Moxifloxacin Hydrochloride is a broad-spectrum fourth-generation fluoroquinolone antibiotic that can be used against the bacteria causing respiratory infections. It also has anti-cancer activity. Moxifloxacin Hydrochloride is sparingly soluble in aqueous solution.
| Mechanism of Action |
Fluoroquinolone antibiotics target bacterial DNA gyrase, an enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited. The anticancer properties is lined to anti-human Topoisomerase II activity. Many studies suggest that various different cancer tissues have own unique microbiota and that bacteria associated with theise tumors could in fact contribute to DNA damage and the progression of hte umors including angiogeneiss. Some Moxifloxacin drivatives have activity agaisnt various cancer cells in vitro. An example is some Moxifloxacin-isatin hybrids which showed anticancer activity agaisnt liver cancer cells HepG2, breast cancer cells MCF-7, MCF-7/DOX, prostate cancer cells DU-145 and MDR DU-145. All 7, novel moxifloxacin-fatty acid amides tested showed cytostatic (or cytotoxic) activity agasint colorectal and prostate cancer cell lines but were not toxic agaisnt normal keratinocytes. (Chrzanowska et al, 2023). |
| Spectrum | Moxifloxacin is a broad-spectrum antibiotic commonly used Gram-positive and Gram-negative bacteria. It is effective against bacteria that case respiratory infections including S. pneumonia. It is also effective for obligate anaerobes including Bacteriodes, Fusobacterium, Bilophila, and Clostridium. |
| Impurity Profile | Impurity A| 1-Cyclopropyl-6,8-difluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Moxifloxacin Difluoro Analog|151213-15-9|C20H21F2N3O3|389.40| Impurity B| 1-Cyclopropyl-6,8-dimethoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Moxifloxacin Dimethoxy Analog||C22H27N3O5|413.47| Impurity C| 1-Cyclopropyl-8-ethoxy-6-fluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo [3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Moxifloxacin Ethyl Analog||C22H26FN3O4|415.46| Impurity D| 1-Cyclopropyl-8-fluoro-6-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo [3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Moxifloxacin Isomer|1029364-77-9|C21H24FN3O4|401.43| Impurity E| 1-Cyclopropyl-6-fluoro-8-hydroxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo [3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; Moxifloxacin Desmethyl Analog||C20H22FN3O4|387.4| Moxifloxacin Decarboxy Analog| Decarboxy Moxifloxacin;1-Cyclopropyl-6-fluoro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline||C20H24FN3O2|357.42| Moxifloxacin Difluoro Hydroxy Impurity| 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinoline carboxylic acid|154093-72-8|C13H9F2NO4|281.21| Moxifloxacin Difluoro Methoxy Impurity| 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid|112811-72-0|C14H11F2NO4|295.24| Moxifloxacin N-Methyl Analog| 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-1-methyl-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid hydrochloride||C22H27ClFN3O4|451.92| Moxifloxacin Trifluoro Ethyl Ester| 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid ethyl ester|94242-51-0|C15H12F3NO3|311.26| Moxifloxacin Trifluoro Impurity| 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid|94695-52-0|C13H8F3NO3|283.20| Moxifloxacin Methyl Ester| 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid methyl ester|721970-35-0|C22H26FN3O4|415.46| Moxifloxacin Hydrochloride| 1-Cyclopropyl-6-fluoro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride|186826-86-8|C21H25ClFN3O4|437.89| |
| Microbiology Applications | Moxifloxacin Hydrochloride is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
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| Eukaryotic Cell Culture Applications | A cell culture model to investigate the safety of Moxifloxacin for intracameral application was investigated in cultured human corneas to review endothelial toxicity. Moxifloxacin at 10-750 µg/ml was evaluated in endothelial cells, primary human trabecular meshwork cells (TMC), and primary human retinal pigment epithelial (RPE) cells. Concentrations up to 150 µg/ml had no influence on endothelial cells, TMC, or RPE when exposed for up to 24 hours (MIC90 is 0.25-2.5 µg/ml)(Kernt et al, 2009). |
| Cancer Applications |
The trend in cancer treatment is the search for antineoplastic potential of existing compounds. A good candidate is Moxifloxacin, and researchers reviewed novel Moxifloxacin conjugates with fatty acids and verified the metabolic profile in SW480, SW620 and PC3 cell lines. The cytotoxic potential of these conjugates can be beneficial in oncological studies. Moxifloxacin displayed anti-tumor activity against many cancer cell lines (Barot et al, 2012). |
| Molecular Formula | C21H24FN3O4 · HCl |
| References |
Ackermann G et al (2000) comparative activity of Moxifloxacin in vitro against obligately anaerobic bacteria. Eur. J. Clin. Microbiol. Infect. Dis. 19(3):228-232 Araujo FG, Slifer TL and Remington JS (2002) Effect of Moxifloxacin on secretion of cytokines by human monocytes stimulated with lipopolysaccharide. Clin. Microbiol. Infect. 8(1):26-30 Chrzanowska A et al (2023) Anticancer activity and metabolic alteration in colon and prostate cancer cells by novel Moxifloxacin conjugates with fatty acids. Eur. J. Pharmacol. 940:175481 Dalhoff A (2001) Comparative in vitro and in vivo activity of the C-8 methoxy quinolone moxifloxacin and the C-8 chlorine quinolone BAY y 3118. Clin Infect Dis 32 Suppl 1:S16-22 PMID 11249824 Dalhoff A, Krasemann C, Wegener S, Tillotson G (2001) Penicillin-resistant Streptococcus pneumoniae: Review of Moxifloxacin activity. Clin Infect Dis. 32 Suppl 1:S22-9 PMID 11249825 Kernt M et al (2009) Intracameral Moxifloxacin: In vitro safety on human ocular cells. Cornia 28(5):553-561 Wolfson JS and Hooper DC (1985) The Fluoroquinolones: Structures, mechanisms of action and resistance, and spectra of activity in vitro. 28:581-86 |
| MIC | Bacillus cereus| 0.078|| Bacteroides caccae| 0.25 － 64|| Bacteroides distasonis| ≤0.06 － 32|| Bacteroides eggerthii| 1 － 64|| Bacteroides fragilis| ≤0.06 － 128|| Bacteroides merdae| 0.064 － 32|| Bacteroides ovatus| 0.064 － 64|| Bacteroides stercoris| 1 － 64|| Bacteroides thetaiotaomicron| 0.06 － 64|| Bacteroides uniformis| ≤0.06 － 128|| Bacteroides vulgatus| 0.06 － 128|| Bifidobacterium adolescentis| 0.064 － 4|| Bifidobacterium sp.| 0.064 － 4|| Brucella melitensis| ≥1|| Burkholderia cepacia| 0.12 － >16|| Campylobacter coli| 0.0125 － 128|| Campylobacter jejuni| 0.0125 － 128|| Capnocytophaga spp.| 0.016 － 0.5|| Chlamydia pneumonia| 0.125 － 1|| Chlamydia trachomatis| 0.031 － 1|| Chlamydophila pneumonia| 0.06 － 0.125|| Citrobacter freundii| 0.03 － 32|| Citrobacter koseri| 0.015 － >8|| Citrobacter spp.| 0.015 － 32|| Clostridium baratii| 0.25 － 2|| Clostridium bifermentans| 0.25 － 2|| Clostridium butyricum| 0.12 － 2|| Clostridium cadaveris| 0.25 － 2|| Clostridium clostridioforme| 0.12 － 2|| Clostridium difficile| ≤0.06 － 128|| Clostridium hastiforme| 0.25 － 2|| Clostridium histolyticum | 0.25 － 2|| Clostridium innocuum| 0.25 － 2|| Clostridium paraputrificum| 0.25 － 2|| Clostridium perfringens| 0.12 － 2|| Clostridium ramosum| 0.12 － 2|| Clostridium sordellii| 0.25 － 2|| Clostridium sporogenes| 0.12 － 2|| Clostridium spp.| 0.12 － 2|| Clostridium tertium| 0.25 － 2|| Enterobacter aerogenes| 0.03 － 64|| Enterobacter cloacae| ≤0.015 － >64|| Enterobacter spp.| 0.015 － 32|| Enterobacteriaceae (fluoroquinolone-resistant)| 4 － >64|| Enterococcus faecalis| 0.016 － >32|| Enterococcus faecium| 0.06 － 64|| Escherichia coli| 0.002 － 128|| Eubacterium lentum| ≥0.5|| Eubacterium spp.| 0.25 － 2|| Finegoldia magna| 0.047 － 64|| Fusobacteria| 0.03 － >8|| Fusobacterium mortiferum| 0.06 － 4|| Fusobacterium necrophorum| 0.03 － 4|| Fusobacterium nucleatum| 0.06 － 4|| Fusobacterium spp.| 0.06 － >16|| Fusobacterium varium| 0.06 － >16|| Gemella morbillorum| 0.016 － 0.5|| Haemophilus influenzae| ≤0.015 － 0.5|| Haemophilus parainfluenzae| 0.016 － 0.5|| Haemophilus spp.| 0.19 - 4|| Helicobacter pylori| 0.008 － >32|| Hemolytic streptococci| 0.032 － 0.5|| Klebsiella oxytoca| 0.03 － 8|| Klebsiella pneumonia| 0.008 － >64|| |
