TOSUFLOXACIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15F3N4O3.ClH
Molecular Weight	440.804
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=CIHZSSCESOLBRQ-UHFFFAOYSA-N

InChI=1S/C19H15F3N4O3.ClH/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);1H

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
Comparative in-vitro activities of the new quinolone, Bay y 3118, and ciprofloxacin, sparfloxacin, tosufloxacin, CI-960 and CI-990.	1993 Apr	7605398
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
History of quinolones and their side effects.	2001	11549783
[An adult case of systemic cat-scratch disease with hepatosplenic involvement].	2001 Jun	11494569
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.	2001 Nov	11885973
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species.	2002 Mar	11957133
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
In vitro activity of pazufloxacin, tosufloxacin and other quinolones against Legionella species.	2005 Dec	16260445
[Study on the accumulation of fluoroquinolones in clinical isolates of susceptible and multi-drug-resistant Escherichia coli strains].	2005 Jan	15702790
Antimicrobial safety: focus on fluoroquinolones.	2005 Jul 15	15942881
[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
Multidrug-resistant typhoid fever outbreak in travelers returning from Bangladesh.	2007 Dec	18258058
[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
Antibiotic prophylaxis for transrectal prostate biopsy: a prospective randomized study of tosufloxacin versus levofloxacin.	2008 Jul	18462354
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.	2009	19430173
[Antibacterial activity of quinolones against various clinically isolated strains and evaluation of efficacy based on the pharmacokinetics/pharmacodynamics theory].	2009 Jun	19882980
[Efficacy of tosufloxacin in genital chlamydial infections].	2009 Oct	20055118
[Intractable pediatric infectious disease: examining the ability of a new drug, tosufloxacin tosilate hydrate for pediatric].	2010 Dec	21425593
[Antibiotic susceptibility of blood-borne Streptococcus pneumoniae and efficacy assessment of respiratory quinolones using Monte Carlo simulation].	2010 Feb	20836402
Risk factors for acute prostatitis after transrectal biopsy of the prostate.	2010 Jun	20577611

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 HYDROCHLORIDE

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, HYDROCHLORIDE

Systematic Name

English

ABBOTT-60969

Code

English

A-60969

Code

English

TOSUFLOXACIN HYDROCHLORIDE, (±)-

Common Name

English

Tosufloxacin hydrochloride [WHO-DD]

Common Name

English

TOSUFLOXACIN HYDROCHLORIDE [MI]

Common Name

English

1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7-(3-AMINO-1-PYRROLIDINYL)-1-(2,4-DIFLUOROPHENYL)-6-FLUORO-1,4-DIHYDRO-4-OXO-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60908770