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Details

Stereochemistry RACEMIC
Molecular Formula C19H15F3N4O3
Molecular Weight 404.3426
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOSUFLOXACIN

SMILES

NC1CCN(C1)C2=NC3=C(C=C2F)C(=O)C(=CN3C4=CC=C(F)C=C4F)C(O)=O

InChI

InChIKey=WUWFMDMBOJLQIV-UHFFFAOYSA-N
InChI=1S/C19H15F3N4O3/c20-9-1-2-15(13(21)5-9)26-8-12(19(28)29)16(27)11-6-14(22)18(24-17(11)26)25-4-3-10(23)7-25/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29)

HIDE SMILES / InChI

Description

Tosufloxacin is a fluoroquinolone antibacterial agent. Tosufloxacin is an inhibitor of bacterial DNA gyrase and topoisomerase IV. Tosufloxacin is indicated for the treatment of various infections such as skin, respiratory, urinary, gynecologic, ophthalmologic, otolaryngologic, dental infections. Fluoroquinolones including tosufloxacin have a potential risk of inducing cartilage and joint toxicity in children. It is also associated with severe thrombocytopenia and nephritis, and hepatotoxicity.

CNS Activity

Originator

PMID

PMID

TitleDatePMID
Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8- naphthyridine-3-carboxylic acids.
1992 Feb 7
Comparative in-vitro activities of the new quinolone, Bay y 3118, and ciprofloxacin, sparfloxacin, tosufloxacin, CI-960 and CI-990.
1993 Apr
In-vitro activity of quinolones and macrolides against mycobacteria.
1994 Sep
Trovafloxacin is active against Toxoplasma gondii.
1996 Aug
Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice.
1996 Dec
N-1-tert-butyl-substituted quinolones: in vitro anti-Mycobacterium avium activities and structure-activity relationship studies.
1996 Nov
Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position.
1996 Oct
[In vitro anti-MAC activities of new quinolones in focus (2)].
1996 Sep
Terbium sensitized determination of tosufloxacin using electrochemiluminescence method.
2005 Apr
In vitro activity of pazufloxacin, tosufloxacin and other quinolones against Legionella species.
2005 Dec
Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones.
2005 Jul
Antimicrobial safety: focus on fluoroquinolones.
2005 Jul 15
[Clinical experience of streptococcal balanoposthitis in 47 healthy adult males].
2005 Nov
In vitro activity of fluoroquinolones against Mycoplasma genitalium and their bacteriological efficacy for treatment of M. genitalium-positive nongonococcal urethritis in men.
2005 Nov 1
Antimicrobial activities of tosufloxacin against Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella branhamella catarrhalis isolated from otolaryngological infectious diseases.
2005 Oct
[Successful treatment with voriconazole for disseminated cutaneous and visceral infection by Fusarium solani in a patient with acute myeloid leukemia].
2006 Aug
[Evaluation of efficacy of oral quinolone against Streptococcus pneumoniae AND Haemophilus influenzae with the use of Monte Carlo simulation].
2006 Dec
Pharmacodynamic evaluation of tosufloxacin against Streptococcus pneumoniae in an in vitro model simulating serum concentration.
2006 Feb
In vitro activity of sitafloxacin compared with several fluoroquinolones against Streptococcus anginosus and Streptococcus constellatus.
2006 Feb
Azithromycin failure in Mycoplasma genitalium urethritis.
2006 Jul
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].
2006 Jun
Antibacterial activity of tosufloxacin against major organisms detected from patients with respiratory or otorhinological infections: comparison with the results obtained from organisms isolated about 10 years ago.
2006 Jun
[Antibacterial activity of tosufloxacin against major organisms detected from patients with respiratory infections].
2007 Apr
[Effectiveness of switch therapy for peritonitis].
2007 Aug
A novel in vivo rabbit model that mimics human dosing to determine the distribution of antibiotics in ocular tissues.
2007 Aug
Multidrug-resistant typhoid fever outbreak in travelers returning from Bangladesh.
2007 Dec
[Susceptibility of clinical isolates from primary care clinics to oral antibacterial agents].
2007 Feb
Tosufloxacin tosilate-induced thrombocytopenic purpura.
2007 Jul
[A case of acute bronchitis caused by Neisseria meningitidis associated with HIV infection].
2007 Nov
Effect of GrlA mutation on the development of quinolone resistance in Staphylococcus aureus in an in vitro pharmacokinetic model.
2007 Nov
[Sensitivity surveillance of Haemophilus influenzae isolates for several antibiotics in Gifu Prefecture (2006)].
2008 Aug
Antibiotic prophylaxis for transrectal prostate biopsy: a prospective randomized study of tosufloxacin versus levofloxacin.
2008 Jul
Mutations in the quinolone resistance determining region in Staphylococcus epidermidis recovered from conjunctiva and their association with susceptibility to various fluoroquinolones.
2008 Jun
In vitro susceptibilities of bacterial isolates from conjunctival flora to gatifloxacin, levofloxacin, tosufloxacin, and moxifloxacin.
2008 Mar
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.
2009
Fluoroquinolones reduce carrageenan-induced edema in rats and the involvement of the glucocorticoid receptor system.
2009 Apr
Measurement of AQCmax of five different ophthalmic solutions and discussion of its new application.
2009 Aug
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones.
2009 Feb
Corneal deposits after topical tosufloxacin in a patient with poor tear secretion.
2009 Jan
[Antibacterial activity of quinolones against various clinically isolated strains and evaluation of efficacy based on the pharmacokinetics/pharmacodynamics theory].
2009 Jun
Levofloxacin 0.5% ophthalmic solution: a review of its use in the treatment of external ocular infections and in intraocular surgery.
2009 Jun 18
[Efficacy of tosufloxacin in genital chlamydial infections].
2009 Oct
Antituberculosis activity of the molecular libraries screening center network library.
2009 Sep
[Intractable pediatric infectious disease: examining the ability of a new drug, tosufloxacin tosilate hydrate for pediatric].
2010 Dec
[Antibiotic susceptibility of blood-borne Streptococcus pneumoniae and efficacy assessment of respiratory quinolones using Monte Carlo simulation].
2010 Feb
[Epidemiological analysis of Streptococcus pneumoniae in Gifu prefecture].
2010 Jun
Risk factors for acute prostatitis after transrectal biopsy of the prostate.
2010 Jun
Legionella pneumophila induces cathepsin B-dependent necrotic cell death with releasing high mobility group box1 in macrophages.
2010 Nov 22
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.
2010 Sep 20
Patent

Sample Use Guides

In Vivo Use Guide
In general, for adults, take 2 to 3 tablets (300 to 450 mg of the active ingredient) a day, in 2 to 3 divided doses. The dosage may be adjusted according to disease, symptoms, etc. of the patient. If symptoms are severe or the effect is insufficient, take 4 tablets (600 mg) a day. Osteomyelitis, arthritis: In general, for adults, take 1 tablet (150 mg of the active ingredient) at a time, 3 times a day. The dosage may be adjusted according to disease, symptoms, etc. of the patient. If symptoms are severe or the effect is insufficient, take 4 tablets (600 mg) a day. Typhoid/paratyphoid fever: In general, for adults, take 1 tablet (150 mg of the active ingredient) at a time, 4 times a day for 14 days.
Route of Administration: Oral
In Vitro Use Guide
The MIC90s of tosufloxacin among the 27 isolates of macrolide-resistant Mycoplasma pneumoniae (MRMP) was 0.25 ug/ml and those among the 23 isolates of macrolide-sensitive Mycoplasma pneumoniae (MSMP) was 0.5 μg/ml.
Name Type Language
TOSUFLOXACIN
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
A 67107
Code English
ABBOTT-61827
Code English
TOSUFLOXACIN [INN]
Common Name English
ABBOTT 61827
Code English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7-(3-AMINO-1-PYRROLIDINYL)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-4-OXO-, (+/-)-
Common Name English
TOSUFLOXACIN [MI]
Common Name English
(+/-)-7-(3-AMINO-1-PYRROLIDINYL)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID
Systematic Name English
TOSUFLOXACIN [MART.]
Common Name English
TOSUFLOXACIN [USAN]
Common Name English
A 61827
Code English
TOSUFLOXACIN [WHO-DD]
Common Name English
A-67107
Code English
A-61827
Code English
Code System Code Type Description
EPA CompTox
100490-36-6
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
ChEMBL
CHEMBL273348
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
INN
6242
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
EVMPD
SUB11201MIG
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
NCI_THESAURUS
C80642
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
WIKIPEDIA
TOSUFLOXACIN
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
CAS
100490-36-6
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY
MERCK INDEX
M10984
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY Merck Index
PUBCHEM
5517
Created by admin on Tue Mar 06 11:54:38 UTC 2018 , Edited by admin on Tue Mar 06 11:54:38 UTC 2018
PRIMARY SWITZERF