Identification

Name
Lomefloxacin
Accession Number
DB00978
Description

Lomefloxacin is a fluoroquinolone antibiotic, used to treat bacterial infections including bronchitis and urinary tract infections (UTIs). Additionally, it has been employed for the prophylaxis of UTIs prior to surgery as well.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 351.3479
Monoisotopic: 351.139447899
Chemical Formula
C17H19F2N3O3
Synonyms
  • (±)-1-ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
  • 1,4-Dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
  • LFLX
  • Lomefloxacin
  • Lomefloxacine
  • Lomefloxacino
  • Lomefloxacinum

Pharmacology

Indication

For the treatment of bacterial infections of the respiratory tract (chronic bronchitis) and urinary tract, and as a pre-operative prophylactic to prevent urinary tract infection caused by: S.pneumoniae, H.influenzae, S.aureus, P.aeruginosa, E. cloacae, P. mirabilis, C. civersus, S. asprphyticus, E.coli, and K.pneumoniae.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Lomefloxacin is a fluoroquinolone antibiotic used to treat chronic bronchitis, as well as complicated and uncomplicated urinary tract infections. It is also used as a prophylactic or preventative treatment to prevent urinary tract infections in patients undergoing transrectal or transurethral surgical procedures. Flouroquinolones such as lomefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.

Mechanism of action

Lomefloxacin is a bactericidal fluoroquinolone agent with activity against a wide range of gram-negative and gram-positive organisms. The bactericidal action of lomefloxacin results 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 results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.

TargetActionsOrganism
ADNA topoisomerase 4 subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
ADNA gyrase subunit A
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UDNA topoisomerase 2-alpha
inhibitor
Humans
Absorption

Rapid and nearly complete with approximately 95% to 98% of a single oral dose being absorbed.

Volume of distribution
Not Available
Protein binding

10%

Metabolism

Minimally metabolized although 5 metabolites have been identified in human urine. 65% appears as the parent drug in urine and 9% as the glucuronide metabolite.

Route of elimination

The urinary excretion of lomefloxacin was virtually complete within 72 hours after cessation of dosing, with approximately 65% of the dose being recovered as parent drug and 9% as its glucuronide metabolite.

Half-life

8 hours

Clearance
  • 271 mL/min/1.73 m2 [creatinine clearance of 110 mL/min/1.73 m2]
  • 31 mL/min/1.73 m2 [creatinine clearance of 0 mL/min/1.73 m2]
Adverse Effects
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Toxicity

Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Lomefloxacin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Lomefloxacin can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Lomefloxacin can be increased when it is combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Lomefloxacin.
AcebutololThe risk or severity of QTc prolongation can be increased when Lomefloxacin is combined with Acebutolol.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Lomefloxacin.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Lomefloxacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Lomefloxacin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Lomefloxacin.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Lomefloxacin.
Additional Data Available
  • Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
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Food Interactions
  • Avoid multivalent ions. Separate the administration polyvalent ions, including magnesium and aluminum-containing antacids, from lomefloxacin by at least 4 hours before and 2 hours after lomefloxacin dosing.
  • Take with or without food. The rate and extent of absorption may be reduced when lomefloxacin is taken with food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lomefloxacin hydrochloride9VC7S3ZXXB98079-52-8KXEBLAPZMOQCKO-UHFFFAOYSA-N
International/Other Brands
Bareon
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MaxaquinTablet, film coated400 mg/1OralG.D. Searle LLC2006-05-11Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
S01AE04 — LomefloxacinJ01MA07 — Lomefloxacin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Fluoroquinolones / N-arylpiperazines / Haloquinolines / Hydroquinolones / Aminoquinolines and derivatives / Hydroquinolines / Pyridinecarboxylic acids / Dialkylarylamines / Benzenoids / Aryl fluorides
show 12 more
Substituents
1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, quinolone antibiotic, fluoroquinolone antibiotic, quinolone, quinolinemonocarboxylic acid (CHEBI:116278)

Chemical Identifiers

UNII
L6BR2WJD8V
CAS number
98079-51-7
InChI Key
ZEKZLJVOYLTDKK-UHFFFAOYSA-N
InChI
InChI=1S/C17H19F2N3O3/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25)
IUPAC Name
1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N3CCNC(C)C3)C(F)=C12

References

Synthesis Reference
US4528287
General References
  1. FDA Approved Products: Maxaquin (lomeafloxacin hydrochloride) oral tablets [Link]
Human Metabolome Database
HMDB0015113
KEGG Drug
D02318
KEGG Compound
C07078
PubChem Compound
3948
PubChem Substance
46508499
ChemSpider
3811
BindingDB
50417952
RxNav
28872
ChEBI
116278
ChEMBL
CHEMBL561
Therapeutic Targets Database
DAP000653
PharmGKB
PA164749165
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Lomefloxacin
FDA label
Download (88 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Unknown StatusTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
  • Pharmacia corp
Packagers
  • GD Searle LLC
  • Unimed Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
TabletOral400 MG
Tablet, coatedOral400 MG
Tablet, film coatedOral400 mg/1
Solution / dropsOphthalmic3 mg/ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)239-240.5 °CPhysProp
water solubility27.2 mg/mLNot Available
logP-0.30TAKACS-NOVAK,K ET AL. (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.106 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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.11 m3·mol-1ChemAxon
Polarizability34.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9919
Blood Brain Barrier-0.9856
Caco-2 permeable-0.5416
P-glycoprotein substrateSubstrate0.8953
P-glycoprotein inhibitor INon-inhibitor0.8699
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.7933
CYP450 2C9 substrateNon-substrate0.8591
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7284
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.933
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8497
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6283
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7701
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9971 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8282
hERG inhibition (predictor II)Non-inhibitor0.6392
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Topoisomerase IV is essential for chromosome segregation. It relaxes supercoiled DNA. Performs the decatenation events required during the replication of a circular DNA molecule.
Gene Name
parC
Uniprot ID
P43702
Uniprot Name
DNA topoisomerase 4 subunit A
Molecular Weight
83366.24 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Didier ES, Bowers L, Stovall ME, Kuebler D, Mittleider D, Brindley PJ, Didier PJ: Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo. Folia Parasitol (Praha). 2005 May;52(1-2):173-81. [PubMed:16004377]
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
DNA gyrase negatively supercoils closed circular double-stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, inc...
Gene Name
gyrA
Uniprot ID
P43700
Uniprot Name
DNA gyrase subunit A
Molecular Weight
97817.145 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Takenouchi T, Ishii C, Sugawara M, Tokue Y, Ohya S: Incidence of various gyrA mutants in 451 Staphylococcus aureus strains isolated in Japan and their susceptibilities to 10 fluoroquinolones. Antimicrob Agents Chemother. 1995 Jul;39(7):1414-8. [PubMed:7492077]
  4. Drusano GL, Johnson DE, Rosen M, Standiford HC: Pharmacodynamics of a fluoroquinolone antimicrobial agent in a neutropenic rat model of Pseudomonas sepsis. Antimicrob Agents Chemother. 1993 Mar;37(3):483-90. [PubMed:8384815]
  5. Gushchin AE, Ladygina VG, Govorun VM: [Role of mutations in parC and gyrA in forming resistance of Mycoplasma hominis to fluoroquinolones]. Mol Gen Mikrobiol Virusol. 1999;(4):19-24. [PubMed:10621934]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
This drug is a fluoroquinolone, and these agents are known to inhibit CYP1A2.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zhang L, Wei MJ, Zhao CY, Qi HM: Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes. Acta Pharmacol Sin. 2008 Dec;29(12):1507-14. doi: 10.1111/j.1745-7254.2008.00908.x. [PubMed:19026171]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter 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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2020 21:00

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