Basic information
- CAS
98079-51-7- Standard SMILES
CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNC(C)C3)c(F)c21- InChIKey
ZEKZLJVOYLTDKK-UHFFFAOYSA-N- Molecular formula
- C17H19F2N3O3
- Average molar mass
- 351.35 g/mol
- Monoisotopic mass
- 351.13944791
Overview
Lomefloxacin is a fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery. It has a role as an antitubercular agent, an antimicrobial agent and a photosensitizing agent. It is a quinolone, a quinolinemonocarboxylic acid, a N-arylpiperazine, a quinolone antibiotic and a fluoroquinolone antibiotic.
Names & identifiers
- Preferred name
- Lomefloxacin
- IUPAC
- 1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
- English name
- Lomefloxacin
- Molecular formula
- C17H19F2N3O3
- Molecular weight
- 351.35
Names & synonyms
lomefloxacin98079-51-7LomefloxacineLomefloxacinoLomefloxacinumLFLX1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidSC-47111AL6BR2WJD8V1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid1,4-Dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidDTXSID4040680
Show more names
dm-10ClfimonoSC 47111ALomel9actLEMOFLOXACIN
CHEBI:116278(+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidLogifloxOkacinSC-4711lomefloxacinalomenfloxacin1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
Database identifiers
- CAS
98079-51-7- PubChem CID
- 3948
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 72.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 585
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
LogP2.8
Solubility1.06e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones
Melting Point
239-240.5 °C
239 - 240.5 °C
Physical DescriptionSolid
Dissociation Constants5.742
Collision Cross Section
191.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
191.04 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationStatus: Active Update: 17-03-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19305
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
lomefloxacin
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- VB1997500
- hs_code
- 29419000
- Toxicity
- LD50 in mice (mg/kg): 245.6 i.v.; >4000 orally (Itoh)
- risk_code
- 22-36/37/38
- Signal word
- Warning
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QS - Sensory organs
Protein Binding10%
Pharmacodynamics
Lomefloxacin is a fluoroquinolone antibiotic 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 <i>E.coli</i> and <i>Neisseria gonorrhoea</i> as well as gram-positive bacteria including <i>S. pneumoniae</i> and <i>Staphylococcus aureus</i>. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter.
Mechanism of Action
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.
Biological Half-Life8 hours
Metabolism/MetabolitesMinimally metabolized although 5 metabolites have been identified in human urine. 65% appears as the parent drug in urine and 9% as the glucuronide metabolite.
MeSH Pharmacological Classification
Related reactions
4 records
Compound notes
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