Finafloxacin

Identification

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Name
Finafloxacin
Accession Number
DB09047
Type
Small Molecule
Groups
Approved, Investigational
Description

Finafloxacin is a fluoroquinolone antibiotic indicated in the treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. Finafloxacin is marketed by Novartis under the brand Xtoro™, and was approved by the FDA in December 2014.

Structure
Thumb
Synonyms
  • 8-Cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
  • Finafloxacin
  • gastrochinolon
  • gastroquinolone
External IDs
AL-60371 / BY 377 / BY-377
Product Ingredients
IngredientUNIICASInChI Key
finafloxacin hydrochloride2G22PNZ052209342-41-6CQMSQUOHWYYEKM-MOGJOVFKSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
XtoroSuspension0.3 %Auricular (otic)Alcon, Inc.Not applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
D26OSN9Q4R
CAS number
209342-40-5
Weight
Average: 398.394
Monoisotopic: 398.139033271
Chemical Formula
C20H19FN4O4
InChI Key
FYMHQCNFKNMJAV-HOTGVXAUSA-N
InChI
InChI=1S/C20H19FN4O4/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28)/t15-,16-/m0/s1
IUPAC Name
7-[(4aS,7aS)-octahydropyrrolo[3,4-b]morpholin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
[H][C@]12CN(C[C@]1([H])OCCN2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1C#N)C(O)=O

Pharmacology

Indication

Finafloxacin is indicated for the treatment of acute otitis externa (AOE) with or without an otowick, caused by susceptible strains of Pseudomonas aeruginosa and Staphylococcus aureus in patients age 1 year and older.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

Finafloxacin is a fluoroquinolone antibiotic, which selectively inhibit bacterial type II topoisomerase enzymes, DNA gyrase and topoisomerase IV, which are required for bacterial DNA replication, transcription, 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
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

-Finafloxacin was shown to be genotoxic and clastogenic in vitro, with and without metabolic activation, and in vivo. -General toxicity studies in rats have confirmed sperm toxicity following oral and intravenous dosing. -At 500 mg/kg/day, males were completely infertile, presumably due to low sperm count and sperm immobility.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-positive Bacteria
  • Pseudomonas aeruginosa
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [PubMed:25808831]
External Links
KEGG Drug
D10575
PubChem Compound
11567473
PubChem Substance
310264991
ChemSpider
9742243
ChEBI
85176
ChEMBL
CHEMBL1908370
Wikipedia
Finafloxacin
AHFS Codes
  • 52:04.04 — Antibacterials
FDA label
Download (389 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHelicobacter Infections / Urinary Tract Infections (UTIs)1
1CompletedTreatmentPharmacokinetic and Tolerability of Finafloxacin1
1WithdrawnBasic ScienceOtitis Media (OM)1
2CompletedTreatmentGram-Negative Bacterial Infections / Helicobacter Infections / Indigestion1
2CompletedTreatmentUrinary Tract Infections (UTIs)1
2TerminatedTreatmentAcute Otitis Media1
3CompletedTreatmentAcute Otitis Externa2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionAuricular (otic)0.3 %
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6133206No2000-10-172017-04-04Us
US8536167No2013-09-172031-08-08Us
US9119859No2015-09-012030-07-02Us
US6432948No2002-08-132017-04-12Us
US6133260No2000-10-172017-04-12Us
US9504691No2016-11-292033-11-21Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Liquid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.208 mg/mLALOGPS
logP-0.59ALOGPS
logP-1.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
pKa (Strongest Basic)7.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.9 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.08 m3·mol-1ChemAxon
Polarizability39.75 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Fluoroquinolones / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides / Morpholines
show 15 more
Substituents
Quinoline-3-carboxylic acid / Fluoroquinolone / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Tertiary aliphatic/aromatic amine / Dialkylarylamine
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, tertiary amino compound, monocarboxylic acid, secondary amino compound, nitrile, cyclopropanes, quinolone (CHEBI:85176)

Targets

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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [PubMed:25808831]
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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [PubMed:25808831]
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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [PubMed:25808831]

Drug created on April 30, 2015 16:28 / Updated on June 19, 2019 12:52