Gemifloxacin mesylate (LB-20304; SB-265805;LB20304; SB265805;Factive), the mesylate salt ofGemifloxacin, is athird generation, orally bioavailable, broad-spectrum quinolone antibacterial agent, used in the treatment of acute bacterial exacerbation of chronic bronchitis, and mild-to-moderate pneumonia. Gemifloxacin has been shown to be active against most strains of the aerobic gram-positive microorganisms- Streptococcus pneumoniae- including multi-drug resistant Streptococcus pneumoniae.
Physicochemical Properties
| Molecular Formula | C19H24FN5O7S |
| Molecular Weight | 485.4866 |
| Exact Mass | 485.138 |
| Elemental Analysis | C, 47.01; H, 4.98; F, 3.91; N, 14.43; O, 23.07; S, 6.60 |
| CAS # | 210353-53-0 |
| Related CAS # | Gemifloxacin;175463-14-6 |
| PubChem CID | 9588170 |
| Appearance | White to off-white solid powder |
| Boiling Point | 638.9ºC at 760mmHg |
| Melting Point | 235-237ºC |
| Flash Point | 340.2ºC |
| LogP | 2.316 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 33 |
| Complexity | 817 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | S(C([H])([H])[H])(=O)(=O)O[H].FC1C([H])=C2C(C(C(=O)O[H])=C([H])N(C2=NC=1N1C([H])([H])/C(/C([H])(C([H])([H])N([H])[H])C1([H])[H])=N\OC([H])([H])[H])C1([H])C([H])([H])C1([H])[H])=O |
| InChi Key | JIYMVSQRGZEYAX-CWUUNJJBSA-N |
| InChi Code | InChI=1S/C18H20FN5O4.CH4O3S/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17;1-5(2,3)4/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27);1H3,(H,2,3,4)/b22-14+; |
| Chemical Name | 7-[(4Z)-3-(aminomethyl)-4-methoxyiminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;methanesulfonic acid |
| Synonyms | CHEBI:53749; LB-20304a; SB-265805-S; gemifloxacin mesylate; LB 20304; SB-265805S; LB-20304a; LB-20304; LB20304; SB 265805; SB-265805; SB 265805S; LB 20304a; SB-265805-S; LB-20304-a |
| 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 | Quinolone |
| ln Vitro |
With a MIC90 of 0.06 μg/mL, gemifloxacin exhibits greater antibacterial activity against Streptococcus pneumoniae than doxifloxacin (HY-66011A)[2]. With a MIC90 of 0.03 μg/mL, gemifloxacin exhibits extremely strong antibacterial activity against S. pneumoniae strains that are resistant to penicillin[2]. |
| ln Vivo | Gemifloxacin has favorable pharmacokinetic profile in animals after oral administration[1]. |
| References |
[1]. Hong CY. Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. Farmaco. 2001 Jan-Feb;56(1-2):41-4. [2]. Multiple-dose pharmacokinetics and tolerability of gemifloxacin administered orally to healthy volunteers. Antimicrob Agents Chemother. 2001 Feb;45(2):540-5. [3]. Ingestion of the anti-bacterial agent, gemifloxacin mesylate, leads to increased gst activity and peroxidation products in hemolymph of Galleria mellonella l. (lepidoptera: pyralidae). Arch Insect Biochem Physiol. 2016 Dec;93(4):202-209. |
| Additional Infomation |
Gemifloxacin mesylate is the mesylate salt of gemifloxacin. It has a role as an antimicrobial agent and a topoisomerase IV inhibitor. It contains a gemifloxacin. Gemifloxacin Mesylate is the mesylate salt form of gemifloxacin, a synthetic broad-spectrum fluoroquinolone with antibacterial activity. Gemifloxacin mesylate inhibits activities of DNA gyrase and topoisomerase IV, thereby inhibiting DNA replication and eventually bacterial growth. This fluoroquinolone exerts an enhanced spectrum of activity against gram-positive bacteria such as Streptococcus pneumoniae and Staphylococcus aureus, in addition to its activity against gram-negative bacteria. A naphthyridine and fluoroquinolone derivative antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used for the treatment of community-acquired pneumonia and acute bacterial infections associated with chronic bronchitis. See also: Gemifloxacin (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
DMSO : 97~100 mg/mL ( 199.79 ~205.98 mM ) H2O : 50~97 mg/mL (~102.99 mM ) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.15 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 (5.15 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: ≥ 2.5 mg/mL (5.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.15 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0598 mL | 10.2989 mL | 20.5977 mL | |
| 5 mM | 0.4120 mL | 2.0598 mL | 4.1195 mL | |
| 10 mM | 0.2060 mL | 1.0299 mL | 2.0598 mL |