Gemifloxacin

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"Factive" redirects here. For the linguistic sense, see factive verb.
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
category
  • C
Legal status
  • ℞ (Prescription only)
Routes of
administration		 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 (WHO)
PubChem CID: 9571107
DrugBank DB01155 YesY
ChemSpider 7845573 YesY
UNII OKR68Y0E4T YesY
KEGG D08012 N
ChEBI CHEBI:101853 YesY
ChEMBL CHEMBL430 YesY
Chemical data
Formula C18H20FN5O4
Molecular mass 389.381 g/mol
  • Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN
  • 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+ YesY
  • Key:ZRCVYEYHRGVLOC-HYARGMPZSA-N YesY
 NYesY (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.

Indications

Gemifloxacin is indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions listed below.

  • Acute bacterial exacerbation of chronic bronchitis caused by S. pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, or Moraxella catarrhalis
  • Community-acquired pneumonia (of mild to moderate severity) caused by S. pneumoniae (including multi-drug resistant strains, Haemophilus influenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, Chlamydia pneumoniae, or Klebsiella pneumoniae

Microbiology

Gemifloxacin has been shown to be active against most strains of the following microorganisms:

Aerobic gram-positive microorganisms - Streptococcus pneumoniae[1]

including multi-drug resistant Streptococcus pneumoniae (MDRSP). MDRSP includes isolates previously known as PRSP (penicillin-resistant Streptococcus pneumoniae), and are strains resistant to two or more of the following antibiotics: penicillin, 2nd generation cephalosporins, e.g., cefuroxime, macrolides, tetracyclines and trimethoprim/sulfamethoxazole.

Staphylococcus aureus and Streptococcus pyogenes
Aerobic gram-negative microorganisms - Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae (many strains are moderately susceptible), Moraxella catarrhalis, Acinetobacter lwoffii, Klebsiella oxytoca, Legionella pneumophila, Proteus vulgaris.
Other microorganisms - Chlamydia pneumoniae, Mycoplasma pneumoniae

Adverse effects

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See also: Adverse effects of fluoroquinolones

Fluoroquinolones are generally well tolerated with most side effects being mild and serious adverse effects being rarely.[2][3] Some of the serious adverse effects which occur more commonly with fluoroquinolones than with other antibiotic drug classes include CNS and tendon toxicity.[4][5] The currently marketed quinolones have safety profiles similar to that of other antimicrobial classes.[4]

The serious events may occur with therapeutic or with acute overdose. At therapeutic doses they include: central nervous system toxicity, cardiovascular toxicity, tendon / articular toxicity, and rarely hepatic toxicity.[6] Events that may occur in acute overdose are rare and include: renal failure and seizure.[6] Children and the elderly are at greater risk.[2][5] Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy.[7]

The FDA ordered a black box warnings on all fluoroquinolones advising consumers of the possible toxic effects of fluoroquinolones on tendons.[8]

On August 15, 2013 the FDA issued a Safety Announcement where they described that they are requiring the medication guides and drug labels for all fluoroquinolones to be updated and better describe the risk for peripheral neuropathy.[9] The peripheral neuropathy may occur very quickly, and may be irreversible. This warning applies to fluoroquinolones taken by mouth and injection, but does not apply to fluoroquinolones taken topically.

Current findings

One recent study showed that Gemifloxacin possess anti-metastatic activities against breast cancer in vitro and in vivo (in mice).[10]

See also

References

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  9. ↑ http://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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