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Details

Stereochemistry RACEMIC
Molecular Formula C17H19F2N3O3
Molecular Weight 351.3485
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOMEFLOXACIN

SMILES

CCn1cc(c(=O)c2cc(c(c(c21)F)N3CCNC(C)C3)F)C(=O)O

InChI

InChIKey=ZEKZLJVOYLTDKK-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C17H19F2N3O3
Molecular Weight 351.3485
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Lomefloxacin hydrochloride (marketed under the following brand names in English speaking countries Maxaquin, Okacyn, Uniquin) is a fluoroquinolone antibiotic used to treat bacterial infections. It is 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. 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.

CNS Activity

Curator's Comment:: Small amount of lomefloxacin crosses the blood–brain barrier and enter the extracellular space

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MAXAQUIN

Approved Use

Maxaquin (lomefloxacin HCl) film-coated tablets are indicated for the treatment of adults with mild to moderate infections caused by susceptible strains of the designated microorganisms in the conditions listed below: (See Dosage and Administration for specific dosing recommendations.) LOWER RESPIRATORY TRACT Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae or Moraxella catarrhalis.* NOTE: MAXAQUIN IS NOT INDICATED FOR THE EMPIRIC TREATMENT OF ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS WHEN IT IS PROBABLE THAT S PNEUMONIAE IS A CAUSATIVE PATHOGEN. S PNEUMONIAE EXHIBITS IN VITRO RESISTANCE TO LOMEFLOXACIN, AND THE SAFETY AND EFFICACY OF LOMEFLOXACIN IN THE TREATMENT OF PATIENTS WITH ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS CAUSED BY S PNEUMONIAE HAVE NOT BEEN DEMONSTRATED. IF LOMEFLOXACIN IS TO BE PRESCRIBED FOR GRAMSTAIN–GUIDED EMPIRIC THERAPY OF ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS, IT SHOULD BE USED ONLY IF SPUTUM GRAM STAIN DEMONSTRATES AN ADEQUATE QUALITY OF SPECIMEN (> 25 PMNs/LPF) AND THERE IS BOTH A PREDOMINANCE OF GRAM-NEGATIVE MICROORGANISMS AND NOT A PREDOMINANCE OF GRAM-POSITIVE MICROORGANISMS. URINARY TRACT Uncomplicated Urinary Tract Infections (cystitis) caused by Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, or Staphylococcus saprophyticus. (See DOSAGE AND ADMINISTRATION and CLINICAL STUDIES— UNCOMPLICATED CYSTITIS.) Complicated Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Citrobacter diversus,* or Enterobacter cloacae.* NOTE: In clinical trials with patients experiencing complicated urinary tract infections (UTIs) due to P aeruginosa, 12 of 16 patients had the microorganism eradicated from the urine after therapy with lomefloxacin. None of the patients had concomitant bacteremia. Serum levels of lomefloxacin do not reliably exceed the MIC of Pseudomonas isolates. THE SAFETY AND EFFICACY OF LOMEFLOXACIN IN TREATING PATIENTS WITH PSEUDOMONAS BACTEREMIA HAVE NOT BEEN ESTABLISHED. Prevention / prophylaxis: Maxaquin is indicated preoperatively for the prevention of infection in the following situations: •Transrectal prostate biopsy: to reduce the incidence of urinary tract infection, in the early and late postoperative periods (3–5 days and 3–4 weeks postsurgery). •Transurethral surgical procedures: to reduce the incidence of urinary tract infection in the early postoperative period (3–5 days postsurgery).

Launch Date

6.9863041E11
Curative
MAXAQUIN

Approved Use

Maxaquin (lomefloxacin HCl) film-coated tablets are indicated for the treatment of adults with mild to moderate infections caused by susceptible strains of the designated microorganisms in the conditions listed below: (See Dosage and Administration for specific dosing recommendations.) LOWER RESPIRATORY TRACT Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae or Moraxella catarrhalis.* NOTE: MAXAQUIN IS NOT INDICATED FOR THE EMPIRIC TREATMENT OF ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS WHEN IT IS PROBABLE THAT S PNEUMONIAE IS A CAUSATIVE PATHOGEN. S PNEUMONIAE EXHIBITS IN VITRO RESISTANCE TO LOMEFLOXACIN, AND THE SAFETY AND EFFICACY OF LOMEFLOXACIN IN THE TREATMENT OF PATIENTS WITH ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS CAUSED BY S PNEUMONIAE HAVE NOT BEEN DEMONSTRATED. IF LOMEFLOXACIN IS TO BE PRESCRIBED FOR GRAMSTAIN–GUIDED EMPIRIC THERAPY OF ACUTE BACTERIAL EXACERBATION OF CHRONIC BRONCHITIS, IT SHOULD BE USED ONLY IF SPUTUM GRAM STAIN DEMONSTRATES AN ADEQUATE QUALITY OF SPECIMEN (> 25 PMNs/LPF) AND THERE IS BOTH A PREDOMINANCE OF GRAM-NEGATIVE MICROORGANISMS AND NOT A PREDOMINANCE OF GRAM-POSITIVE MICROORGANISMS. URINARY TRACT Uncomplicated Urinary Tract Infections (cystitis) caused by Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, or Staphylococcus saprophyticus. (See DOSAGE AND ADMINISTRATION and CLINICAL STUDIES— UNCOMPLICATED CYSTITIS.) Complicated Urinary Tract Infections caused by Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Citrobacter diversus,* or Enterobacter cloacae.* NOTE: In clinical trials with patients experiencing complicated urinary tract infections (UTIs) due to P aeruginosa, 12 of 16 patients had the microorganism eradicated from the urine after therapy with lomefloxacin. None of the patients had concomitant bacteremia. Serum levels of lomefloxacin do not reliably exceed the MIC of Pseudomonas isolates. THE SAFETY AND EFFICACY OF LOMEFLOXACIN IN TREATING PATIENTS WITH PSEUDOMONAS BACTEREMIA HAVE NOT BEEN ESTABLISHED. Prevention / prophylaxis: Maxaquin is indicated preoperatively for the prevention of infection in the following situations: •Transrectal prostate biopsy: to reduce the incidence of urinary tract infection, in the early and late postoperative periods (3–5 days and 3–4 weeks postsurgery). •Transurethral surgical procedures: to reduce the incidence of urinary tract infection in the early postoperative period (3–5 days postsurgery).

Launch Date

6.9863041E11
Curative
OKACYN

Approved Use

Bacterial conjuctivitis due to susceptible organisms.

Launch Date

9.6716161E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 μg/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LOMEFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
25.9 μg × h/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LOMEFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.75 h
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LOMEFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
healthy, 21 - 24 years
n = 5
Health Status: healthy
Age Group: 21 - 24 years
Sex: M
Population Size: 5
Sources:
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 22–87 years
n = 165
Health Status: unhealthy
Condition: urinary tract infections
Age Group: 22–87 years
Sex: M+F
Population Size: 165
Sources:
Disc. AE: Gastrointestinal disorders, Herpes labialis...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorders (14 patients)
Herpes labialis (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Herpes labialis 1 patient
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 22–87 years
n = 165
Health Status: unhealthy
Condition: urinary tract infections
Age Group: 22–87 years
Sex: M+F
Population Size: 165
Sources:
Gastrointestinal disorders 14 patients
Disc. AE
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 22–87 years
n = 165
Health Status: unhealthy
Condition: urinary tract infections
Age Group: 22–87 years
Sex: M+F
Population Size: 165
Sources:
PubMed

PubMed

TitleDatePubMed
In-vitro activity of lomefloxacin against pathogenic and environmental mycobacteria.
1992 Aug
In vitro activity of the new quinolone lomefloxacin against Mycobacterium tuberculosis.
1992 Dec
[Study on the direct determination of lomefloxacin in urine by derivative-synchronous fluorescence].
2002 Jun
[The history of the development and changes of quinolone antibacterial agents].
2003
Levofloxacin: a review of its use in the treatment of bacterial infections in the United States.
2003
[Levofloxacin (Tavanic) in the treatment of corneal ulcers].
2003
[Formation of virulent antigen-modified mutants (Fra-, Fra-Tox-) of plague bacteria resistant to rifampicin and quinolones].
2003
Binding characteristics of fluoroquinolones to synthetic levodopa melanin.
2003 Aug
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.
2003 Dec
Photocarcinogenesis in the Tg.AC mouse: lomefloxacin and 8-methoxypsoralen.
2003 Jan
Alteration of constitutive apoptosis in neutrophils by quinolones.
2003 Jun
Fluorescence spectroscopy determination of fluoroquinolones by charge-transfer reaction.
2003 Nov 24
[Analysis of the response factors of different quinolones detected by evaporative light-scattering detector].
2003 Sep
Aqueous humor levels of topically applied levofloxacin, norfloxacin, and lomefloxacin in the same human eyes.
2003 Sep
Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: from DNA damage to apoptosis.
2003 Sep
Failure of erythromycin to eliminate airway colonization with ureaplasma urealyticum in very low birth weight infants.
2003 Sep 4
[Optimization of tuberculosis complex chemotherapy with the use of moxifloxacin].
2004
Levofloxacin in the treatment of urinary tract infections and prostatitis.
2004 Apr
Permeability classification of representative fluoroquinolones by a cell culture method.
2004 Apr 5
Vibrio vulnificus in Taiwan.
2004 Aug
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.
2004 Dec
[Fluorescence spectroscopy determination of lomefloxacin by charge transfer complex formation with chloranilic acid].
2004 Dec
Effects of 25 pharmaceutical compounds to Lemna gibba using a seven-day static-renewal test.
2004 Feb
Compare two methods of measuring DNA damage induced by photogenotoxicity of fluoroquinolones.
2004 Feb
Synthesis and antibacterial activity of 7-(substituted)aminomethyl quinolones.
2004 Jan 19
Comparison of topical lomefloxacin 0.3 per cent versus topical ciprofloxacin 0.3 per cent for the treatment of presumed bacterial corneal ulcers.
2004 Mar
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux.
2004 Nov-Dec
[Simultaneous determination of quinolones in foods by LC/MS/MS].
2004 Oct
Clinical evaluation of ophthalmic lomefloxacin 0.3% in comparison with fortified cefazolin and gentamicin ophthalmic solutions in the treatment of presumed bacterial keratitis.
2004 Sep
Fluoroquinolone-dependent DNA supercoiling by Vaccinia topoisomerase I.
2004 Sep 10
[Comparative efficiency of treatment with moxyfloxacin and lomefloxacin for generalized murine tuberculosis caused by drug-resistant Mycobacterium strains].
2005
In vitro activity of fluoroquinolones against Mycobacterium tuberculosis.
2005 Apr
Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods.
2005 Apr 4
[Antimicrobial susceptibility surveillance of recent isolates from ophthalmological infections to gatifloxacin and other antimicrobial drugs].
2005 Feb
Toxicity of fluoroquinolone antibiotics to aquatic organisms.
2005 Feb
Demand for prophylaxis after bioterrorism-related anthrax cases, 2001.
2005 Jan
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.
2005 Jan 10
High-throughput mass spectrometer using atmospheric pressure ionization and a cylindrical ion trap array.
2005 Jan 15
A simplified search strategy for identifying randomised controlled trials for systematic reviews of health care interventions: a comparison with more exhaustive strategies.
2005 Jul 23
Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.
2005 Jul 4
Chlamydia trachomatis survival in the presence of two fluoroquinolones (lomefloxacin versus levofloxacin) in patients with chronic prostatitis syndrome.
2005 Jun
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.
2005 Jun 15
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005 May
Vibrational spectroscopic characterization of fluoroquinolones.
2005 May
Ocular pharmacokinetics of moxifloxacin after topical treatment of animals and humans.
2005 Nov
The photocarcinogenesis of antibiotic lomefloxacin and UVA radiation is enhanced in xeroderma pigmentosum group A gene-deficient mice.
2005 Sep
The simultaneous separation and determination of five quinolone antibiotics using isocratic reversed-phase HPLC: application to stability studies on an ofloxacin tablet formulation.
2005 Sep 15
In vitro activities of 11 fluoroquinolones against 816 non-typhoidal strains of Salmonella enterica isolated from Finnish patients with special reference to reduced ciprofloxacin susceptibility.
2005 Sep 5
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.
2006 Apr
Quantitative determination of gatifloxacin, levofloxacin, lomefloxacin and pefloxacin fluoroquinolonic antibiotics in pharmaceutical preparations by high-performance liquid chromatography.
2006 Jan 23
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Also can be used topically: At the beginning of therapy on Day 1 instil 5 drops into the conjuctival sac within 20 minutes. Thereafter, until Day 7-9 instil 1 drop 3 times daily into the conjuctival sac. http://home.intekom.com/pharm/adcock/okacyned.html
The recommended daily dose of Maxaquin (Lomefloxacin) is: Acute bacterial exacerbation of chronic bronchitis 400 mg qd 10 days 400 mg Uncomplicated cystitis in females caused by E coli 400 mg qd 3 days 400 mg
Route of Administration: Oral
In Vitro Use Guide
DNA synthesis in intact cells of E. cloacae, S. marcescens, and K. pneumoniae after 90 min of exposure was inhibited 90% (IC90) by 1 ug of lomefloxacin per ml. For E. coli, the IC50 and the IC90 of lomefloxacin were of the same order of magnitude, regardless of the growth stage of the culture, with IC90s of 0.12 and 0.37 ug/ml obtained for the early and late logarithmic phases, respectively.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:55:33 UTC 2021
Edited
by admin
on Fri Jun 25 22:55:33 UTC 2021
Record UNII
L6BR2WJD8V
Record Status Validated (UNII)
Record Version
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Name Type Language
LOMEFLOXACIN
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
SC-47111A
Code English
3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6,8-DIFLUORO-1,4-DIHYDRO-7-(3-METHYL-1-PIPERAZINYL)-4-OXO-, (+/-)-
Common Name English
LOMEFLOXACIN [VANDF]
Common Name English
(+/-)-1-ETHYL-6,8-DIFLUORO-1,4-DIHYDRO-7-(3-METHYL-1-PIPERAZINYL)-4-
Common Name English
LOMEFLOXACIN [INN]
Common Name English
LOMEFLOXACIN [USAN]
Common Name English
LOMEFLOXACIN [MI]
Common Name English
LOMEFLOXACIN [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 565
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
NCI_THESAURUS C795
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WHO-VATC QS01AE04
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WHO-VATC QJ01MA07
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WHO-ATC J01MA07
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WHO-ATC S01AX17
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WHO-ATC S01AE04
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
Code System Code Type Description
MESH
C053091
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
DRUG CENTRAL
1594
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PRIMARY
DRUG BANK
DB00978
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PRIMARY
LACTMED
Lomefloxacin
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
PUBCHEM
3948
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PRIMARY
EVMPD
SUB08561MIG
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PRIMARY
EPA CompTox
98079-51-7
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
WIKIPEDIA
LOMEFLOXACIN
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
NCI_THESAURUS
C61814
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PRIMARY
RXCUI
28872
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PRIMARY RxNorm
MERCK INDEX
M6889
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PRIMARY Merck Index
CAS
98079-51-7
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
FDA UNII
L6BR2WJD8V
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL561
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PRIMARY
INN
6222
Created by admin on Fri Jun 25 22:55:33 UTC 2021 , Edited by admin on Fri Jun 25 22:55:33 UTC 2021
PRIMARY
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