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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:58 UTC
HMDB IDHMDB0014610
Secondary Accession Numbers
  • HMDB14610
Metabolite Identification
Common NameEnoxacin
DescriptionEnoxacin, also known as penetrex or ENX, belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. Some isozymes of the cytochrome P-450 hepatic microsomal enzyme system are inhibited by enoxacin. 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). Enoxacin is a quinolone/fluoroquinolone antibiotic. Enoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. Enoxacin is only found in individuals that have used or taken this drug. After a single dose, greater than 40% was recovered in urine by 48 hours as unchanged drug. Enoxacin may be active against pathogens resistant to drugs that act by different mechanisms.
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 barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point220 - 224 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.09 g/LNot Available
LogP2.3Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-1093000000-241451e66e16daabab83Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-2039000000-3aaed983f26fc10675b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0pc0-2691000000-70495182f5d53b3e2f3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0009000000-c343d2455564f9c283abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0039000000-c8fb064ca8dcd22fd051Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0069000000-6f1cc68c72c995af1700Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fr-0195000000-f089fb10889524908bb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0391000000-342a8fc923e2f74b2c2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0970000000-ad4c54479d1e64d34d71Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0pc0-2691000000-70495182f5d53b3e2f3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0029000000-b768a8766a208143ef4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi9-3095000000-4d791244c2706826943aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3090000000-449abf1ea9e4d691dee5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0094000000-2dfdf64dcd801c343137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0190000000-6184732185fc1f37ecefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-6490000000-d025aca1fd56c040e757Spectrum
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 ID
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 ]