Human Metabolome Database: Showing metabocard for Levofloxacin (HMDB0001929)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:43:18 UTC

Update Date

2020-02-26 21:23:37 UTC

HMDB ID

HMDB0001929

Secondary Accession Numbers

HMDB01929

Metabolite Identification

Common Name

Levofloxacin

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-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

Chemical Formula

C₁₈H₂₀FN₃O₄

Average Molecular Weight

361.3675

Monoisotopic Molecular Weight

361.143784348

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 Number

100986-85-4

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 Key

GSDSWSVVBLHKDQ-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).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:51380 )
pyridines (CHEBI:51380 )

Ontology

Physiological effect

Health effect:

Health condition:

Gastrointestinal disorders:

Nausea

Ingestion

Parenteral:

Dermal

Biological location:

Biofluid and excreta:

Organ and components:

Prostate

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	0.65	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.94 m³·mol⁻¹	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Prostate

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.135 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	17549677	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.206 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.569 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.510 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.907 uM	Adult (>18 years old)	Not Specified	disseminated multidrug-resistant tuberculosis (MDRTB)	11181130	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.242 +/- 9.802 uM	Adult (>18 years old)	Both	external ventriculostomy	14506016	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	19.383 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.763 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.297 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	12.599 uM	Adult (>18 years old)	Not Specified	Tuberculosis	19109477	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.652 +/- 0.692 uM	Not Specified	Not Specified	4hrs after administration of 300mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.510 uM	Not Specified	Not Specified	2hrs after administration of 500mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.206 uM	Not Specified	Not Specified	5hrs after administration of 750mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.242 +/- 9.802 uM	Not Specified	Not Specified	2hrs after IV administration of 500mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	11.297 uM	Not Specified	Not Specified	2hrs after administration of 750mg	20959502	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	4.652 +/- 0.692 uM	Not Specified	Not Specified	neurosurgical operations	12016861	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Tuberculosis
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
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

607948 (Tuberculosis)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB01137

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022746

KNApSAcK ID

Not Available

Chemspider ID

131410

KEGG Compound ID

C07660

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levofloxacin

METLIN ID

Not Available

PubChem Compound

149096

PDB ID

Not Available

ChEBI ID

63598

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

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

Enzyme Details

2. DNA topoisomerase 2-alpha

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

Showing metabocard for Levofloxacin (HMDB0001929)

Structure for HMDB0001929 (Levofloxacin)

Enzymes