NAV
Explore a selection of essential drug information below, or:
Unlock enhanced features & extensive drug insights. Create a free account.
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

Fleroxacin

Explore a selection of our essential drug information below, or:

CREATE FREE ACCOUNT
Full Drug Profiles
Unlock enhanced features & extensive drug insights, including detailed interaction data & regulatory status. Create a free account.
SUBSCRIBERECOMMENDED FOR PHARMA
Data Packages
Explore the full scope of our drug knowledge tailored for pharmaceutical research needs in our data library. Learn more.

Identification

Generic Name
Fleroxacin
DrugBank Accession Number
DB04576
Background

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It strongly inhibits the DNA-supercoiling activity of DNA gyrase. Fleroxacin is not an inhibitor of CYP1A2.1

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 369.344
Monoisotopic: 369.130025941
Chemical Formula
C17H18F3N3O3
Synonyms
  • Fleroxacin
  • Fleroxacine
  • Fleroxacino
  • Fleroxacinum
  • Fleroxicin
  • FLRX
External IDs
  • AM 833
  • Ro 23-6240
  • RO 23-6240/000
  • RO-236240
  • RO-236240000
Unlock the secrets to drugging the undruggable
Discover how groundbreaking research is turning "undruggable" targets into therapeutic opportunities.
Download eBook
Unlock the secrets to drugging the undruggable
Download eBook

Pharmacology

Indication

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It strongly inhibits the DNA-supercoiling activity of DNA gyrase.

Mechanism of action

The inhibition of DNA gyrase and DNA topoisomerase 2 leads ultimately to cell death as these enzymes are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.

TargetActionsOrganism
ADNA topoisomerase 2-beta
inhibitor
Humans
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA topoisomerase 2-alpha
inhibitor
Humans
Absorption

Rapidly and well absorbed from the gastrointestinal tract after oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Fleroxacin.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Fleroxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Fleroxacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Fleroxacin.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Fleroxacin.
Food Interactions
  • Avoid milk and dairy products.
  • Limit caffeine intake.
  • Take with a full glass of water.
  • Take with or without food.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Megalocin / Megalone / Megalosin / Quinodis

Categories

ATC Codes
J01MA08 — Fleroxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
N-arylpiperazines / Fluoroquinolones / Aminoquinolines and derivatives / Hydroquinolones / Haloquinolines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-methylpiperazines / Aryl fluorides
show 14 more
Substituents
1,4-diazinane / Alkyl fluoride / Alkyl halide / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, fluoroquinolone antibiotic (CHEBI:31810)
Affected organisms
Not Available

Chemical Identifiers

UNII
N804LDH51K
CAS number
79660-72-3
InChI Key
XBJBPGROQZJDOJ-UHFFFAOYSA-N
InChI
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)
IUPAC Name
6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CN1CCN(CC1)C1=C(F)C=C2C(=O)C(=CN(CCF)C2=C1F)C(O)=O

References

Synthesis Reference
US4398029
General References
  1. Fuhr U, Anders EM, Mahr G, Sorgel F, Staib AH: Inhibitory potency of quinolone antibacterial agents against cytochrome P450IA2 activity in vivo and in vitro. Antimicrob Agents Chemother. 1992 May;36(5):942-8. [Article]
KEGG Drug
D01716
KEGG Compound
C13179
PubChem Compound
3357
PubChem Substance
46506357
ChemSpider
3240
RxNav
42322
ChEBI
31810
ChEMBL
CHEMBL6273
ZINC
ZINC000003786299
Therapeutic Targets Database
DAP000928
PharmGKB
PA164774762
Wikipedia
Fleroxacin

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)270 dec °CPhysProp
logP0.24ROSS,DL ET AL. (1992) (ION-CORRECT)
Caco2 permeability-4.81ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.284 mg/mLALOGPS
logP0.3ALOGPS
logP1.12Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)5.44Chemaxon
pKa (Strongest Basic)6.06Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area64.09 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity90.84 m3·mol-1Chemaxon
Polarizability34.71 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-0169000000-c300db33eb5021a5c529
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0169000000-c300db33eb5021a5c529
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0009000000-571ea80a29e45af56558
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-432ed2ecbfe407d959c7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-ca67fefe1afd57d18a96
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-0049000000-a72982dd2249e507f35e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ffx-0019000000-467be39811017734c143
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0097000000-3d6a9072bc44ca583dbe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.8585
predicted
DeepCCS 1.0 (2019)
[M+H]+183.2165
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.47551
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. DNA topoisomerase 2-beta
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand. Plays a role in B-cell differentiation
Specific Function
ATP binding
Gene Name
TOP2B
Uniprot ID
Q02880
Uniprot Name
DNA topoisomerase 2-beta
Molecular Weight
183265.825 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. DNA gyrase subunit A
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
A type II topoisomerase that negatively supercoils closed circular double-stranded (ds) DNA in an ATP-dependent manner to modulate DNA topology and maintain chromosomes in an underwound state. Negative supercoiling favors strand separation, and DNA replication, transcription, recombination and repair, all of which involve strand separation. Also able to catalyze the interconversion of other topological isomers of dsDNA rings, including catenanes and knotted rings. Type II topoisomerases break and join 2 DNA strands simultaneously in an ATP-dependent manner.
Specific Function
ATP binding
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
References
  1. Naber KG: Fleroxacin overview. Chemotherapy. 1996 Mar;42 Suppl 1:1-9. [Article]
  2. Asahina Y, Iwase K, Iinuma F, Hosaka M, Ishizaki T: Synthesis and antibacterial activity of 1-(2-fluorovinyl)-7-substituted-4-quinolone-3-carboxylic acid derivatives, conformationally restricted analogues of fleroxacin. J Med Chem. 2005 May 5;48(9):3194-202. [Article]
Details3. DNA topoisomerase 4 subunit A
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Specific Function
ATP binding
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
References
  1. Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92. [Article]
  2. Chaudhry U, Ray K, Bala M, Saluja D: Mutation patterns in gyrA and parC genes of ciprofloxacin resistant isolates of Neisseria gonorrhoeae from India. Sex Transm Infect. 2002 Dec;78(6):440-4. [Article]
  3. Lee JK, Lee YS, Park YK, Kim BS: Mutations in the gyrA and parC genes in ciprofloxacin-resistant clinical isolates of Acinetobacter baumannii in Korea. Microbiol Immunol. 2005;49(7):647-53. [Article]
  4. Leavis HL, Willems RJ, Top J, Bonten MJ: High-level ciprofloxacin resistance from point mutations in gyrA and parC confined to global hospital-adapted clonal lineage CC17 of Enterococcus faecium. J Clin Microbiol. 2006 Mar;44(3):1059-64. [Article]
Details4. DNA topoisomerase 2-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand (PubMed:17567603, PubMed:18790802, PubMed:22013166, PubMed:22323612). May play a role in regulating the period length of BMAL1 transcriptional oscillation (By similarity)
Specific Function
ATP binding
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Robinson MJ, Martin BA, Gootz TD, McGuirk PR, Osheroff N: Effects of novel fluoroquinolones on the catalytic activities of eukaryotic topoisomerase II: Influence of the C-8 fluorine group. Antimicrob Agents Chemother. 1992 Apr;36(4):751-6. [Article]
  3. Hussy P, Maass G, Tummler B, Grosse F, Schomburg U: Effect of 4-quinolones and novobiocin on calf thymus DNA polymerase alpha primase complex, topoisomerases I and II, and growth of mammalian lymphoblasts. Antimicrob Agents Chemother. 1986 Jun;29(6):1073-8. [Article]
  4. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at September 11, 2007 15:20 / Updated at August 26, 2024 19:23