You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:06 UTC
Update Date2018-03-12 22:11:01 UTC
HMDB IDHMDB0029861
Secondary Accession Numbers
  • HMDB29861
Metabolite Identification
Common NameEnrofloxacin
DescriptionEnrofloxacin is a veterinary antibacterial agent, used in poultry. Enrofloxacin is a fluoroquinolone antibiotic sold by the Bayer Corporation under the trade name Baytril(r). Enrofloxacin is currently FDA-approved for treatment of individual pets and domestic animals in the United States. In September 2005, the FDA withdrew approval of Baytril for use in water to treat flocks of poultry, as this practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium Campylobacter, a human pathogen. Fluoroquinolones such as ciprofloxacin are widely used in the treatment of human disease. Enrofloxacin is a synthetic chemotherapeutic agent from the class of the fluoroquinolone carboxylic acid derivatives. It has antibacterial activity against a broad spectrum of Gram-negative and Gram-positive bacteria. Its mechanism of action is not thoroughly understood, but it is believed to act by inhibiting bacterial DNA gyrase (a type-II topoisomerase), thereby preventing DNA supercoiling and DNA synthesis. It is a bactericidal agent. The bactericidal activity of enrofloxacin is concentration dependent, with susceptible bacteria cell death occurring within 20-30 minutes of exposure. Enrofloxacin has demonstrated a significant post-antibiotic effect for both Gram-negative and Gram-positive bacteria and is active in both stationary and growth phases of bacterial replication. http://www.fda.gov/cvm/Documents/baytrilDDL.pdf is a broken lin
Structure
Thumb
Synonyms
ValueSource
BaytrilChEBI
1-Cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 9ciHMDB
Bay VP 2674HMDB
CFPQHMDB
EndrofloxicinHMDB
EnrofloxacineHMDB
EnrofloxacinoHMDB
EnrofloxacinumHMDB
EnroxilHMDB
ERFXHMDB
N-EthylciprofloxacinHMDB
Bay-VP-2674MeSH
Chemical FormulaC19H22FN3O3
Average Molecular Weight359.3947
Monoisotopic Molecular Weight359.16451979
IUPAC Name1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namebaytril
CAS Registry Number93106-60-6
SMILES
CCN1CCN(CC1)C1=CC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O
InChI Identifier
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)
InChI KeySPFYMRJSYKOXGV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • Fluoroquinolone
  • N-arylpiperazine
  • Aminoquinoline
  • Haloquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • N-alkylpiperazine
  • Benzenoid
  • Pyridine
  • Aryl fluoride
  • Piperazine
  • Aryl halide
  • 1,4-diazinane
  • Vinylogous amide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Amine
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.61 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.98 m³·mol⁻¹ChemAxon
Polarizability37.53 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fyo-3039000000-59b648670bc1f1afc988View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-5007900000-0b5cc8ff0efe2333a5f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0089-0910000000-4fa87f5d615526253c23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0911000000-9ce11eb4989b09ec8c84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fr2-2693000000-3679c40c5dc700dbf56eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0019000000-e7a949a1162db1f03652View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08fr-0096000000-feb7821fd491a2011266View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0cdr-0290000000-0c9063320cd19d05594cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0009000000-0ceccd896185c92779f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02t9-0009000000-7c4f963eafeedb87df04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-2097000000-387e4f1c103c53c8ecc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ula-2290000000-89a0cbe2960439c00dc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uki-4890000000-a3285b7b0c6fedababb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uki-2940000000-22b987c1b1a6c35f6cfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ka2-1900000000-253c46c9c07205bffb6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-057i-3900000000-3d251200ff423bd15d97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a6r-8900000000-4692d2e949c698cfe6a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-4993689e3911744859f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udr-2490000000-1289668cde8adf202d13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0009000000-bb587a05511f39f01449View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0009000000-34f80939d0727bed0ca0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-398409151b5424b8f1f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-4029000000-1c66a6a32ad70a114cf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9030000000-08910ee7cc238036b863View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0009000000-82765856b0d615cad425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0179000000-f208ae885a779eee2c64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w2i-2190000000-c85c2f6bc3548f8bce76View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001086
KNApSAcK IDNot Available
Chemspider ID64326
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnrofloxacin
METLIN IDNot Available
PubChem Compound71188
PDB IDNot Available
ChEBI ID35720
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .