Difloxacin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Difloxacin
Accession Number
DB11511
Type
Small Molecule
Groups
Vet approved
Description

Difloxacin is a synthetic fluoroquinolone used in veterinary. As an antibacterial, it presents a broad bactericidal spectrum and its effects are dependent on its concentration. However, it presents a reduced efficacy when compared to other fluoroquinolone antibacterials.

Structure
Thumb
Synonyms
  • Difloxacin
  • difloxacino
Product Ingredients
IngredientUNIICASInChI Key
Difloxacin hydrochlorideXJ0260HJ0O91296-86-5JFMGBGLSDVIOHL-UHFFFAOYSA-N
Categories
UNII
5Z7OO9FNFD
CAS number
98106-17-3
Weight
Average: 399.398
Monoisotopic: 399.13944781
Chemical Formula
C21H19F2N3O3
InChI Key
NOCJXYPHIIZEHN-UHFFFAOYSA-N
InChI
InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)
IUPAC Name
6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CN1CCN(CC1)C1=C(F)C=C2C(=C1)N(C=C(C(O)=O)C2=O)C1=CC=C(F)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Difloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Difloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Difloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Difloxacin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Difloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Difloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Difloxacin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Difloxacin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Difloxacin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Difloxacin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Atef M, el-Banna HA, Abd El-Aty AM, Goudah A: Pharmacokinetics of difloxacin in goats. Dtsch Tierarztl Wochenschr. 2002 Jul;109(7):320-3. [PubMed:12161971]
  2. Prabhakaran D, Sukul P, Lamshoft M, Maheswari MA, Zuhlke S, Spiteller M: Photolysis of difloxacin and sarafloxacin in aqueous systems. Chemosphere. 2009 Oct;77(6):739-46. doi: 10.1016/j.chemosphere.2009.08.031. Epub 2009 Sep 13. [PubMed:19751946]
  3. Olchowy TW, TerHune TN, Herrick RL: Efficacy of difloxacin in calves experimentally infected with Mannheimia haemolytica. Am J Vet Res. 2000 Jun;61(6):710-3. [PubMed:10850850]
  4. Granneman GR, Snyder KM, Shu VS: Difloxacin metabolism and pharmacokinetics in humans after single oral doses. Antimicrob Agents Chemother. 1986 Nov;30(5):689-93. [PubMed:3800345]
  5. Mavrogianni VS, Fthenakis GC: Efficacy of difloxacin against respiratory infections of lambs. J Vet Pharmacol Ther. 2005 Jun;28(3):325-8. [PubMed:15953209]
  6. van den Hoven R, Wagenaar JA, Walker RD: In vitro activity of difloxacin against canine bacterial isolates. J Vet Diagn Invest. 2000 May;12(3):218-23. [PubMed:10826834]
  7. Sukul P, Lamshoft M, Kusari S, Zuhlke S, Spiteller M: Metabolism and excretion kinetics of 14C-labeled and non-labeled difloxacin in pigs after oral administration, and antimicrobial activity of manure containing difloxacin and its metabolites. Environ Res. 2009 Apr;109(3):225-31. doi: 10.1016/j.envres.2008.12.007. Epub 2009 Jan 31. [PubMed:19181312]
  8. Fernandes PB, Chu DT, Bower RR, Jarvis KP, Ramer NR, Shipkowitz N: In vivo evaluation of A-56619 (difloxacin) and A-56620: new aryl-fluoroquinolones. Antimicrob Agents Chemother. 1986 Feb;29(2):201-8. [PubMed:3521473]
  9. Bansal MB, Thadepalli H: Activity of difloxacin (A-56619) and A-56620 against clinical anaerobic bacteria in vitro. Antimicrob Agents Chemother. 1987 Apr;31(4):619-21. [PubMed:3606066]
  10. Lamshoft M, Sukul P, Zuhlke S, Spiteller M: Behaviour of (14)C-sulfadiazine and (14)C-difloxacin during manure storage. Sci Total Environ. 2010 Mar 1;408(7):1563-8. doi: 10.1016/j.scitotenv.2009.12.010. Epub 2009 Dec 21. [PubMed:20022355]
External Links
KEGG Drug
D07828
KEGG Compound
C11234
ChemSpider
50725
ChEBI
4537
ChEMBL
CHEMBL6259
Wikipedia
Difloxacin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.126 mg/mLALOGPS
logP1.16ALOGPS
logP2.36ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)5.64ChemAxon
pKa (Strongest Basic)6.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.09 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.19 m3·mol-1ChemAxon
Polarizability39.25 Å3ChemAxon
Number of Rings4ChemAxon
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
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0013900000-2f0533cdd6722829bba3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0001900000-39559042c9c17f22b056
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0003900000-eeb11a494a85c69cc39d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0037900000-24e9d598116abf61643a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zfs-0196200000-7e5e7b2e464e8cee97c2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000900000-eb816b59e49880b716fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0000900000-45746cb99dbc2c1e8a5a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0pc0-0019500000-7c3ad675ae6a4c089ac6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f6t-1097400000-e4426c10a3fca116fd72
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052b-1192000000-dcd995c8456a1135ae84
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-2390000000-790df0725e0d72ae05b4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-2590000000-91ae82904bc16c72ce22
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-056r-3970000000-3d9a266fce5e4c244a56
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a7i-4930000000-6b3e52ca9dd7c42c65ee
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a7i-7910000000-6721a1b8ea16086eaca1

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Phenylquinolines
Direct Parent
Phenylquinolines
Alternative Parents
Quinoline carboxylic acids / Fluoroquinolones / N-arylpiperazines / Aminoquinolines and derivatives / Haloquinolines / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Fluorobenzenes
show 14 more
Substituents
Phenylquinoline / Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines (CHEBI:4537)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
This drug is a quinolone derivative, and these agents are known to inhibit CYP1A2.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [PubMed:19026171]

Drug created on February 26, 2016 10:28 / Updated on June 04, 2019 07:23