Gemifloxacin

Title: Gemifloxacin
CAS Registry Number: 175463-14-6
CAS Name: 7-[3-(Aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
Manufacturers' Codes: SB-265805; LB-20304
Molecular Formula: C18H20FN5O4
Molecular Weight: 389.38
Percent Composition: C 55.52%, H 5.18%, F 4.88%, N 17.99%, O 16.44%
Literature References: Third generation fluorinated quinolone antibacterial. Prepn: J. H. Kwak et al., EP 688772; C. Y. Hong et al., US 5633262 (1995, 1997 both to LG Chemical); C. Y. Hong et al., J. Med. Chem. 40, 3584 (1997). Antibacterial spectrum in vitro: R. Wise, J. M. Andrews, J. Antimicrob. Chemother. 44, 679 (1999). HPLC-tandem MS determn in human plasma: E. Doyle et al., J. Chromatogr. B 746, 191 (2000). Clinical pharmacokinetics: A. Allen et al., Antimicrob. Agents Chemother. 44, 1604 (2000). Review of antibacterial activity, pharmacology, and clinical trials: J. M. Blondeau, B. Missaghi, Expert Opin. Pharmacother. 5, 1117-1152 (2004).
Properties: Off-white, amorphous solid from chloroform-ethanol, mp 235-237°.
Melting point: mp 235-237°
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Quinolones and Analogs.
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Gemifloxacin
Gemifloxacin.svg
Systematic (IUPAC) name
7-[(4Z)-3-(Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a604014
Pregnancy cat. C
Legal status Prescription only
Routes Oral/IV under development
Pharmacokinetic data
Bioavailability 71%
Protein binding 60-70%
Metabolism Limited metabolism by the liver to minor metabolites
Excretion Feces (61%); urine (36%)
Identifiers
CAS number 175463-14-6 YesY
ATC code J01MA15
PubChem CID 9571107
DrugBank DB01155
ChemSpider 7845573 YesY
UNII OKR68Y0E4T YesY
KEGG D08012 N
ChEBI CHEBI:101853 YesY
ChEMBL CHEMBL430 YesY
Chemical data
Formula C18H20FN5O4 
Mol. mass 389.381 g/mol
 N (what is this?)  (verify)

Gemifloxacin mesylate (trade name Factive, Oscient Pharmaceuticals) is an oral broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. Vansen Pharma Inc. has licensed the active ingredient from LG Life Sciences of Korea.