Lomefloxacin

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Lomefloxacin


Systematic (IUPAC) name
(RS)-1-Ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
Clinical data
Trade names	Maxaquin
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a600002
Legal status	?
Pharmacokinetic data
Protein binding	10%
Half-life	8 hours
Identifiers
CAS number	98079-51-7^Y
ATC code	J01MA07 S01AE04
PubChem	CID 3948
DrugBank	DB00978
ChemSpider	3811^Y
UNII	9VC7S3ZXXB^Y
KEGG	D02318^Y
ChEBI	CHEBI:116278^Y
ChEMBL	CHEMBL561^Y
Chemical data
Formula	C₁₇H₁₉F₂N₃O₃
Mol. mass	351.348 g/mol
SMILES Fc1c(c(F)c2c(c1)C(=O)C(\C(=O)O)=C/N2CC)N3CC(NCC3)C
InChI InChI=1S/C17H19F2N3O3/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)^Y Key:ZEKZLJVOYLTDKK-UHFFFAOYSA-N^Y
Y (what is this?) (verify)

Lomefloxacin hydrochloride (sold under the following brand names in English speaking countries Maxaquin, Okacyn, Uniquin) is a fluoroquinolone antibiotic used to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery. Lomefloxacin is associated with phototoxicity and central nervous system adverse effects.^[1]

October 2008 the FDA added the following black box warning to the product insert for Maxaquin: Lomefloxacin is unique in that it forms a magnesium chelate with itself. The chelate is formed between the 2-carbonyl group of two separate lomefloxacin molecules.

References

↑ Rubinstein, E. (2001). "History of quinolones and their side effects.". Chemotherapy 47 (Suppl 3): 3–8; discussion 44–8. doi:10.1159/000057838. PMID 11549783.

Antibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Enoxacin^‡ Fleroxacin^‡ Lomefloxacin Nadifloxacin Ofloxacin Norfloxacin Pefloxacin Rufloxacin

3rd g.	Balofloxacin Grepafloxacin^‡ Levofloxacin Pazufloxacin Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin

4th g.	Besifloxacin Clinafloxacin^† Garenoxacin Gemifloxacin Moxifloxacin Gatifloxacin^‡ Sitafloxacin Trovafloxacin^‡/Alatrofloxacin^‡ Prulifloxacin

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Related (DG)	Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a (t)/gr-p (c)/gr-o

drug (J1p, w, n, m, vacc)

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Lomefloxacin

See also

References