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Record Information
Version3.6
Creation Date2006-05-18 08:43:18 UTC
Update Date2016-02-11 01:05:07 UTC
HMDB IDHMDB01929
Secondary Accession NumbersNone
Metabolite Identification
Common NameLevofloxacin
DescriptionLevofloxacin is a synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication. Levofloxacin is marketed by Ortho-McNeil under the trade name Levaquin. Chemically, levofloxacin is the S-enantiomer (L-isomer) of ofloxacin. -- Wikipedia.
Structure
Thumb
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
(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
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[7.3.1.0⁵,¹³]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
Traditional Namelevofloxacin
CAS Registry Number100986-85-4
SMILES
C[C@H]1COC2=C(N3CCN(C)CC3)C(F)=CC3=C2N1C=C(C(O)=O)C3=O
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 KeyInChIKey=GSDSWSVVBLHKDQ-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-arylpiperazine
  • Fluoroquinolone
  • Hydroxyquinoline
  • Dihydroquinolone
  • Aminoquinoline
  • Dihydroquinoline
  • Benzoxazine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Dialkylarylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Fluorobenzene
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.94 m3·mol-1ChemAxon
Polarizability36.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00gm-1315975420-b0c4e6cdef799fda69b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0abc-3459425420-e8a4ecd2f8aea93fa660View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0h9p-3513893500-1d5c8069419fa2c37ebbView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.135 +/- 0.015 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022746
KNApSAcK IDNot Available
Chemspider ID131410
KEGG Compound IDC07660
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01929
Metagene LinkHMDB01929
METLIN IDNot Available
PubChem Compound149096
PDB IDLFX
ChEBI ID63598
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [19212411 ]
  2. Norrby SR: Levofloxacin. Expert Opin Pharmacother. 1999 Nov;1(1):109-19. [11249554 ]
  3. 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. [11975700 ]
  4. 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. [14581720 ]

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