| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H18ClF2N3O3.H2O |
| Molecular Weight | 427.83 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.N[C@@H]1CN(CC12CC2)C3=C(Cl)C4=C(C=C3F)C(=O)C(=CN4[C@@H]5C[C@@H]5F)C(O)=O
InChI
InChIKey=ANCJYRJLOUSQBW-JJZGMWGRSA-N
InChI=1S/C19H18ClF2N3O3.H2O/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19;/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28);1H2/t10-,12+,13+;/m0./s1
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C19H18ClF2N3O3 |
| Molecular Weight | 409.814 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Sitafloxacin hydrate (DU-6859a, Gracevit), a new-generation, broad-spectrum oral fluoroquinolone that is very active against many Gram-positive, Gram-negative and anaerobic clinical isolates, including strains resistant to other fluoroquinolones, was recently approved in Japan for the treatment of respiratory and urinary tract infections. This is a new quinolone oral antibacterial to inhibit DNA replication of bacteria at the time of infection, and shows antibacterial action. Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci. Sitafloxacin has also demonstrated activity against clinical isolates of Klebsiella pneumoniae (including about 67% of strains producing extended-spectrum, beta-lactamases and resistant to ciprofloxacin), Enterobacter cloacae, Pseudomonas aeruginosa with some activity against quinolone-resistant strains and Acinetobacter baumannii. The in vitro activity against anaerobes is comparable to imipenem or metronidazole. Sitafloxacin showed dual inhibitory activity against both enzymes: Streptococcus pneumoniae DNA gyrase and topoisomerase IV.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
for adults: 1 tablet (50 mg of sitafloxacin) at a time, twice daily, or 2 tablets (100 mg) at a time, once daily. If the effect is insufficient, the dosage may be increased to 2 tablets (100 mg) at a time, twice daily.
Route of Administration:
Oral
The minimum inhibitory concentration of sitafloxacin (STFX) at which 90% of isolates (MIC90) was 0.5 microg/mL for methicillin-susceptible Staphylococcus aureus. STFX inhibited the growth of all the isolates of Streptococcus pneumoniae at 0.06 microg/mL or less. The MIC90 of STFX was 0.03 microg/mL. Against Streptococcus pyogenes, the MIC90 of STFX was 0.06 microg/mL. The MIC90 of STFX was 2 microg/mL for Enterococcus faecalis. The MIC90 of STFX for Escherichia coli was 2 microg/mL. The MIC90 of STFX for Pseudomonas aeruginosa isolates recovered from urinary infections was 4 microg/mL. The MIC90 of STFX for P. aeruginosa isolates recovered from respiratory infections was 4 microg/mL. STFX inhibited the growth of all the isolates of Haemophilus influenzae at 0.004 microg/mL or less. The MIC90 of STFX was 0.015 microg/mL for Moraxella catarrhalis. The MIC90(s) of STFX ranged from 0.03 to 0.25 microg/mL for all the species of anaerobic bacteria and were the lowest values of all the antimicrobial agents tested
