Gemifloxacin

Gemifloxacin
Clinical data
Trade names	Factive
AHFS/Drugs.com	Monograph
MedlinePlus	a604014
License data	US DailyMed: Gemifloxacin;
Routes of; administration	By mouth
ATC code	J01MA15 (WHO) ;
Legal status
Legal status	US: WARNINGRx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	71%
Protein binding	60–70%
Metabolism	Limited metabolism by the liver to minor metabolites
Excretion	Feces (61%); urine (36%)
Identifiers
	IUPAC name 7-[(4Z)-3-(Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid;
CAS Number	175463-14-6 ;
PubChem CID	9571107;
DrugBank	DB01155 ;
ChemSpider	7845573 ;
UNII	OKR68Y0E4T;
KEGG	D08012 ;
ChEBI	CHEBI:101853 ;
ChEMBL	ChEMBL430 ;
CompTox Dashboard (EPA)	DTXSID3048495 ;
Chemical and physical data
Formula	C18H20FN5O4
Molar mass	389.387 g·mol−1
3D model (JSmol)	Interactive image;
	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+ ; Key:ZRCVYEYHRGVLOC-HYARGMPZSA-N ;
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Gemifloxacin mesylate, sold under the brand name Factive among others, is a broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. It is taken by mouth. Vansen Pharma Inc. licensed the active ingredient from LG Life Sciences of Korea.^{[citation needed]}

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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^[2]

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

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

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.^[3]^[5] Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy.^[7]

The FDA added a boxed warnings on all fluoroquinolones about the possible toxic effects of fluoroquinolones on tendons.^[8]

In August 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.

Research

A study showed that gemifloxacin possess anti-metastatic activities against breast cancer in vitro and in vivo (in mice).^[10]

References

[1]
"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
[2]
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.
[3]
Owens RC, Ambrose PG (July 2005). "Antimicrobial safety: focus on fluoroquinolones". Clinical Infectious Diseases. 41 (Suppl 2): S144 – S157. doi:10.1086/428055. PMID 15942881.
[4]
Ball P, Mandell L, Niki Y, Tillotson G (November 1999). "Comparative tolerability of the newer fluoroquinolone antibacterials". Drug Safety. 21 (5): 407–421. doi:10.2165/00002018-199921050-00005. PMID 10554054. S2CID 26842570.
[5]
Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations". Current Medical Research and Opinion. 23 (6): 1403–1413. doi:10.1185/030079907X188099. PMID 17559736. S2CID 34091286.
[6]
Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (2006). Goldfrank's toxicologic emergencies. New York: McGraw-Hill, Medical Pub. Division. ISBN 978-0-07-143763-9.
[7]
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 French). 86 (5): 495–7. PMID 10970974.
[8]
"FDA orders 'black box' label on some antibiotics". CNN. 8 July 2008. Retrieved 8 July 2008.
[9]
https://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf ^{[bare URL PDF]}
[10]
Chen TC (January 2014). "Gemifloxacin inhibits migration and invasion and induces mesenchymal-epithelial transition in human breast adenocarcinoma cells". J Mol Med (Berl). 92 (1): 53–64. doi:10.1007/s00109-013-1083-4. PMID 24005829. S2CID 11279701.

[FDA-AllBoxedWarnings-1] [1]
"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[Calvo2002-2] [2]
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.

[Owens_RC,_Ambrose_PG_2005_S144–57-3] [3]
Owens RC, Ambrose PG (July 2005). "Antimicrobial safety: focus on fluoroquinolones". Clinical Infectious Diseases. 41 (Suppl 2): S144 – S157. doi:10.1086/428055. PMID 15942881.

[Bel1999-4] [4]
Ball P, Mandell L, Niki Y, Tillotson G (November 1999). "Comparative tolerability of the newer fluoroquinolone antibacterials". Drug Safety. 21 (5): 407–421. doi:10.2165/00002018-199921050-00005. PMID 10554054. S2CID 26842570.

[pmid17559736-5] [5]
Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations". Current Medical Research and Opinion. 23 (6): 1403–1413. doi:10.1185/030079907X188099. PMID 17559736. S2CID 34091286.

[Gold2006-6] [6]
Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (2006). Goldfrank's toxicologic emergencies. New York: McGraw-Hill, Medical Pub. Division. ISBN 978-0-07-143763-9.

[pmid10970974-7] [7]
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 French). 86 (5): 495–7. PMID 10970974.

[8] [8]
"FDA orders 'black box' label on some antibiotics". CNN. 8 July 2008. Retrieved 8 July 2008.

[9] [9]
https://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf ^{[bare URL PDF]}

[pmid_=_24005829-10] [10]
Chen TC (January 2014). "Gemifloxacin inhibits migration and invasion and induces mesenchymal-epithelial transition in human breast adenocarcinoma cells". J Mol Med (Berl). 92 (1): 53–64. doi:10.1007/s00109-013-1083-4. PMID 24005829. S2CID 11279701.

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