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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:37 UTC
Update Date2019-07-23 06:35:12 UTC
HMDB IDHMDB0041895
Secondary Accession Numbers
  • HMDB41895
Metabolite Identification
Common NameFlumequine
DescriptionCiprofloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division. Flumequine is a 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The molecular formula is C14H12FNO3 It is a white powder, odorless, flavorless, insoluble in water but soluble in organic solvent. Flumequine is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed. It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries. It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone. However this was a limited indication because only minimal serum levels were achieved. The first quinolone used was nalidixic acid (was marketed in many countries as Negram) followed by the fluoroquinolone flumequine. The first-generation fluoroquinolone agents, such as flumequine, had poor distribution into the body tissues and limited activity. As such they were used mainly for treatment of urinary tract infections. Flumequine (benzo quinolizine) was first patented in 1973, (German Patent) by Rikker Labs. Flumequine is a known antimicrobial compound described and claimed in U.S. Pat. No. 3,896,131 (Example 3), July 22, 1975. Flumequine is the first quinolone compound with a fluorine atom at the C6-position of the related quinolone basic molecular structure. Even though this was the first fluoroquinolone, it is oftentimes overlooked when classifying the drugs within this class by generations and excluded from such a list. There continues to be considerable debate as to whether or not this DNA damage is to be considered one of the mechanisms of action concerning the severe adverse reactions experienced by some patients following fluoroquinolone therapy.
Structure
Data?1563863712
Synonyms
ValueSource
FLMKegg
ApuroneKegg
9-Fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylateGenerator
FlumequineMeSH
Chemical FormulaC14H12FNO3
Average Molecular Weight261.2484
Monoisotopic Molecular Weight261.08012146
IUPAC Name7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0⁵,¹³]trideca-2,5(13),6,8-tetraene-3-carboxylic acid
Traditional Nameflumequine
CAS Registry Number42835-25-6
SMILES
CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O
InChI Identifier
InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)
InChI KeyDPSPPJIUMHPXMA-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Dihydroquinolone
  • Haloquinoline
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Benzenoid
  • Pyridine
  • Aryl fluoride
  • Aryl halide
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organofluoride
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point253 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.60Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.24 g/LALOGPS
logP1.62ALOGPS
logP2.42ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.87 m³·mol⁻¹ChemAxon
Polarizability25.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02td-0190000000-d99bc59675d12cd5e4a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9166000000-57d63f1f1cfe90f640bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ukc-2690000000-7afb48e267c7b334213bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-4562bd1b09907dc3b700Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uk9-0190000000-0bac3ec6458648a725c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fk9-0980000000-91b57386bd019dd7838bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-938a6d39c487a729e57eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dl-0090000000-73779217b6427d238ce0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ox-0090000000-13657a0f167139ce56f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0h2f-0090000000-def6112d5472cfde4da7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fk9-0190000000-56e0b22aa033cf49c8c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fk9-0980000000-e04498a4742bec91275eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ufs-2900000000-068e7a9b1ae656d70d01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f92-9800000000-b99a0e425235a9128533Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f6t-9300000000-164deed4d2600172d871Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01ox-0090000000-7b3c06efa7853de57efbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ukc-2690000000-7afb48e267c7b334213bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0090000000-9604f2662310bea2bfe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-3bd1178d60063e7ccbdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-0090000000-dd8fd2eb769868a3ed15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbd-0490000000-b900a0ae75214bdfabeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0090000000-dfabe88649d6507b3599Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0290000000-8169716cf15c21437036Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0hn1-1950000000-cb83bcde14854f583e5dSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDDB08972
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3257
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFlumequine
METLIN IDNot Available
PubChem Compound3374
PDB IDNot Available
ChEBI ID85269
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available