FLEROXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)C2=C(F)C3=C(C=C2F)C(=O)C(=CN3CCF)C(O)=O

InChI

InChIKey=XBJBPGROQZJDOJ-UHFFFAOYSA-N

InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8861529
Curator's Comment: description was created based on several sources, including, http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf

Fleroxacin is an anti-bacterial agent developed for the treatment of uncomplicated cystitis in women, uncomplicated gonococcal infections, bacterial enteritis, and traveler's diarrea, urinary tract infection, pyelonephritis, skin, soft tissue, bone and joint infections, and lower respiratory tract infections. Fleroxacin acts on bacterials by inhibiting DNA gyrase and topoisomerase IV. Although the current status of the drug in Europe and in the USA is unknown, there is information about its approval and usage in China.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf	Inhibitor 8504
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8861529	Curative		Approved 8583	QUINODIS Approved Use Unknown

C_max

Value	Dose	Analyte	Population
8.7 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.7 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN sputum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.3 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN sputum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
6.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
99 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
149 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN sputum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10606835/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN sputum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
90 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
82.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
104 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
89 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8851614/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
96.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
83.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
86.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
77.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
8.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8203844/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	FLEROXACIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / 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: https://pubmed.ncbi.nlm.nih.gov/2110437/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	Disc. AE: Psychosis, Nausea... Other AEs: Photosensitivity, vomiting... AEs leading to discontinuation/dose reduction: Psychosis (1 pt) Nausea (5 patients) Other AEs: Photosensitivity (1 pt) vomiting (8 patients) Hot flushes (1 pt) Sleeplessness (2 patients) Angina pectoris (1 pt) Dysgeusia (2 patients) Eosinophilia (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/
200 mg 1 times / day steady-state, oral Studied dose Dose: 200 mg, 1 times / day Route: oral Route: steady-state Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	Disc. AE: Oliguria, Photosensitivity... Other AEs: Nausea, vomiting... AEs leading to discontinuation/dose reduction: Oliguria (1 pt) Photosensitivity (1 pt) Nausea (1 pt) Other AEs: Nausea (2 patients) vomiting (2 patients) Sleeplessness (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/
400 mg 1 times / day steady-state, oral Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady-state Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	Disc. AE: oliguria, psychosis... AEs leading to discontinuation/dose reduction: oliguria (1 pt) psychosis (1 pt) photosensitivity (1 pt) insomnia (1 pt) nausea (9 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/
400 mg 1 times / day steady-state, oral Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady-state Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/	Disc. AE: Nausea, vomiting... Other AEs: Hot flushes, Sleeplessness... AEs leading to discontinuation/dose reduction: Nausea (3 patients) vomiting (3 patients) Sleeplessness (1 pt) Other AEs: Hot flushes (1 pt) Sleeplessness (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/2110437/
400 mg 1 times / day steady-state, oral Studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady-state Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8452177/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8452177/	Disc. AE: gastrointestinal disorders, gastrointestinal disorders... Other AEs: gastrointestinal disorders, nervous system disorders... AEs leading to discontinuation/dose reduction: gastrointestinal disorders (7 patients) gastrointestinal disorders (7 patients) Other AEs: gastrointestinal disorders (25 patients) nervous system disorders (25 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8452177/

AEs

PubMed

Title	Date	PubMed
Preparation of high-affinity rabbit monoclonal antibodies for ciprofloxacin and development of an indirect competitive ELISA for residues in milk.	2010-10	20872990
Cephalosporin Resistance in Neisseria gonorrhoeae.	2010-09	20927291
Biopsy proven acute interstitial nephritis after treatment with moxifloxacin.	2010-08-23	20731847
Comparative in vitro activity of Meropenem, Imipenem and Piperacillin/tazobactam against 1071 clinical isolates using 2 different methods: a French multicentre study.	2010-03-18	20298555
Determination of fluoroquinolone antibiotics in environmental water samples based on magnetic molecularly imprinted polymer extraction followed by liquid chromatography-tandem mass spectrometry.	2010-03-03	20152262
Multifocal aggressive squamous cell carcinomas induced by prolonged voriconazole therapy: a case report.	2010	21209800
Synergistic antitumor effects of fleroxacin with 5-fluorouracil in vitro and in vivo for bladder cancer cell lines.	2009-12	19428092
Fluoroquinolone antibiotic determination in bovine, ovine and caprine milk using solid-phase extraction and high-performance liquid chromatography-fluorescence detection with ionic liquids as mobile phase additives.	2009-10-23	19268960
Application of ionic liquids in high performance reversed-phase chromatography.	2009-06-04	19582220
A comparison of fluoroquinolones versus other antibiotics for treating enteric fever: meta-analysis.	2009-06-03	19493939
Inter- and intramolecular photochemical reactions of fleroxacin.	2009-05-07	19385669
Enhanced separation of seven quinolones by capillary electrophoresis with silica nanoparticles as additive.	2009-03-15	19159781
Urinary tract infections and reduced risk of bladder cancer in Los Angeles.	2009-03-10	19174821
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009-03	19680903
Capillary electrophoresis with electrochemiluminescence detection for simultaneous determination of proline and fleroxacin in human urine.	2009-02	20355181
[Interaction of cucurbit[8]urils with ofloxacin, fleroxacin, gatifloxacin and sparfloxacin].	2009-02	19445224
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009-01	19449537
CE determination of quinolones in the presence of bovine serum albumin.	2009-01	19035388
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.	2009	19430173
Ionic liquids as mobile phase additives for the high-performance liquid chromatographic analysis of fluoroquinolone antibiotics in water samples.	2008-12	18854988
Utility of a single adjusting compartment: a novel methodology for whole body physiologically-based pharmacokinetic modelling.	2008-08-08	18687151
Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae.	2008-06	18471102
[Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry].	2008-05	18724674
Solution equilibria between aluminum(III) ion and some fluoroquinolone family members. Spectroscopic and potentiometric study.	2007-12	18057741
A rapid CE-potential gradient detection method for determination of quinolones.	2007-11	17941113
A flow injection chemiluminescence method for the determination of fluoroquinolone derivative using the reaction of luminol and hydrogen peroxide catalyzed by gold nanoparticles.	2007-05-15	19071726
1H and 19F NMR relaxation studies of fleroxacin with Micrococcus luteus.	2007-04-11	17254731
[Study on the ternary complex of FLRX, zinc(II) and BSA by the method of fluorescence].	2007-04	17608194
Interaction between fluoroquinolones and bovine serum albumin studied by affinity capillary electrophoresis.	2006-12	17159308
Moxifloxacin enhances antiproliferative and apoptotic effects of etoposide but inhibits its proinflammatory effects in THP-1 and Jurkat cells.	2006-10-23	17047652
Preparation of anti-pefloxacin antibody and development of an indirect competitive enzyme-linked immunosorbent assay for detection of pefloxacin residue in chicken liver.	2006-09-20	16968054
[Clinical observation on shufei granule in improving right ventricular function of patients with chronic pulmonary heart disease].	2006-08	16970099
The use of microscopy and three-dimensional visualization to evaluate the structure of microbial biofilms cultivated in the Calgary Biofilm Device.	2006	17242736
Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography.	2005-11	16318219
High-throughput metal susceptibility testing of microbial biofilms.	2005-10-03	16202124
[Determination of fleroxacin by photochemical fluorescence of zinc-fleroxacin complex].	2005-09	16379292
High-performance liquid chromatographic assay of fleroxacin in human serum using fluorescence detection.	2001-09-13	18968409
Fleroxacin 400 mg once daily versus ofloxacin 400 mg twice daily in skin and soft tissue infections.	1997-10-06	9309373
Atypical pneumonia in the Nordic countries: aetiology and clinical results of a trial comparing fleroxacin and doxycycline. Nordic Atypical Pneumonia Study Group.	1997-04	9145823
[In vitro anti-MAC activities of new quinolones in focus (2)].	1996-09	8999137
Trovafloxacin is active against Toxoplasma gondii.	1996-08	8843293
Two cases of fleroxacin-induced insomnia.	1994	7868853
In-vitro activities of quinolones against mycobacteria.	1993-12	8144420
Activity of topoisomerase inhibitors against Pneumocystis carinii in vitro and in an inoculated mouse model.	1993-07	8395791
Comparative in vitro and in vivo activity of fleroxacin and ofloxacin against various mycobacteria.	1991-09	1771676
Central nervous system toxicity of quinolones: human and animal findings.	1990-10	2124211
The antimicrobial activity of Fleroxacin RO 23-6240, a third generation fluoroquinolone derivative, tested in vitro.	1990	2112571
Adverse reactions in a dose-ranging study with a new long-acting fluoroquinolone, fleroxacin.	1989-10	2511802
Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.	1988-10	3144550
Activity of ciprofloxacin and other fluorinated quinolones against mycobacteria.	1987-04-27	3107379

Patents

Sample Use Guides

In Vivo Use Guide

400mg once daily (uncomplicated cystitis in women, uncomplicated gonococcal infections, bacterial enteritis, and traveler's diarrhea), 200 mg administered for 3 days (uncomplicated urinary tract infection).

Route of Administration: Oral

In Vitro Use Guide

In vitro activity of fleroxacin was tested against different bacteria isolates. The drug inhibited E.Coli (MIC 0.06-0.12 ug/ml), Klebsiella pneumoniae and K. oxytoca (MIC 0.12-1 ug/ml), Enterobacter cloacae and E. aerogenes (MIC <= 0.06-0.5 ug/ml), Citrobacterfreundii and C. diversus (MIC 0.06-1), Streptococcus faecalis (MIC 4-16 ug/ml), Pseudomonas aeruginosa (MIC 0.5-32 ug/ml), Salmonella spp. (MIC 0.06-0.12 ug/ml), etc.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:35 GMT 2025`
Record UNII	N804LDH51K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEGALOCIN

Preferred Name

English

FLEROXACIN

Official Name

English

RO-236240

Code

English

6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

Systematic Name

English

RO 23-6240/000

Code

English

fleroxacin [INN]

Common Name

English

RO-236240000

Code

English

FLEROXACIN [MART.]

Common Name

English

RO-23-6240/000

Code

English

FLEROXACIN [USAN]

Common Name

English

MEGALONE

Brand Name

English

FLEROXACIN [JAN]

Common Name

English

Fleroxacin [WHO-DD]

Common Name

English

FLEROXACIN [MI]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 6,8-DIFLUORO-1-(2-FLUOROETHYL)-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA08