TOSUFLOXACIN MONOHYDRATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15F3N4O3.H2O
Molecular Weight	422.3579
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=FCHGAGZTPICOSW-UHFFFAOYSA-N

InChI=1S/C19H15F3N4O3.H2O/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);1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Inhibitor 8,504
Topoisomerase IV 62	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Infectious enteritis 5	Curative	Approved 8,583	Ozex
Cystitis 27	Curative	Approved 8,583	Ozex
Prostatitis 25	Curative	Approved 8,583	Ozex
Pneumonia 91	Curative	Approved 8,583	Ozex

C_max

Value	Dose	Analyte	Population
0.45 μg/L	150 mg 3 times / day multiple, oral	TOSUFLOXACIN plasma	Homo sapiens
0.6 μg/L	150 mg 3 times / day multiple, oral	TOSUFLOXACIN plasma	Homo sapiens
0.83 μg/L	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
0.62 μg/L	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
0.73 μg/L	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
0.82 μg/L	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4.09 μg × h/mL	150 mg 3 times / day multiple, oral		TOSUFLOXACIN plasma	Homo sapiens
3.84 μg × h/mL	150 mg 3 times / day multiple, oral		TOSUFLOXACIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.5 h	150 mg 3 times / day multiple, oral	TOSUFLOXACIN plasma	Homo sapiens
3.59 h	150 mg 3 times / day multiple, oral	TOSUFLOXACIN plasma	Homo sapiens
3.85 h	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
4 h	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
9.8 h	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens
10.5 h	150 mg single, oral	TOSUFLOXACIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Anaphylactoid shock, Toxic epidermal necrolysis...
300 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT

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AEs

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AE	Significance	Dose	Population
Acute renal failure	Disc. AE	200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT
Anaphylactoid shock	Disc. AE	200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT
Consciousness abnormal	Disc. AE	200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT
Convulsion	Disc. AE	200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT
Interstitial nephritis	Disc. AE	200 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT

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PubMed

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Title	Date	PubMed
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
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.	1999 Oct	10588315
Evaluation of in-vitro and in-vivo antibacterial activity of tosufloxacin tosilate.	2001 Dec	11810586

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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.

Substance Class	Chemical
Record UNII	6239812J7L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOSUFLOXACIN MONOHYDRATE

Preferred Name

English

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Classification Tree

Code System

Code

Antibiotic

NCI_THESAURUS

C795

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Code System

Code

Type

Description

FDA UNII

6239812J7L

PRIMARY

EPA CompTox

DTXSID80910234

PRIMARY

PUBCHEM

44154493

PRIMARY

NCI_THESAURUS

C76233

PRIMARY

CAS

107097-79-0

PRIMARY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2