditions, and the skill of the chemist. The yield of the synthesis process is typically around 50%, which is considered to be moderate. Environmental and safety considerations are also important factors to consider when synthesizing moxifloxacin. The process involves the use of several hazardous chemicals, including chloroform and acetic anhydride, which can be harmful to both humans and the environment.
The efficiency and yield of the synthesis process depend on several factors, including the purity of the starting materials, the reaction conditions, and the skill of the chemist. The yield of the synthesis process is typically around 50%, which is considered to be moderate. Environmental and safety considerations are also important factors to consider when synthesizing moxifloxacin. The process involves the use of several hazardous chemicals, including chloroform and acetic anhydride, which can be harmful to both humans and the environment.
Chemical Structure and Biological Activity
Moxifloxacin has a unique chemical structure that is characterized by a fluoroquinolone core with a cyclopropyl group and a carboxylic acid moiety. The drug works by inhibiting the activity of bacterial DNA gyrase and topoisomerase IV, which are essential enzymes for bacterial DNA replication and transcription. This mechanism of action results in the inhibition of bacterial growth and the eventual death of the bacteria.
Moxifloxacin has a broad spectrum of activity against both gram-positive and gram-negative bacteria, including Streptococcus pneumoniae, Haemophilus influenzae, and Escherichia coli. The drug is also effective against atypical bacteria, such as Mycoplasma pneumoniae and Chlamydia pneumoniae. Moxifloxacin has a high bioactivity and potency, with a minimum inhibitory concentration (MIC) of less than 1 μg/mL against most bacterial strains.
Moxifloxacin has a broad spectrum of activity against both gram-positive and gram-negative bacteria, including Streptococcus pneumoniae, Haemophilus influenzae, and Escherichia coli. The drug is also effective against atypical bacteria, such as Mycoplasma pneumoniae and Chlamydia pneumoniae. Moxifloxacin has a high bioactivity and potency, with a minimum inhibitory concentration (MIC) of less than 1 μg/mL against most bacterial strains.
Biological Effects
Moxifloxacin has several biological effects on cell function and signal transduction. The drug can disrupt the normal functioning of bacterial DNA gyrase and topoisomerase IV, leading to the inhibition of bacterial DNA replication and transcription. This disruption can also lead to the formation of DNA breaks and the activation of bacterial stress responses.
Moxifloxacin has both potential therapeutic and toxic effects. The drug is effective in treating bacterial infections, but it can also cause adverse effects, such as gastrointestinal disturbances, skin reactions, and central nervous system effects. Moxifloxacin has also been associated with the development of tendonitis and tendon rupture, particularly in elderly patients and those taking corticosteroids.
Moxifloxacin has both potential therapeutic and toxic effects. The drug is effective in treating bacterial infections, but it can also cause adverse effects, such as gastrointestinal disturbances, skin reactions, and central nervous system effects. Moxifloxacin has also been associated with the development of tendonitis and tendon rupture, particularly in elderly patients and those taking corticosteroids.
Applications
Moxifloxacin has several applications in medical, environmental, and industrial research. In medical research, the drug has been used in drug development and clinical trials. Moxifloxacin has been shown to be effective in treating respiratory, skin, and urinary tract infections, and has been used in clinical trials for the treatment of tuberculosis and other bacterial infections.
In environmental research, moxifloxacin has been studied for its effects on ecosystems and its role in pollution management. The drug has been found to have a low environmental impact, with a low potential for bioaccumulation and toxicity to aquatic organisms. Moxifloxacin has also been used in wastewater treatment to remove bacterial contaminants.
In industrial research, moxifloxacin has been used in manufacturing processes to improve product quality and efficiency. The drug has been used in the production of pharmaceuticals, agrochemicals, and other chemical products. Health and safety considerations are important when using moxifloxacin in industrial settings, as the drug can be harmful to humans and the environment.
In environmental research, moxifloxacin has been studied for its effects on ecosystems and its role in pollution management. The drug has been found to have a low environmental impact, with a low potential for bioaccumulation and toxicity to aquatic organisms. Moxifloxacin has also been used in wastewater treatment to remove bacterial contaminants.
In industrial research, moxifloxacin has been used in manufacturing processes to improve product quality and efficiency. The drug has been used in the production of pharmaceuticals, agrochemicals, and other chemical products. Health and safety considerations are important when using moxifloxacin in industrial settings, as the drug can be harmful to humans and the environment.
Future Perspectives and Challenges
Despite its effectiveness in treating bacterial infections, moxifloxacin has several limitations in its use and study. The drug can cause adverse effects, and its use has been associated with the development of antibiotic resistance. There is also a need for further research to understand the long-term effects of moxifloxacin on human health and the environment.
Possible solutions and improvements include the development of new antibiotics with different mechanisms of action, the use of combination therapies to reduce the risk of antibiotic resistance, and the implementation of sustainable practices in the production and use of antibiotics. Future trends and prospects in the application of moxifloxacin in scientific research include the development of new formulations and delivery methods, the use of moxifloxacin in combination with other drugs, and the exploration of its potential in the treatment of viral infections.
Conclusion:
Moxifloxacin is a versatile antibiotic that has several applications in medical, environmental, and industrial research. The drug has a unique chemical structure and mechanism of action that make it effective against a wide range of bacterial infections. However, its use is associated with several adverse effects, and there is a need for further research to understand its long-term effects on human health and the environment. The development of new antibiotics and sustainable practices in the production and use of antibiotics are important steps in the fight against bacterial infections.
Possible solutions and improvements include the development of new antibiotics with different mechanisms of action, the use of combination therapies to reduce the risk of antibiotic resistance, and the implementation of sustainable practices in the production and use of antibiotics. Future trends and prospects in the application of moxifloxacin in scientific research include the development of new formulations and delivery methods, the use of moxifloxacin in combination with other drugs, and the exploration of its potential in the treatment of viral infections.
Conclusion:
Moxifloxacin is a versatile antibiotic that has several applications in medical, environmental, and industrial research. The drug has a unique chemical structure and mechanism of action that make it effective against a wide range of bacterial infections. However, its use is associated with several adverse effects, and there is a need for further research to understand its long-term effects on human health and the environment. The development of new antibiotics and sustainable practices in the production and use of antibiotics are important steps in the fight against bacterial infections.
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