LOMEFLOXACIN MESYLATE

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

Structure Search

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)

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H19F2N3O3
Molecular Weight	351.3479
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf | http://home.intekom.com/pharm/adcock/okacyned.html

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://home.intekom.com/pharm/adcock/okacyned.html \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/10621934 \| https://www.ncbi.nlm.nih.gov/pubmed/10590273	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Chronic bronchitis 51 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf	Curative	Approved 8429	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 1992
Uncomplicated urinary tract infections 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf	Curative	Approved 8429	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 1992
Bacterial conjunctivitis 34 Sources: http://home.intekom.com/pharm/adcock/okacyned.html	Curative	Approved 8429	OKACYN Approved Use Bacterial conjuctivitis due to susceptible organisms. Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
2.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.75 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf	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 Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3214495/	healthy, 21 - 24 years n = 5 Health Status: healthy Age Group: 21 - 24 years Sex: M Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/3214495/	Sources: https://pubmed.ncbi.nlm.nih.gov/3214495/
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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5	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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5	Disc. AE: Gastrointestinal disorders, Herpes labialis... AEs leading to discontinuation/dose reduction: Gastrointestinal disorders (14 patients) Herpes labialis (1 patient) Sources: https://sci-hub.do/10.1016/s0090-4295(97)00708-5

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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5	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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5
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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5	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: https://sci-hub.do/10.1016/s0090-4295(97)00708-5

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478	UGT 192 OCT2 355

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no

Drug as victim

Target	Modality	Activity
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
OCT2 355	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30309202/	no
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/20013s015lbl.pdf#page=	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/17027138/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:116278	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:116278
MolPort	MolPort-003-949-739	https://www.molport.com/shop/molecule-link/MolPort-003-949-739
eMolecules	566238	https://www.emolecules.com/cgi-bin/more?vid=566238

PubMed

Title	Date	PubMed
In-vitro activity of lomefloxacin against pathogenic and environmental mycobacteria.	1992 Aug	1328136
In vitro activity of the new quinolone lomefloxacin against Mycobacterium tuberculosis.	1992 Dec	1333738
[Study on the direct determination of lomefloxacin in urine by derivative-synchronous fluorescence].	2002 Jun	12938329
[The history of the development and changes of quinolone antibacterial agents].	2003	15143768
Levofloxacin: a review of its use in the treatment of bacterial infections in the United States.	2003	14664657
[Levofloxacin (Tavanic) in the treatment of corneal ulcers].	2003	14558414
[Formation of virulent antigen-modified mutants (Fra-, Fra-Tox-) of plague bacteria resistant to rifampicin and quinolones].	2003	13677133
Binding characteristics of fluoroquinolones to synthetic levodopa melanin.	2003 Aug	12956903
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.	2003 Dec	14691652
Photocarcinogenesis in the Tg.AC mouse: lomefloxacin and 8-methoxypsoralen.	2003 Jan	12856886
Alteration of constitutive apoptosis in neutrophils by quinolones.	2003 Jun	12875364
Fluorescence spectroscopy determination of fluoroquinolones by charge-transfer reaction.	2003 Nov 24	14623595
[Analysis of the response factors of different quinolones detected by evaporative light-scattering detector].	2003 Sep	14730921
Aqueous humor levels of topically applied levofloxacin, norfloxacin, and lomefloxacin in the same human eyes.	2003 Sep	14522299
Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: from DNA damage to apoptosis.	2003 Sep	12925221
Failure of erythromycin to eliminate airway colonization with ureaplasma urealyticum in very low birth weight infants.	2003 Sep 4	12956892
[Optimization of tuberculosis complex chemotherapy with the use of moxifloxacin].	2004	15628798
Levofloxacin in the treatment of urinary tract infections and prostatitis.	2004 Apr	15255558
Permeability classification of representative fluoroquinolones by a cell culture method.	2004 Apr 5	15760043
Vibrio vulnificus in Taiwan.	2004 Aug	15496235
Validation of HPLC method for determination of six fluoroquinolones: cinoxacin, ciprofloxacin, enoxacin, lomefloxacin, norfloxacin and ofloxacin.	2004 Dec	15909943
[Fluorescence spectroscopy determination of lomefloxacin by charge transfer complex formation with chloranilic acid].	2004 Dec	15828343
Effects of 25 pharmaceutical compounds to Lemna gibba using a seven-day static-renewal test.	2004 Feb	14982384
Compare two methods of measuring DNA damage induced by photogenotoxicity of fluoroquinolones.	2004 Feb	14769204
Synthesis and antibacterial activity of 7-(substituted)aminomethyl quinolones.	2004 Jan 19	14698166
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	15117040
Cotransport of macrolide and fluoroquinolones, a beneficial interaction reversing P-glycoprotein efflux.	2004 Nov-Dec	15543082
[Simultaneous determination of quinolones in foods by LC/MS/MS].	2004 Oct	15678937
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	16083168
Fluoroquinolone-dependent DNA supercoiling by Vaccinia topoisomerase I.	2004 Sep 10	15327948
[Comparative efficiency of treatment with moxyfloxacin and lomefloxacin for generalized murine tuberculosis caused by drug-resistant Mycobacterium strains].	2005	15881962
In vitro activity of fluoroquinolones against Mycobacterium tuberculosis.	2005 Apr	15920901
Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods.	2005 Apr 4	15792876
[Antimicrobial susceptibility surveillance of recent isolates from ophthalmological infections to gatifloxacin and other antimicrobial drugs].	2005 Feb	15847222
Toxicity of fluoroquinolone antibiotics to aquatic organisms.	2005 Feb	15720004
Demand for prophylaxis after bioterrorism-related anthrax cases, 2001.	2005 Jan	15705321
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.	2005 Jan 10	15659296
High-throughput mass spectrometer using atmospheric pressure ionization and a cylindrical ion trap array.	2005 Jan 15	15649041
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	16042789
Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.	2005 Jul 4	15917145
Chlamydia trachomatis survival in the presence of two fluoroquinolones (lomefloxacin versus levofloxacin) in patients with chronic prostatitis syndrome.	2005 Jun	16026425
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.	2005 Jun 15	16047783
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005 May	16004377
Vibrational spectroscopic characterization of fluoroquinolones.	2005 May	15820884
Ocular pharmacokinetics of moxifloxacin after topical treatment of animals and humans.	2005 Nov	16257309
The photocarcinogenesis of antibiotic lomefloxacin and UVA radiation is enhanced in xeroderma pigmentosum group A gene-deficient mice.	2005 Sep	16117798
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	15953703
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	16143044
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.	2006 Apr	16171969
Quantitative determination of gatifloxacin, levofloxacin, lomefloxacin and pefloxacin fluoroquinolonic antibiotics in pharmaceutical preparations by high-performance liquid chromatography.	2006 Jan 23	16095864

Patents

Sample Use Guides

In Vivo Use Guide

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 Dec 15 15:57:24 GMT 2023` Edited by `admin` on `Fri Dec 15 15:57:24 GMT 2023`
Record UNII	6908F93PY1
Record Status	`Validated (UNII)`
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Name

Type

Language

LOMEFLOXACIN MESYLATE

Official Name

English

LOMEFLOXACIN MESYLATE [USAN]

Common Name

English

LOMEFLOXACIN MESILATE

Common Name

English

SC-47111B

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C795