TOSUFLOXACIN TOSYLATE MONOHYDRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15F3N4O3.C7H8O3S.H2O
Molecular Weight	594.56
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TOSUFLOXACIN TOSYLATE MONOHYDRATE

Structure Search

SMILES

O.CC1=CC=C(C=C1)S(O)(=O)=O.NC2CCN(C2)C3=NC4=C(C=C3F)C(=O)C(=CN4C5=C(F)C=C(F)C=C5)C(O)=O

InChI

InChIKey=SSULTCPIIYRGFQ-UHFFFAOYSA-N

InChI=1S/C19H15F3N4O3.C7H8O3S.H2O/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;1-6-2-4-7(5-3-6)11(8,9)10;/h1-2,5-6,8,10H,3-4,7,23H2,(H,28,29);2-5H,1H3,(H,8,9,10);1H2

HIDE SMILES / InChI

Description
Sources: http://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=33966
Curator's Comment: description was created based on several sources, including: http://medical.taishotoyama.co.jp/data/if/pdf/ozx.pdf

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://medical.taishotoyama.co.jp/data/if/pdf/ozx.pdf	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://medical.taishotoyama.co.jp/data/if/pdf/ozx.pdf	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Infectious enteritis 5 Sources: http://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=33966	Curative	Approved 8429	Ozex Approved Use It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections. Launch Date 1990
Cystitis 27 Sources: http://www.rad-ar.or.jp/siori/english/kekka_plain.cgi?n=33966	Curative	Approved 8429	Ozex Approved Use It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections. Launch Date 1990
Prostatitis 25 Sources: http://medical.taishotoyama.co.jp/data/if/pdf/ozx.pdf	Curative	Approved 8429	Ozex Approved Use It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections. Launch Date 1991
Pneumonia 90 Sources: http://medical.taishotoyama.co.jp/data/if/pdf/ozx.pdf	Curative	Approved 8429	Ozex Approved Use It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections. Launch Date 1990

PubMed

Title	Date	PubMed
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	1738144
In-vitro activity of quinolones and macrolides against mycobacteria.	1994 Sep	7829409
Trovafloxacin is active against Toxoplasma gondii.	1996 Aug	8843293
Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice.	1996 Dec	9006794
N-1-tert-butyl-substituted quinolones: in vitro anti-Mycobacterium avium activities and structure-activity relationship studies.	1996 Nov	8913479
Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position.	1996 Oct	8891145
[In vitro anti-MAC activities of new quinolones in focus (2)].	1996 Sep	8999137
[The history of the development and changes of quinolone antibacterial agents].	2003	15143768
[Alteration of antibacterial activity of tosufloxacin and various antibacterial agents against Streptococcus pneumoniae].	2003 Feb	12723396
[Salmonella infections].	2003 Feb	12722251
Alteration of constitutive apoptosis in neutrophils by quinolones.	2003 Jun	12875364
Anaphylaxis due to tosufloxacin tosilate.	2003 Sep	14578563
[Molecular epidemiology of fluoroquinolone-resistant Streptococcus pneumoniae in Japan].	2004 May	15211865
In vitro activity of pazufloxacin, tosufloxacin and other quinolones against Legionella species.	2005 Dec	16260445
VapB-positive Rhodococcus equi infection in an HIV-infected patient in Japan.	2005 Feb	15729486
Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones.	2005 Jul	15942701
[Clinical experience of streptococcal balanoposthitis in 47 healthy adult males].	2005 Nov	16363705
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	16206116
Antimicrobial activities of tosufloxacin against Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella branhamella catarrhalis isolated from otolaryngological infectious diseases.	2005 Oct	16258823
[Successful treatment with voriconazole for disseminated cutaneous and visceral infection by Fusarium solani in a patient with acute myeloid leukemia].	2006 Aug	16986714
[Evaluation of efficacy of oral quinolone against Streptococcus pneumoniae AND Haemophilus influenzae with the use of Monte Carlo simulation].	2006 Dec	17334064
Azithromycin failure in Mycoplasma genitalium urethritis.	2006 Jul	16836839
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].	2006 Jun	16913401
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	16826349
[Antibacterial activity of tosufloxacin against major organisms detected from patients with respiratory infections].	2007 Apr	17612257
[Effectiveness of switch therapy for peritonitis].	2007 Aug	18018417
A novel in vivo rabbit model that mimics human dosing to determine the distribution of antibiotics in ocular tissues.	2007 Aug	17803431
Multidrug-resistant typhoid fever outbreak in travelers returning from Bangladesh.	2007 Dec	18258058
[Susceptibility of clinical isolates from primary care clinics to oral antibacterial agents].	2007 Feb	17436860
Tosufloxacin tosilate-induced thrombocytopenic purpura.	2007 Jul	17584324
[A case of acute bronchitis caused by Neisseria meningitidis associated with HIV infection].	2007 Nov	18095474
Effect of GrlA mutation on the development of quinolone resistance in Staphylococcus aureus in an in vitro pharmacokinetic model.	2007 Nov	17827137
[Sensitivity surveillance of Haemophilus influenzae isolates for several antibiotics in Gifu Prefecture (2006)].	2008 Aug	19024643
Antibiotic prophylaxis for transrectal prostate biopsy: a prospective randomized study of tosufloxacin versus levofloxacin.	2008 Jul	18462354
Mutations in the quinolone resistance determining region in Staphylococcus epidermidis recovered from conjunctiva and their association with susceptibility to various fluoroquinolones.	2008 Jun	18460536
In vitro susceptibilities of bacterial isolates from conjunctival flora to gatifloxacin, levofloxacin, tosufloxacin, and moxifloxacin.	2008 Mar	18327047
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.	2009	19430173
Fluoroquinolones reduce carrageenan-induced edema in rats and the involvement of the glucocorticoid receptor system.	2009 Apr	19396522
Measurement of AQCmax of five different ophthalmic solutions and discussion of its new application.	2009 Aug	19650709
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009 Dec 2	19956587
Functional characterization of multidrug and toxin extrusion protein 1 as a facilitative transporter for fluoroquinolones.	2009 Feb	19004926
Corneal deposits after topical tosufloxacin in a patient with poor tear secretion.	2009 Jan	19092422
[Antibacterial activity of quinolones against various clinically isolated strains and evaluation of efficacy based on the pharmacokinetics/pharmacodynamics theory].	2009 Jun	19882980
Levofloxacin 0.5% ophthalmic solution: a review of its use in the treatment of external ocular infections and in intraocular surgery.	2009 Jun 18	19537841
[Efficacy of tosufloxacin in genital chlamydial infections].	2009 Oct	20055118
Antituberculosis activity of the molecular libraries screening center network library.	2009 Sep	19783214
[Antibiotic susceptibility of blood-borne Streptococcus pneumoniae and efficacy assessment of respiratory quinolones using Monte Carlo simulation].	2010 Feb	20836402
[Epidemiological analysis of Streptococcus pneumoniae in Gifu prefecture].	2010 Jun	20976879
Risk factors for acute prostatitis after transrectal biopsy of the prostate.	2010 Jun	20577611
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.	2010 Sep 20	20922036

Patents

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 TOSYLATE MONOHYDRATE

Common Name

English

TOSUFLOXACIN TOSILATE HYDRATE

Common Name

English

TOSUXACIN

Brand Name

English

Tosufloxacin tosilate monohydrate [WHO-DD]

Common Name

English

TOSUFLOXACIN TOSILATE MONOHYDRATE

Common Name

English

TOSUFLOXACIN TOSILATE HYDRATE [JAN]

Common Name

English

OZEX

Brand Name

English

Code System Code Type Description

SMS_ID

100000164913