ULIFLOXACIN

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 Search

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
Sources: http://www.leespharm.com/file/product/Unidrox%20PIL%20HK%20ver%202012.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/16286954 | https://adisinsight.springer.com/drugs/800015025 | https://www.ncbi.nlm.nih.gov/pubmed/15456336
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12621742	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12621742	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Lower urinary tract infections 4 Sources: http://www.leespharm.com/file/product/Unidrox%20PIL%20HK%20ver%202012.pdf	Curative	Approved 8429	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.
Chronic bronchitis 51 Sources: http://www.leespharm.com/file/product/Unidrox%20PIL%20HK%20ver%202012.pdf	Curative	Approved 8429	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.
Gastroenteritis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19114678	Curative	Approved 8429	Quisnon Approved Use The treatment of gastroenteritis, including infectious diarrheas.

PubMed

Title	Date	PubMed
Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice.	1996 Dec	9006794
Involvement of multiple transport systems in the disposition of an active metabolite of a prodrug-type new quinolone antibiotic, prulifloxacin.	2003	15618759
Prulifloxacin.	2004	15456336
Molecular characterization of clinical Streptococcus pneumoniae isolates with reduced susceptibility to fluoroquinolones emerging in Italy.	2004 Fall	15383164
Interpretive criteria for disk diffusion susceptibility testing of ulifloxacin, the active metabolite of prulifloxacin.	2005 Apr	15920898
Synergistic effect of fosfomycin and fluoroquinolones against Pseudomonas aeruginosa growing in a biofilm.	2005 Oct	16286954
Prulifloxacin: a new fluoroquinolone for the treatment of acute exacerbation of chronic bronchitis.	2006	16359895
Determination of the active metabolite of prulifloxacin in human plasma by liquid chromatography-tandem mass spectrometry.	2006 Mar 7	16490405
Penetration of prulifloxacin into gynaecological tissues after single and repeated oral administrations.	2007	17963428
Transporter-mediated hepatic uptake of ulifloxacin, an active metabolite of a prodrug-type new quinolone antibiotic prulifloxacin, in rats.	2007 Oct	17965518
Effects of prulifloxacin on cardiac repolarization in healthy subjects: a randomized, crossover, double-blind versus placebo, moxifloxacin-controlled study.	2010	19995094
Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine.	2010 Apr 16	20177059
[In vitro synergism of ulifloxacin plus piperacillin/tazobactam against clinical isolates of Enterobacteriaceae producing extended-spectrum or AmpC-type β-lactamases].	2010 Dec	21196818
[Susceptibility surveillance of clinical isolates to fluoroquinolone antimicrobial agents from 2003 to 2008: post-marketing study of prulifloxacin].	2010 Jun	20976880

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

Official Name

English

Ulifloxacin [WHO-DD]

Common Name

English

ulifloxacin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795