Gallamine triethiodide: Difference between revisions

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			{{Short description\|Muscle relaxant}}
	{{Drugbox		{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~396142022~~		\| verifiedrevid = 461118216
	\| IUPAC_name = 2,2’,2’’-tris(N,N,N-triethylethanaminium) triiodide		\| IUPAC_name = 2,2’,2’’-tris(N,N,N-triethylethanaminium) triiodide
	\| image = Gallamine triethiodide.svg		\| image = Gallamine triethiodide.svg

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename = Flaxedil
	\| Drugs.com = {{drugs.com\|international\|gallamine-triethiodide}}		\| Drugs.com = {{drugs.com\|international\|gallamine-triethiodide}}
	\| pregnancy_category =		\| pregnancy_category =
	\| legal_status =		\| legal_status =
	\| routes_of_administration =		\| routes_of_administration =

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| bioavailability =		\| bioavailability =
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	\| elimination_half-life =		\| elimination_half-life =
	\| excretion =		\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 65-29-2		\| CAS_number = 65-29-2
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	\| IUPHAR_ligand = 356		\| IUPHAR_ligand = 356
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = ~~APRD00712~~		\| DrugBank = DB00483
	\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| ChemSpiderID = 5937		\| ChemSpiderID = 5937
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = Q3254X40X2		\| UNII = Q3254X40X2
	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D02292		\| KEGG = D02292
	\| ChEBI_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 503442		\| ChEBI = 503442
	\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChEMBL = 1200993		\| ChEMBL = 1200993

	<!--Chemical data-->		<!--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)		\| 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 = ...O(c1c(OCC(CC)(CC)CC)cccc1OCC(CC)(CC)CC)CC(CC)(CC)CC
⚫	\| molecular_weight = 891.529 g/mol (gallamine triethiodide)<br />423.633 g/mol<br> (gallamine)
⚫	\| ~~smiles~~ = ...O(c1c(OCC(CC)(CC)CC)cccc1OCC(CC)(CC)CC)CC(CC)(CC)CC
	\| InChI = 1S/C30H60N3O3.3HI/c1-10-31(11-2,12-3)22-25-34-28-20-19-21-29(35-26-23-32(13-4,14-5)15-6)30(28)36-27-24-33(16-7,17-8)18-9;;;/h19-21H,10-18,22-27H2,1-9H3;3*1H/q+3;;;/p-3
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| 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		\| 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
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	\| StdInChIKey = ICLWTJIMXVISSR-UHFFFAOYSA-N		\| StdInChIKey = ICLWTJIMXVISSR-UHFFFAOYSA-N
	}}		}}
			]

	'''Gallamine triethiodide''' ('''Flaxedil''') is a ].<ref>{{cite web \| title=Webster's Online Dictionary - Flaxedil \| url=http://www.websters-online-dictionary.org/Fl/Flaxedil.html\| ~~accessdate~~=2008-12-15}}</ref> It acts by combining with the ] sites in ] and competitively blocking the transmitter action of ].<ref>{{ cite web \| title=RxMed: Pharmaceutical Information - FLAXEDIL \| url=http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20F)/FLAXEDIL.html\| ~~accessdate~~=2008-12-15}}</ref> Gallamine triethiodide has a ] effect on the cardiac ] which causes ] and occasionally ]. Very high doses cause ] release.		'''Gallamine triethiodide''' ('''Flaxedil''') is a ].<ref>{{cite web\|title=Webster's Online Dictionary - Flaxedil \|url=http://www.websters-online-dictionary.org/Fl/Flaxedil.html \|access-date=2008-12-15 }}{{dead link\|date=January 2017 \|bot=InternetArchiveBot \|fix-attempted=yes }}</ref> It acts by combining with the ] sites in ] and competitively blocking the transmitter action of ].<ref>{{ cite web \| title=RxMed: Pharmaceutical Information - FLAXEDIL \| url=http://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 ] of acetyl choline. Gallamine triethiodide has a ] effect on the cardiac ], which causes ]<ref name="pmid4380161">{{cite journal \| vauthors = Morgenstern C, Splith G \| title = \| 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 ]. Very high doses cause ] release.{{fact\|date=March 2018}}<br>
			Presence of ] makes it ], and its ] in a bag at airport's ] raise the false suspicion of a ] in the bag.

		⚫	Gallamine triethiodide was commonly used to prevent muscle contractions during surgical procedures, but is now superseded by new ] with less ].

		⚫	It was developed by ] 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>
⚫	Gallamine triethiodide is commonly used to ~~stabilize~~ muscle contractions during surgical procedures.

			The drug is no longer marketed in the United States, according to the FDA Orange Book.
⚫	It was developed by ] in 1947.<ref name="pmid12091515">{{cite journal \|~~author~~=Raghavendra T \|title=Neuromuscular blocking drugs: discovery and development \|journal=J R ~~Soc~~ ~~Med~~ \|volume=95 \|issue=7 \|pages=363–7 \|~~year=2002~~ ~~\|month~~=July \|pmid=12091515 \|pmc=1279945 \|doi= 10.~~1258~~/~~jrsm.95.7.363~~\|url=http://www.jrsm.org/cgi/pmidlookup?view=long&pmid=12091515}}</ref>

			==See also==
			* ]
			* ]

	== References ==		== References ==
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	{{Muscle relaxants}}		{{Muscle relaxants}}
			{{Nicotinic acetylcholine receptor modulators}}
	{{Cholinergics}}
			{{Muscarinic acetylcholine receptor modulators}}

			]
	]		]
	]		]
			]
	]		]
			]

			{{musculoskeletal-drug-stub}}
	]
	]
	]
	]

Latest revision as of 04:22, 26 October 2024

Muscle relaxant Pharmaceutical compound

Gallamine triethiodide
Clinical data

Trade names	Flaxedil
AHFS/Drugs.com	International Drug Names
ATC code	M03AC02 (WHO)
Identifiers
IUPAC name 2,2’,2’’-tris(N,N,N-triethylethanaminium) triiodide
CAS Number	65-29-2
PubChem CID	6172
IUPHAR/BPS	356
DrugBank	DB00483
ChemSpider	5937
UNII	Q3254X40X2
KEGG	D02292
ChEBI	CHEBI:503442
ChEMBL	ChEMBL1200993
Chemical and physical data
Formula	C₃₀H₆₀N₃O₃ · 3 I (gallamine triethiodide) C₂₄H₄₅N₃O₃ (gallamine)
Molar mass	891.529 g/mol (gallamine triethiodide) 423.633 g/mol (gallamine)
3D model (JSmol)	Interactive image
SMILES ...O(c1c(OCC(CC)(CC)CC)cccc1OCC(CC)(CC)CC)CC(CC)(CC)CC
InChI InChI=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 Key:ICLWTJIMXVISSR-UHFFFAOYSA-N
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Gallamine triethiodide (Flaxedil) is a non-depolarising muscle relaxant. It acts by combining with the cholinergic receptor sites in muscle and competitively blocking the transmitter action of acetylcholine. 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 and occasionally hypertension. Very high doses cause histamine release.
Presence of iodine makes it radio opaque, and its ampule in a bag at airport's x-ray scanner raise the false suspicion of a bullet in the bag.

Gallamine triethiodide was commonly used to prevent muscle contractions during surgical procedures, but is now superseded by new neuromuscular blocking drugs with less side effects.

It was developed by Daniel Bovet in 1947.

The drug is no longer marketed in the United States, according to the FDA Orange Book.

References

"Webster's Online Dictionary - Flaxedil". Retrieved 2008-12-15.
"RxMed: Pharmaceutical Information - FLAXEDIL". Retrieved 2008-12-15.
Morgenstern C, Splith G (October 1965). "". Der Anaesthesist (in German). 14 (10): 298–301. PMID 4380161.
Walts LF (1963). "Ventricular tachycardia with gallamine and cyclopropane anesthesia". Anesthesiology. 24: 119. doi:10.1097/00000542-196301000-00024. PMID 13998750.
Raghavendra T (July 2002). "Neuromuscular blocking drugs: discovery and development". Journal of the Royal Society of Medicine. 95 (7): 363–7. doi:10.1177/014107680209500713. PMC 1279945. PMID 12091515.

Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids

4° ammonium agents

ultra-short duration: Gantacurium

short duration: Rapacuronium
Mivacurium
Chandonium

unsorted: Hexafluronium (Hexafluorenium)

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine)

Polyalkylene derivatives: Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Phenprobamate Styramate Tybamate
Benzodiazepines	Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam
Nonbenzodiazepines	Eszopiclone
Thienodiazepines	Etizolam
Quinazolines	Methaqualone
Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine
Other	Arbaclofen placarbil Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Eperisone Fenyramidol Flopropione Gabapentin GHB Inaperisone Lanperisone Mephenesin Mephenoxalone Metaxalone Methocarbamol Phenibut Pregabalin Pridinol Promoxolane Quinine Silperisone Thiocolchicoside Tizanidine Tolperisone Zoxazolamine