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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:37 UTC
Update Date2022-03-07 02:57:13 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-carboxylateHMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point253 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2186 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.60Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available149.762http://allccs.zhulab.cn/database/detail?ID=AllCCS00001009
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+161.22430932474
DeepCCS[M-H]-158.86630932474
DeepCCS[M-2H]-191.75230932474
DeepCCS[M+Na]+167.31730932474
AllCCS[M+H]+157.932859911
AllCCS[M+H-H2O]+154.032859911
AllCCS[M+NH4]+161.532859911
AllCCS[M+Na]+162.532859911
AllCCS[M-H]-161.032859911
AllCCS[M+Na-2H]-160.532859911
AllCCS[M+HCOO]-160.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlumequineCC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O2870.4Standard polar33892256
FlumequineCC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O2053.3Standard non polar33892256
FlumequineCC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O2766.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Flumequine,1TMS,isomer #1CC1CCC2=C3C(=CC(F)=C2)C(=O)C(C(=O)O[Si](C)(C)C)=CN312430.4Semi standard non polar33892256
Flumequine,1TBDMS,isomer #1CC1CCC2=C3C(=CC(F)=C2)C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=CN312645.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flumequine GC-MS (Non-derivatized) - 70eV, Positivesplash10-02td-0190000000-d99bc59675d12cd5e4a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flumequine GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9166000000-57d63f1f1cfe90f640bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flumequine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flumequine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-qTof , Positive-QTOFsplash10-0ukc-2690000000-7afb48e267c7b334213b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOFsplash10-03di-0090000000-4562bd1b09907dc3b7002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOFsplash10-0uk9-0190000000-0bac3ec6458648a725c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QTOF , positive-QTOFsplash10-0fk9-0980000000-91b57386bd019dd7838b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-03di-0090000000-938a6d39c487a729e57e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-03dl-0090000000-73779217b6427d238ce02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-01ox-0090000000-13657a0f167139ce56f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0h2f-0090000000-def6112d5472cfde4da72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0fk9-0190000000-56e0b22aa033cf49c8c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0fk9-0980000000-e04498a4742bec91275e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0ufs-2900000000-068e7a9b1ae656d70d012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0f92-9800000000-b99a0e425235a91285332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-0f6t-9300000000-164deed4d2600172d8712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine , positive-QTOFsplash10-01ox-0090000000-7b3c06efa7853de57efb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine , positive-QTOFsplash10-0ukc-2690000000-7afb48e267c7b334213b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine LC-ESI-QFT , positive-QTOFsplash10-03di-0090000000-9604f2662310bea2bfe72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 90V, Positive-QTOFsplash10-0fk9-0890000000-c7445bd8c0c09c1feef72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 20V, Positive-QTOFsplash10-03dl-0090000000-305e228c2c2a38446f192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 35V, Positive-QTOFsplash10-03di-0090000000-4565c8d43013294a9ff42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 75V, Positive-QTOFsplash10-0fk9-0190000000-60944c1b22ed1678b2162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 30V, Positive-QTOFsplash10-03dl-0090000000-920a27df0f353f1bcdce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 60V, Positive-QTOFsplash10-0h2f-0090000000-50b738ad21bc91a53f532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 30V, Positive-QTOFsplash10-03dl-0090000000-73779217b6427d238ce02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 40V, Positive-QTOFsplash10-0uk9-0190000000-3a4831235aafed28688d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flumequine 10V, Positive-QTOFsplash10-03di-0090000000-fa10da39611fc93932622021-09-20HMDB team, MONAView Spectrum
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 IDNot Available
Good Scents IDrw1080101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available