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
Enrofloxacin
Accession Number
DB11404
Type
Small Molecule
Groups
Vet approved
Description

Enrofloxacin is an antibiotic agent from the fluoroquinolone family produced by the Bayer Corporation. Enrofloxacin is approved by the FDA for its veterinary use. Due to the identification of fluoroquinolone-resistant strains of Campylobacter, in September 2005, the FDA withdrew the approval of enrofloxacin for its use in water to treat flocks of poultry.

Structure
Thumb
Synonyms
  • Enrofloxacin
  • Enrofloxacine
  • Enrofloxacino
  • Enrofloxacinum
External IDs
BAY VP 2674
International/Other Brands
Baytril
Categories
UNII
3DX3XEK1BN
CAS number
93106-60-6
Weight
Average: 359.3947
Monoisotopic: 359.16451979
Chemical Formula
C19H22FN3O3
InChI Key
SPFYMRJSYKOXGV-UHFFFAOYSA-N
InChI
InChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26)
IUPAC Name
1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CCN1CCN(CC1)C1=CC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O

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
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
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Enrofloxacin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Enrofloxacin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Enrofloxacin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Enrofloxacin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Enrofloxacin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Enrofloxacin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Enrofloxacin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Enrofloxacin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Enrofloxacin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Enrofloxacin.
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. Dick GC: Use of enrofloxacin. Vet Rec. 1993 Jun 12;132(24):616. [PubMed:8393228]
  2. Lizondo M, Pons M, Gallardo M, Estelrich J: Physicochemical properties of enrofloxacin. J Pharm Biomed Anal. 1997 Aug;15(12):1845-9. [PubMed:9278889]
  3. Bowser PR, Babish JG: Enrofloxacin in salmonids. Vet Hum Toxicol. 1991;33 Suppl 1:46-8. [PubMed:1926748]
  4. e Souza MJ, Bittencourt CF, Morsch LM: LC determination of enrofloxacin. J Pharm Biomed Anal. 2002 Jun 15;28(6):1195-9. [PubMed:12049983]
  5. Wu Y, Liao X, Wang Z, Chen Z, Zhou Y: [Hydrolysis characteristics of enrofloxacin]. Ying Yong Sheng Tai Xue Bao. 2006 Jun;17(6):1086-90. [PubMed:16964946]
  6. e Souza MJ, Bittencourt CF, e Souza Filho Pda S: Microbiological assay for enrofloxacin injection. Int J Pharm. 2004 Mar 1;271(1-2):287-91. [PubMed:15129996]
  7. Kan CA: Pharmacokinetics of enrofloxacin in chicken. Br Poult Sci. 1997 Dec;38(5):614. [PubMed:9511011]
  8. Dimitrova DJ, Lashev LD, Yanev SG, Pandova B: Pharmacokinetics of enrofloxacin in turkeys. Res Vet Sci. 2007 Jun;82(3):392-7. Epub 2006 Nov 14. [PubMed:17107697]
  9. Schroder J: Enrofloxacin: a new antimicrobial agent. J S Afr Vet Assoc. 1989 Jun;60(2):122-4. [PubMed:2691696]
  10. Salmon SA, Watts JL, Case CA, Hoffman LJ, Wegener HC, Yancey RJ Jr: Comparison of MICs of ceftiofur and other antimicrobial agents against bacterial pathogens of swine from the United States, Canada, and Denmark. J Clin Microbiol. 1995 Sep;33(9):2435-44. [PubMed:7494042]
  11. Aguilera R, Gutierrez OL, Sumano LH: Enhancement of enrofloxacin serum antibacterial activity by calcium primed broilers. Res Vet Sci. 2007 Feb;82(1):80-4. Epub 2006 Apr 18. [PubMed:16624360]
  12. Otker HM, Akmehmet-Balcioglu I: Adsorption and degradation of enrofloxacin, a veterinary antibiotic on natural zeolite. J Hazard Mater. 2005 Jul 15;122(3):251-8. [PubMed:15967281]
  13. Wu CC, Lin CH, Wang WS: Development of an enrofloxacin immunosensor based on label-free electrochemical impedance spectroscopy. Talanta. 2009 Jun 30;79(1):62-7. doi: 10.1016/j.talanta.2009.03.006. Epub 2009 Mar 14. [PubMed:19376344]
  14. Rico A, Dimitrov MR, Van Wijngaarden RP, Satapornvanit K, Smidt H, Van den Brink PJ: Effects of the antibiotic enrofloxacin on the ecology of tropical eutrophic freshwater microcosms. Aquat Toxicol. 2014 Feb;147:92-104. doi: 10.1016/j.aquatox.2013.12.008. Epub 2013 Dec 15. [PubMed:24380725]
  15. Suckow MA, Martin BJ, Bowersock TL, Douglas FA: Derivation of Pasteurella multocida-free rabbit litters by enrofloxacin treatment. Vet Microbiol. 1996 Jul;51(1-2):161-8. [PubMed:8828132]
  16. Miranda-Calderon JE, Gutierrez L, Flores-Alamo M, Garcia-Gutierrez P, Sumano H: Enrofloxacin hydro-chloride dihydrate. Acta Crystallogr Sect E Struct Rep Online. 2014 Mar 26;70(Pt 4):o468-9. doi: 10.1107/S1600536814006059. eCollection 2014 Apr 1. [PubMed:24826167]
  17. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
External Links
Human Metabolome Database
HMDB0029861
KEGG Drug
D02473
ChemSpider
64326
ChEBI
35720
ChEMBL
CHEMBL15511
Wikipedia
Enrofloxacin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedBasic ScienceHealthy Volunteers1

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 Solubility0.612 mg/mLALOGPS
logP0.58ALOGPS
logP1.15ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.69ChemAxon
pKa (Strongest Basic)6.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.09 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.98 m3·mol-1ChemAxon
Polarizability37.53 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0019000000-e7a949a1162db1f03652
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-08fr-0096000000-feb7821fd491a2011266
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0cdr-0290000000-0c9063320cd19d05594c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0009000000-0ceccd896185c92779f2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-02t9-0009000000-7c4f963eafeedb87df04
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ot-2097000000-387e4f1c103c53c8ecc9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ula-2290000000-89a0cbe2960439c00dc5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uki-4890000000-a3285b7b0c6fedababb2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uki-2940000000-22b987c1b1a6c35f6cfb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ka2-1900000000-253c46c9c07205bffb6f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-057i-3900000000-3d251200ff423bd15d97
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a6r-8900000000-4692d2e949c698cfe6a2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-4993689e3911744859f5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udr-2490000000-1289668cde8adf202d13
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-bb587a05511f39f01449
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0009000000-34f80939d0727bed0ca0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-08fr-0139000000-a48011f21becc5da55a9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0089-0910000000-4fa87f5d615526253c23
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-0149000000-977dbdede4137a9e8b1a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0911000000-9ce11eb4989b09ec8c84
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fr2-2693000000-3679c40c5dc700dbf56e

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
N-arylpiperazines / Fluoroquinolones / Aminoquinolines and derivatives / Hydroquinolones / Haloquinolines / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / N-alkylpiperazines / Aryl fluorides
show 13 more
Substituents
Quinoline-3-carboxylic acid / Fluoroquinolone / N-arylpiperazine / Aminoquinoline / Haloquinoline / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Dialkylarylamine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, N-arylpiperazine, cyclopropanes, N-alkylpiperazine, quinolone, quinolinemonocarboxylic acid (CHEBI:35720)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Sasaki K, Shimoda M: Possible drug-drug interaction in dogs and cats resulted from alteration in drug metabolism: A mini review. J Adv Res. 2015 May;6(3):383-92. doi: 10.1016/j.jare.2015.02.003. Epub 2015 Feb 24. [PubMed:26257936]

Drug created on February 25, 2016 11:26 / Updated on November 02, 2019 02:44