Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H19F2N3O3.ClH |
Molecular Weight | 387.809 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N3CCNC(C)C3)C(F)=C12
InChI
InChIKey=KXEBLAPZMOQCKO-UHFFFAOYSA-N
InChI=1S/C17H19F2N3O3.ClH/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);1H
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 Date1992 |
|||
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 Date1992 |
|||
Curative | OKACYN Approved UseBacterial conjuctivitis due to susceptible organisms. Launch Date2000 |
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 |
---|---|---|
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening. | 2000 Oct |
|
History of quinolones and their side effects. | 2001 |
|
Unusual cause of hematuria. | 2001 |
|
Analysis of fluoroquinolone-mediated photosensitization of 2'-deoxyguanosine, calf thymus and cellular DNA: determination of type-I, type-II and triplet-triplet energy transfer mechanism contribution. | 2001 Mar |
|
Is more than one quinolone needed in clinical practice? | 2001 Sep |
|
In vitro phototoxic properties of new 6-desfluoro and 6-fluoro-8-methylquinolones. | 2002 Dec |
|
Accumulation of ciprofloxacin and lomefloxacinin fluoroquinolone-resistant strains of Escherichia coli. | 2002 Jan |
|
[Lemofloxacin: antimicrobial ability and clinico-pharmacokinetic basis for use in urogenital infections]. | 2002 Jan-Feb |
|
Lomefloxacin versus ciprofloxacin in the treatment of chronic bacterial prostatitis. | 2002 Jul |
|
The expanding role of fluoroquinolones. | 2002 Jul 8 |
|
[Study on the direct determination of lomefloxacin in urine by derivative-synchronous fluorescence]. | 2002 Jun |
|
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin. | 2002 Mar |
|
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation. | 2002 May 27 |
|
Determination of bioequivalence of lomefloxacin tablets using urinary excretion data. | 2002 Nov 7 |
|
Determination of moxifloxacin in human plasma by liquid chromatography electrospray ionization tandem mass spectrometry. | 2002 Nov 7 |
|
[Analysis of the response factors of different quinolones detected by evaporative light-scattering detector]. | 2003 Sep |
|
Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: from DNA damage to apoptosis. | 2003 Sep |
|
Permeability classification of representative fluoroquinolones by a cell culture method. | 2004 Apr 5 |
|
Vibrio vulnificus in Taiwan. | 2004 Aug |
|
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux. | 2004 Nov-Dec |
|
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 |
|
[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 |
|
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101. | 2006 Apr |
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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