Gemifloxacin

{{Short description|Medication to treat chronic bronchitis}} {{redirect|Factive|the linguistic sense|factive verb}} {{Use dmy dates|date=June 2024}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461119364 | image = Gemifloxacin.svg | image_class = skin-invert-image | alt =

| tradename = Factive | Drugs.com = {{drugs.com|monograph|gemifloxacin}} | MedlinePlus = a604014 | DailyMedID = Gemifloxacin | pregnancy_category = | routes_of_administration = By mouth | ATC_prefix = J01 | ATC_suffix = MA15

| bioavailability = 71% | protein_bound = 60–70% | metabolism = Limited metabolism by the liver to minor metabolites | excretion = Feces (61%); urine (36%)

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 175463-14-6 | PubChem = 9571107 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01155 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7845573 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = OKR68Y0E4T | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = D08012 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 101853 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 430

| IUPAC_name = 7-[(4''Z'')-3-(Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid | C=18 | H=20 | F=1 | N=5 | O=4 | smiles = Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZRCVYEYHRGVLOC-HYARGMPZSA-N }}

'''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.{{cn|date=June 2024}}

==Common Uses (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''<ref name=Calvo2002>{{cite journal |vauthors=Calvo A, Gimenez MJ |title=Ex Vivo Serum Activity (Killing Rates) After Gemifloxacin 320 mg Versus Trovafloxacin 200 mg Single Doses Against Ciprofloxacin-Susceptible and -Resistant Streptococcus pneumoniae |journal=Int. J. Antimicrob. Agents |volume=20 |issue=2 |pages=144–6 | date= 2002 |pmid=12297365 |doi= 10.1016/S0924-8579(02)00119-X}}</ref> 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== {{See also|Adverse effects of fluoroquinolones}}

Fluoroquinolones are generally well tolerated with most side effects being mild and serious adverse effects being rarely.<ref name="Owens RC, Ambrose PG 2005 S144–57">{{cite journal | vauthors = Owens RC, Ambrose PG | title = Antimicrobial safety: focus on fluoroquinolones | journal = Clinical Infectious Diseases | volume = 41 | pages = S144–S157 | date = July 2005 | issue = Suppl 2 | pmid = 15942881 | doi = 10.1086/428055 | doi-access = free }}</ref><ref name=Bel1999>{{cite journal | vauthors = Ball P, Mandell L, Niki Y, Tillotson G | title = Comparative tolerability of the newer fluoroquinolone antibacterials | journal = Drug Safety | volume = 21 | issue = 5 | pages = 407–421 | date = November 1999 | pmid = 10554054 | doi = 10.2165/00002018-199921050-00005 | s2cid = 26842570 }}</ref> Some of the serious adverse effects which occur more commonly with fluoroquinolones than with other antibiotic drug classes include CNS and tendon toxicity.<ref name="Owens RC, Ambrose PG 2005 S144–57"/><ref name="pmid17559736">{{cite journal | vauthors = Iannini PB | title = The safety profile of moxifloxacin and other fluoroquinolones in special patient populations | journal = Current Medical Research and Opinion | volume = 23 | issue = 6 | pages = 1403–1413 | date = June 2007 | pmid = 17559736 | doi = 10.1185/030079907X188099 | s2cid = 34091286 }}</ref> The currently marketed quinolones have safety profiles similar to that of other antimicrobial classes.<ref name="Owens RC, Ambrose PG 2005 S144–57"/>

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.<ref name=Gold2006>{{Cite book| vauthors = Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA |title=Goldfrank's toxicologic emergencies |publisher=McGraw-Hill, Medical Pub. Division |location=New York |year=2006 |isbn=978-0-07-143763-9 | url=https://books.google.com/books?id=cvJuLqBxGUcC&q=goldfranks+Fluoroquinolone+toxicity&pg=PA849}}</ref> Events that may occur in acute overdose are rare and include: renal failure and seizure.<ref name=Gold2006/> Children and the elderly are at greater risk.<ref name="Owens RC, Ambrose PG 2005 S144–57"/><ref name="pmid17559736"/> Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy.<ref name="pmid10970974">{{cite journal |vauthors=Saint F, Gueguen G, Biserte J, Fontaine C, Mazeman E |title=[Rupture of the patellar ligament one month after treatment with fluoroquinolone] |language=fr |journal=Rev Chir Orthop Reparatrice Appar mot |volume=86 |issue=5 |pages=495–7 |date=September 2000 |pmid=10970974 |url=http://www.masson.fr/masson/MDOI-RCO-09-2000-86-5-0035-1040-101019-ART7}}</ref>

The FDA added a boxed warnings on all fluoroquinolones about the possible toxic effects of fluoroquinolones on tendons.<ref>{{cite news |url=http://www.cnn.com/2008/HEALTH/07/08/antibiotics.risk/index.html|title=FDA orders 'black box' label on some antibiotics |access-date=2008-07-08 |work=CNN | date=2008-07-08}}</ref>

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.<ref>{{Cite web |title=www.fda.gov/ |url=http://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf |archive-url=https://web.archive.org/web/20131008061801/http://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf |archive-date=2013-10-08 |access-date=2026-03-19 |website=www.fda.gov}}</ref> 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).<ref name=" pmid = 24005829 ">{{cite journal | vauthors = Chen TC | title = Gemifloxacin inhibits migration and invasion and induces mesenchymal-epithelial transition in human breast adenocarcinoma cells | journal = J Mol Med (Berl) | volume = 92 | issue = 1|date=January 2014 | pmid = 24005829 | pages = 53–64 | doi=10.1007/s00109-013-1083-4| s2cid = 11279701 }}</ref>

==References== {{Reflist}}

Category:Fluoroquinolone antibiotics Category:Naphthyridines Category:Pyrrolidines Category:Ketoxime ethers Category:Cyclopropyl compounds Category:Carboxylic acids Category:Aminomethyl compounds