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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 of TOSUFLOXACIN HYDROCHLORIDE

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 ( + / - )

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

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

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ozex

Approved Use

It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections.

Launch Date

1990
Curative
Ozex

Approved Use

It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections.

Launch Date

1990
Curative
Ozex

Approved Use

It is usually used to treat various infections such as skin/respiratory/urinary/gynecologic/ophthalmologic/otolaryngologic/dental infections.

Launch Date

1991
Curative
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

PubMed

TitleDatePubMed
Comparative in-vitro activities of the new quinolone, Bay y 3118, and ciprofloxacin, sparfloxacin, tosufloxacin, CI-960 and CI-990.
1993 Apr
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
Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position.
1996 Oct
[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
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.
2001 Dec
[An adult case of systemic cat-scratch disease with hepatosplenic involvement].
2001 Jun
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.
2001 Nov
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species.
2002 Mar
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin.
2002 Mar
[The history of the development and changes of quinolone antibacterial agents].
2003
[Alteration of antibacterial activity of tosufloxacin and various antibacterial agents against Streptococcus pneumoniae].
2003 Feb
[Salmonella infections].
2003 Feb
Terbium sensitized determination of tosufloxacin using electrochemiluminescence method.
2005 Apr
In vitro activity of pazufloxacin, tosufloxacin and other quinolones against Legionella species.
2005 Dec
[Clinical study of male urethritis in Oogaki Municipal Hospital].
2005 Jan
Prevalence of Ile-460-Val/ParE substitution in clinical Streptococcus pneumoniae isolates that were less susceptible to fluoroquinolones.
2005 Jul
Antimicrobial activities of tosufloxacin against Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella branhamella catarrhalis isolated from otolaryngological infectious diseases.
2005 Oct
Pharmacodynamic evaluation of tosufloxacin against Streptococcus pneumoniae in an in vitro model simulating serum concentration.
2006 Feb
In vitro activity of sitafloxacin compared with several fluoroquinolones against Streptococcus anginosus and Streptococcus constellatus.
2006 Feb
[Sensitivity surveillance of Streptococcus pneumoniae isolates for several antibiotics in Gifu prefecture (2004)].
2006 Jun
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
Multidrug-resistant typhoid fever outbreak in travelers returning from Bangladesh.
2007 Dec
[A case of acute bronchitis caused by Neisseria meningitidis associated with HIV infection].
2007 Nov
Mutations in the quinolone resistance determining region in Staphylococcus epidermidis recovered from conjunctiva and their association with susceptibility to various fluoroquinolones.
2008 Jun
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.
2009
Fluoroquinolones reduce carrageenan-induced edema in rats and the involvement of the glucocorticoid receptor system.
2009 Apr
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
[Efficacy of tosufloxacin in genital chlamydial infections].
2009 Oct
[Intractable pediatric infectious disease: examining the ability of a new drug, tosufloxacin tosilate hydrate for pediatric].
2010 Dec
Risk factors for acute prostatitis after transrectal biopsy of the prostate.
2010 Jun
Patents

Sample Use Guides

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
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
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on Sat Dec 16 09:23:54 GMT 2023
Edited
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on Sat Dec 16 09:23:54 GMT 2023
Record UNII
M1FK9581QZ
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Name Type Language
TOSUFLOXACIN HYDROCHLORIDE
MI  
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
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY
CAS
100490-92-4
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
M1FK9581QZ
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY
SMS_ID
100000176623
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY
MERCK INDEX
m10984
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY Merck Index
PUBCHEM
10433396
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY
CAS
104051-69-6
Created by admin on Sat Dec 16 09:23:54 GMT 2023 , Edited by admin on Sat Dec 16 09:23:54 GMT 2023
PRIMARY
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