Moxifloxacin Basic information

Description Quinolones Mechanism of action Preparation Adverse effects References

Product Name: Moxifloxacin

Synonyms: MOXIFLOXACIN;(1'S,6'S)-1-Cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;MAXIOFFOXACIN;(4αS-cis)-1-Cydopropyl-6-fluoro-1，4-dihydro-8-methoxy-7-(octahydro-6H-pyrrolo[3，4-b]pyridin-6-y1)-4-oxo-3-quinolinecarboxylic acid;Avdox;186826-86-8 (Hydrochloride);192927-63-2 (Hydrochloride hydrate);Actira (*hydrochloride*)

CAS: 151096-09-2

MF: C21H24FN3O4

MW: 401.43

EINECS:

Product Categories: API

Mol File: 151096-09-2.mol

Moxifloxacin Structure

Moxifloxacin Chemical Properties

Melting point 203-208 C

alpha 23D -193°

CAS DataBase Reference 151096-09-2(CAS DataBase Reference)

EPA Substance Registry System 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4- dihydro-8-methoxy-7-[(4aS, 7aS)-octahydro-6H-pyrrolo[ 3,4-b]pyridin-6-yl]-4-oxo-(151096-09-2)

Safety Information

Hazard Codes Xn

Risk Statements 22-40

Safety Statements 36/37

MSDS Information

Moxifloxacin Usage And Synthesis

Description Moxifloxacin is a fourth-generation synthetic fluoroquinolone antibacterial agent developed by Bayer AG (initially called BAY 12-8039), used to treat a number of infections, including: respiratory tract infections, cellulitis, anthrax, intraabdominal infections, endocarditis, meningitis, and tuberculosis. It is marketed worldwide (as the hydrochloride) under the brand names Avelox, Avalox, and Avelon for oral treatment. In most countries, the drug is also available in parenteral form for intravenous infusion.

In the United States, moxifloxacin is licensed for the treatment of acute bacterial sinusitis, acute bacterial exacerbation of chronic bronchitis, community acquired pneumonia, complicated and uncomplicated skin and skin structure infections, and complicated intra-abdominal infections.[5] In the European Union, it is licensed for acute bacterial exacerbations of chronic bronchitis, non-severe community-acquired pneumonia, and acute bacterial sinusitis.

Quinolones Moxifloxacin and levofloxacin, gatifloxacin, gemifloxacin are quinolone antibacterial drugs newly developed in recent years. The position of C-7 ring structure of the nitrogen enhances antibacterial effect of gram positive bacteria, and methoxy strengthens the role of anaerobic bacteria. Such new varieties significantly increased excellent antibacterial activity against Streptococcus pneumoniae and other respiratory tract infections common pathogens antibacterial activity. Penicillin-resistant Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhal and Mycoplasma pneumoniae, Chlamydia pneumoniae Atypical pathogens, also known as "quinolones breathing". Moxifloxacin has bactericidal effect by interfering Ⅱ, Ⅳ topoisomerase. It also has strong antibacterial effect on gram-positive bacteria, Gram-negative bacteria, anaerobic bacteria, Mycoplasma pneumoniae, Chlamydia pneumoniae and Legionella bacteria. It has no cross-resistance situation between penicillins, cephalosporins, glycopeptides, macrolides, tetracyclines and other antibiotics. Bactericidal activity of moxifloxacin is similar with isoniazid, and is better than levofloxacin to rapid growth of Mycobacterium tuberculosis, as well as it is slightly lower than levofloxacin to quiescent Mycobacterium tuberculosis. It is for the treatment of acute bronchitis, chronic obstructive pulmonary disease exacerbations, community acquired pneumonia and bronchiectasis. General oral 400mg/times, 1 times/d; the course is 5 to 7 days. Adverse reactions are nausea, upset stomach and abdominal pain. The quinolones allergies, pregnant women, breastfeeding women and children should not use it.

Mechanism of action Moxifloxacin mechanism is mainly inhibition of bacterial DNA synthesis, since rapid bactericidal effect, which can act on bacterial DNA gyrase and topoisomerase Ⅳ, resulting in breakage enzyme-DNA complex. DNA gyrase, also known as topoisomerase Ⅱ, composed of the gyrA, gyrB subunit. DNA gyrase and topoisomerase Ⅰ common regulate DNA replication. Throughout the replication process, DNA gyrase mainly have the effect of the maintenance of DNA coiled modest role. Topoisomerase Ⅳ is composed of the parC and parE subunits. Its structure and DNA gyrase have similarities, which parC and gyrA, parE and gyrB have some homology. Topoisomerase Ⅳ can copy the complete distribution of progeny DNA to progeny cells, together with DNA gyrase to complete bacterial DNA replication. Moxifloxacin enzyme-DNA complexes can be stable in the DNA chain cut off state, terminating the DNA replication, resulting in a cytotoxic effect. Moxifloxacin on site is the main function of most gram-negative bacteria DNA gyrase, and effect on gram-positive bacteria loci with topoisomerase Ⅳ primarily.

Preparation 1-cyclopropyl-6, 7-difluoro-1, 4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid was dissolved in acetonitrile and dimethylformamide, and then added 1,4-diazabicyclo [2.2.2] octane and the (+)-[S, S]-2,8-diazabicyclo [4.3.0] nonane, refluxed for 1h. Cooling, precipitate was obtained by filtering, and washed with water. Stirring together with water for a moment, filtered and dried. The residue was purified by silica gel chromatography, dichloromethane/methanol/17% aqueous ammonia = 30: 8: 1 start, and moxifloxacin was obtained, melting point 203~208 ℃.

Adverse effects

Moxifloxacin is associated with an increased risk of tendon problems. These include pain, swelling, inflammation, and possible breakage of tendons. Moxifloxacin may worsen muscle weakness and breathing problems in patients with myasthenia gravis. Do not use moxifloxacin if you have a history of myasthenia gravis.

Rare but serious adverse effects that may occur as a result of moxifloxacin therapy include irreversible peripheral neuropathy, spontaneous tendon rupture and tendonitis, hepatitis, psychiatric effects (hallucinations, depression), torsades de pointes, Stevens-Johnson syndrome and Clostridium difficile-associated disease, and photosensitivity/phototoxicity reactions.

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Definition ChEBI: A quinolone that consits of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b /ital>]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.

Moxifloxacin Preparation Products And Raw materials

Raw materials N-OCTANE-->QUINOLINE-3-CARBOXYLIC ACID