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L2906

Sigma-Aldrich

Lomefloxacin hydrochloride

Synonym(s):

1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C17H19F2N3O3 · HCl
CAS Number:
98079-52-8
Molecular Weight:
387.81
MDL number:
MFCD00214312
UNSPSC Code:
51282927
PubChem Substance ID:
24278514
NACRES:
NA.85

biological source

synthetic

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

−20°C

SMILES string

Cl.CCN1C=C(C(O)=O)C(=O)c2cc(F)c(N3CCNC(C)C3)c(F)c12

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

InChI key

KXEBLAPZMOQCKO-UHFFFAOYSA-N

General description

Chemical structure: fluoroquinolone

Application

Lomefloxacin is a fluoroquinolone antibiotic that is commonly used to treat bacterial infections, including bronchitis and urinary tract infections. It is used as a pre-operative prophylactic to prevent urinary tract infection caused by S. pneumoniae, H. influenzae, S. aureus, P. aeruginosa, E. cloacae, P. mirabilis, C. civersus, S. asprphyticus, E. coli, and K. pneumoniae. It is used to induce genomic instability in mice and modification of the kinetics of growth of Gram-negative bacteria.

Biochem/physiol Actions

Lomefloxacin is a bactericidal fluoroquinolone agent that is active against gram-negative and gram-positive organisms. Lomefloxacin inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase is thought to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV is thought to be the primary target in gram-positive organisms. The inhibition of the topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. Therefore, DNA replication and transcription is inhibited.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yiruhan et al.
Environmental pollution (Barking, Essex : 1987), 158(7), 2350-2358 (2010-05-04)
Four fluoroquinolone antibiotics (norfloxacin, ciprofloxacin, lomefloxacin, and enrofloxacin) in tap water in Guangzhou and Macao were analyzed using high performance liquid chromatography fluorescence detection. The results showed that all target antibiotics were detected in high rate both in Guangzhou (77.5%)
Yongnian Ni et al.
The Analyst, 134(9), 1840-1847 (2009-08-18)
Three commonly used fluoroquinolone antibiotics (norfloxacin (NFX), ofloxacin (OFX) and lomefloxacin (LMFX)) were used as examples of molecules which can interact with a biomacromolecule, such as DNA, separately or in a mixture. Such interactions were investigated with the use of
Yoko Yoshihisa et al.
Experimental dermatology, 19(11), 1000-1006 (2010-09-04)
Intracellular reactive oxygen species (ROS) and apoptosis play important roles in the ultraviolet (UV)-induced inflammatory responses in the skin. Metal nanoparticles have been developed to increase the catalytic activity of metals, which is because of the large surface area of
Maria Rambla-Alegre et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(31), 3975-3981 (2009-10-27)
A sensitive and robust method was developed and validated for the routine identification and quantification of five quinolones in urine samples directly injected into a micellar liquid chromatographic system without any pre-treatment step. Since the simultaneous elution of the five
H Pruul et al.
The Journal of antimicrobial chemotherapy, 25(1), 91-101 (1990-01-01)
The post-antibiotic effect (PAE) of lomefloxacin against Escherichia coli and Pseudomonas aeruginosa was determined and compared with various other antibiotics. All the quinolones tested, and chloramphenicol and gentamicin, possessed PAE activity. At 10 x MIC and 30 min exposure, the
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