| Revision as of 15:12, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 450475378 of page Gatifloxacin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
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 |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{Drugbox |
|
{{Drugbox |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 443833018 |
|
| verifiedrevid = 461119081 |
|
| IUPAC_name = 1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid |
|
| IUPAC_name = 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid |
|
| image = Gatifloxacin.svg |
|
| image = Gatifloxacin.svg |
|
|
| image2 = Gatifloxacin ball-and-stick.png |
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = Zymar |
|
| tradename = Gatiflo, Tequin, Zymar, others |
|
| Drugs.com = {{drugs.com|monograph|gatifloxacin}} |
|
| Drugs.com = {{drugs.com|monograph|gatifloxacin}} |
|
| MedlinePlus = a605012 |
|
| MedlinePlus = a605012 |
|
| pregnancy_category = |
|
| pregnancy_category = |
|
| legal_status = Rx only |
|
| legal_status = Rx only |
|
| routes_of_administration = Oral (discontinued),<br> ] (discontinued)<br>ophthalmic |
|
| routes_of_administration = Oral (discontinued),<br> ] (discontinued)<br>ophthalmic |
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!--Pharmacokinetic data--> |
|
| bioavailability = |
|
| bioavailability = |
|
| protein_bound = 20% |
|
| protein_bound = 20% |
|
| metabolism = |
|
| metabolism = |
|
| elimination_half-life = 7 to 14 hours |
|
| elimination_half-life = 7 to 14 hours |
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number = 112811-59-3 |
|
| CAS_number = 112811-59-3 |
|
| ATC_prefix = J01 |
|
| ATC_prefix = J01 |
|
| ATC_suffix = MA16 |
|
| ATC_suffix = MA16 |
|
| ATC_supplemental = {{ATC|S01|AX21}} |
|
| ATC_supplemental = {{ATC|S01|AE06}} |
|
| PubChem = 5379 |
|
| PubChem = 5379 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| Line 39: |
Line 37: |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| ChEMBL = 31 |
|
| ChEMBL = 31 |
|
|
| NIAID_ChemDB = 044913 |
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=19 | H=22 | F=1 | N=3 | O=4 |
|
| C=19 | H=22 | F=1 | N=3 | O=4 |
|
⚫ |
| SMILES = Fc1c(c(OC)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CC(NCC4)C |
|
| molecular_weight = 375.394 ]/] |
|
| ⚫ |
| smiles = Fc1c(c(OC)c2c(c1)C(=O)C(\C(=O)O)=C/N2C3CC3)N4CC(NCC4)C |
|
|
| InChI = 1/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26) |
|
|
| InChIKey = XUBOMFCQGDBHNK-UHFFFAOYAS |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26) |
|
| StdInChI = 1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26) |
| Line 51: |
Line 46: |
|
| StdInChIKey = XUBOMFCQGDBHNK-UHFFFAOYSA-N |
|
| StdInChIKey = XUBOMFCQGDBHNK-UHFFFAOYSA-N |
|
}} |
|
}} |
|
|
<!-- Definition and medical uses --> |
|
|
'''Gatifloxacin''' (brand names '''Gatiflo''', '''Tequin''', and '''Zymar''') is an ] of the fourth-generation ] family,<ref name="pmid15953577">{{cite journal | vauthors = Burka JM, Bower KS, Vanroekel RC, Stutzman RD, Kuzmowych CP, Howard RS | title = The effect of fourth-generation fluoroquinolones gatifloxacin and moxifloxacin on epithelial healing following photorefractive keratectomy | journal = American Journal of Ophthalmology | volume = 140 | issue = 1 | pages = 83–87 | date = July 2005 | pmid = 15953577 | doi = 10.1016/j.ajo.2005.02.037 | url = https://zenodo.org/record/1258684 }}</ref> that like other members of that family, inhibits the ]l ]s ] and ]. |
|
|
|
|
|
<!-- Society and culture --> |
|
|
It was patented in 1986 and approved for medical use in 1999.<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> |
|
|
|
|
|
==Side effects== |
|
|
A ] study published in the '']'' in March 2006, claimed that Tequin can have significant ] including ].<ref>{{cite journal | vauthors = Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM | display-authors = 6 | title = Outpatient gatifloxacin therapy and dysglycemia in older adults | journal = The New England Journal of Medicine | volume = 354 | issue = 13 | pages = 1352–1361 | date = March 2006 | pmid = 16510739 | doi = 10.1056/NEJMoa055191 | hdl-access = free | author5-link = Thérèse Stukel | hdl = 1807/16915 }} ''Note: publication date 30 March; available on-line 1 March''</ref> An ] by |
|
|
Jerry Gurwitz in the same issue called for the ] (FDA) to consider giving Tequin a ].<ref>{{cite journal | vauthors = Gurwitz JH | title = Serious adverse drug effects--seeing the trees through the forest | journal = The New England Journal of Medicine | volume = 354 | issue = 13 | pages = 1413–1415 | date = March 2006 | pmid = 16510740 | doi = 10.1056/NEJMe068051 | url = https://escholarship.umassmed.edu/meyers_pp/54 }}</ref> This editorial followed distribution of a letter dated February 15 by Bristol-Myers Squibb to health care providers indicating action taken with the FDA to strengthen warnings for the medication.<ref>{{cite web | vauthors = Lewis-Hall F | date = February 15, 2006 | url = https://www.fda.gov/medwatch/safety/2006/tequin_DHCP.pdf | title = Dear Healthcare Provider | publisher = Bristol-Myers Squibb | access-date = May 1, 2006 }}</ref> Subsequently, Bristol-Myers Squibb reported it would stop manufacture of Tequin, end sales of the drug after existing stockpiles were exhausted, and return all rights to Kyorin.<ref>{{cite news |vauthors = Schmid RE |url = http://www.sfgate.com/cgi-bin/article.cgi?file=/news/archive/2006/05/01/national/w120748D88.DTL&type=health |title = Drug Company Taking Tequin Off Market |publisher = ] |date = May 1, 2006 |access-date = 2006-05-01 |archive-url = https://web.archive.org/web/20071125104959/http://www.sfgate.com/cgi-bin/article.cgi?file=%2Fnews%2Farchive%2F2006%2F05%2F01%2Fnational%2Fw120748D88.DTL&type=health |archive-date = November 25, 2007 |url-status = dead }}</ref> |
|
|
|
|
|
By contrast, ophthalmic gatifloxacin is generally well tolerated. The observed ] concentration of the drug following oral administration of 400 mg (0.01 ounces) gatifloxacin is approximately 800 times higher than that of the 0.5% gatifloxacin eye drop. Given as an eye drop, gatifloxacin has very low systemic exposure. Therefore, the systemic exposures resulting from the gatifloxacin ophthalmic solution are not likely to pose any risk for systemic toxicities.{{citation needed|date=March 2017}} |
|
|
|
|
|
==Contraindications== |
|
|
]<ref>{{cite web| url = http://www.medpagetoday.com/PrimaryCare/PreventiveCare/3212| title = Bristol-Myers Squibb Hangs No Sale Sign on Tequin| access-date = 24 February 2009| author = Peggy Peck| date = 2 May 2006| publisher = Med Page Today}}</ref>{{not in source|date=May 2018}} |
|
|
|
|
|
==Society and culture== |
|
|
===Availability=== |
|
|
Gatifloxacin is currently available in the US and Canada only as an ophthalmic solution.{{cn|date=August 2022}} |
|
|
|
|
|
In 2011, the Union Health and Family Welfare Ministry of India banned the manufacture, sale, and distribution of gatifloxacin because of its adverse side effects.<ref>{{cite news| url=http://www.thehindu.com/news/national/article1551233.ece | archive-url = https://web.archive.org/web/20120306234052/https://www.thehindu.com/news/national/article1551233.ece | archive-date = 6 March 2012| location=Chennai, India | work=The Hindu | title=Two drugs banned | date=19 March 2011}}</ref> |
|
|
|
|
|
In China, gatifloxacin is sold in tablet as well as in eye drop formulations.{{cn|date=August 2022}} |
|
|
|
|
|
===Brand names=== |
|
|
] introduced gatifloxacin in 1999 under the ] Tequin for the treatment of respiratory tract infections, having licensed the medication from ] of Japan. Allergan produces it in eye-drop formulation under the names Zymar, Zymaxid and Zylopred. In many countries, gatifloxacin is also available as ] and in various ]s for ].{{cn|date=August 2022}} |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{QuinoloneAntiBiotics}} |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |