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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 of TOSUFLOXACIN TOSYLATE

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
Molecular Formula C19H15F3N4O3
Molecular Weight 404.3426
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula C7H8O3S
Molecular Weight 172.202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

CNS Penetrant
2554
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Toyama
24
Curator's Comment: http://adisinsight.springer.com/drugs/800005704 | http://www.chemdrug.com/article/8/3285/16420748.html

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

6.3296641E11
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

6.3296641E11
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

6.645024E11
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

6.3296641E11
PubMed

PubMed

TitleDatePubMed
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
[In vitro anti-MAC activities of new quinolones in focus (2)].
1996 Sep
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.
1999 Oct
The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors.
2000 Jul
History of quinolones and their side effects.
2001
Evaluation of in-vitro and in-vivo antibacterial activity of tosufloxacin tosilate.
2001 Dec
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.
2001 Dec
Quinolones alter defense reactions mediated by macrophages.
2001 Feb
Pulmonary infiltration with eosinophilia (PIE) syndrome induced by antibiotics, PIPC and TFLX during cancer treatment.
2001 Jul
[An adult case of systemic cat-scratch disease with hepatosplenic involvement].
2001 Jun
Accumulation of ofloxacin and tosufloxacin in fluoroquinolone-resistant E coli.
2001 Mar
Emergence of cephem- and aztreonam-high-resistant Neisseria gonorrhoeae that does not produce beta-lactamase.
2001 Mar
Effect of hydrophobicity and molecular mass on the accumulation of fluoroquinolones by Staphylococcus aureus.
2001 Mar
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.
2001 Nov
[In vitro antibacterial activity of prulifloxacin, a new oral fluoroquinolone].
2002 Dec
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species.
2002 Mar
Clinical assessment of tosufloxacin tosilate.
2002 Mar
Pharmacokinetics and safety assessment of tosufloxacin tosilate.
2002 Mar
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin.
2002 Mar
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.
2002 Mar
[Alteration of antibacterial activity of tosufloxacin and various antibacterial agents against Streptococcus pneumoniae].
2003 Feb
[Salmonella infections].
2003 Feb
Pharmacokinetic-pharmacodynamic analysis of fluoroquinolones against Bacillus anthracis.
2004 Apr
[Molecular epidemiology of fluoroquinolone-resistant Streptococcus pneumoniae in Japan].
2004 May
Terbium sensitized determination of tosufloxacin using electrochemiluminescence method.
2005 Apr
Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones.
2005 Jul
[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
In vitro activity of sitafloxacin compared with several fluoroquinolones against Streptococcus anginosus and Streptococcus constellatus.
2006 Feb
[Effectiveness of switch therapy for peritonitis].
2007 Aug
[Susceptibility of clinical isolates from primary care clinics to oral antibacterial agents].
2007 Feb
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
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
[Antibiotic susceptibility of blood-borne Streptococcus pneumoniae and efficacy assessment of respiratory quinolones using Monte Carlo simulation].
2010 Feb
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.
2010 Sep 20
Patents

Patents

JP2003515526A
462

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:06:50 UTC 2023
Edited
by admin
on Fri Dec 15 16:06:50 UTC 2023
Record UNII
NO6NM634EH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOSUFLOXACIN TOSYLATE
Common Name English
TOSUFLOXACIN TOSILATE
JAN   MART.   WHO-DD  
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
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
Code System Code Type Description
FDA UNII
NO6NM634EH
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID8047842
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL273348
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
MERCK INDEX
m10984
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY Merck Index
CHEBI
77605
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
SMS_ID
100000084639
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
CAS
115964-29-9
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
NCI_THESAURUS
C76234
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
EVMPD
SUB04924MIG
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
MESH
C055185
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
PUBCHEM
93858
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
PRIMARY
CAS
100490-94-6
Created by admin on Fri Dec 15 16:06:50 UTC 2023 , Edited by admin on Fri Dec 15 16:06:50 UTC 2023
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
Structure of TOSUFLOXACIN TOSYLATE MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of TOSUFLOXACIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of TOSUFLOXACIN
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