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
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)
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | MAXAQUIN Approved UseMaxaquin (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 Date6.9863041E11 |
|||
Curative | MAXAQUIN Approved UseMaxaquin (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 Date6.9863041E11 |
|||
Curative | OKACYN Approved UseBacterial conjuctivitis due to susceptible organisms. Launch Date9.6716161E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
800 mg single, oral Highest studied dose |
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) Sources: Herpes labialis (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
In vitro activity of the new quinolone lomefloxacin against Mycobacterium tuberculosis. | 1992 Dec |
|
[Study on photodegradation kinetics of lomefloxacin hydrochloride aqueous solution]. | 2001 Mar |
|
[Efficacy of some new antibiotics in treating experimental brucellosis]. | 2002 |
|
[New technologies in the surgical treatment of tuberculous spondylitis]. | 2002 |
|
Comparative study on salivary distribution of fluoroquinolones in rats. | 2002 Aug |
|
Lomefloxacin versus ciprofloxacin in the treatment of chronic bacterial prostatitis. | 2002 Jul |
|
[Study on the direct determination of lomefloxacin in urine by derivative-synchronous fluorescence]. | 2002 Jun |
|
[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration]. | 2002 Jun |
|
Laser flash photolysis study of photoionization in fluoroquinolones. | 2002 Nov |
|
Determination of moxifloxacin in human plasma by liquid chromatography electrospray ionization tandem mass spectrometry. | 2002 Nov 7 |
|
In vivo photochemical micronucleus induction due to certain quinolone antimicrobial agents in the skin of hairless mice. | 2002 Sep 26 |
|
[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 |
|
Genotoxicity of lomefloxacin--an antibacterial drug in somatic and germ cells of Swiss albino mice in vivo. | 2003 Feb 5 |
|
Photocarcinogenesis in the Tg.AC mouse: lomefloxacin and 8-methoxypsoralen. | 2003 Jan |
|
Alteration of constitutive apoptosis in neutrophils by quinolones. | 2003 Jun |
|
Effects of lomefloxacin and norfloxacin on pancreatic beta-cell ATP-sensitive K(+) channels. | 2003 Jun 13 |
|
In vitro activity of amphotericin B and itraconazole in combination with flucytosine, sulfadiazine and quinolones against Exophiala spinifera. | 2003 May |
|
[Experience in using the new drug moxifloxacin (Avelox, "Bayer", Germaniia) in urologic practice]. | 2003 May-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 |
|
Permeability classification of representative fluoroquinolones by a cell culture method. | 2004 Apr 5 |
|
Vibrio vulnificus in Taiwan. | 2004 Aug |
|
[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 |
|
[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 |
|
Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. | 2005 Apr 4 |
|
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 |
|
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 |
|
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2168142
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.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
565
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NCI_THESAURUS |
C795
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QS01AE04
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QJ01MA07
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J01MA07
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S01AX17
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S01AE04
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C053091
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1594
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DB00978
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Lomefloxacin
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3948
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SUB08561MIG
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98079-51-7
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LOMEFLOXACIN
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C61814
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28872
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M6889
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98079-51-7
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L6BR2WJD8V
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CHEMBL561
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6222
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)