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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-18 08:43:18 UTC |
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Update Date | 2020-02-26 21:23:37 UTC |
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HMDB ID | HMDB0001929 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Levofloxacin |
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Description | Levofloxacin, 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. |
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Structure | |
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Synonyms | Value | Source |
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(-)-Ofloxacin | ChEBI | (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 acid | ChEBI | (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 acid | ChEBI | (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 acid | ChEBI | (S)-Ofloxacin | ChEBI | L-Ofloxacin | ChEBI | Levofloxacine | ChEBI | Levofloxacino | ChEBI | Levofloxacinum | ChEBI | Ofloxacin S-(-)-form | ChEBI | Cravit | Kegg | Levaquin | Kegg | (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-carboxylate | Generator | (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-carboxylate | Generator | (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-carboxylate | Generator | Floxin | HMDB | Levofloxacin hydrate | HMDB | Ofloxacin | HMDB | Quixin | HMDB | Ofloxacin, (S)-isomer | HMDB | Anhydrous, levofloxacin | HMDB | Levofloxacin anhydrous | HMDB |
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Chemical Formula | C18H20FN3O4 |
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Average Molecular Weight | 361.3675 |
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Monoisotopic Molecular Weight | 361.143784348 |
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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 |
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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 |
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CAS Registry Number | 100986-85-4 |
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SMILES | C[C@H]1COC2=C3N1C=C(C(O)=O)C(=O)C3=CC(F)=C2N1CCN(C)CC1 |
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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 |
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InChI Key | GSDSWSVVBLHKDQ-JTQLQIEISA-N |
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Chemical Taxonomy |
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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). |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzylethers |
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Direct Parent | Benzylethers |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-2019000000-30d77332fe9feb70a82d | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01dl-7009600000-d322709717558bd09e25 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-00gm-1315975420-b0c4e6cdef799fda69b4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0abc-3459425420-e8a4ecd2f8aea93fa660 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-0h9p-3513893500-1d5c8069419fa2c37ebb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-03di-0009000000-63138044688fa3ab0792 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-02t9-0019000000-265eec70cbb77077fbfa | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-03di-1290000000-3ff2c315dfac97ded8c5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0axr-1980000000-e31472e2487627c51cea | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0adl-1930000000-3cd445f16118ecf3f610 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-0049000000-3cbab894a4b0d1165e7d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-2492000000-62b30ac9148b06791816 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0009000000-6e3992e2c7f71e2e2d60 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02tc-0009000000-8e0f1b0fc3b80969c0dd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pi3-7097000000-363d82fc0e563a2423b0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-02t9-0009000000-bf579599f29511ea990c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0670-0096000000-9d4af124e757cd0455bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014r-0091000000-c5e349004a62406fb095 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.135 +/- 0.015 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.206 uM | Adult (>18 years old) | Not Specified | disseminated multidrug-resistant tuberculosis (MDRTB) | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.569 uM | Adult (>18 years old) | Not Specified | disseminated multidrug-resistant tuberculosis (MDRTB) | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.510 uM | Adult (>18 years old) | Not Specified | disseminated multidrug-resistant tuberculosis (MDRTB) | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.907 uM | Adult (>18 years old) | Not Specified | disseminated multidrug-resistant tuberculosis (MDRTB) | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.242 +/- 9.802 uM | Adult (>18 years old) | Both | external ventriculostomy | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 19.383 uM | Adult (>18 years old) | Not Specified | Tuberculosis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.763 uM | Adult (>18 years old) | Not Specified | Tuberculosis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.297 uM | Adult (>18 years old) | Not Specified | Tuberculosis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 12.599 uM | Adult (>18 years old) | Not Specified | Tuberculosis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.652 +/- 0.692 uM | Not Specified | Not Specified | 4hrs after administration of 300mg | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.510 uM | Not Specified | Not Specified | 2hrs after administration of 500mg | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 5.206 uM | Not Specified | Not Specified | 5hrs after administration of 750mg | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.242 +/- 9.802 uM | Not Specified | Not Specified | 2hrs after IV administration of 500mg | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.297 uM | Not Specified | Not Specified | 2hrs after administration of 750mg | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 4.652 +/- 0.692 uM | Not Specified | Not Specified | neurosurgical operations | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Predicted Concentrations |
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Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | Tuberculosis |
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- 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 |
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- 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 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB01137 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022746 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 131410 |
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KEGG Compound ID | C07660 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Levofloxacin |
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METLIN ID | Not Available |
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PubChem Compound | 149096 |
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PDB ID | Not Available |
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ChEBI ID | 63598 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Norrby SR: Levofloxacin. Expert Opin Pharmacother. 1999 Nov;1(1):109-19. [PubMed:11249554 ]
- 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 ]
- 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 ]
- 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 ]
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