Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H19F2N3O3.CH4O3S |
| Molecular Weight | 447.454 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(N3CCNC(C)C3)C(F)=C12
InChI
InChIKey=QHLKJRAHRXUJLD-UHFFFAOYSA-N
InChI=1S/C17H19F2N3O3.CH4O3S/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;1-5(2,3)4/h6,8-9,20H,3-5,7H2,1-2H3,(H,24,25);1H3,(H,2,3,4)
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 |
|---|---|---|
| In-vitro activity of lomefloxacin against pathogenic and environmental mycobacteria. | 1992 Aug |
|
| Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques. | 2000 Oct |
|
| History of quinolones and their side effects. | 2001 |
|
| Lomefloxacin is an effective treatment of experimental bacterial keratitis. | 2001 Apr |
|
| Pulmonary disposition of lomefloxacin in patients with acute exacerbation of chronic obstructive pulmonary disease. A multiple-dose study. | 2001 Aug |
|
| Peripheral neuropathy associated with fluoroquinolones. | 2001 Dec |
|
| In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
|
| Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
|
| [Study on photodegradation kinetics of lomefloxacin hydrochloride aqueous solution]. | 2001 Mar |
|
| 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 |
|
| Disposable 1-day Acuvue contact lenses for the delivery of lomefloxacin to rabbits' eyes. | 2001 Oct |
|
| Is more than one quinolone needed in clinical practice? | 2001 Sep |
|
| Determination of lomefloxacin by terbium sensitized chemiluminescence method. | 2002 Dec |
|
| [Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies]. | 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 |
|
| Laser flash photolysis study of photoionization in fluoroquinolones. | 2002 Nov |
|
| Adverse drug reactions related to the use of fluoroquinolone antimicrobials: an analysis of spontaneous reports and fluoroquinolone consumption data from three italian regions. | 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 |
|
| 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 |
|
| Effects of lomefloxacin and norfloxacin on pancreatic beta-cell ATP-sensitive K(+) channels. | 2003 Jun 13 |
|
| Failure of erythromycin to eliminate airway colonization with ureaplasma urealyticum in very low birth weight infants. | 2003 Sep 4 |
|
| Permeability classification of representative fluoroquinolones by a cell culture method. | 2004 Apr 5 |
|
| [Fluorescence spectroscopy determination of lomefloxacin by charge transfer complex formation with chloranilic acid]. | 2004 Dec |
|
| Synthesis and antibacterial activity of 7-(substituted)aminomethyl quinolones. | 2004 Jan 19 |
|
| 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 |
|
| High-throughput mass spectrometer using atmospheric pressure ionization and a cylindrical ion trap array. | 2005 Jan 15 |
|
| Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation. | 2005 Jul 4 |
|
| 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
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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C795
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
60622
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
C76231
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
AA-85
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
114394-67-1
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
DTXSID40921346
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
CHEMBL561
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY | |||
|
6908F93PY1
Created by
admin on Fri Dec 15 15:57:24 GMT 2023 , Edited by admin on Fri Dec 15 15:57:24 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
