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
SMILES
CC1SC2=C(C(O)=O)C(=O)C3=C(C=C(N4CCNCC4)C(F)=C3)N12
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)
| 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 | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16286954 | https://adisinsight.springer.com/drugs/800015025 | https://www.ncbi.nlm.nih.gov/pubmed/15456336http://www.leespharm.com/file/product/Unidrox%20PIL%20HK%20ver%202012.pdfCurator's Comment: description was created based on several sources, including
https://hal.archives-ouvertes.fr/hal-00679605/document
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16286954 | https://adisinsight.springer.com/drugs/800015025 | https://www.ncbi.nlm.nih.gov/pubmed/15456336http://www.leespharm.com/file/product/Unidrox%20PIL%20HK%20ver%202012.pdf
Curator's Comment: description was created based on several sources, including
https://hal.archives-ouvertes.fr/hal-00679605/document
Prulifloxacin is a prodrug of ulifloxacin which has been approved in Italy, Japan, China, India and Greece, for treatment of infections caused by susceptible bacteria, in the following conditions: acute uncomplicated lower urinary tract infections (simple cystitis); complicated lower urinary tract infections; acute exacerbation of chronic bronchitis; gastroenteritis, including infectious diarrheas. Like other fluoroquinolones, prulifloxacin prevents bacterial DNA replication, transcription, repair and recombination through inhibition of bacterial DNA gyrase.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311224 |
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Target ID: CHEMBL2363076 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unidrox Approved UseUnidrox 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 UseUnidrox 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 UseThe treatment of gastroenteritis, including infectious diarrheas. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.03 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.68 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.88 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.09 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.81 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1.41 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.99 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.72 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.41 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.13 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
9.67 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
450 mg single, oral dose: 450 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12705176/ |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.92 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
54.8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7983237/ |
300 mg 2 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ULIFLOXACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 mg 1 times / day steady-state, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Gastric pain, Diarrhoea... Other AEs: Gastric pain (9 patients) Sources: Diarrhoea (1 pt) Dyspepsia (1 pt) Vomiting (2 patients) Headache (1 pt) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diarrhoea | 1 pt | 600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Dyspepsia | 1 pt | 600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Headache | 1 pt | 600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | 2 patients | 600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastric pain | 9 patients | 600 mg 1 times / day steady-state, oral Studied dose Dose: 600 mg, 1 times / day Route: oral Route: steady-state Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [In vitro synergism of ulifloxacin plus piperacillin/tazobactam against clinical isolates of Enterobacteriaceae producing extended-spectrum or AmpC-type β-lactamases]. | 2010-12 |
|
| [Susceptibility surveillance of clinical isolates to fluoroquinolone antimicrobial agents from 2003 to 2008: post-marketing study of prulifloxacin]. | 2010-06 |
|
| Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine. | 2010-04-16 |
|
| Effects of prulifloxacin on cardiac repolarization in healthy subjects: a randomized, crossover, double-blind versus placebo, moxifloxacin-controlled study. | 2010 |
|
| Active uptake of ulifloxacin from plasma to lung that controls its concentration in epithelial lining fluid. | 2009-06 |
|
| Prulifloxacin: clinical studies of a broad-spectrum quinolone agent. | 2009-02 |
|
| Penetration of orally administered prulifloxacin into human prostate tissue. | 2009 |
|
| Determination of ulifloxacin, the active metabolite of prulifloxacin, in human plasma by a 96-well format solid-phase extraction and capillary zone electrophoresis. | 2008-09-01 |
|
| Proposal of membrane transport mechanism of protein-unbound ulifloxacin into epithelial lining fluid determined by improved microdialysis. | 2008-09 |
|
| Simultaneous determination of Ciprofloxacin and the active metabolite of Prulifloxacin in aqueous human humor by high-performance liquid chromatography. | 2008-07-15 |
|
| Effects of fluoroquinolones on bacterial adhesion and on preformed biofilm of strains isolated from urinary double J stents. | 2008-04 |
|
| Determination of ulifloxacin by terbium-sensitized fluorescence with second-order scattering and its applications. | 2007-12 |
|
| Transporter-mediated hepatic uptake of ulifloxacin, an active metabolite of a prodrug-type new quinolone antibiotic prulifloxacin, in rats. | 2007-10 |
|
| Involvement of breast cancer resistance protein (ABCG2) in the biliary excretion mechanism of fluoroquinolones. | 2007-10 |
|
| Activity of ulifloxacin against clinical hospital isolates. | 2007-09 |
|
| 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 the active metabolite of prulifloxacin in human plasma by liquid chromatography-tandem mass spectrometry. | 2006-03-07 |
|
| Prulifloxacin: a new antibacterial fluoroquinolone. | 2006-02 |
|
| Pharmacologic characteristics of prulifloxacin. | 2006 |
|
| Prulifloxacin: a new fluoroquinolone for the treatment of acute exacerbation of chronic bronchitis. | 2006 |
|
| Synergistic effect of fosfomycin and fluoroquinolones against Pseudomonas aeruginosa growing in a biofilm. | 2005-10 |
|
| Interpretive criteria for disk diffusion susceptibility testing of ulifloxacin, the active metabolite of prulifloxacin. | 2005-04 |
|
| Penetration of orally administered prulifloxacin into human lung tissue. | 2005 |
|
| Prulifloxacin. | 2004 |
|
| Molecular characterization of clinical Streptococcus pneumoniae isolates with reduced susceptibility to fluoroquinolones emerging in Italy. | 2004 |
|
| Involvement of multiple transport systems in the disposition of an active metabolite of a prodrug-type new quinolone antibiotic, prulifloxacin. | 2003 |
|
| Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice. | 1996-12 |
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
Ulifloxacin was highly active against many Enterobacteriaceae, including Italian community or nosocomial isolates including Streptococcus spp., Staphylococcus aureus, and Spanish clinical isolates of E. coli (with activity against some nalidixic acid-resistant isolates) and Klebsiella spp. (MIC90 ≤0.015–4.0 mg/L). Ulifloxacin showed good activity against Spanish clinical isolates of ciprofloxacin-susceptible P. aeruginosa (MIC90 1.0 mg/L) and gentamicin resistant P. aeruginosa (MIC90 0.2 mg/L).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:31:19 GMT 2025
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on
Mon Mar 31 18:31:19 GMT 2025
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| Record UNII |
C38638H76Y
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Name | Type | Language | ||
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C795
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124225
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C074190
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112984-60-8
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CHEMBL345937
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C76925
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8346
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DTXSID0057621
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C38638H76Y
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300000037003
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TARGET ORGANISM->INHIBITOR |
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ENANTIOMER -> RACEMATE |
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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ENANTIOMER -> RACEMATE |
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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PRODRUG -> METABOLITE ACTIVE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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