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Details

Stereochemistry RACEMIC
Molecular Formula C18H20FN5O4
Molecular Weight 389.3809
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GEMIFLOXACIN

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+

HIDE SMILES / InChI

Description

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

Targets

Primary TargetPharmacologyConditionPotency
500.0 nM [IC50]
300.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FACTIVE
Curative
FACTIVE

Cmax

ValueDoseCo-administeredAnalytePopulation
1.61 μg/mL
320 mg 1 times / day multiple, oral
GEMIFLOXACIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
9.93 μg × h/mL
320 mg 1 times / day multiple, oral
GEMIFLOXACIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
320 mg 1 times / day multiple, oral
GEMIFLOXACIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
320 mg 1 times / day multiple, oral
GEMIFLOXACIN plasma
Homo sapiens

Doses

AEs

Overview

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.