| Revision as of 15:15, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456887783 of page Gemifloxacin for the Chem/Drugbox validation project (updated: 'DrugBank', 'KEGG'). |
Latest revision as of 11:35, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Cyclopropanes; added Category:Cyclopropyl compounds using HotCat |
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{{Short description|Medication to treat chronic bronchitis}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{redirect|Factive|the linguistic sense|factive verb}} |
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{{Use dmy dates|date=June 2024}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 443833589 |
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| verifiedrevid = 461119364 |
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| IUPAC_name = 7-- 1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid |
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| image = Gemifloxacin.svg |
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| image = Gemifloxacin.svg |
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| alt = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Factive |
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| Drugs.com = {{drugs.com|monograph|factive}} |
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| Drugs.com = {{drugs.com|monograph|gemifloxacin}} |
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| MedlinePlus = a604014 |
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| MedlinePlus = a604014 |
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| DailyMedID = Gemifloxacin |
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| pregnancy_category = C |
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| pregnancy_category = |
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| routes_of_administration = ] |
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| ATC_prefix = J01 |
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| ATC_suffix = MA15 |
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<!-- Legal status --> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_AU_comment = |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| legal_BR_comment = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US_comment = |
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| legal_EU = |
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| legal_EU_comment = |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = Rx-only |
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| legal_status = Rx-only |
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| routes_of_administration = Oral/IV under development |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 71% |
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| bioavailability = 71% |
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| protein_bound = 60-70% |
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| protein_bound = 60–70% |
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| metabolism = Limited metabolism by the liver to minor metabolites |
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| metabolism = Limited metabolism by the liver to minor metabolites |
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| excretion = Feces (61%); urine (36%) |
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| excretion = Feces (61%); urine (36%) |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 175463-14-6 |
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| CAS_number = 175463-14-6 |
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| ATC_prefix = J01 |
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| ATC_suffix = MA15 |
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| PubChem = 9571107 |
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| PubChem = 9571107 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| UNII = OKR68Y0E4T |
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| UNII = OKR68Y0E4T |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = <!-- blanked - oldvalue: D02471 --> |
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| KEGG = D08012 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 101853 |
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| ChEBI = 101853 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| IUPAC_name = 7--1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid |
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| C=18 | H=20 | F=1 | N=5 | O=4 |
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| C=18 | H=20 | F=1 | N=5 | O=4 |
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| molecular_weight = 389.381 g/mol |
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| smiles = Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN |
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| smiles = Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN |
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| InChI = 1/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+ |
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| InChIKey = ZRCVYEYHRGVLOC-HYARGMPZBL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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+ |
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| 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+ |
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| StdInChIKey = ZRCVYEYHRGVLOC-HYARGMPZSA-N |
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| StdInChIKey = ZRCVYEYHRGVLOC-HYARGMPZSA-N |
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}} |
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}} |
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'''Gemifloxacin mesylate''', sold under the brand name '''Factive''' among others, is a ] ] agent used in the treatment of acute bacterial exacerbation of chronic ] and mild-to-moderate ]. It is taken ]. Vansen Pharma Inc. licensed the active ingredient from LG Life Sciences of Korea.{{cn|date=June 2024}} |
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==Indications== |
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Gemifloxacin is indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions listed below. |
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* Acute bacterial exacerbation of ] caused by ''S. pneumoniae'', ''Haemophilus influenzae'', ''Haemophilus parainfluenzae'', or ''Moraxella catarrhalis'' |
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* ] (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'' |
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==Microbiology== |
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Gemifloxacin has been shown to be active against most strains of the following microorganisms: |
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:Aerobic ] microorganisms – '']''<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> |
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including ] ''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 ], e.g., ], ], ] and ]/]. |
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:'']'' and '']'' |
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:Aerobic ] microorganisms – '']'', '']'', ] (many strains are moderately susceptible), ], '']'', '']'', '']'', '']''. |
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:Other microorganisms – '']'', '']'' |
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==Adverse effects== |
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{{See also|Adverse effects of fluoroquinolones}} |
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] 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 ] 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"/> |
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The serious events may occur with therapeutic or with acute overdose. At therapeutic doses they include: central nervous system 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= |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> |
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The FDA added a ]s 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> |
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In August 2013, the FDA issued a Safety Announcement where they described that they are requiring the medication guides and drug labels for all ] to be updated and better describe the risk for ].<ref>https://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf {{Bare URL PDF|date=March 2022}}</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. |
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== Research == |
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A study showed that gemifloxacin possess anti-metastatic activities against ] 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> |
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==References== |
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{{Reflist}} |
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{{QuinoloneAntiBiotics}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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