Fleroxacin

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
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

Pharmacology

Indication

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone.

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Contraindications & Blackbox Warnings
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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 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
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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
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

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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
PhaseStatusPurposeConditionsCount

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

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insights and accelerate drug research.
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Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
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]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific 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.
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]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
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]

Drug created at September 11, 2007 15:20 / Updated at February 21, 2021 18:51