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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014610
Secondary Accession Numbers
  • HMDB14610
Metabolite Identification
Common NameEnoxacin
DescriptionEnoxacin, also known as ENX or penetrex, belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group. Enoxacin is a drug which is used for the treatment of adults (≥18 years of age) with the following infections caused by susceptible strains of the designated microorganisms: (1) uncomplicated urethral or cervical gonorrhea due to neisseria gonorrhoeae, (2) uncomplicated urinary tract infections (cystitis) due to escherichia coli, staphylococcus epidermidis, or staphylococcus saprophyticus, and (3) complicated urinary tract infections due to escherichia coli, klebsiella pneumoniae, proteus mirabilis, pseudomonas aeruginosa, staphylococcus epidermidis, or enterobacter cloacae. Enoxacin is a very strong basic compound (based on its pKa).
Structure
Data?1582753198
Synonyms
ValueSource
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acidChEBI
1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidChEBI
EnoxacineChEBI
EnoxacinoChEBI
EnoxacinumChEBI
ENXKegg
PenetrexKegg
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylateGenerator
EnoxinHMDB
Rhône poulenc rorer brand OF enoxacin sesquihydrateHMDB
EnoxorHMDB
Enoxacin sesquihydrateHMDB
Faulding brand OF enoxacinHMDB
Pierre fabre brand OF enoxacin sesquihydrateHMDB
Rhône-poulenc rorer brand OF enoxacin sesquihydrateHMDB
Sesquihydrate, enoxacinHMDB
Chemical FormulaC15H17FN4O3
Average Molecular Weight320.3189
Monoisotopic Molecular Weight320.128468635
IUPAC Name1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Nameenoxacin
CAS Registry Number74011-58-8
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC1
InChI Identifier
InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
InChI KeyIDYZIJYBMGIQMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Fluoroquinolone
  • N-arylpiperazine
  • Pyridinylpiperazine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyridine
  • Aryl fluoride
  • Aryl halide
  • 1,4-diazinane
  • Piperazine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Azacycle
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 - 224 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.09 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.09 g/LALOGPS
logP-0.97ALOGPS
logP-0.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)5.5ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.95 m³·mol⁻¹ChemAxon
Polarizability31.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-200.73430932474
DeepCCS[M+Na]+175.96230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EnoxacinCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC13362.4Standard polar33892256
EnoxacinCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC12625.6Standard non polar33892256
EnoxacinCCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N=C12)N1CCNCC13173.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enoxacin,1TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCNCC3)N=C212783.3Semi standard non polar33892256
Enoxacin,1TMS,isomer #2CCN1C=C(C(=O)O)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C)CC3)N=C213021.5Semi standard non polar33892256
Enoxacin,2TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C)CC3)N=C212909.9Semi standard non polar33892256
Enoxacin,2TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C)CC3)N=C212874.3Standard non polar33892256
Enoxacin,2TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C)CC3)N=C213660.4Standard polar33892256
Enoxacin,1TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCNCC3)N=C212978.6Semi standard non polar33892256
Enoxacin,1TBDMS,isomer #2CCN1C=C(C(=O)O)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213227.8Semi standard non polar33892256
Enoxacin,2TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213292.2Semi standard non polar33892256
Enoxacin,2TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213281.7Standard non polar33892256
Enoxacin,2TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN([Si](C)(C)C(C)(C)C)CC3)N=C213798.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enoxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-1093000000-241451e66e16daabab832017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enoxacin GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-2039000000-3aaed983f26fc10675b92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enoxacin 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 - Enoxacin LC-ESI-qTof , Positive-QTOFsplash10-0pc0-2691000000-70495182f5d53b3e2f3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-00di-0009000000-c343d2455564f9c283ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-00di-0039000000-c8fb064ca8dcd22fd0512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-00di-0069000000-6f1cc68c72c995af17002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-05fr-0195000000-f089fb10889524908bb92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-0udi-0391000000-342a8fc923e2f74b2c2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin LC-ESI-QFT , positive-QTOFsplash10-0udi-0970000000-ad4c54479d1e64d34d712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin , positive-QTOFsplash10-0pc0-2691000000-70495182f5d53b3e2f3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 90V, Positive-QTOFsplash10-0udi-0970000000-bb0d7bb58daaabaa5d302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 60V, Positive-QTOFsplash10-05fr-0095000000-e5aecf8dae20a8173ba72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 75V, Positive-QTOFsplash10-0udi-0391000000-9c0a1a78d2583bd883392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 45V, Positive-QTOFsplash10-00di-0069000000-0e21ce47b095471d4c882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 30V, Positive-QTOFsplash10-00di-0039000000-56c5deec0bec46a6ccc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enoxacin 15V, Positive-QTOFsplash10-00di-0009000000-be580c5bfc772c5089912021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 10V, Positive-QTOFsplash10-00di-0029000000-b768a8766a208143ef4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 20V, Positive-QTOFsplash10-0fi9-3095000000-4d791244c2706826943a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 40V, Positive-QTOFsplash10-002f-3090000000-449abf1ea9e4d691dee52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 10V, Negative-QTOFsplash10-00or-0094000000-2dfdf64dcd801c3431372016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 20V, Negative-QTOFsplash10-002b-0190000000-6184732185fc1f37ecef2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 40V, Negative-QTOFsplash10-000e-6490000000-d025aca1fd56c040e7572016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 10V, Positive-QTOFsplash10-00di-0009000000-a42c0b05ac20f28b16b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 20V, Positive-QTOFsplash10-0udi-0029000000-7012f2139eff8aba307f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 40V, Positive-QTOFsplash10-0059-0091000000-8e32867f3fee05370a412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 10V, Negative-QTOFsplash10-0axs-0092000000-89be0bf06b51a26e9b3d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enoxacin 20V, Negative-QTOFsplash10-0002-0090000000-bbe88efb18ff81eade782021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00467 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00467 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00467
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3116
KEGG Compound IDC06979
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnoxacin
METLIN IDNot Available
PubChem Compound3229
PDB IDNot Available
ChEBI ID157175
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Maki T, Hirono I, Kondo H, Aoki T: Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae. J Fish Dis. 2008 Jun;31(6):461-8. doi: 10.1111/j.1365-2761.2008.00927.x. [PubMed:18471102 ]
  3. Snyder RD, Cooper CS: Photogenotoxicity of fluoroquinolones in Chinese hamster V79 cells: dependency on active topoisomerase II. Photochem Photobiol. 1999 Mar;69(3):288-93. [PubMed:10089819 ]