Lomefloxacin

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 462093329

| IUPAC_name = (RS)-1-Ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid

| image = Lomefloxacin.svg

| image2 = Lomefloxacin ball-and-stick.png

| tradename = Maxaquin

| Drugs.com = {{drugs.com|CDI|lomefloxacin}}

| MedlinePlus = a600002

| pregnancy_AU =

| pregnancy_category =

| routes_of_administration =

| ATC_prefix = J01

| ATC_suffix = MA07

| ATC_supplemental = {{ATC|J04|AM09}}, {{ATC|S01|AE04}}

| legal_AU =

| legal_UK =

| legal_US =

| legal_status =

| bioavailability =

| protein_bound = 10%

| metabolism =

| elimination_half-life = 8 hours{{cite book | last=Al-Wabli | first=Reem I. | name-list-style = vanc | title=Profiles of Drug Substances, Excipients and Related Methodology | chapter=Lomefloxacin | journal=Profiles of Drug Substances, Excipients, and Related Methodology | publisher=Elsevier | year=2017 | volume=42 | isbn=978-0-12-812226-6 | issn=1871-5125 | doi=10.1016/bs.podrm.2017.02.004 | pages=193–240| pmid=28431777 |quote=Lomefloxacin elimination half-life is about 7–8 h and is prolonged in patients with renal impairment. }}

| excretion =

| index2_label = HCl

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 98079-52-8

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 9VC7S3ZXXB

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 98079-51-7

| PubChem = 3948

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00978

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3811

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L6BR2WJD8V

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02318

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 116278

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 561

| C=17 | H=19 | F=2 | N=3 | O=3

| smiles = Fc1c(c(F)c2c(c1)C(=O)C(\C(=O)O)=C/N2CC)N3CC(NCC3)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZEKZLJVOYLTDKK-UHFFFAOYSA-N

| melting_point = 239

| melting_high = 240.5

}}

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.{{cite journal | vauthors = Rubinstein E | title = History of quinolones and their side effects | journal = Chemotherapy | volume = 47 | issue = Suppl 3 | pages = 3–8; discussion 44-8 | year = 2001 | pmid = 11549783 | doi = 10.1159/000057838 | s2cid = 21890070 }}

In 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."

It was patented in 1983 and approved for medical use in 1989.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=500 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA500 |language=en}}