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
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
[In vitro anti-MAC activities of new quinolones in focus (2)].	1996 Sep	8999137
History of quinolones and their side effects.	2001	11549783
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.	2001 Dec	11698174
[An adult case of systemic cat-scratch disease with hepatosplenic involvement].	2001 Jun	11494569
Emergence of cephem- and aztreonam-high-resistant Neisseria gonorrhoeae that does not produce beta-lactamase.	2001 Mar	11406757
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.	2001 Nov	11885973
[In vitro antibacterial activity of prulifloxacin, a new oral fluoroquinolone].	2002 Dec	12621732
Pharmacokinetics and safety assessment of tosufloxacin tosilate.	2002 Mar	11957114
[Salmonella infections].	2003 Feb	12722251
Alteration of constitutive apoptosis in neutrophils by quinolones.	2003 Jun	12875364
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
VapB-positive Rhodococcus equi infection in an HIV-infected patient in Japan.	2005 Feb	15729486
[Study on the accumulation of fluoroquinolones in clinical isolates of susceptible and multi-drug-resistant Escherichia coli strains].	2005 Jan	15702790
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
Azithromycin failure in Mycoplasma genitalium urethritis.	2006 Jul	16836839
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
A novel in vivo rabbit model that mimics human dosing to determine the distribution of antibiotics in ocular tissues.	2007 Aug	17803431
Mutations in the quinolone resistance determining region in Staphylococcus epidermidis recovered from conjunctiva and their association with susceptibility to various fluoroquinolones.	2008 Jun	18460536
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.	2009	19430173
Measurement of AQCmax of five different ophthalmic solutions and discussion of its new application.	2009 Aug	19650709
Antituberculosis activity of the molecular libraries screening center network library.	2009 Sep	19783214

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