Gemifloxacin

Gemifloxacin
Names
Other namesGemifloxacin mesylate
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
Drug classFluoroquinolone[1]
Main usesCOPD exacerbation, pneumonia[1]
Side effectsDiarrhea, nausea, rash, headache, abdominal pain[1]
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Pregnancy
category
  • C
Routes of
use		By mouth
Typical dose320 mg OD[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa604014
Legal
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetics
Bioavailability71%
Protein binding60–70%
MetabolismLimited metabolism by the liver to minor metabolites
ExcretionFeces (61%); urine (36%)
Chemical and physical data
FormulaC18H20FN5O4
Molar mass389.387 g·mol−1
3D model (JSmol)
SMILES
  • Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN
InChI
  • 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+ checkY
  • Key:ZRCVYEYHRGVLOC-HYARGMPZSA-N checkY

Gemifloxacin, sold under the brand name Factive, is an antibiotic used to treat COPD exacerbations and mild-to-moderate pneumonia.[1] It may also be used for gonorrhea.[2] It is generally only used when other options are not suitable.[1] It is taken by mouth.[1]

Common side effects include diarrhea, nausea, rash, headache, and abdominal pain.[1] Other side effects may include tendon rupture, prolonged QT, anaphylaxis, peripheral neuropathy, psychosis, and Clostridioides difficile infection.[3] There are concerns that use in pregnancy may harm the baby.[1] It is in the fluoroquinolone family.[1]

Gemifloxacin was approved for medical use in the United States in 2003.[1] In the United States 5 tablets of 320 mg costs about 220 USD as of 2021.[4] There; however, has been a shortage of the medication due to a dispute over the right to manufacture it, which has been ongoing since 2015.[5]

Medical uses

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

Spectrum of activity

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

Aerobic gram-positive microorganisms – Streptococcus pneumoniae[6]

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

Dosage

It is generally used at a dose of 320 mg per day for 5 to 7 days.[1]

Side effects

See also: Adverse effects of fluoroquinolones

Fluoroquinolones are generally well tolerated with most side effects being mild and serious adverse effects being rarely.[7] Some of the serious adverse effects which occur more commonly with fluoroquinolones than with other antibiotic drug classes include CNS and tendon toxicity.[8][9] The currently marketed quinolones have safety profiles similar to that of other antimicrobial classes.[8]

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.[10] Events that may occur in acute overdose are rare and include: renal failure and seizure.[10] Children and the elderly are at greater risk.[7][9] Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy.[11]

The FDA ordered a black box warnings on all fluoroquinolones advising consumers of the possible toxic effects of fluoroquinolones on tendons.[12]

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.[13] 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.

Society and culture

There was a shortage in the United States as of 2021.[14] The shortage is due to a legal dispute regarding permission to manufacture the medication which has been ongoing since 2015.[5]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 "Gemifloxacin Monograph for Professionals". Drugs.com. Archived from the original on 21 January 2021. Retrieved 3 December 2021.
  2. ↑ Canada, Public Health Agency of (28 July 2017). "Treatment of N. gonorrhoeae in response to the discontinuation of spectinomycin". www.canada.ca. Archived from the original on 1 October 2021. Retrieved 3 December 2021.
  3. ↑ "DailyMed - FACTIVE- gemifloxacin mesylate tablet". dailymed.nlm.nih.gov. Archived from the original on 21 December 2016. Retrieved 3 December 2021.
  4. ↑ "Factive Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 3 December 2021.
  5. 1 2 "FDA Drug Shortages". www.accessdata.fda.gov. Archived from the original on 29 April 2021. Retrieved 3 December 2021.
  6. ↑ Calvo A, Gimenez MJ (2002). "Ex Vivo Serum Activity (Killing Rates) After Gemifloxacin 320 mg Versus Trovafloxacin 200 mg Single Doses Against Ciprofloxacin-Susceptible and -Resistant Streptococcus pneumoniae". Int. J. Antimicrob. Agents. 20 (2): 144–6. doi:10.1016/S0924-8579(02)00119-X. PMID 12297365.
  7. 1 2 Owens RC, Ambrose PG (July 2005). "Antimicrobial safety: focus on fluoroquinolones". Clin. Infect. Dis. 41 Suppl 2: S144–57. doi:10.1086/428055. PMID 15942881.
  8. 1 2 Owens RC, Ambrose PG (July 2005). "Antimicrobial safety: focus on fluoroquinolones". Clin. Infect. Dis. 41 Suppl 2: S144–57. doi:10.1086/428055. PMID 15942881.
  9. 1 2 Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations". Curr Med Res Opin. 23 (6): 1403–13. doi:10.1185/030079907X188099. PMID 17559736. S2CID 34091286.
  10. 1 2 Nelson, Lewis H.; Flomenbaum, Neal; Goldfrank, Lewis R.; Hoffman, Robert Louis; Howland, Mary Deems; Neal A. Lewin (2006). Goldfrank's toxicologic emergencies. New York: McGraw-Hill, Medical Pub. Division. ISBN 978-0-07-143763-9. Archived from the original on 2014-06-12. Retrieved 2021-09-23.
  11. ↑ Saint F, Gueguen G, Biserte J, Fontaine C, Mazeman E (September 2000). "[Rupture of the patellar ligament one month after treatment with fluoroquinolone]". Rev Chir Orthop Reparatrice Appar mot (in français). 86 (5): 495–7. PMID 10970974.
  12. ↑ "FDA orders 'black box' label on some antibiotics". CNN. 2008-07-08. Archived from the original on 2021-04-13. Retrieved 2008-07-08.
  13. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 2019-03-17. Retrieved 2021-09-23.{{cite web}}: CS1 maint: archived copy as title (link)
  14. ↑ "Drug Shortage Detail: Gemifloxacin Mesylate Tablets". www.ashp.org. Archived from the original on 18 September 2021. Retrieved 3 December 2021.
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