U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H20FN5O4.CH4O3S
Molecular Weight 485.487
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GEMIFLOXACIN MESYLATE

SMILES

CS(O)(=O)=O.CO\N=C1/CN(CC1CN)C2=C(F)C=C3C(=O)C(=CN(C4CC4)C3=N2)C(O)=O

InChI

InChIKey=JIYMVSQRGZEYAX-CWUUNJJBSA-N
InChI=1S/C18H20FN5O4.CH4O3S/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;1-5(2,3)4/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27);1H3,(H,2,3,4)/b22-14+;

HIDE SMILES / InChI

Molecular Formula C18H20FN5O4
Molecular Weight 389.3809
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FACTIVE

Approved Use

Acute bacterial exacerbation of chronic bronchitis caused by Streptococcus pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, or Moraxella catarrhalis. Community-acquired pneumonia (of mild to moderate severity) caused by Streptococcus pneumoniae (including multi-drug resistant strains [MDRSP])*, Haemophilus influenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, Chlamydia pneumoniae, or Klebsiella pneumoniae. *MDRSP: multi-drug resistant Streptococcus pneumoniae, includes isolates previously known as PRSP (penicillin-resistant Streptococcus pneumoniae), and are strains resistant to two or more of the following antibiotics: penicillin (MIC ≥2 µg/mL), 2nd generation cephalosporins (e.g., cefuroxime), macrolides, tetracyclines and trimethoprim/sulfamethoxazole.

Launch Date

1.0494144E12
Curative
FACTIVE

Approved Use

FACTIVE is indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions listed below. (See DOSAGE AND ADMINISTRATION and CLINICAL STUDIES .) Acute bacterial exacerbation of chronic bronchitis caused by Streptococcus pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, or Moraxella catarrhalis. Community-acquired pneumonia (of mild to moderate severity) caused by Streptococcus pneumoniae (including multi-drug resistant strains [MDRSP

Launch Date

1.0494144E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.61 μg/mL
320 mg 1 times / day multiple, oral
dose: 320 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GEMIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.93 μg × h/mL
320 mg 1 times / day multiple, oral
dose: 320 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GEMIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
320 mg 1 times / day multiple, oral
dose: 320 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GEMIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
320 mg 1 times / day multiple, oral
dose: 320 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GEMIFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Disc. AE: Hepatic enzymes increased, Pneumonia...
AEs leading to
discontinuation/dose reduction:
Hepatic enzymes increased (grade 3-4, 1.8%)
Pneumonia (grade 3-4, 0.6%)
Diarrhea (grade 3-4, 0.6%)
Flatulence (grade 3-4, 0.6%)
Intestinal obstruction (grade 3-4, 0.6%)
Nausea (grade 3-4, 0.6%)
Vomiting (grade 3-4, 0.6%)
Aortic stenosis (grade 3-4, 0.6%)
Myocardial infarction (grade 3-4, 0.6%)
Somnolence (grade 3-4, 0.6%)
Pleurisy (grade 3-4, 0.6%)
Respiratory insufficiency (grade 3-4, 0.6%)
Rash (grade 3-4, 0.6%)
Leucocytosis NOS (grade 3-4, 0.6%)
Sources: Page: Study 185
AEs

AEs

AESignificanceDosePopulation
Aortic stenosis grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Diarrhea grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Flatulence grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Intestinal obstruction grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Leucocytosis NOS grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Myocardial infarction grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Nausea grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Pleurisy grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Pneumonia grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Rash grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Respiratory insufficiency grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Somnolence grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Vomiting grade 3-4, 0.6%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Hepatic enzymes increased grade 3-4, 1.8%
Disc. AE
320 mg 1 times / day multiple, oral
Recommended
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: Study 185
unhealthy, 59.6
n = 172
Health Status: unhealthy
Condition: Community-Acquired Pneumonia
Age Group: 59.6
Sex: M+F
Population Size: 172
Sources: Page: Study 185
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
In vitro activities of six fluoroquinolones against 250 clinical isolates of Mycobacterium tuberculosis susceptible or resistant to first-line antituberculosis drugs.
2000 Sep
Pharmacokinetics and tissue penetration of gemifloxacin following a single oral dose.
2001 Apr
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.
2002 Mar
Fluoroquinolones as chemotherapeutics against mycobacterial infections.
2004
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:10:15 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:15 UTC 2023
Record UNII
X4S9F8RL01
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEMIFLOXACIN MESYLATE
ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
(±)-7-(3-(AMINOMETHYL)-4-OXO-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7(SUP 4)-(Z)-(O-METHYLOXIME), MONOMETHANESULPHONATE
Common Name English
GEMIFLOXACIN MESYLATE [USAN]
Common Name English
LB-20304A
Code English
(Z)-7-(3-(AMINOMETHYL)-4-(METHOXYIMINO)-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID MONOMETHANESULFONATE
Systematic Name English
GEMIFLOXACIN MESILATE
MART.   WHO-DD  
Common Name English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7-((4Z)-3-(AMINOMETHYL)-4-(METHOXYIMINO)-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4- OXO-, MONOMETHANESULPHONATE
Common Name English
LB 20304A
Code English
FACTIVE
Brand Name English
GEMIFLOXACIN MESILATE [MART.]
Common Name English
Gemifloxacin Mesilate [WHO-DD]
Common Name English
GEMIFLOXACIN METHANESULFONATE [MI]
Common Name English
(±)-7-(3-(AMINOMETHYL)-4-OXO-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7(SUP 4)-(Z)-(O-METHYLOXIME), MONOMETHANESULFONATE
Common Name English
SB-265805-S
Code English
(Z)-7-(3-(AMINOMETHYL)-4-(METHOXYIMINO)-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID MONOMETHANESULPHONATE
Systematic Name English
GEMIFLOXACIN MESYLATE [VANDF]
Common Name English
GEMIFLOXACIN MESYLATE [ORANGE BOOK]
Common Name English
GEMIFLOXACIN MESYLATE [USP-RS]
Common Name English
GEMIFLOXACIN METHANESULFONATE
MI  
Common Name English
GEMIFLOXACIN MESYLATE [USP MONOGRAPH]
Common Name English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 7-((4Z)-3-(AMINOMETHYL)-4-(METHOXYIMINO)-1-PYRROLIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4- OXO-, MONOMETHANESULFONATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
Code System Code Type Description
DAILYMED
X4S9F8RL01
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
MERCK INDEX
M5693
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY Merck Index
EVMPD
SUB21851
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
PUBCHEM
9588170
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
DRUG BANK
DBSALT002832
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
RS_ITEM_NUM
1288667
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
RXCUI
402429
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY RxNorm
USAN
KK-82
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
SMS_ID
100000090463
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
FDA UNII
X4S9F8RL01
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL430
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID7045948
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
CAS
210353-53-0
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
NCI_THESAURUS
C47548
Created by admin on Wed Jul 05 23:10:15 UTC 2023 , Edited by admin on Wed Jul 05 23:10:15 UTC 2023
PRIMARY
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