 Chemical Structure.png)
Moxifloxacin HCl (formerly BAY12-8039; BAY12-8039; BAY 12-8039; Avelox, Avalox, Avelon, Vigamox, Moxeza),the hydrochloride salt of moxifloxacin, is an orally bioactive, broad spectrum and 4th generation antibacterial drug of the fluoroquinolone class with high activity against both Gram positive and Gram negative bacteria. It functions as a topoisomerase II and IV DNA inhibitor.
Physicochemical Properties
| Molecular Formula | C21H24FN3O4.HCL | |
| Molecular Weight | 437.89 | |
| Exact Mass | 437.151 | |
| Elemental Analysis | C, 57.60; H, 5.75; Cl, 8.10; F, 4.34; N, 9.60; O, 14.61 | |
| CAS # | 186826-86-8 | |
| Related CAS # | 151096-09-2; 192927-63-2; Moxifloxacin Hydrochloride;186826-86-8;(Rac)-Moxifloxacin;354812-41-2;Moxifloxacin-d4;2596386-23-9;Moxifloxacin-d3 hydrochloride;2734919-98-1;Moxifloxacin-d3-1 hydrochloride;1246816-75-0;Moxifloxacin-13C,d3 hydrochloride;rac cis-Moxifloxacin-d4 hydrochloride;1217802-65-7 | |
| PubChem CID | 101526 | |
| Appearance | Light yellow to green yellow solid powder | |
| Boiling Point | 636.4ºC at 760 mmHg | |
| Flash Point | 338.7ºC | |
| Vapour Pressure | 4.56E-17mmHg at 25°C | |
| LogP | 3.566 | |
| 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 | Cl[H].FC1C([H])=C2C(C(C(=O)O[H])=C([H])N(C2=C(C=1N1C([H])([H])[C@]2([H])[C@@]([H])(C([H])([H])C([H])([H])C([H])([H])N2[H])C1([H])[H])OC([H])([H])[H])C1([H])C([H])([H])C1([H])[H])=O |
|
| 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 |
|
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
|
| 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 II; Topoisomerase IV | |
| ln Vitro |
|
|
| ln Vivo |
|
|
| Cell Assay | The antibiotic agent doxifloxacin (hydrochloride) is a synthetic fluoroquinolone. When compared to earlier fluoroquinolone agents, antibacterial doxifloxacin, an extended-spectrum fluoroquinolone, exhibits better coverage against gram-positive cocci and atypical pathogens while maintaining good activity against gram-negative bacteria. All common upper and lower respiratory tract pathogens are included in moxifloxacin's antibacterial spectrum, making it one of the most effective fluoroquinolones against pneumococci, including strains resistant to macrolides and penicillin. Moxifloxacin's potential for phototoxicity is limited. Moxifloxacin demonstrated bacteriologic eradication rates of 90–97% and clinical success rates of 88–97% in clinical trials. Moxifloxacin is an antimicrobial agent that is both safe and effective in treating community-acquired pneumonia, acute bacterial exacerbations of chronic bronchitis, and acute sinusitis. As shown by the production of MDA and the prolongation of survival, movifloxacin may promote lipid peroxidation and improve phagocytosis without being toxic, as shown by the white blood cell count. Clinical recommendations: Acute sinusitis, bacterial infection, acute bronchitis, and abdominal abscess toxicity CNS and gastrointestinal side effects, such as reduced activity, sleepiness, trembling, convulsions, vomiting, and diarrhea, are signs of an overdose. In rats and mice, a minimal lethal intravenous dose is 100 mg/kg. | |
| Animal Protocol |
144 white male Wistar rats (18-22 weeks; 300-400 g) infected Stenotrophomonas maltophilia 12 mg/kg Intravenous injection; once per day, twice per day, three times per day; for 7 days 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 saline-treated 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.[2] |
|
| 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]. Tuberculosis (Edinb). 2008 Mar;88(2):127-31. [2]. 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) |
|
|||
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: 30% PEG400+0.5% Tween80+5% Propylene glycol : 30mg/mL Solubility in Formulation 4: 4 mg/mL (9.13 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2837 mL | 11.4184 mL | 22.8368 mL | |
| 5 mM | 0.4567 mL | 2.2837 mL | 4.5674 mL | |
| 10 mM | 0.2284 mL | 1.1418 mL | 2.2837 mL |