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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-18 08:43:18 UTC
Update Date2020-02-26 21:23:37 UTC
HMDB IDHMDB0001929
Secondary Accession Numbers
  • HMDB01929
Metabolite Identification
Common NameLevofloxacin
DescriptionLevofloxacin, also known as (S)-ofloxacin or cravit, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin. Levofloxacin is a drug which is used for the treatment of bacterial conjunctivitis caused by susceptible strains of the following organisms: corynebacterium species, staphylococus aureus, staphylococcus epidermidis, streptococcus pneumoniae, streptococcus (groups c/f/g), viridans group streptococci, acinetobacter lwoffii, haemophilus influenzae, serratia marcescens. Levofloxacin is a very strong basic compound (based on its pKa). Levofloxacin is a bitter tasting compound. Outside of the human body,. Levofloxacin is a potentially toxic compound. Levofloxacin is a synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin inhibits bacterial type II topoisomerases, topoisomerase IV and DNA gyrase.
Structure
Data?1582752217
Synonyms
ValueSource
(-)-OfloxacinChEBI
(3S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acidChEBI
(S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acidChEBI
(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acidChEBI
(S)-OfloxacinChEBI
L-OfloxacinChEBI
LevofloxacineChEBI
LevofloxacinoChEBI
LevofloxacinumChEBI
Ofloxacin S-(-)-formChEBI
CravitKegg
LevaquinKegg
(3S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylateGenerator
(S)-(-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylateGenerator
(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylateGenerator
FloxinHMDB
Levofloxacin hydrateHMDB
OfloxacinHMDB
QuixinHMDB
Ofloxacin, (S)-isomerHMDB
Anhydrous, levofloxacinHMDB
Levofloxacin anhydrousHMDB
Chemical FormulaC18H20FN3O4
Average Molecular Weight361.3675
Monoisotopic Molecular Weight361.143784348
IUPAC Name(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
Traditional Name(2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^{5,13}]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
CAS Registry Number100986-85-4
SMILES
C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1
InChI Identifier
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
InChI KeyGSDSWSVVBLHKDQ-JTQLQIEISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzylethers
Direct ParentBenzylethers
Alternative Parents
Substituents
  • Benzylether
  • Pyridine
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP-0.02ALOGPS
logP0.65ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.45ChemAxon
pKa (Strongest Basic)6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.94 m³·mol⁻¹ChemAxon
Polarizability36.69 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0006-2019000000-30d77332fe9feb70a82dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01dl-7009600000-d322709717558bd09e25Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00gm-1315975420-b0c4e6cdef799fda69b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0abc-3459425420-e8a4ecd2f8aea93fa660Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0h9p-3513893500-1d5c8069419fa2c37ebbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0009000000-63138044688fa3ab0792Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02t9-0019000000-265eec70cbb77077fbfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-1290000000-3ff2c315dfac97ded8c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0axr-1980000000-e31472e2487627c51ceaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0adl-1930000000-3cd445f16118ecf3f610Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0049000000-3cbab894a4b0d1165e7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2492000000-62b30ac9148b06791816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-6e3992e2c7f71e2e2d60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-0009000000-8e0f1b0fc3b80969c0ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi3-7097000000-363d82fc0e563a2423b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0009000000-bf579599f29511ea990cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0670-0096000000-9d4af124e757cd0455bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0091000000-c5e349004a62406fb095Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.135 +/- 0.015 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified5.206 uMAdult (>18 years old)Not Specifieddisseminated multidrug-resistant tuberculosis (MDRTB) details
Cerebrospinal Fluid (CSF)Detected and Quantified4.569 uMAdult (>18 years old)Not Specifieddisseminated multidrug-resistant tuberculosis (MDRTB) details
Cerebrospinal Fluid (CSF)Detected and Quantified5.510 uMAdult (>18 years old)Not Specifieddisseminated multidrug-resistant tuberculosis (MDRTB) details
Cerebrospinal Fluid (CSF)Detected and Quantified2.907 uMAdult (>18 years old)Not Specifieddisseminated multidrug-resistant tuberculosis (MDRTB) details
Cerebrospinal Fluid (CSF)Detected and Quantified11.242 +/- 9.802 uMAdult (>18 years old)Bothexternal ventriculostomy details
Cerebrospinal Fluid (CSF)Detected and Quantified19.383 uMAdult (>18 years old)Not SpecifiedTuberculosis details
Cerebrospinal Fluid (CSF)Detected and Quantified4.763 uMAdult (>18 years old)Not SpecifiedTuberculosis details
Cerebrospinal Fluid (CSF)Detected and Quantified11.297 uMAdult (>18 years old)Not SpecifiedTuberculosis details
Cerebrospinal Fluid (CSF)Detected and Quantified12.599 uMAdult (>18 years old)Not SpecifiedTuberculosis details
Cerebrospinal Fluid (CSF)Detected and Quantified4.652 +/- 0.692 uMNot SpecifiedNot Specified4hrs after administration of 300mg details
Cerebrospinal Fluid (CSF)Detected and Quantified5.510 uMNot SpecifiedNot Specified2hrs after administration of 500mg details
Cerebrospinal Fluid (CSF)Detected and Quantified5.206 uMNot SpecifiedNot Specified5hrs after administration of 750mg details
Cerebrospinal Fluid (CSF)Detected and Quantified11.242 +/- 9.802 uMNot SpecifiedNot Specified2hrs after IV administration of 500mg details
Cerebrospinal Fluid (CSF)Detected and Quantified11.297 uMNot SpecifiedNot Specified2hrs after administration of 750mg details
Cerebrospinal Fluid (CSF)Detected and Quantified4.652 +/- 0.692 uMNot SpecifiedNot Specifiedneurosurgical operations details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Tuberculosis
  1. Upton A, Woodhouse A, Vaughan R, Newton S, Ellis-Pegler R: Evolution of central nervous system multidrug-resistant Mycobacterium tuberculosis and late relapse of cryptic prosthetic hip joint tuberculosis: complications during treatment of disseminated isoniazid-resistant tuberculosis in an immunocompromised host. J Clin Microbiol. 2009 Feb;47(2):507-10. doi: 10.1128/JCM.01473-08. Epub 2008 Dec 24. [PubMed:19109477 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB01137
Phenol Explorer Compound IDNot Available
FooDB IDFDB022746
KNApSAcK IDNot Available
Chemspider ID131410
KEGG Compound IDC07660
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevofloxacin
METLIN IDNot Available
PubChem Compound149096
PDB IDNot Available
ChEBI ID63598
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Norrby SR: Levofloxacin. Expert Opin Pharmacother. 1999 Nov;1(1):109-19. [PubMed:11249554 ]
  2. Chow AT, Chen A, Lattime H, Morgan N, Wong F, Fowler C, Williams RR: Penetration of levofloxacin into skin tissue after oral administration of multiple 750 mg once-daily doses. J Clin Pharm Ther. 2002 Apr;27(2):143-50. [PubMed:11975700 ]
  3. Bielecka-Grzela S, Klimowicz A: Evaluation of ofloxacin penetration into the skin after a single oral dose assessed by cutaneous microdialysis. Pol J Pharmacol. 2003 Jul-Aug;55(4):613-8. [PubMed:14581720 ]
  4. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

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
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