Sitafloxacin

• CAT Number: I009498
• CAS Number: 127254-12-0
• Molecular Formula: C19H18ClF2N3O3
• Molecular Weight: 409.818
• Purity: ≥95%
• Target: Type II DNA topoisomerase
• Solubility: Soluble in DMSO
• Storage: RT
• IUPAC Name: 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid
• InChI: InChI=1S/C19H18ClF2N3O3/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)/t10-,12+,13+/m0/s1
• InChIKey: PNUZDKCDAWUEGK-CYZMBNFOSA-N
• SMILES: C1CC12CN(CC2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)C5CC5F)F

Sitafloxacin(CAT: I009498) is 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. Sitafloxacin is active against methicillin-resistant staphylococci, Streptococcus pneumoniae and other streptococci with reduced susceptibility to levofloxacin and other quinolones and enterococci.

Reference

1. Drugs Today (Barc). 2008 Jul;44(7):489-501. doi: 10.1358/dot.2008.44.7.1219561.

Sitafloxacin hydrate for bacterial infections.

Anderson DL(1).

Author information:
(1)Medical Information Department, Prous Science, Barcelona, Spain.


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. 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. In a published phase II randomized,
open-label, multicenter study of patients hospitalized with pneumonia,
sitafloxacin (400 mg once daily) was comparable to imipenem/cilastatin (500 mg
three times a day). Results of the phase III trials of sitafloxacin are not
available in English. The clinical safety profile of sitafloxacin has been
characterized from 1,059 patients who participated in 10 clinical trials. The
most common events with 50 or 100 mg twice daily were gastrointestinal disorders
(17.2%), mostly diarrhea, and abnormal laboratory test results (16.2%), mostly
liver enzyme elevations. For Japanese patients, sitafloxacin provides the
broad-spectrum coverage promised by clinafloxacin and trovafloxacin and
comparable to carbapenems. While it is currently limited by its potential for
phototoxicity in Caucasians, phototoxicity is essentially irrelevant if
sitafloxacin is used in hospitals and especially in intensive care units.