-Moxifloxacin ((Rac)-BAY 12-8039 free base) Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C21H24FN3O4 |
| Molecular Weight | 401.43 |
| Exact Mass | 401.175 |
| Elemental Analysis | C, 62.83; H, 6.03; F, 4.73; N, 10.47; O, 15.94 C, 62.83; H, 6.03; F, 4.73; N, 10.47; O, 15.94 |
| CAS # | 354812-41-2 |
| Related CAS # | Moxifloxacin Hydrochloride;186826-86-8;Moxifloxacin;151096-09-2;Moxifloxacin-d4;2596386-23-9;Moxifloxacin-d3 hydrochloride;2734919-98-1;Moxifloxacin-d3-1 hydrochloride;1246816-75-0;Moxifloxacin-13C,d3 hydrochloride |
| PubChem CID | 101526 |
| Appearance | Typically exists as Off-white to yellow solid at room temperatureOff-white to yellow |
| Density | 1.409 g/cm3 |
| Boiling Point | 636.382ºC at 760 mmHg |
| Flash Point | 338.672ºC |
| LogP | 2.764 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 30 |
| Complexity | 727 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C1(N2C3C(=CC(F)=C(N4CC5C(NCCC5)C4)C=3OC)C(=O)C(C(O)=O)=C2)CC1 |
| InChi Key | IDIIJJHBXUESQI-DFIJPDEKSA-N |
| InChi Code | InChI=1S/C21H24FN3O4.ClH/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);1H/t11-,16+;/m0./s1 |
| Chemical 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;hydrochloride |
| Synonyms | 354812-41-2; (Rac)-Moxifloxacin; CID 4259; 1-cyclopropyl-6-fluoro-8-methoxy-7-(octahydro-6h-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-(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; 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-8-methoxy-4 -oxo-quinoline-3-carboxylic acid; 158060-78-7; 1-CYCLOPROPYL-7-(2,8-DIAZABICYCLO[4.3.0]NON-8-YL)-6-FLUORO-8-METHOXY-4-OXOQUINOLINE-3-CARBOXYLIC ACID; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Topoisomerase |
| ln Vitro | Using a bone marrow-derived mouse macrophage model infected with Listeria, time-kill curve and intracellular growth inhibition tests were used to compare the in vitro actions of moxifloxacin hydrochloride (BAY 12-8039) and amoxicillin. EGDe mononucleosis. Moxifloxacin works more quickly; it begins to work during the first three hours of incubation and completely sterilizes the broth in about twenty-four hours. Numerous cells continue to exist during a 24-hour incubation period, suggesting that doxifloxacin may have a protective effect against macrophage lysis [3]. |
| ln Vivo | Treatment every 8 hours with doxifloxacin (BAY 12-8039; 12 mg/kg; intravenously administered; once to three times daily; 7 days; white male Wistar rats) increased survival. Thirty hours after the bacterial challenge, tissue culture revealed no toxicity and much reduced bacterial overgrowth in the lungs and spleen of moxifloxacin-treated animals than saline-treated animals [4]. |
| Cell Assay |
Bacterial strains.[2] Antimicrobial susceptibility to moxifloxacin was determined for a representative selection of the collection strains from the French National Reference Centre for Listeria. The strains studied included Listeria type strains and L. monocytogenes serovar reference strains (n = 16) (see Table S1 in the supplemental material), L. monocytogenes strains isolated from humans in 2005 (n = 205), a set of randomly selected L. monocytogenes strains isolated from food and the environment in 2005 (n = 183), and L. monocytogenes strains resistant to ciprofloxacin isolated from humans since 2000 (n = 8). Susceptibility testing.[2] The MICs of moxifloxacin and ciprofloxacin were determined by the Etest procedure (AB Biodisk, Solna, Sweden), according to the guidelines of the Antibiogram Committee of the French Society for Microbiology. To the best of our knowledge, there are no interpretative criteria for moxifloxacin and L. monocytogenes from any breakpoint committee (CA-SFM, EUCAST, and CLSI). The isolates were categorized as susceptible, intermediate, or resistant according to the following breakpoints: 1 μg/ml ≤ MIC > 2 μg/ml. Time-kill curves.[2] The in vitro bactericidal activities of moxifloxacin and moxifloxacin were determined against a virulent strain of L. monocytogenes (strain EGDe) (11). Five milliliters of Mueller-Hinton (MH) broth was inoculated with 5 × 108 bacteria, and the mixture was incubated at 37°C. Moxifloxacin and amoxicillin were added to the MH broth suspension at various concentrations: 1× MIC, 4× MIC, 8× MIC, or 400× MIC. The last two concentrations correspond to the maximum serum concentration (Cmax) after the administration of clinically relevant doses of moxifloxacin and amoxicillin to humans, respectively (31). Bacterial counts were determined in triplicate at the indicated times of incubation with antibiotics by subculturing 10 μl of serial 10-fold dilutions of the MH broth suspension on brain heart infusion agar plates and on BHI agar supplemented with 2 μg/ml of moxifloxacin and incubation for 48 h. The results were expressed as the number of CFU per milliliter and corresponded to the means ± standard errors from three experiments. Bactericidal activity was defined as the killing of more than 99.9% of the initial inoculum after 24 h of incubation (i.e., a ≥3-log10 CFU/ml decrease in viable counts). The killing rate was defined as the decrease in the initial inoculum within the first 3 h. |
| Animal Protocol | In order to investigate the effect of moxifloxacin on survival, lipid peroxidation and inflammation in immunosuppressed rats with soft tissue infection caused by Stenotrophomonas maltophilia, 144 white male Wistar rats were randomized into six groups: Groups A and B received saline or moxifloxacin once per day, respectively; Groups C and D received saline or moxifloxacin twice per day, respectively, and Groups E and F received saline or moxifloxacin three times per day, respectively. Blood samples were taken at 6 and 30 hr after administration of S. maltophilia. Malonodialdehyde (MDA), WBC counts, bacterial tissue overgrowth, serum concentrations of moxifloxacin and survival were assessed. Survival analysis proved that treatment with moxifloxacin every 8 hr was accompanied by longer survival than occurred in any other group. Tissue cultures 30 hr after bacterial challenge showed considerably less bacterial overgrowth in the spleens and lungs of moxifloxacin-treated than in salinetreated animals, but not in their livers. At 6 hr there were no statistically significant differences between groups. However, at 30 hr, MDA concentrations were significantly greater (P = 0.044) and WBC counts significantly lower (P = 0.026) in group D than in group C. No statistically significant variations were observed between the other groups. Moxifloxacin possibly stimulates lipid peroxidation and enhances phagocytosis, as indicated by MDA production and survival prolongation, without being toxic, as indicated by WBC count. Therefore, under the appropriate conditions, moxifloxacin has a place in treatment of infections in immunosuppressed patients and of infections caused by S. maltophilia.[4] |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No information is available on the use of moxifloxacin during breastfeeding. Fluoroquinolones have traditionally not been used in infants because of concern about adverse effects on the infants' developing joints. However, recent studies indicate little risk. The calcium in milk might prevent absorption of the small amounts of fluoroquinolones in milk, but insufficient data exist to prove or disprove this assertion. Use of moxifloxacin is acceptable in nursing mothers with monitoring of the infant for possible effects on the gastrointestinal flora, such as diarrhea or candidiasis (thrush, diaper rash). However, it is preferable to use an alternate drug for which safety information is available. Maternal use of an eye drop that contains moxifloxacin presents negligible risk for the nursing infant. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. Culley CM, et al. Moxifloxacin: clinical efficacy and safety. Am J Health Syst Pharm. 2001 Mar 1;58(5):379-88. [2]. Balfour JA, et al. Moxifloxacin: a review of its clinical potential in the management of community-acquired respiratory tract infections. Drugs. 2000 Jan;59(1):115-39. [3]. Grayo S, et al. Comparison of the in vitro efficacies of moxifloxacin and amoxicillin against Listeria monocytogenes. Antimicrob Agents Chemother. 2008 May;52(5):1697-702. [4]. Ioannidis O, et al. Effect of moxifloxacin on survival, lipid peroxidation and inflammation in immunosuppressed rats with soft tissue infection caused by Stenotrophomonas maltophilia. Microbiol Immunol. 2014 Feb;58(2):96-102. |
| Additional Infomation |
Moxifloxacin hydrochloride is a hydrochloride comprising equimolar amounts of moxifloxacin and hydrogen chloride. It has a role as an antibacterial drug. It contains a moxifloxacinium(1+). Moxifloxacin hydrochloride is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as community-acquired pneumonia, acute worsening of chronic bronchitis, acute sinus infections, plague, and skin and abdominal infections. Community-acquired pneumonia, a bacterial respiratory infection, can be an opportunistic infection (OI) of HIV. Moxifloxacin Hydrochloride is the hydrochloride salt of a fluoroquinolone antibacterial antibiotic. Moxifloxacin binds to and inhibits the bacterial enzymes DNA gyrase (topoisomerase II) and topoisomerase IV, resulting in inhibition of DNA replication and repair and cell death in sensitive bacterial species. A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent. See also: Moxifloxacin (has active moiety). Drug Indication Acute Exacerbation of Chronic Bronchitis, Community Acquired Pneumonia, Complicated Intra-Abdominal Infection, Complicated Skin and Skin Structure Infections, Pelvic Inflammatory Disease, Treatment of acute bacterial sinusitis Acute Exacerbation of Chronic Bronchitis, Community Acquired Pneumonia, Complicated Intra-Abdominal Infection, Complicated Skin and Skin Structure Infections, Pelvic Inflammatory Disease, Treatment of acute bacterial sinusitis Acute Exacerbation of Chronic Bronchitis, Community Acquired Pneumonia, Complicated Intra-Abdominal Infection, Complicated Skin and Skin Structure Infections, Pelvic Inflammatory Disease, Treatment of acute bacterial sinusitis Acute Exacerbation of Chronic Bronchitis, Community Acquired Pneumonia, Complicated Intra-Abdominal Infection, Complicated Skin and Skin Structure Infections, Pelvic Inflammatory Disease, Treatment of acute bacterial sinusitis |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4911 mL | 12.4555 mL | 24.9109 mL | |
| 5 mM | 0.4982 mL | 2.4911 mL | 4.9822 mL | |
| 10 mM | 0.2491 mL | 1.2455 mL | 2.4911 mL |