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Revision as of 13:10, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456624997 of page Moxifloxacin for the Chem/Drugbox validation project (updated: 'DrugBank', 'UNII').  Latest revision as of 08:53, 21 December 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,136 edits rank 
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{{Short description|Antibiotic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=January 2024}}
{{drugbox
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 462255811
| UNII_Ref = {{fdacite|changed|FDA}}
| image = Moxifloxacin.svg
| image2 = Moxifloxacin-cation-from-xtal-3D-balls.png

<!--Clinical data-->
| tradename = Avelox, Vigamox, Moxiflox, others
| Drugs.com = {{drugs.com|monograph|moxifloxacin-hydrochloride}}
| MedlinePlus = a600002
| licence_US = Moxifloxacin
| pregnancy_AU = B3
| routes_of_administration = ], ], ]
| class = ] (])
| ATC_prefix = J01
| ATC_suffix = MA14
| ATC_supplemental = {{ATC|S01|AE07}}

| legal_AU = S4
| legal_UK =
| legal_US = Rx-only

<!--Pharmacokinetic data-->
| bioavailability = 86%<ref name="pmid17154673">{{cite journal | vauthors = Zhanel GG, Fontaine S, Adam H, Schurek K, Mayer M, Noreddin AM, Gin AS, Rubinstein E, Hoban DJ | display-authors = 6 | title = A Review of New Fluoroquinolones : Focus on their Use in Respiratory Tract Infections | journal = Treatments in Respiratory Medicine | volume = 5 | issue = 6 | pages = 437–465 | year = 2006 | pmid = 17154673 | doi = 10.2165/00151829-200605060-00009 | s2cid = 26955572 }}</ref>
| protein_bound = 47%<ref name="pmid17154673" />
| metabolism = ] and ] ]; {{abbrlink|CYP450|cytochrome P450}} system not involved<ref name="WHO2008">{{cite book|author=World Health Organization|title=Guidelines for the Programmatic Management of Drug-resistant Tuberculosis|url=https://books.google.com/books?id=XKsLsl4_v4QC&pg=PA189|year=2008|publisher=World Health Organization|isbn=978-92-4-154758-1|pages=189–}}</ref>
| elimination_half-life = 12.1 hours<ref name="pmid17154673" />
| excretion = ], ]

<!--Identifiers-->
| index2_label = as HCl
| CAS_number_Ref = {{cascite|correct|yes}}
| CAS_number = 151096-09-2
| PubChem = 152946
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00218
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 134802
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = U188XYD42P | UNII = U188XYD42P
| KEGG = D08237
| verifiedrevid = 408764902
| KEGG2 = D00874
|
| IUPAC_name = 1-cyclopropyl-7-[(1''S'',6''S'')-2,8-diazabicyclo
non-8-yl]-6-fluoro-8-methoxy-4-oxo-
quinoline-3-carboxylic acid
| image = Moxifloxacin Structural Formulae V.1.svg
| image2 = Moxifloxacin-cation-from-xtal-3D-balls.png
| CASNo_Ref = {{cascite|correct|CAS}}
| InChI = 1/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
| InChIKey = FABPRXSRWADJSP-MEDUHNTEBH
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 32 | ChEMBL = 32
| NIAID_ChemDB = 070017
| synonyms = Moxifloxacine; BAY 12-8039

<!--Chemical data-->
| IUPAC_name = 1-Cyclopropyl-7-nonan-8-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
| C=21 | H=24 | N=3 | F=1 | O=4
| SMILES = COc1c2c(cc(c1N3C4CCCN4C3)F)c(=O)c(cn2C5CC5)C(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1 | StdInChI = 1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FABPRXSRWADJSP-MEDUHNTESA-N | StdInChIKey = FABPRXSRWADJSP-MEDUHNTESA-N
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 354812-41-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 134802
| ATC_prefix = J01
| ATC_suffix = MA14
| ATC_supplemental = {{ATC|S01|AX22}}
| PubChem = 152946
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00218
| chemical_formula =
| C=21 |H=24 |N=3 |F=1 |O=4
| molecular_weight = 401.431 ]/]
| smiles = COc1c2c(cc(c1N3C4CCCN4C3)F)c(=O)c(cn2C5CC5)C(=O)O
| bioavailability = 86 to 92%
| protein_bound = 30 to 50%
| metabolism = ] and ] conjugation<br>] system not involved
| elimination_half-life = 12 hours
| excretion = hepatic
| pregnancy_category = C <small>(United States)</small><br>B3 <small>(Australia)</small>
| legal_status = ]
| routes_of_administration = ], ], local (eyedrops)
}} }}
<!-- Definition and treatment -->
'''Moxifloxacin''' is an ], used to treat ]s,<ref name=AHFS2017/> including ], ], ], ], and ].<ref name=AHFS2017>{{cite web|title=Moxifloxacin Hydrochloride|url=https://www.drugs.com/monograph/moxifloxacin-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date= 29 August 2017}}</ref><ref name=BNF69/> It can be given by mouth, by ], and as an ].<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=408, 757|edition=69}}</ref>

<!-- Side effects and mechanism -->
Common side effects include ], dizziness, and headache.<ref name=AHFS2017/> Severe side effects may include spontaneous ]s, ], and worsening of ].<ref name=AHFS2017/> Safety of use in ] and ] is unclear.<ref>{{cite web|title=Moxifloxacin Use During Pregnancy|url=https://www.drugs.com/pregnancy/moxifloxacin.html|website=Drugs.com|access-date=10 December 2017}}</ref> Moxifloxacin is in the ] family of medications.<ref name=AHFS2017/> It usually ] by blocking their ability to duplicate ].<ref name=AHFS2017/>

<!-- History and culture -->
Moxifloxacin was patented in 1988 and approved for use in the United States in 1999.<ref name="Details for NDA:021085">{{cite web |title=Details for NDA:021085 |url=http://www.drugpatentwatch.com/p/NDA/021085 |publisher=DrugPatentWatch |access-date=17 July 2009}}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=501 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA501 |language=en}}</ref> It is on the ].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> In 2022, it was the 273rd most commonly prescribed medication in the United States, with more than 800,000 prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Moxifloxacin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Moxifloxacin | access-date = 30 August 2024 }}</ref>

==Medical uses==
Moxifloxacin treats a number of infections, including ], ], ], ], ], ], ], and ].<ref name=AHFS>{{cite web|title=Avelox|url=https://www.drugs.com/monograph/avelox.html|work=The American Society of Health-System Pharmacists|access-date=3 April 2011}}</ref>

In the United States, moxifloxacin is licensed for the treatment of acute bacterial sinusitis, acute bacterial exacerbation of chronic bronchitis, community-acquired pneumonia, complicated and uncomplicated infections of the skin and of the skin structure, and complicated intra-abdominal infections.<ref name="www.accessdata.fda.gov">{{cite web |url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021085s55-021277s052lbl.pdf |title=Documents |website=accessdata.fda.gov }}</ref> In the European Union, it is licensed for acute bacterial exacerbations of chronic bronchitis, non-severe community-acquired pneumonia, and acute bacterial sinusitis. On the basis of its investigation into reports of rare but severe cases of liver toxicity and skin reactions, the European Medicines Agency recommended in 2008 that the use of the oral (but not the intravenous) form of moxifloxacin be restricted to infections in which other antibacterial agents cannot be used or have failed.<ref name="www.emea.europa.eu">{{cite web |url=http://www.emea.europa.eu/docs/en_GB/documednt_library/Press_release/2010/08/WC500095423.pdf |title=Press release|publisher=Europa (web portal) }}</ref> In the United States, the marketing approval does not contain these restrictions, though the label contains prominent warnings of skin reactions.

The initial approval by the Food and Drug Administration of the United States (December 1999)<ref>{{cite web|url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/1999/21085ltr.pdf |title=Application letter |year=1999 |website=accessdata.fda.gov |access-date=7 June 2019}}</ref> encompassed these indications:
* Acute exacerbations of chronic bronchitis
* Acute bacterial sinusitis
* Community acquired pneumonia

Additional indications approved by the Food and Drug Administration:
* April 2001: Uncomplicated skin and skin-structure infections<ref>{{cite web|url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-085S010_Avelox_Approv.pdf |title=Approval of supplements |year=2001 |website=accessdata.fda.gov |access-date=7 June 2019}}</ref>
* May 2004: Community-acquired pneumonia caused by multidrug-resistant ''Streptococcus pneumoniae''<ref>{{cite web |url= http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2004/21085se1-022,21277se1-017ltr.pdf|title=Application letter|website= accessdata.fda.gov|year=2004|access-date=7 June 2019}}</ref>
* June 2005: Complicated skin and skin-structure infections<ref>{{cite web|url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2005/021085s026,021277s022ltr.pdf |title=Approval of supplements |year=2005 |website=accessdata.fda.gov |access-date=7 June 2019}}</ref>
* November 2005: Complicated intra-abdominal infections<ref>{{cite web |url= http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2005/021085s027,029,021277s024,025ltr.pdf|title=Application letter |website= accessdata.fda.gov|access-date=7 June 2019}}</ref>

The ] has advised that, for pneumonia, acute bacterial sinusitis, and acute exacerbations of COPD, it should only be used when other antibiotics are inappropriate.<ref>{{cite web|title=Moxifloxacin: increased risk of life-threatening liver reactions and other serious risks|url=https://www.gov.uk/drug-safety-update/moxifloxacin-increased-risk-of-life-threatening-liver-reactions-and-other-serious-risks|access-date=8 February 2022|website=gov.uk}}</ref><ref>{{cite web |publisher=European Medicines Agency |title=European Medicines Agency recommends restricting the use of oral moxifloxacin-containing medicines |url=http://www.emea.europa.eu/pdfs/human/press/pr/38292708en.pdf |date=24 July 2008 |access-date=20 July 2009 |archive-url=https://web.archive.org/web/20090708125020/http://www.emea.europa.eu/pdfs/human/press/pr/38292708en.pdf |archive-date=8 July 2009 |url-status=dead}}</ref>

Oral and intravenous moxifloxacin have not been approved for children. Several drugs in this class, including moxifloxacin, are not licensed by the Food and Drug Administration for use in children, because of the risk of permanent injury to the musculoskeletal system.<ref name=s2009>{{cite web| url = http://download.veritasmedicine.com/PDF/CR002392_CSR.pdf| title = SYNOPSIS | access-date =29 January 2009 }}</ref><ref name="pmid1592498">{{cite journal | vauthors = Karande SC, Kshirsagar NA | title = Adverse drug reaction monitoring of ciprofloxacin in pediatric practice | journal = Indian Pediatrics | volume = 29 | issue = 2 | pages = 181–188 | date = February 1992 | pmid = 1592498 }}</ref><ref name="Dolui">{{cite journal | vauthors = Dolui SK, Das M, Hazra A | title = Ofloxacin-induced reversible arthropathy in a child | journal = Journal of Postgraduate Medicine | volume = 53 | issue = 2 | pages = 144–145 | year = 2007 | pmid = 17495385 | doi = 10.4103/0022-3859.32220 | doi-access = free }}</ref> Moxifloxacin eye drops are approved for ]l infections caused by susceptible bacteria.<ref>{{cite web |title=Center for drug evaluation and research Application number 21-598 |url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-598_Vigamox_approv.PDF |publisher=] (FDA) |date=15 April 2005 |access-date=21 July 2009}}</ref>

Recently, alarming reports of moxifloxacin resistance rates among anaerobes have been published. In Austria 36% of ''Bacteroides'' have been reported to be resistant to moxifloxacin,<ref>{{cite journal | vauthors = König E, Ziegler HP, Tribus J, Grisold AJ, Feierl G, Leitner E | title = Surveillance of Antimicrobial Susceptibility of Anaerobe Clinical Isolates in Southeast Austria: ''Bacteroides fragilis'' Group Is on the Fast Track to Resistance | journal = Antibiotics | volume = 10 | issue = 5 | pages = 479 | date = April 2021 | pmid = 33919239 | pmc = 8143075 | doi = 10.3390/antibiotics10050479 | doi-access = free }}</ref> while in Italy resistance rates as high as 41% have been reported.<ref>{{cite journal | vauthors = Principe L, Sanson G, Luzzati R, Aschbacher R, Pagani E, Luzzaro F, Di Bella S | title = Time to reconsider moxifloxacin anti-anaerobic activity? | journal = Journal of Chemotherapy | pages = 367–368 | date = August 2022 | volume = 35 | issue = 4 | pmid = 35947127 | doi = 10.1080/1120009X.2022.2106637 | s2cid = 251470489 }}</ref>

===Susceptible bacteria===
A broad spectrum of bacteria is susceptible, including the following:
* '']''
* '']''
* '']''
* '']''
* '']'' spp.
* '']''
* '']'' spp.
* '']'' spp.
* '']''
* '']''<ref>{{cite journal | vauthors = Unemo M, Jensen JS | title = Antimicrobial-resistant sexually transmitted infections: gonorrhoea and Mycoplasma genitalium | journal = Nature Reviews. Urology | volume = 14 | issue = 3 | pages = 139–152 | date = March 2017 | pmid = 28072403 | doi = 10.1038/nrurol.2016.268 | s2cid = 205521926 }}</ref>
* ] (found to be effective in vitro) <ref>{{cite journal | vauthors = Pothineni VR, Wagh D, Babar MM, Inayathullah M, Solow-Cordero D, Kim KM, Samineni AV, Parekh MB, Tayebi L, Rajadas J | display-authors = 6 | title = Identification of new drug candidates against Borrelia burgdorferi using high-throughput screening | journal = Drug Design, Development and Therapy | volume = 10 | pages = 1307–1322 | date = 1 April 2016 | pmid = 27103785 | pmc = 4827596 | doi = 10.2147/DDDT.S101486 | doi-access = free }}</ref>

==Adverse effects==
{{See also|Adverse effects of fluoroquinolones}}

Rare but serious adverse effects that may occur as a result of moxifloxacin therapy include irreversible ], spontaneous tendon rupture and ],<ref>{{cite web | vauthors = Albrecht R |title = NDA 21-085/S-024, NDA 21-277/S-019 |url = http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2004/21277s019,21085s024ltr.pdf |work = Center for Drug Evaluation and Research |publisher = ] (FDA) |date = 28 July 2004 |access-date =31 July 2009 }}</ref> ], psychiatric effects (hallucinations, depression), '']'', ] and '']''-associated disease,<ref>{{cite web | vauthors = Albrecht R |title=NDA 21-085/S-036, NDA 21-277/S-030 |url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2007/021085s036,021277s030ltr.pdf |work=Center for Drug Evaluation and Research |publisher=] (FDA) |date=31 May 2007 |access-date=31 July 2009}}</ref> and photosensitivity/phototoxicity reactions.<ref>{{cite web | vauthors = Albrecht R |title=NDA 21-085/S-038, NDA 21-277/S-031 |url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2008/021085s038ltr.pdf |work=Division of Special Pathogen and Transplant Products |publisher=] (FDA) |date=15 February 2008 |access-date=31 July 2009}}</ref><ref>{{cite web |author=DEPARTMENT OF HEALTH & HUMAN SERVICES |title=NDA 21-085/S-014, S-015, S-017 |url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2003/21085slr014se1-015slr017,21277slr006se1-007slr009ltr.pdf |publisher=] (FDA) |date=28 February 2008 |access-date=17 July 2009}}</ref>

Several reports suggest the use of moxifloxacin may lead to ].<ref name=JAMA_Ophthalmology>{{cite web|title=Risk for Uveitis With Oral Moxifloxacin|url=http://archopht.jamanetwork.com/article.aspx?articleid=1913582|publisher=JAMA Ophthalmology online|date=2 October 2014}}</ref>

===Pregnancy and breastfeeding===
Exposure of the developing fetus to quinolones, including levofloxacin, during the first-trimester is not associated with an increased risk of stillbirths, premature births, birth defects, or low birth weight.<ref>{{cite journal | vauthors = Ziv A, Masarwa R, Perlman A, Ziv D, Matok I | title = Pregnancy Outcomes Following Exposure to Quinolone Antibiotics - a Systematic-Review and Meta-Analysis | journal = Pharmaceutical Research | volume = 35 | issue = 5 | pages = 109 | date = March 2018 | pmid = 29582196 | doi = 10.1007/s11095-018-2383-8 | s2cid = 4724821 }}</ref> There is limited data about the appearance of moxifloxacin in human breastmilk. Animal studies have found that moxifloxacin appears in significant concentration in breastmilk.<ref>{{cite journal | vauthors = Balfour JA, Lamb HM | title = Moxifloxacin: a review of its clinical potential in the management of community-acquired respiratory tract infections | journal = Drugs | volume = 59 | issue = 1 | pages = 115–139 | date = January 2000 | pmid = 10718103 | doi = 10.2165/00003495-200059010-00010 | s2cid = 195694147 }}</ref> Decisions as to whether to continue therapy during pregnancy or while breast feeding should take the potential risk of harm to the fetus or child into account, as well as the importance of the drug to the well-being of the mother.<ref name="www.merck.com">{{cite web |url=https://www.merck.com/product/usa/pi_circulars/a/avelox/avelox_pi.pdf |title=merck.com }}</ref>

==Contraindications==
Only two listed contraindications are found within the 2008 package insert:
* "] (NSAIDs): Although not observed with moxifloxacin in preclinical and clinical trials, the concomitant administration of a nonsteroidal anti-inflammatory drug with a fluoroquinolone may increase the risks of ] stimulation and convulsions."<ref name="insert">{{cite web |author=Bayer |title=AVELOX (moxifloxacin hydrochloride) Tablets AVELOX I.V. (moxifloxacin hydrochloride in sodium chloride injection) |url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021085s039,021277s033lbl.pdf |publisher=] (FDA) |date=December 2008 |page= 19 |access-date=2 November 2010}}</ref>
* "Moxifloxacin is contraindicated in persons with a history of hypersensitivity to moxifloxacin, any member of the quinolone class of antimicrobial agents, or any of the product components."<ref name="insert" />

Though not stated as such within the package insert, ziprasidone is also considered to be contraindicated, as it may have the potential to prolong QT interval. Moxifloxacin should also be avoided in patients with uncorrected hypokalemia, or concurrent administration of other medications known to prolong the QT interval (antipsychotics and tricyclic antidepressants).<ref name="umm.edu">{{cite web |title=Moxifloxacin |url=http://www.umm.edu/altmed/drugs/moxifloxacin-088848.htm |archive-url=https://web.archive.org/web/20090307063002/http://www.umm.edu/altmed/drugs/moxifloxacin-088848.htm |url-status=dead |archive-date=7 March 2009 |publisher=University of Maryland Medical Center |year=2009 |access-date=22 July 2009}}</ref>

Moxifloxacin should be used with caution in patients with ], as glucose regulation may be significantly altered.<ref name="umm.edu"/>

Moxifloxacin is also considered to be contraindicated within the pediatric population, ], nursing mothers, patients with a history of tendon disorder, patients with documented QT prolongation,<ref>{{cite web|url=http://www.akdae.de/Arzneimittelsicherheit/RHB/Archiv/2009/20090119.pdf |title=Microsoft Word - Rote Hand Brief Avalox an BfArM.doc |access-date=7 June 2019}}</ref> and patients with ] or other seizure disorders. Coadministration of moxifloxacin with other drugs that also prolong the QT interval or induce bradycardia (e.g., beta-blockers, amiodarone) should be avoided. Careful consideration should be given in the use of moxifloxacin in patients with cardiovascular disease, including those with conduction abnormalities.<ref name="umm.edu"/>

===Children and adolescents===
The safety of moxifloxacin in human patients under age 18 has not been established. Animal studies suggest a risk of musculoskeletal harm in juveniles.<ref name="www.merck.com"/>

== Interactions ==

Moxifloxacin is not believed to be associated with clinically significant drug interactions due to inhibition or stimulation of hepatic metabolism. Thus, it should not, for the most part, require special clinical or laboratory monitoring to ensure its safety.<ref>{{cite journal | vauthors = Nightingale CH | title = Moxifloxacin, a new antibiotic designed to treat community-acquired respiratory tract infections: a review of microbiologic and pharmacokinetic-pharmacodynamic characteristics | journal = Pharmacotherapy | volume = 20 | issue = 3 | pages = 245–256 | date = March 2000 | pmid = 10730681 | doi = 10.1592/phco.20.4.245.34880 | s2cid = 11448163 }}</ref> Moxifloxacin has a potential for a serious drug interaction with NSAIDs.<ref name="wl121599">{{cite letter|date=15 December 1999|author=U.S. Food and Drug Administration|author-link=U.S. Food and Drug Administration|recipient=Martina Ziska|subject=RE: NDA # 21-085 Avelox (moxifloxacin hydrochloride) Tablets MACMIS # 8577|url=https://www.fda.gov/cder/warn/dec99/wl121599.pdf|archive-url=https://web.archive.org/web/20090309204016/https://www.fda.gov/cder/warn/dec99/wl121599.pdf|archive-date=9 March 2009|access-date=11 April 2009}}</ref>

The combination of ] and moxifloxacin has increased potential to result in tendonitis and disability.<ref>{{cite web | vauthors = Albrecht R |title=NDA 21-085/S-012 |url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2002/21-085s012ltr.pdf |publisher=] (FDA) |date=16 May 2002 |access-date=17 July 2009}}</ref>

Antacids containing ] or ] ]s inhibit the absorption of moxifloxacin. Drugs that prolong the ] (e.g., ]) may have an additive effect on QT prolongation and lead to increased risk of ventricular arrhythmias. The ] may be increased or decreased in patients treated with ].<ref name="wl121599"/>

==Overdose==
"In the event of acute overdose, the stomach should be emptied and adequate hydration maintained. ECG monitoring is recommended due to the possibility of QT interval prolongation. The patient should be carefully observed and given supportive treatment. The administration of ] as soon as possible after oral overdose may prevent excessive increase of systemic moxifloxacin exposure. About 3% and 9% of the dose of moxifloxacin, as well as about 2% and 4.5% of its glucuronide metabolite are removed by continuous ambulatory peritoneal dialysis and hemodialysis, respectively." (Quoting from 29 December 2008 package insert for Avelox)<ref name="insert" />

==Pharmacology==

===Mechanism of action===
Moxifloxacin is a ] that is active against both ] and ] bacteria. It functions by inhibiting ], a type II ], and topoisomerase IV,<ref>{{cite journal | vauthors = Drlica K, Zhao X | title = DNA gyrase, topoisomerase IV, and the 4-quinolones | journal = Microbiology and Molecular Biology Reviews | volume = 61 | issue = 3 | pages = 377–392 | date = September 1997 | pmid = 9293187 | pmc = 232616 | doi = 10.1128/mmbr.61.3.377-392.1997 }}</ref> enzymes necessary to separate bacterial DNA, thereby inhibiting cell replication.

===Pharmacokinetics===
About 52% of an oral or intravenous dose of moxifloxacin is metabolized via glucuronide and sulfate conjugation. The cytochrome P450 system is not involved in moxifloxacin metabolism, and is not affected by moxifloxacin.<ref name="WHO2008" /> The sulfate conjugate (M1) accounts for around 38% of the dose, and is eliminated primarily in the feces. Approximately 14% of an oral or intravenous dose is converted to a glucuronide conjugate (M2), which is excreted exclusively in the urine. Peak plasma concentrations of M2 are about 40% those of the parent drug, while plasma concentrations of M1 are, in general, less than 10% those of moxifloxacin.<ref name="insert" />

''In vitro'' studies with cytochrome (CYP) P450 enzymes indicate that moxifloxacin does not inhibit 80 CYP3A4, CYP2D6, CYP2C9, CYP2C19, or CYP1A2, suggesting that moxifloxacin is unlikely to alter the pharmacokinetics of drugs metabolized by these enzymes.<ref name="insert" /><ref name="WHO2008" />

The pharmacokinetics of moxifloxacin in pediatric subjects have not been studied.<ref name="insert" />

The ] of moxifloxacin is 11.5 to 15.6 hours (single-dose, oral).<ref name="drugbank.ca">{{cite web |title=Drug card for Moxifloxacin (DB00218) |url=http://www.drugbank.ca/drugs/DB00218 |publisher=DrugBank |location=Canada |date=19 February 2009 |access-date=3 August 2009}}</ref> About 45% of an oral or intravenous dose of moxifloxacin is excreted as unchanged drug (about 20% in urine and 25% in feces). A total of 96 ± 4% of an oral dose is excreted as either unchanged drug or known metabolites. The mean (± SD) apparent total body clearance and renal clearance are 12 ± 2&nbsp;L/h and 2.6 ± 0.5&nbsp;L/h, respectively.<ref name="drugbank.ca"/> The CSF penetration of moxifloxacin is 70% to 80% in patients with ].<ref>{{cite journal | vauthors = Alffenaar JW, van Altena R, Bökkerink HJ, Luijckx GJ, van Soolingen D, Aarnoutse RE, van der Werf TS | title = Pharmacokinetics of moxifloxacin in cerebrospinal fluid and plasma in patients with tuberculous meningitis | journal = Clinical Infectious Diseases | volume = 49 | issue = 7 | pages = 1080–1082 | date = October 2009 | pmid = 19712035 | doi = 10.1086/605576 | doi-access = free | hdl = 2066/79494 | hdl-access = free }}</ref>

==Chemistry==
Moxifloxacin monohydrochloride is a slightly yellow to yellow crystalline substance.<ref name="insert" /> It is synthesized in several steps, the first involving the preparation of ] 2,8-diazabicyclononane which is then ] using ]. A suitably derivatised quinolinecarboxylic acid is then introduced, in the presence of ], followed by acidification to form moxifloxacin hydrochloride.<ref>{{cite book | vauthors = Peterson U |chapter = Quinolone Antibiotics: The Development of Moxifloxacin |chapter-url = https://books.google.com/books?id=FjKfqkaKkAAC&q=discovery+benzylamine&pg=PA338 | veditors = Fischer J, Ganellin CR |title = Analogue-based Drug Discovery |pages = 338–342 |publisher = ]|isbn = 9783527607495|year = 2006}}</ref>

==History==
Moxifloxacin was first patented (United States patent) in 1991 by Bayer A.G., and again in 1997.<ref name="Inventors/Applicants">{{cite web |title=Inventors/Applicants |url=http://www.patentlens.net/patentlens/search_ajax.cgi?patnum=US/7115744 |archive-url=https://archive.today/20130221225050/http://www.patentlens.net/patentlens/search_ajax.cgi?patnum=US/7115744 |url-status=dead |archive-date=21 February 2013 |publisher=patentlens.net |date=3 October 2006 |access-date=17 July 2009 }}</ref> Avelox was subsequently approved by the U.S. Food and Drug Administration (FDA) for use in the United States in 1999 to treat specific bacterial infections.<ref name="Details for NDA:021085"/> Ranking 140th within the top 200 prescribed drugs in the United States for 2007,<ref>{{cite web | vauthors = Lamb E |title=Top 200 Prescription Drugs of 2007 |url=http://www.pharmacytimes.com/issues/articles/2008-05_003.asp |work=Pharmacy Times|date=1 May 2008 |access-date=21 July 2009 |archive-url=https://web.archive.org/web/20090207090521/http://pharmacytimes.com/issues/articles/2008-05_003.asp |archive-date=7 February 2009 |url-status=dead }}</ref> Avelox generated sales of $697.3 million worldwide.<ref name=euarrmu>{{cite news |title=EU agency recommends restricting moxifloxacin use |url=https://www.reuters.com/article/rbssHealthcareNews/idUSL2453307820080724 |work=Reuters|date=24 July 2008 |access-date=21 July 2009}}</ref>

Moxifloxacin is also manufactured by ] as Vigamox.<ref>{{cite web|url=http://www.infectioncontroltoday.com/news/2003/04/alcon-s-newest-antibiotic-vigamox-ophthalmic-solu.aspx|title=Alcon's Newest Antibiotic, Vigamox Ophthalmic Solution, Earns FDA Approval|date=22 June 2003|website=Infection Control Today|publisher=]|access-date=25 June 2016|archive-date=16 August 2016|archive-url=https://web.archive.org/web/20160816004257/http://www.infectioncontroltoday.com/news/2003/04/alcon-s-newest-antibiotic-vigamox-ophthalmic-solu.aspx|url-status=dead}}</ref>

===Patent===
A United States patent application was made on 30 June 1989, for Avelox, Bayer A.G. being the assignee, which was subsequently approved on 5 February 1991. This patent was scheduled to expire on 30 June 2009. However, this patent was extended for an additional two and one half years on 16 September 2004, and as such was not expected to expire until 2012.<ref>{{cite web|url=http://www.uspto.gov/web/offices/pac/dapp/opla/term/certs/4990517.pdf |title=Patent form |date=1 February 1991 |website=uspto.gov |access-date=7 June 2019}}</ref>
Moxifloxacin was subsequently (ten years later) approved by the FDA for use in the United States in 1999. At least four additional United States patents have been filed regarding moxifloxacin hydrochloride since the 1989 United States application,<ref name="Inventors/Applicants"/><ref>US 4990517 A (Feb 1991) Petersen ''et al.'' See US 5051509 A (Sep 1991) Nagano ''et al.'' See US 5059597 A (Oct 1991) Petersen ''et al.'' See US 5395944 A (Mar 1995) Petersen ''et al.'' See US 5416096 A (May 1995) Petersen ''et al.'' See </ref> as well as patents outside of the US.

==Society and culture==

===Regulatory actions===
Regulatory agencies have taken actions to address certain rare but serious adverse events associated with moxifloxacin therapy.{{citation needed|date=December 2022}}

Based on its investigation into reports of rare but severe cases of liver toxicity and skin reactions, the European Medicines Agency recommended in 2008 that the use of the oral (but not the IV) form of moxifloxacin be restricted to infections in which other antibacterial agents cannot be used or have failed.<ref name="www.emea.europa.eu"/> Similarly, the Canadian label includes a warning of the risk of liver injury.<ref>{{cite web | title = Updated Labelling for Antibiotic Avelox (Moxifloxacin) Regarding Rare Risk of Severe Liver Injury | quote = Information Update: 2010-42 | date = 22 March 2010 | url = http://www.hc-sc.gc.ca/ahc-asc/media/advisories-avis/_2010/2010_42-eng.php | work = Health Canada }}</ref>

The U.S. label does not contain restrictions similar to the European label, but a carries a "black box" warning of the risk of tendon damage and/or rupture and warnings regarding the risk of irreversible peripheral neuropathy.<ref>{{cite web | vauthors = Albrecht R |title=NDA 21-085/S-040, NDA 21-277/S-034 |url=http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2008/021085s040,%20021277s034ltr.pdf |work=Center for Drug Evaluation and Research |publisher=Food and Drug Administration |date=3 October 2008 |access-date=31 July 2009}}</ref>

===Generic equivalents===
In 2007, the U.S. District Court for the District of Delaware held that two Bayer patents on Avelox are valid and enforceable, and infringed by Dr. Reddy's ANDA for a generic version of Avelox.<ref name="ribfoap">{{cite web |author=Bayer AG |author-link=Bayer AG |title=Ruling in Bayer's favor over Avelox patents |url=http://www.stockholders-newsletter-q3-07.bayer.com/en/avelox-patents.aspx |publisher=Bayer |date=6 November 2007 |access-date=29 August 2009 |archive-url=https://web.archive.org/web/20081211130541/http://www.stockholders-newsletter-q3-07.bayer.com/en/Avelox-patents.aspx |archive-date=11 December 2008 |url-status=dead}}</ref><ref>{{cite web |url= http://www.orangebookblog.com/Bayer_20v._20Dr._20Reddy_27s.pdf|title= Opinion form |date=5 October 2007 |website= orangebookblog.com|access-date=7 June 2019}}</ref> The district court sided with Bayer, citing the Federal Circuit's prior decision in ''Takeda v. Alphapharm''<ref>{{cite web|title=United States Court of Appeals for the Federal Circuit |url=http://www.cafc.uscourts.gov/opinions/06-1329.pdf |publisher=uscourts.gov |date=28 June 2007 |access-date=29 August 2009 |url-status=dead |archive-url=https://web.archive.org/web/20090826202547/http://www.cafc.uscourts.gov/opinions/06-1329.pdf |archive-date=26 August 2009 }}</ref> as "affirming the district court's finding that defendant failed to prove a prima facie case of obviousness where the ] disclosed a broad selection of compounds, any one of which could have been selected as a lead compound for further investigation, and defendant did not prove that the prior art would have led to the selection of the particular compound singled out by defendant." According to Bayer's press release<ref name="ribfoap" /> announcing the court's decision, it was noted that Teva had also challenged the validity of the same Bayer patents at issue in the Dr. Reddy's case. Within Bayer's first-quarter 2008 stockholder's newsletter<ref>{{cite web |author=Bayer AG |author-link=Bayer AG |title=Risk Report |url=http://www.stockholders-newsletter-q1-08.bayer.com/en/Risk-Report.aspx |publisher=Bayer |date=24 April 2008 |access-date=29 August 2009 |archive-url=https://web.archive.org/web/20090309014517/http://www.stockholders-newsletter-q1-08.bayer.com/en/Risk-Report.aspx |archive-date=9 March 2009 |url-status=dead}}</ref> Bayer stated that they had reached an agreement with Teva Pharmaceuticals USA, Inc., the adverse party, to settle their patent litigation with regard to the two Bayer patents. Under the settlement terms agreed upon, Teva would obtain a license to sell its generic moxifloxacin tablet product in the U.S. shortly before the second of the two Bayer patents expires in March 2014. In Bangladesh, it is available with brand name of Optimox.{{citation needed|date=August 2022}}

== References ==
{{Reflist}}

{{QuinoloneAntiBiotics}}
{{Portal bar|Medicine}}

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