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Details

Stereochemistry RACEMIC
Molecular Formula C16H16FN3O3S
Molecular Weight 349.38
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ULIFLOXACIN

SMILES

CC1SC2=C(C(O)=O)C(=O)C3=CC(F)=C(C=C3N12)N4CCNCC4

InChI

InChIKey=SUXQDLLXIBLQHW-UHFFFAOYSA-N
InChI=1S/C16H16FN3O3S/c1-8-20-11-7-12(19-4-2-18-3-5-19)10(17)6-9(11)14(21)13(16(22)23)15(20)24-8/h6-8,18H,2-5H2,1H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C16H16FN3O3S
Molecular Weight 349.38
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 https://hal.archives-ouvertes.fr/hal-00679605/document

Ulifloxacin is a fluoroquinolone with potent antibacterial activity against a broad spectrum of Gram-positive and -negative bacteria. Ulifloxacin is the active form of the prodrug prulifloxacin and shows a highly potent antipseudomonal activity. Ulifloxacin is generally more active in vitro than other fluoroquinolones against a variety of clinical isolates of Gram-negative bacteria, including community and nosocomial isolates of Escherichia coli, Klebsiella spp., Proteus, Providencia and Morganella spp., Moraxella catarrhalis and Haemophilus spp. The activity of ulifloxacin against Pseudomonas aeruginosa varies between countries. Gram-positive organisms, including meticillin- or oxacillin-susceptible Staphylococcus aureus, Enterococcus spp. and Italian community isolates of Streptococcus pneumoniae are susceptible to ulifloxacin. Activity against Spanish strains of S. pneumoniae is moderate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unidrox

Approved Use

Unidrox is indicated in the treatment of infections caused by susceptible organisms, in the following conditions: acute uncomplicated lower urinary tract infections (simple cystitis); complicated lower urinary tract infections; acute exacerbation of chronic bronchitis.
Curative
Unidrox

Approved Use

Unidrox is indicated in the treatment of infections caused by susceptible organisms, in the following conditions: acute uncomplicated lower urinary tract infections (simple cystitis); complicated lower urinary tract infections; acute exacerbation of chronic bronchitis.
Curative
Quisnon

Approved Use

The treatment of gastroenteritis, including infectious diarrheas.
PubMed

PubMed

TitleDatePubMed
Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice.
1996 Dec
Involvement of multiple transport systems in the disposition of an active metabolite of a prodrug-type new quinolone antibiotic, prulifloxacin.
2003
Prulifloxacin.
2004
Molecular characterization of clinical Streptococcus pneumoniae isolates with reduced susceptibility to fluoroquinolones emerging in Italy.
2004 Fall
Penetration of orally administered prulifloxacin into human lung tissue.
2005
Interpretive criteria for disk diffusion susceptibility testing of ulifloxacin, the active metabolite of prulifloxacin.
2005 Apr
Synergistic effect of fosfomycin and fluoroquinolones against Pseudomonas aeruginosa growing in a biofilm.
2005 Oct
Pharmacologic characteristics of prulifloxacin.
2006
Prulifloxacin: a new fluoroquinolone for the treatment of acute exacerbation of chronic bronchitis.
2006
Prulifloxacin: a new antibacterial fluoroquinolone.
2006 Feb
Determination of the active metabolite of prulifloxacin in human plasma by liquid chromatography-tandem mass spectrometry.
2006 Mar 7
Prulifloxacin: a brief review of its potential in the treatment of acute exacerbation of chronic bronchitis.
2007
Penetration of prulifloxacin into gynaecological tissues after single and repeated oral administrations.
2007
Determination of ulifloxacin by terbium-sensitized fluorescence with second-order scattering and its applications.
2007 Dec
Transporter-mediated hepatic uptake of ulifloxacin, an active metabolite of a prodrug-type new quinolone antibiotic prulifloxacin, in rats.
2007 Oct
Involvement of breast cancer resistance protein (ABCG2) in the biliary excretion mechanism of fluoroquinolones.
2007 Oct
Activity of ulifloxacin against clinical hospital isolates.
2007 Sep
Effects of fluoroquinolones on bacterial adhesion and on preformed biofilm of strains isolated from urinary double J stents.
2008 Apr
Simultaneous determination of Ciprofloxacin and the active metabolite of Prulifloxacin in aqueous human humor by high-performance liquid chromatography.
2008 Jul 15
Proposal of membrane transport mechanism of protein-unbound ulifloxacin into epithelial lining fluid determined by improved microdialysis.
2008 Sep
Determination of ulifloxacin, the active metabolite of prulifloxacin, in human plasma by a 96-well format solid-phase extraction and capillary zone electrophoresis.
2008 Sep 1
Penetration of orally administered prulifloxacin into human prostate tissue.
2009
Prulifloxacin: clinical studies of a broad-spectrum quinolone agent.
2009 Feb
Active uptake of ulifloxacin from plasma to lung that controls its concentration in epithelial lining fluid.
2009 Jun
Effects of prulifloxacin on cardiac repolarization in healthy subjects: a randomized, crossover, double-blind versus placebo, moxifloxacin-controlled study.
2010
Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine.
2010 Apr 16
[In vitro synergism of ulifloxacin plus piperacillin/tazobactam against clinical isolates of Enterobacteriaceae producing extended-spectrum or AmpC-type β-lactamases].
2010 Dec
[Susceptibility surveillance of clinical isolates to fluoroquinolone antimicrobial agents from 2003 to 2008: post-marketing study of prulifloxacin].
2010 Jun
Patents

Sample Use Guides

One 600 mg tablet is sufficient. For patients with complicated lower urinary tract infections or acute exacerbation of bronchitis - one 600 mg tablet once daily for up to a maximum of 10 days of treatment
Route of Administration: Oral
Activity of prulifloxacin against Gram-negative and -positive bacteria (MIC50) is 0.015-2 mg/L
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:33:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:33:24 GMT 2023
Record UNII
C38638H76Y
Record Status Validated (UNII)
Record Version
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Name Type Language
ULIFLOXACIN
INN   WHO-DD  
INN  
Official Name English
Ulifloxacin [WHO-DD]
Common Name English
ulifloxacin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
Code System Code Type Description
PUBCHEM
124225
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
MESH
C074190
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
CAS
112984-60-8
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL345937
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
NCI_THESAURUS
C76925
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
INN
8346
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID0057621
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
FDA UNII
C38638H76Y
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
SMS_ID
300000037003
Created by admin on Fri Dec 15 16:33:24 GMT 2023 , Edited by admin on Fri Dec 15 16:33:24 GMT 2023
PRIMARY
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