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Lomefloxacin

Lomefloxacin
Clinical data
Trade namesMaxaquin
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa600002
ATC code
Pharmacokinetic data
Protein binding10%
Elimination half-life8 hours[1]
Identifiers
  • (RS)-1-Ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.117.399 Edit this at Wikidata
Chemical and physical data
FormulaC17H19F2N3O3
Molar mass351.354 g·mol−1
3D model (JSmol)
Melting point239 to 240.5 °C (462.2 to 464.9 °F)
  • Fc1c(c(F)c2c(c1)C(=O)C(\C(=O)O)=C/N2CC)N3CC(NCC3)C
  • 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) checkY
  • Key:ZEKZLJVOYLTDKK-UHFFFAOYSA-N checkY
  (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.[2]

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.[3]

References

  1. ^ Al-Wabli RI (2017). "Lomefloxacin". Profiles of Drug Substances, Excipients and Related Methodology. Vol. 42. Elsevier. pp. 193–240. doi:10.1016/bs.podrm.2017.02.004. ISBN 978-0-12-812226-6. ISSN 1871-5125. PMID 28431777. Lomefloxacin elimination half-life is about 7–8 h and is prolonged in patients with renal impairment.
  2. ^ 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. S2CID 21890070.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.
Quelle: https://en.wikipedia.org/wiki/Lomefloxacin