This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Difloxacin
- DrugBank Accession Number
- DB11511
- Background
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.
- Type
- Small Molecule
- Groups
- Vet approved
- Structure
Structure for Difloxacin (DB11511)
- Weight
- Average: 399.398
Monoisotopic: 399.13944781 - Chemical Formula
- C21H19F2N3O3
- Synonyms
- Difloxacin
- difloxacino
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Difloxacin. Aceclofenac Aceclofenac may increase the neuroexcitatory activities of Difloxacin. Acemetacin Acemetacin may increase the neuroexcitatory activities of Difloxacin. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Difloxacin. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Difloxacin. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Difloxacin. Acetylsalicylic acid Acetylsalicylic acid may increase the neuroexcitatory activities of Difloxacin. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Difloxacin. Acyclovir The metabolism of Acyclovir can be decreased when combined with Difloxacin. Adenosine The risk or severity of QTc prolongation can be increased when Difloxacin is combined with Adenosine. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Difloxacin hydrochloride XJ0260HJ0O 91296-86-5 JFMGBGLSDVIOHL-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- quinolines (CHEBI:4537)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 5Z7OO9FNFD
- CAS number
- 98106-17-3
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Mavrogianni VS, Fthenakis GC: Efficacy of difloxacin against respiratory infections of lambs. J Vet Pharmacol Ther. 2005 Jun;28(3):325-8. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D07828
- KEGG Compound
- C11234
- ChemSpider
- 50725
- ChEBI
- 4537
- ChEMBL
- CHEMBL6259
- ZINC
- ZINC000004099034
- Wikipedia
- Difloxacin
Clinical Trials
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
Property Value Source Water Solubility 0.126 mg/mL ALOGPS logP 1.16 ALOGPS logP 2.36 ChemAxon logS -3.5 ALOGPS pKa (Strongest Acidic) 5.64 ChemAxon pKa (Strongest Basic) 6.45 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 64.09 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 105.19 m3·mol-1 ChemAxon Polarizability 39.25 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- 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
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Munro AW: Cytochrome P450 1A1 opens up to new substrates. J Biol Chem. 2018 Dec 14;293(50):19211-19212. doi: 10.1074/jbc.H118.006715. Epub 2018 Dec 14. [Article]
Drug created at February 26, 2016 17:28 / Updated at February 21, 2021 18:53