Lomefloxacin

Lomefloxacin
Clinical data
Trade names	Maxaquin
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a600002
ATC code	J01MA07 (WHO) S01AE04 (WHO);
Pharmacokinetic data
Protein binding	10%
Elimination half-life	8 hours[1]
Identifiers
	IUPAC name (RS)-1-Ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid;
CAS Number	98079-51-7 ; HCl: 98079-52-8 ;
PubChem CID	3948;
DrugBank	DB00978 ;
ChemSpider	3811 ;
UNII	L6BR2WJD8V; HCl: 9VC7S3ZXXB ;
KEGG	D02318 ;
ChEBI	CHEBI:116278 ;
ChEMBL	ChEMBL561 ;
CompTox Dashboard (EPA)	DTXSID4040680 ;
ECHA InfoCard	100.117.399
Chemical and physical data
Formula	C17H19F2N3O3
Molar mass	351.354 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	239 to 240.5 °C (462.2 to 464.9 °F)
	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) ; Key:ZEKZLJVOYLTDKK-UHFFFAOYSA-N ;
	(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]

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

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.
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.
Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.

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[Al-Wabli_2017_pp._193–240-1] 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.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 500. ISBN 9783527607495.