Details
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21504249Curator's Comment: description was created based on several sources, including
http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597
https://www.ncbi.nlm.nih.gov/pubmed/18806900
https://www.ncbi.nlm.nih.gov/pubmed/10588315
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21504249
Curator's Comment: description was created based on several sources, including
http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1597
https://www.ncbi.nlm.nih.gov/pubmed/18806900
https://www.ncbi.nlm.nih.gov/pubmed/10588315
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2363033 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10588315 |
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Target ID: CHEMBL2311225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10588315 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Gracevit(R) Approved UseIt is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date2008 |
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Curative | Gracevit(R) Approved UseIt is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date2008 |
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Curative | Gracevit(R) Approved UseIt is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date2008 |
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Curative | Gracevit(R) Approved UseIt is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date2008 |
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Curative | Gracevit(R) Approved UseIt is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection. Launch Date2008 |
PubMed
Title | Date | PubMed |
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In vitro and in vivo antimycobacterial activities of a new quinolone, DU-6859a. | 1994 Dec |
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[In vitro anti-MAC activities of new quinolones in focus (2)]. | 1996 Sep |
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Comparative pharmacokinetics and pharmacodynamics of the newer fluoroquinolone antibacterials. | 2001 |
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Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis. | 2001 Apr |
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Recent advances in the field of quinolones. | 2001 Jan-Feb |
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In vitro activity of sitafloxacin against Clostridium difficile. | 2001 May |
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Pharmacokinetics and absolute bioavailability of sitafloxacin, a new fluoroquinolone antibiotic, in healthy male and female Caucasian subjects. | 2001 Nov |
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Effects of disruption of heat shock genes on susceptibility of Escherichia coli to fluoroquinolones. | 2003 Aug 12 |
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Factors influencing fluoroquinolone resistance. | 2003 Dec |
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In-vitro activity of sitafloxacin (DU-6859a), either singly or in combination with rifampin analogs, against Mycobacterium leprae. | 2003 Mar |
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In vivo susceptibility of Mycobacterium leprae to sitafloxacin (DU-6859a), either singly or in combination with rifampicin analogues. | 2003 Mar |
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Investigational new drugs for the treatment of resistant pneumococcal infections. | 2005 Aug |
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Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes. | 2005 Jun |
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Antimicrobial activity of picolinic acid against extracellular and intracellular Mycobacterium avium complex and its combined activity with clarithromycin, rifampicin and fluoroquinolones. | 2006 Jan |
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New trends in development of antimycobacterial compounds. | 2006 Jun |
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Skin and skin structure infections: treatment with newer generation fluoroquinolones. | 2007 Jun |
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Successful treatment of Mycobacterium ulcerans osteomyelitis with minor surgical debridement and prolonged rifampicin and ciprofloxacin therapy: a case report. | 2008 Apr 27 |
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Dual-targeting properties of the 3-aminopyrrolidyl quinolones, DC-159a and sitafloxacin, against DNA gyrase and topoisomerase IV: contribution to reducing in vitro emergence of quinolone-resistant Streptococcus pneumoniae. | 2008 Jul |
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Quinolones with enhanced bactericidal activity induce autolysis in Streptococcus pneumoniae. | 2009 |
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Convulsant activity of sitafloxacin and its interactions with anti-inflammatory drugs in mice. | 2009 Aug |
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[Pharmacological profile and clinical efficacy of sitafloxacin, a novel quinolone antibacterial agent]. | 2009 Jan |
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Imipenem resistance of Pseudomonas in pneumonia: a systematic literature review. | 2010 Aug 26 |
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[In vitro activity of sitafloxacin against clinical isolates in 2009]. | 2010 Dec |
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Studies on mechanism of thermal crystal transformation of sitafloxacin hydrates through melting and recrystallization, yielding different anhydrates depending on initial crystalline forms. | 2010 Dec 15 |
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Characterization of the quinolone resistant determining regions in clinical isolates of pneumococci collected in Canada. | 2010 Jan 18 |
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Comparative in vitro and in vivo antimicrobial activities of sitafloxacin, gatifloxacin and moxifloxacin against Mycobacterium avium. | 2011 Apr |
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24649797
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
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45IP57B62B
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163253-37-0
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6918203
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ACTIVE MOIETY
SUBSTANCE RECORD