Finafloxacin

Identification

Generic Name
Finafloxacin
DrugBank Accession Number
DB09047
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 398.394
Monoisotopic: 398.139033271
Chemical Formula
C20H19FN4O4
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

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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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.

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
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Finafloxacin.
MagnesiumMagnesium can cause a decrease in the absorption of Finafloxacin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Vibrio cholerae CVD 103-HgR strain live antigenThe therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Finafloxacin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
finafloxacin hydrochloride2G22PNZ052209342-41-6CQMSQUOHWYYEKM-MOGJOVFKSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
XtoroSuspension0.3 % w/vAuricular (otic)Merlion Pharmaceuticals GmbhNot applicableNot applicableCanada flag

Categories

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
Fluoroquinolones / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides / Morpholines
show 15 more
Substituents
Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonitrile
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)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-positive Bacteria
  • Pseudomonas aeruginosa

Chemical Identifiers

UNII
D26OSN9Q4R
CAS number
209342-40-5
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

References

General References
  1. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [Article]
KEGG Drug
D10575
PubChem Compound
11567473
PubChem Substance
310264991
ChemSpider
9742243
RxNav
1598641
ChEBI
85176
ChEMBL
CHEMBL1908370
ZINC
ZINC000003985346
Wikipedia
Finafloxacin
FDA label
Download (389 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Otitis Externa2
2CompletedTreatmentAcute Pyelonephritis(APN) / Urinary Tract Infection1
2CompletedTreatmentDyspepsia / Gram-Negative Bacterial Infections / Helicobacter Infections1
2CompletedTreatmentUrinary Tract Infection1
2TerminatedTreatmentAcute Otitis Media (AOM)1
1CompletedTreatmentHealthy Subjects (HS)1
1CompletedTreatmentHelicobacter Infections / Urinary Tract Infection1
1CompletedTreatmentPharmacokinetic and Tolerability of Finafloxacin1
1CompletedTreatmentSafety and Tolerability1
1WithdrawnBasic ScienceOtitis Media (OM)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionAuricular (otic)0.3 % w/v
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6133206No2000-10-172017-04-04US flag
US8536167No2013-09-172031-08-08US flag
US9119859No2015-09-012030-07-02US flag
US6432948No2002-08-132017-04-12US flag
US6133260No2000-10-172017-04-12US flag
US9504691No2016-11-292033-11-21US flag

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

Targets

Drugtargets2
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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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [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. McKeage K: Finafloxacin: first global approval. Drugs. 2015 Apr;75(6):687-93. doi: 10.1007/s40265-015-0384-z. [Article]

Drug created on April 30, 2015 22:28 / Updated on September 16, 2021 13:04