{{Short description|Muscle relaxant}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461118216 | IUPAC_name = 2,2’,2’’-[benzene-1,2,3-triyltris(oxy)]tris(N,N,N-triethylethanaminium) triiodide | image = Gallamine triethiodide.svg | image_class = skin-invert-image <!--Clinical data--> | tradename = Flaxedil | Drugs.com = {{drugs.com|international|gallamine-triethiodide}} | pregnancy_category = | legal_status = | routes_of_administration = <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 65-29-2 | ATC_prefix = M03 | ATC_suffix = AC02 | ATC_supplemental = | PubChem = 6172 | IUPHAR_ligand = 356 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00483 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 5937 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Q3254X40X2 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02292 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 503442 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1200993 <!--Chemical data--> | chemical_formula = C<sub>30</sub>H<sub>60</sub>N<sub>3</sub>O<sub>3</sub><sup>+3</sup> · 3 I<sup>−</sup> (gallamine triethiodide)<br />C<sub>24</sub>H<sub>45</sub>N<sub>3</sub>O<sub>3</sub> (gallamine) | molecular_weight = 891.529 g/mol (gallamine triethiodide)<br />423.633 g/mol<br /> (gallamine) | SMILES = [I-].[I-].[I-].O(c1c(OCC[N+](CC)(CC)CC)cccc1OCC[N+](CC)(CC)CC)CC[N+](CC)(CC)CC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C24H45N3O3/c1-7-25(8-2)16-19-28-22-14-13-15-23(29-20-17-26(9-3)10-4)24(22)30-21-18-27(11-5)12-6/h13-15H,7-12,16-21H2,1-6H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ICLWTJIMXVISSR-UHFFFAOYSA-N }} thumb|right|An ampoule of gallamine.
'''Gallamine triethiodide''' ('''Flaxedil''') is a non-depolarising muscle relaxant.<ref>{{cite web |title=Webster's Online Dictionary - Flaxedil |url=http://www.websters-online-dictionary.org/Fl/Flaxedil.html |access-date=2008-12-15 |archive-date=2023-06-11 |archive-url=https://web.archive.org/web/20230611130826/http://www.websters-online-dictionary.org/Fl/Flaxedil.html |url-status=dead }}</ref> It acts by combining with the cholinergic receptor sites in muscle and competitively blocking the transmitter action of acetylcholine.<ref>{{ cite web | title=RxMed: Pharmaceutical Information - FLAXEDIL | url=https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20F)/FLAXEDIL.html| access-date=2008-12-15}}</ref> Gallamine is a non-depolarising type of blocker as it binds to the acetylcholine receptor but does not have the biological activity of acetyl choline. Gallamine triethiodide has a parasympatholytic effect on the cardiac vagus nerve, which causes tachycardia<ref name="pmid4380161">{{cite journal | vauthors = Morgenstern C, Splith G | title = [Studies on the causes of gallamine tachycardia and its antagonistic modification by beta adrenolytics] | language = de | journal = Der Anaesthesist | volume = 14 | issue = 10 | pages = 298–301 | date = October 1965 | pmid = 4380161 }}<!--|access-date=2014-09-20--></ref><ref name="pmid13998750">{{cite journal | vauthors = Walts LF | title = Ventricular tachycardia with gallamine and cyclopropane anesthesia | journal = Anesthesiology | volume = 24 | pages = 119 | year = 1963 | pmid = 13998750 | doi = 10.1097/00000542-196301000-00024 | doi-access = free }}</ref> and occasionally hypertension. Very high doses cause histamine release.{{fact|date=March 2018}}. Presence of iodine in the triethiodide salt makes it radio opaque. Gallamine triethiodide was commonly used to prevent muscle contractions during surgical procedures, but is now superseded by new neuromuscular blocking drugs with fewer side effects.
It was developed by Daniel Bovet in 1947.<ref name="pmid12091515">{{cite journal | vauthors = Raghavendra T | title = Neuromuscular blocking drugs: discovery and development | journal = Journal of the Royal Society of Medicine | volume = 95 | issue = 7 | pages = 363–7 | date = July 2002 | pmid = 12091515 | pmc = 1279945 | doi = 10.1177/014107680209500713 | url = http://www.jrsm.org/cgi/pmidlookup?view=long&pmid=12091515 }}</ref>
The drug is no longer marketed in the United States, according to the FDA Orange Book.
==See also== * Neuromuscular-blocking drug * Curare
== References == {{Reflist}}
{{Muscle relaxants}} {{Nicotinic acetylcholine receptor modulators}} {{Muscarinic acetylcholine receptor modulators}}
Category:M2 receptor antagonists Category:Muscle relaxants Category:Neuromuscular blockers Category:Nicotinic antagonists Category:Phenol ethers Category:Quaternary ammonium compounds