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Tosufloxacin tosylate, formerly known as T-3262 and A-61827, is a potent fluoroquinolone antibiotic used to treat susceptible infections. It has a controversial safety profile in relation to other fluoroquinolones. It is associated with severe thrombocytopenia and nephritis, and hepatotoxicity. It is sold in Japan under the brand name Ozex.
Physicochemical Properties
| Molecular Formula | C26H23F3N4O6S |
| Molecular Weight | 576.54422 |
| Exact Mass | 576.129 |
| Elemental Analysis | C, 54.16; H, 4.02; F, 9.89; N, 9.72; O, 16.65; S, 5.56 |
| CAS # | 115964-29-9 |
| Related CAS # | Tosufloxacin tosylate hydrate;1400591-39-0;Tosufloxacin;100490-36-6 |
| PubChem CID | 93858 |
| Appearance | Solid powder |
| Density | 1.558g/cm3 |
| Boiling Point | 614.4ºC at 760mmHg |
| Melting Point | 251-252ºC |
| LogP | 5.126 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 40 |
| Complexity | 915 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C1=CN(C2=CC=C(F)C=C2F)C3=C(C=C(F)C(N4CC(N)CC4)=N3)C1=O)O.O=S(C5=CC=C(C)C=C5)(O)=O |
| InChi Key | CSSQVOKOWWIUCX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C19H15F3N4O3.C7H8O3S/c20-9-1-2-15(13(21)5-9)26-8-12(19(28)29)16(27)11-6-14(22)18(24-17(11)26)25-4-3-10(23)7-251-6-2-4-7(5-3-6)11(8,9)10/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29)2-5H,1H3,(H,8,9,10) |
| Chemical Name | 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid tosylate |
| Synonyms | T-3262 T3262 T 3262 Tosufloxacin tosylate |
| 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
| ln Vitro | Tosifloxacin tosylate hydrate (T-3262) (0.05-3.13 μg/mL; 18 h) possesses antibacterial action that is effective against Streptococcus, Enterococcus, Bacteroides fragilis, Clostridium difficile, and Clostridium perfringens [2]. |
| ln Vivo | Sufloxacin tosylate hydrate (T-3262) treatment (oral gavage; 0.16–13.39 mg/kg; once) showed antibacterial efficacy against Pseudomonas aeruginosa, Escherichia coli, and Staphylococcus aureus in vivo [2]. |
| Cell Assay |
Cell Viability Assay[2] Cell Types: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus, Enterococcus, Bacteroides fragilis, Clostridium difficile and Clostridium perfringens Tested Concentrations: 0.05-3.13 μg/mL Incubation Duration: 18 Hourly Experimental Results: Displays MIC90s (MIC 90) for Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus, and Enterococcus, ranging from 0.05 to 1.56 μg/mL. MIC90 values for Bacteroides fragilis, Clostridium difficile, and Clostridium perfringens were 1.56, 3.13 and 0.20 μg/mL respectively. |
| Animal Protocol |
Animal/Disease Models: Male Slc:ICR mice infected with Staphylococcus aureus [2] Doses: 1.27-2.15 mg/kg Route of Administration: po (oral gavage); 1.27-2.15 mg/kg; primary Experimental Results:7 days after infection demonstrated 50 The % effective dose (ED50) is 1.62 mg/kg (body weight). The displayed MIC value is 0.0125 μg/mL. Animal/Disease Models: Male Slc:ICR mice infected with E. coli [2] Doses: 0.16-0.30 mg/kg Route of Administration: po (oral gavage); 0.16-0.30 mg/kg; Primary Experimental Results:50% effective 7 days after infection The dose (ED50) is 0.22 mg/kg (body weight). The displayed MIC value is 0.0125 μg/mL. Animal/Disease Models: Male Slc:ICR mice infected with Pseudomonas aeruginosa [2] Doses: 7.66-13.39 mg/kg Route of Administration: po (oral gavage); 7.66-13.39 mg/kg; Primary Experimental Results:Displayed 7 days after infection The 50% effective dose (ED50) is 10.13 mg/kg (body weight). The displayed MIC value is 0.78 μg/mL. |
| References |
[1]. Synthesis and biological properties of A-71497: a prodrug of tosufloxacin. Drugs Exp Clin Res. 1990;16(9):435-43. [2]. In vitro and in vivo antibacterial activities of T-3262, a new fluoroquinolone. Antimicrob Agents Chemother. 1988 Jun;32(6):827-33. |
| Additional Infomation | Tosufloxacin tosylate is a racemate comprising equimolar amounts of (R)- and (S)-tosufloxacin tosylate. It has a role as an antimicrobial agent, an antiinfective agent, a DNA synthesis inhibitor, a hepatotoxic agent and a topoisomerase IV inhibitor. It contains a tosufloxacin(1+), a (S)-tosufloxacin tosylate and a (R)-tosufloxacin tosylate. |
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 | 1.7345 mL | 8.6724 mL | 17.3449 mL | |
| 5 mM | 0.3469 mL | 1.7345 mL | 3.4690 mL | |
| 10 mM | 0.1734 mL | 0.8672 mL | 1.7345 mL |