Stereochemistry | RACEMIC |
Molecular Formula | C18H20FN5O4 |
Molecular Weight | 389.3809 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CO\N=C1/CN(CC1CN)C2=C(F)C=C3C(=O)C(=CN(C4CC4)C3=N2)C(O)=O
InChI
InChIKey=ZRCVYEYHRGVLOC-HYARGMPZSA-N
InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
Gemifloxacin is an oral broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. Gemifloxacin mesylate is marketed under the brand name Factive, indicated for the treatment of bacterial infection caused by susceptible strains such as S. pneumoniae, H. influenzae, H. parainfluenzae, or M. catarrhalis, S. pneumoniae (including multi-drug resistant strains [MDRSP]), M. pneumoniae, C. pneumoniae, or K. pneumoniae. Gemifloxacin has in vitro activity against a wide range of Gram-negative and Grampositive
microorganisms. Gemifloxacin is bactericidal with minimum bactericidal concentrations (MBCs) generally within one dilution of the minimum inhibitory
concentrations (MICs). Gemifloxacin acts by inhibiting DNA synthesis through the
inhibition of both DNA gyrase and topoisomerase IV (TOPO IV), which are essential for
bacterial growth. Streptococcus pneumoniae showing mutations in both DNA gyrase and
TOPO IV (double mutants) are resistant to most fluoroquinolones. Gemifloxacin has the
ability to inhibit both enzyme systems at therapeutically relevant drug levels in S.
pneumoniae (dual targeting), and has MIC values that are still in the susceptible range for
some of these double mutants.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
Sample Use Guides
Usual Adult Dose for Bronchitis
320 mg orally once a day for 5 days
Usual Adult Dose for Pneumonia
320 mg orally once a day
Route of Administration:
Oral
Gemifloxacin demonstrates impressive minimal inhibitory concentrations (MIC 90 ) values against clinical isolates of Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Chlamydia pneumoniae and Legionella spp., with MIC 90 values reported to be 0.016-0.06, < 0.0008-0.06, 0.008-0.3, 0.25, 0.125 and 0.016-0.07 ug/ml, respectively.