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
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+;
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 |
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 | ( + / - ) |
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
500.0 nM [IC50] | |||
Target ID: CHEMBL347 |
|||
Target ID: CHEMBL355 |
|||
Target ID: CHEMBL4088 |
300.0 nM [IC50] | ||
Target ID: CHEMBL2311225 |
|||
Target ID: CHEMBL2363033 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | FACTIVE Approved UseAcute 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 Date2003 |
|||
Curative | FACTIVE Approved UseFACTIVE 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 Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Page: Study 185Pneumonia (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%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21158_Factive_pharmr_P2.pdf#page=4 Page: 4.0 |
no | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21158_Factive_pharmr_P1.pdf#page=4 Page: 4.0 |
PubMed
Title | Date | PubMed |
---|---|---|
In vitro activities of six fluoroquinolones against 250 clinical isolates of Mycobacterium tuberculosis susceptible or resistant to first-line antituberculosis drugs. | 2000 Sep |
|
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/gemifloxacin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15155113
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
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admin
on
Edited
Fri Dec 15 15:41:17 GMT 2023
by
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on
Fri Dec 15 15:41:17 GMT 2023
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Record UNII |
X4S9F8RL01
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C795
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |