U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18ClF2N3O3
Molecular Weight 409.814
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SITAFLOXACIN ANHYDROUS

SMILES

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=PNUZDKCDAWUEGK-CYZMBNFOSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H18ClF2N3O3
Molecular Weight 409.814
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Gracevit(R)

Approved Use

It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Launch Date

2008
Curative
Gracevit(R)

Approved Use

It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Launch Date

2008
Curative
Gracevit(R)

Approved Use

It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Launch Date

2008
Curative
Gracevit(R)

Approved Use

It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Launch Date

2008
Curative
Gracevit(R)

Approved Use

It is usually used in the treatment of various infections such as respiratory infection, urologic infection, gynecologic infection, otorhinological infections, and dental infection.

Launch Date

2008
PubMed

PubMed

TitleDatePubMed
In vitro and in vivo antifungal activities of DU-6859a, a fluoroquinolone, in combination with amphotericin B and fluconazole against pathogenic fungi.
1995 Jul
[In vitro anti-MAC activities of new quinolones in focus (2)].
1996 Sep
Comparative pharmacokinetics and pharmacodynamics of the newer fluoroquinolone antibacterials.
2001
Recent advances in the field of quinolones.
2001 Jan-Feb
An open, randomised, multi-centre study comparing the safety and efficacy of sitafloxacin and imipenem/cilastatin in the intravenous treatment of hospitalised patients with pneumonia.
2001 Mar
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.
2001 Nov
Pharmacokinetics and absolute bioavailability of sitafloxacin, a new fluoroquinolone antibiotic, in healthy male and female Caucasian subjects.
2001 Nov
Phototoxic retinal degeneration and toxicokinetics of sitafloxacin, a quinolone antibacterial agent, in mice.
2001 Sep
A critical review of the fluoroquinolones: focus on respiratory infections.
2002
[Prospects for development of new antituberculous drugs].
2002 Aug
Antimicrobial activities of clarithromycin, gatifloxacin and sitafloxacin, in combination with various antimycobacterial drugs against extracellular and intramacrophage Mycobacterium avium complex.
2002 Feb
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.
2002 Mar
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.
2002 May 27
In vitro antibacterial activity and pharmacodynamics of new quinolones.
2003 Apr
Effects of disruption of heat shock genes on susceptibility of Escherichia coli to fluoroquinolones.
2003 Aug 12
A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity.
2003 Dec
MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 2: achieving activity in vivo through the use of alternative scaffolds.
2003 Dec 1
Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.
2003 Feb
Detection of macrolide resistance in Streptococcus pneumoniae.
2003 May
Adverse drug reactions: implications for the development of fluoroquinolones.
2003 May
Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center.
2003 Nov
A topological-substructural molecular design (TOPS-MODE) approach to determining pharmacokinetics and pharmacological properties of 6-fluoroquinolone derivatives.
2003 Sep
Fluoroquinolones as chemotherapeutics against mycobacterial infections.
2004
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
In vivo experimental approach for the risk assessment of fluoroquinolone antibacterial agents-induced long QT syndrome.
2004 Feb 20
Investigational new drugs for the treatment of resistant pneumococcal infections.
2005 Aug
In vitro activities of 11 fluoroquinolones against 226 Campylobacter jejuni strains isolated from Finnish patients, with special reference to ciprofloxacin resistance.
2005 Dec
Quantitative assessment of the hepatic pharmacokinetics of the antimicrobial sitafloxacin in humans using in vivoF magnetic resonance spectroscopy.
2005 Feb
Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes.
2005 Jun
Reproducibility of gemifloxacin and comparison fluoroquinolone MIC results using Sensititre commercial dry-form panels.
2005 Mar
Characterization of fluoroquinolone and carbapenem susceptibilities in clinical isolates of levofloxacin-resistant Pseudomonas aeruginosa.
2005 May
Determination of in vitro synergy when three antimicrobial agents are combined against Mycobacterium tuberculosis.
2005 Oct
In vitro activities of 11 fluoroquinolones against 816 non-typhoidal strains of Salmonella enterica isolated from Finnish patients with special reference to reduced ciprofloxacin susceptibility.
2005 Sep 5
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.
2006 Apr
In vitro activity of sitafloxacin against clinical strains of Streptococcus pneumoniae with defined amino acid substitutions in QRDRs of gyrase A and topoisomerase IV.
2006 Dec
[Separation of sitafloxacin epimers by capillary electrophoresis].
2006 Sep
Susceptibilities of healthcare- and community-associated methicillin-resistant staphylococci to the novel des-F(6)-quinolone DX-619.
2007 Dec
Skin and skin structure infections: treatment with newer generation fluoroquinolones.
2007 Jun
Effects of treatment with antimicrobial agents on the human colonic microflora.
2008 Dec
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
Quinolones: action and resistance updated.
2009
[In vitro susceptibilities to levofloxacin and various antibacterial agents of 12,919 clinical isolates obtained from 72 centers in 2007].
2009 Aug
Convulsant activity of sitafloxacin and its interactions with anti-inflammatory drugs in mice.
2009 Aug
[Present status and future prospect of 3rd rescue regimen for H. pylori infection].
2009 Dec
A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy.
2009 Dec 1
[Pharmacological profile and clinical efficacy of sitafloxacin, a novel quinolone antibacterial agent].
2009 Jan
Comparative mutant prevention concentration and mutant selection window of sitafloxacin versus other quinolones using strains of Haemophilus influenzae with decreasing susceptibility to levofloxacin.
2009 May
[In vitro activity of sitafloxacin against clinical isolates in 2009].
2010 Dec
[Update on antimicrobial chemotherapy].
2010 Mar
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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:44 GMT 2023
Edited
by admin
on Fri Dec 15 16:18:44 GMT 2023
Record UNII
3GJC60U4Q8
Record Status Validated (UNII)
Record Version
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Name Type Language
SITAFLOXACIN ANHYDROUS
Common Name English
Sitafloxacin [WHO-DD]
Common Name English
SITAFLOXACIN [MI]
Common Name English
sitafloxacin [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC J01MA21
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
NCI_THESAURUS C795
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5048847
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
FDA UNII
3GJC60U4Q8
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
PUBCHEM
461399
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
CAS
127254-12-0
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
MERCK INDEX
m9959
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C76923
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
INN
7479
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
EVMPD
SUB10539MIG
Created by admin on Fri Dec 15 16:18:44 GMT 2023 , Edited by admin on Fri Dec 15 16:18:44 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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TARGET ORGANISM->INHIBITOR
TARGET ORGANISM->INHIBITOR
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TARGET ORGANISM->INHIBITOR
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