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Lomefloxacin Hydrochloride

HCID 68624
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Basic information

CAS
98079-52-8
Standard SMILES
CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNC(C)C3)c(F)c21.Cl
InChIKey
KXEBLAPZMOQCKO-UHFFFAOYSA-N
Molecular formula
C17H20ClF2N3O3
Average molar mass
387.8 g/mol
Monoisotopic mass
387.1161255

Overview

Lomefloxacin hydrochloride is the hydrochloride salt of lomefloxacin. It is administered by mouth to treat bacterial infections including bronchitis and urinary tract infections. It is also used topically as eye drops for the treatment of bacterial conjunctivitis, and as ear drops for the treatment of otitis externa and otitis media. It has a role as an antitubercular agent, an antimicrobial agent and a photosensitizing agent. It contains a lomefloxacin.

Names & identifiers

Preferred name
Lomefloxacin Hydrochloride
IUPAC
1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;hydrochloride
English name
Lomefloxacin hydrochloride
Molecular formula
C17H20ClF2N3O3
Molecular weight
387.81

Names & synonyms

Lomefloxacin hydrochloride98079-52-8Lomefloxacin HClNy-198MazaquinSC-47111Lomefloxacin monohydrochlorideDTXSID20455279VC7S3ZXXB1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochlorideNY 198NSC-758168
Show more names
1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid hydrochlorideny198omefLOkacinChimonoUniquinLoMflox
Lomefloxacin (as hydrochloride)CHEBI:6518DTXCID0025527(+-)-1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, monohydrochlorideRefChem:56494MaxaquinBareonOkacyn

Database identifiers

CAS
98079-52-8
PubChem CID
68624
DTXSID
DTXSID2045527

Properties

Computed structural properties

Topological polar surface area
72.9 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
8
Rotatable bonds
3
Heavy atoms
26
Formal charge
0
Complexity
585

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section188.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
290 · 290-3000C
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
1 M · 1 M NaOH: soluble50mg/mL
form
powder to crystal
color
white to off-white
biological source
synthetic
Merck
14 · 14,5562
InChI
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
InChIKey
KXEBLAPZMOQCKO-UHFFFAOYSA-N
SMILES
N1(CC)C2=C(C=C(F)C(N3CCNC(C)C3)=C2F)C(=O)C(C(O)=O)=C1.[H]Cl

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 · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Lomefloxacin hydrochloride

Ambiguous-DILI-concern

4

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
VB1997500
hs_code
29339900
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
Storage Class
11 - Combustible Solids
Hazard statements
H302-H317
Hazard Classifications
Acute Tox. 4 Oral

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that inhibit the growth or reproduction of BACTERIA.

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

Applications · 3 items

DescriptionLomefloxacin is an orally bioavailable, broad-spectrum fluoroquinolone antibiotic. In vitro, it inhibits growth of N. gonorrhoeae, E. coli, K. pneumoniae, P. vulgaris, S. epidermidis, and M. morganii (MIC90s = 0.1, 0.39, 0.39, 0.39, 0.39, and 0.78 μg/ml, respectively). It also inhibits growth of S. aureus and methicillin-resistant S. aureus (MRSA; MIC90 = 3.13 μg/ml for both) and of H. influenzae and ampicillin-resistant H. influenzae (MIC90 = 0.1 μg/ml for both). In vivo, lomefloxacin inhibits the growth of P. mirabilis, E. coli, K. pneumoniae, and S. aureus (ED50s = 1.39, 1.45, 1.78, and 6.66 mg/kg, respectively) in mouse models of systemic infection. It inhibits bacterial DNA gyrase, thereby inhibiting DNA synthesis and bacterial growth. Formulations containing lomefloxacin have been used in the treatment of bronchitis and urinary tract bacterial infections.

DescriptionLomefloxacin hydrochloride is the hydrochloride form of Lomefloxacin. 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. Lomefloxacin can be used to treat many kinds of infections such as respiratory, urinary tract, obstetric, gynaecological, joint, skin, oral, ear, nose, throat and eye infections. Compared with other quinolone antibacterial drugs, lomefloxacin has certain advantages such as convenient administration and no necessity of theophylline dosage adjustment.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL1728
ChEBI
CHEBI:6518
UNII
9VC7S3ZXXB
EC Number
627-337-1
CAS DataBase Reference
98079 · 98079-52-8(CAS DataBase Reference)
FDA UNII
9 VC7S3ZXXB · 9VC7S3ZXXB
UNSPSC Code
51282927 · 51282927
NACRES
85 · NA.85
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H317
Precautionary statements
261 · P261-P264-P270-P272-P280-P301+P312+P330-P302+P352+P333+P313+P363-P501
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
WGK Germany
3 · 3
RTECS
1997500 · VB1997500
HS Code
29339900 · 29339900
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Precautionary statements
P261-P264-P270-P272-P280-P301+P312+P330-P302+P352+P333+P313+P363-P501

UsesFluorinated quinolone antibacterial. DNA gyrase antagonist

Upstream & downstream products

Upstream raw materials

N,N-Dimethylformamide2-Methylpiperazine1,2,3-Trifluoro-4-nitrobenzeneBromoethanePyridineSodium bicarbonate1-Ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-2-quinolinecarboxylic acid

Downstream products

Lomefloxacin
Additional notes · 1 item

DefinitionChEBI: The hydrochloride salt of lomefloxacin. It is administered by mouth to treat bacterial infections including bronchitis and urinary tract infections. It is also used topically as eye drops for the treatment of bacterial conjunctivitis, and as ear drops for he treatment of otitis externa and otitis media.