Lomefloxacin

Common Name

Lomefloxacin Description

Lomefloxacin is only found in individuals that have used or taken this drug. It is a fluoroquinolone antibiotic, used to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.Lomefloxacin is a bactericidal fluoroquinolone agent with activity against a wide range of gram-negative and gram-positive organisms. The bactericidal action of lomefloxacin reslits from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases reslits in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a reslit DNA replication and transcription is inhibited. Structure

Synonyms

Value Source (+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChEBI 1,4-dihydro-6,8-difluoro-1-Ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChEBI LFLXChEBI LomefloxacineChEBI LomefloxacinoChEBI LomefloxacinumChEBI (+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylateGenerator 1,4-dihydro-6,8-difluoro-1-Ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylateGenerator Lomefloxacin hydrochlorideHMDB 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidMeSH OcacinMeSH DécalogifloxMeSH LogifloxMeSH OkacinMeSH LomenfloxacinMeSH OkacynMeSH Pharmacia brand 1 OF lomefloxacin hydrochlorideMeSH MaxaquinMeSH Pharmacia brand 2 OF lomefloxacin hydrochlorideMeSH

Chemical Formlia

C₁₇H₁₉F₂N₃O₃ Average Molecliar Weight

351.3479 Monoisotopic Molecliar Weight

351.139447899 IUPAC Name

1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid Traditional Name

lomefloxacin CAS Registry Number

98079-51-7 SMILES

InChI Identifier

InChI Key

ZEKZLJVOYLTDKK-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Quinolines and derivatives Direct Parent

Quinoline carboxylic acids Alternative Parents

Fluoroquinolones

N-arylpiperazines

Haloquinolines

Hydroquinolones

Aminoquinolines and derivatives

Hydroquinolines

Pyridinecarboxylic acids

Dialkylarylamines

Benzenoids

Aryl fluorides

Heteroaromatic compounds

Vinylogous amides

Amino acids

Azacyclic compounds

Monocarboxylic acids and derivatives

Dialkylamines

Carboxylic acids

Hydrocarbon derivatives

Organic oxides

Organofluorides

Organooxygen compounds

Organopnictogen compounds

Substituents

Quinoline-3-carboxylic acid

Fluoroquinolone

N-arylpiperazine

Aminoquinoline

Haloquinoline

Dihydroquinolone

Dihydroquinoline

Pyridine carboxylic acid

Pyridine carboxylic acid or derivatives

Tertiary aliphatic/aromatic amine

Dialkylarylamine

Aryl fluoride

Aryl halide

1,4-diazinane

Piperazine

Pyridine

Benzenoid

Vinylogous amide

Heteroaromatic compound

Amino acid or derivatives

Amino acid

Tertiary amine

Azacycle

Secondary amine

Carboxylic acid derivative

Monocarboxylic acid or derivatives

Carboxylic acid

Secondary aliphatic amine

Amine

Organic oxygen compound

Organic nitrogen compound

Organopnictogen compound

Organic oxide

Organohalogen compound

Organofluoride

Organonitrogen compound

Organooxygen compound

Hydrocarbon derivative

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

N-arylpiperazine (CHEBI:116278 )

quinolone antibiotic (CHEBI:116278 )

fluoroquinolone antibiotic (CHEBI:116278 )

quinolone (CHEBI:116278 )

quinolinemonocarboxylic acid (CHEBI:116278 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anti-Infective Agents

Anti-Infective Agents, Urinary

Antitubercliar Agents

Photosensitizing Agents

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point239 – 240.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.06e-01 g/LNot Available LogP2.8Not Available

Predicted Properties

Property Value Source Water Solubility0.11 mg/mLALOGPS logP0ALOGPS logP-0.39ChemAxon logS-3.5ALOGPS pKa (Strongest Acidic)5.64ChemAxon pKa (Strongest Basic)8.7ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area72.88 ŲChemAxon Rotatable Bond Count3ChemAxon Refractivity90.11 m³·mol^-1ChemAxon Polarizability34.8 ųChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00978

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00978

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB00978 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

3811 KEGG Compound ID

C07078 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Lomefloxacin NuGOwiki Link

HMDB15113 Metagene Link

HMDB15113 METLIN ID

Not Available PubChem Compound

3948 PDB ID

Not Available ChEBI ID

116278

Product: AGN 196997

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

Transporters

General function:

Involved in ion transmembrane transporter activity

Specific function:

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3

Gene Name:

SLC22A5

Uniprot ID:

O76082

Molecular weight:

62751.1

References

1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]

General function:

Involved in ATP binding

Specific function:

Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter

Gene Name:

ABCC2

Uniprot ID:

Q92887

Molecular weight:

174205.6

References

1. Sasabe H, Tsuji A, Sugiyama Y: Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats. J Pharmacol Exp Ther. 1998 Mar;284(3):1033-9. [PubMed:9495864 ]

PMID: 10052651

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