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mw-list-item"><a href="https://de.wikipedia.org/wiki/Metaflumizon" title="Metaflumizon – German" lang="de" hreflang="de" data-title="Metaflumizon" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Metaflumizon" title="Metaflumizon – Serbian" lang="sr" hreflang="sr" data-title="Metaflumizon" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Metaflumizon" title="Metaflumizon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Metaflumizon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> 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noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Metaflumizone">Metaflumizone</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Metaflumizone_Z-isomer.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Metaflumizone_Z-isomer.svg/220px-Metaflumizone_Z-isomer.svg.png" decoding="async" width="220" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Metaflumizone_Z-isomer.svg/330px-Metaflumizone_Z-isomer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Metaflumizone_Z-isomer.svg/440px-Metaflumizone_Z-isomer.svg.png 2x" data-file-width="620" data-file-height="396" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Metaflumizone_E-isomer.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metaflumizone_E-isomer.svg/220px-Metaflumizone_E-isomer.svg.png" decoding="async" width="220" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metaflumizone_E-isomer.svg/330px-Metaflumizone_E-isomer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metaflumizone_E-isomer.svg/440px-Metaflumizone_E-isomer.svg.png 2x" data-file-width="620" data-file-height="301" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">ProMeris, Alverde</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System#ATCvet" title="Anatomical Therapeutic Chemical Classification System">ATCvet code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AX25</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AX25">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(<i>EZ</i>)-2-{2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene} -N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=139968-49-3">139968-49-3</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.16738643.html">16738643</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/71I50E2UDI">71I50E2UDI</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6040373">DTXSID6040373</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q6822502#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.107.480">100.107.480</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q6822502#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>24</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Fluorine">F</span><sub>6</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002506408000000000♠"></span>506.408</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=FC%28F%29%28F%29Oc1ccc%28cc1%29NC%28%3DO%29N%5CN%3DC%28%5CCc2ccc%28C%23N%29cc2%29c3cccc%28c3%29C%28F%29%28F%29F">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">FC(F)(F)Oc1ccc(cc1)NC(=O)N\N=C(\Cc2ccc(C#N)cc2)c3cccc(c3)C(F)(F)F</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C24H16F6N4O2/c25-23(26,27)18-3-1-2-17(13-18)21(12-15-4-6-16(14-31)7-5-15)33-34-22(35)32-19-8-10-20(11-9-19)36-24(28,29)30/h1-11,13H,12H2,(H2,32,34,35)</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:MIFOMMKAVSCNKQ-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Metaflumizone</b> is a <a href="/wiki/Semicarbazone" title="Semicarbazone">semicarbazone</a> broad-spectrum <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> developed by Nihon Nohyaku with activity on <a href="/wiki/Lepidoptera" title="Lepidoptera">Lepidoptera</a>, <a href="/wiki/Beetle" title="Beetle">Coleoptera</a>, and certain <a href="/wiki/Hemiptera" title="Hemiptera">Hemiptera</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is also used for the <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary treatment</a> of <a href="/wiki/Flea" title="Flea">fleas</a> and <a href="/wiki/Tick" title="Tick">ticks</a>, marketed under the brand name <b>ProMeris</b>. A discontinued variant of <i>ProMeris</i>, called <i>ProMeris Duo</i> or <i>Promeris for Dogs</i>, was indicated for canine use and was a formulated blend of metaflumizone and <a href="/wiki/Amitraz" title="Amitraz">amitraz</a>.<sup id="cite_ref-PetPlaceLib_2-0" class="reference"><a href="#cite_note-PetPlaceLib-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The metaflumizone-only formulation is waterproof and typically remain effective for 30–45 days in a cutaneous application at the base of the neck. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Similar_insecticides">Similar insecticides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metaflumizone&action=edit&section=1" title="Edit section: Similar insecticides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metaflumizone is chemically similar to pyrazoline <a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">sodium channel blocker</a> insecticides (SCBIs) discovered at Philips-Duphar in the early 1970s, but is less dangerous to mammals than earlier compounds.<sup id="cite_ref-Hayashi_3-0" class="reference"><a href="#cite_note-Hayashi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Action">Action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metaflumizone&action=edit&section=2" title="Edit section: Action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metaflumizone belongs to <a href="/wiki/Insecticide_Resistance_Action_Committee#Table_of_modes_of_action_and_classes_of_insecticide" title="Insecticide Resistance Action Committee">IRAC</a> group 22B and works by <a href="/wiki/Sodium_channel_blocker#Other_uses" title="Sodium channel blocker">blocking sodium channels</a> in target insects, resulting in flaccid paralysis. Metaflumizone blocks sodium channels by binding selectively to the slow-inactivated state, which is characteristic of the SCBIs.<sup id="cite_ref-Hayashi_3-1" class="reference"><a href="#cite_note-Hayashi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The toxin has been tested for efficacy against <i><a href="/wiki/Spodoptera_eridania" title="Spodoptera eridania">Spodoptera eridania</a></i> moths<sup id="cite_ref-Hayashi_3-2" class="reference"><a href="#cite_note-Hayashi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and is indicated for control of fleas and ticks. However, in a cross comparison with other veterinary flea control substances, Metaflumizone was not shown to result in a significant reduction in the number of engorged adult female <i><a href="/wiki/Culex" title="Culex">Culex</a></i> mosquitoes.<sup id="cite_ref-Bouhsira_4-0" class="reference"><a href="#cite_note-Bouhsira-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Therefore, its usefulness as a heartworm control treatment is likely to be insignificant when compared with comparable treatments such as <a href="/wiki/Selamectin" title="Selamectin">selamectin</a> that do impact the mosquito disease vector. </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects_reported">Adverse effects reported</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metaflumizone&action=edit&section=3" title="Edit section: Adverse effects reported"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2011, <a href="/wiki/Pfizer#Animal_health_brands" title="Pfizer">Pfizer Animal Care</a> decided to cease production of the drug based on findings which linked its use to an elevated incidence of the autoimmune disorder <a href="/wiki/Pemphigus_foliaceus" title="Pemphigus foliaceus">pemphigus foliaceus</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metaflumizone&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFJeschkeWitschelKrämerSchirmer2019" class="citation book cs1">Jeschke P, Witschel M, Krämer W, Schirmer U (25 January 2019). "33.4.2 Semicarbazone Insecticides: Metaflumizone". <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/book/10.1002/9783527699261"><i>Modern Crop Protection Compounds</i></a> (3rd ed.). Wiley‐VCH. pp. <span class="nowrap">1440–</span>1448. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527699261" title="Special:BookSources/9783527699261"><bdi>9783527699261</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=33.4.2+Semicarbazone+Insecticides%3A+Metaflumizone&rft.btitle=Modern+Crop+Protection+Compounds&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1440-%3C%2Fspan%3E1448&rft.edition=3rd&rft.pub=Wiley%E2%80%90VCH&rft.date=2019-01-25&rft.isbn=9783527699261&rft.aulast=Jeschke&rft.aufirst=P&rft.au=Witschel%2C+M&rft.au=Kr%C3%A4mer%2C+W&rft.au=Schirmer%2C+U&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2Fbook%2F10.1002%2F9783527699261&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetaflumizone" class="Z3988"></span></span> </li> <li id="cite_note-PetPlaceLib-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-PetPlaceLib_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.petplace.com/drug-library/metaflumizone-promeris-and-promeris-duo/page1.aspx">"Metaflumizone (ProMeris and ProMeris Duo) for Dogs and Cats"</a>. <i>PetPlace Drug Library</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PetPlace+Drug+Library&rft.atitle=Metaflumizone+%28ProMeris+and+ProMeris+Duo%29+for+Dogs+and+Cats&rft_id=http%3A%2F%2Fwww.petplace.com%2Fdrug-library%2Fmetaflumizone-promeris-and-promeris-duo%2Fpage1.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetaflumizone" class="Z3988"></span></span> </li> <li id="cite_note-Hayashi-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hayashi_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hayashi_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Hayashi_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSalgadoHayashi2007" class="citation journal cs1">Salgado VL, Hayashi JH (December 2007). "Metaflumizone is a novel sodium channel blocker insecticide". <i>Veterinary Parasitology</i>. <b>150</b> (3): <span class="nowrap">182–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.vetpar.2007.08.032">10.1016/j.vetpar.2007.08.032</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17959312">17959312</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Veterinary+Parasitology&rft.atitle=Metaflumizone+is+a+novel+sodium+channel+blocker+insecticide&rft.volume=150&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E182-%3C%2Fspan%3E9&rft.date=2007-12&rft_id=info%3Adoi%2F10.1016%2Fj.vetpar.2007.08.032&rft_id=info%3Apmid%2F17959312&rft.aulast=Salgado&rft.aufirst=VL&rft.au=Hayashi%2C+JH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetaflumizone" class="Z3988"></span></span> </li> <li id="cite_note-Bouhsira-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bouhsira_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBouhsiraFysikopoulosFranc2009" class="citation journal cs1">Bouhsira E, Fysikopoulos A, Franc M (August 2009). "Efficacy of fipronil-(S)-methoprene, metaflumizone combined with amitraz, and pyriprole commercial spot-on products in preventing Culex pipiens pipiens from feeding on dogs". <i>The Veterinary Record</i>. <b>165</b> (5): <span class="nowrap">135–</span>7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Fvr.165.5.135">10.1136/vr.165.5.135</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19648637">19648637</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Veterinary+Record&rft.atitle=Efficacy+of+fipronil-%28S%29-methoprene%2C+metaflumizone+combined+with+amitraz%2C+and+pyriprole+commercial+spot-on+products+in+preventing+Culex+pipiens+pipiens+from+feeding+on+dogs&rft.volume=165&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E135-%3C%2Fspan%3E7&rft.date=2009-08&rft_id=info%3Adoi%2F10.1136%2Fvr.165.5.135&rft_id=info%3Apmid%2F19648637&rft.aulast=Bouhsira&rft.aufirst=E&rft.au=Fysikopoulos%2C+A&rft.au=Franc%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetaflumizone" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTremayne2011" class="citation news cs1">Tremayne J (18 April 2011). <a rel="nofollow" class="external text" href="http://www.veterinarypracticenews.com/vet-breaking-news/2011/04/18/study-links-promeris-to-pemphigus-foliaceus-pfizer-stopping-its-production.aspx">"Study Links ProMeris to Pemphigus Foliaceus; Pfizer Stopping Its Production"</a>. <i>Veterinary Practice News</i>. California, United States: <a href="/wiki/BowTie_Inc." class="mw-redirect" title="BowTie Inc.">BowTie</a><span class="reference-accessdate">. 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