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=C1C(F)=C(N3CCNC(C)C3)C(F)=C2
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.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Sample Use Guides
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.