TOSUFLOXACIN TOSYLATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15F3N4O3.C7H8O3S
Molecular Weight	576.544
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=CSSQVOKOWWIUCX-UHFFFAOYSA-N

InChI=1S/C19H15F3N4O3.C7H8O3S/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)

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
Trovafloxacin is active against Toxoplasma gondii.	1996 Aug	8843293
N-1-tert-butyl-substituted quinolones: in vitro anti-Mycobacterium avium activities and structure-activity relationship studies.	1996 Nov	8913479
[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
Effect of hydrophobicity and molecular mass on the accumulation of fluoroquinolones by Staphylococcus aureus.	2001 Mar	11222558
[Molecular epidemiology of fluoroquinolone-resistant Streptococcus pneumoniae in Japan].	2004 May	15211865
Terbium sensitized determination of tosufloxacin using electrochemiluminescence method.	2005 Apr	15844328
[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
Pharmacodynamic evaluation of tosufloxacin against Streptococcus pneumoniae in an in vitro model simulating serum concentration.	2006 Feb	16506083
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
Effect of GrlA mutation on the development of quinolone resistance in Staphylococcus aureus in an in vitro pharmacokinetic model.	2007 Nov	17827137
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.	2009	19430173
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009 Dec 2	19956587

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

Common Name

English

TOSUFLOXACIN TOSILATE

Common Name

English

Tosufloxacin tosilate [WHO-DD]

Common Name

English

TOSUFLOXACIN TOLUENESULFONATE, (±)-

Common Name

English

TOSUFLOXACIN TOSILATE [MART.]

Common Name

English

TOSUFLOXACIN TOSILATE [JAN]

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-, 4-METHYLBENZENESULFONATE

Common Name

English

TOSUFLOXACIN TOLUENESULFONATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795