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NameGallamine Triethiodide
Accession NumberDB00483  (APRD00712)
TypeSmall Molecule

A synthetic nondepolarizing blocking drug. The actions of gallamine triethiodide are similar to those of tubocurarine, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. It should be used cautiously in patients at risk from increased heart rate but may be preferred for patients with bradycardia. (From AMA Drug Evaluations Annual, 1992, p198)

Gallamin triethiodid
Gallamini Triethiodidum
Triéthiodure de Gallamine
Trietioduro de galamina
External Identifiers
  • F 2559
  • HL 8583
  • RP 3697
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flaxedil Inj 20mg/mlliquid20 mgintravenousAventis Pharma Inc1951-12-312003-07-22Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
MyraxanYoo Young
SincurarinaCarlo Erba
TricuranNot Available
Brand mixturesNot Available
SaltsNot Available
CAS number65-29-2
WeightAverage: 891.5291
Monoisotopic: 891.176873061
Chemical FormulaC30H60I3N3O3
(2-{2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy}ethyl)triethylazanium triiodide
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
  • Phenol ether
  • Choline
  • Alkyl aryl ether
  • Quaternary ammonium salt
  • Ether
  • Hydrocarbon derivative
  • Organic iodide salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
IndicationFor use as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation
PharmacodynamicsGallamine Triethiodide is a nondepolarizing neuromuscular blocking drug (NDMRD) used as an adjunct to anesthesia to induce skeletal muscle relaxation. The actions of gallamine triethiodide are similar to those of tubocurarine, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. Muscle groups differ in their sensitivity to these types of relaxants with ocular muscles (controlling eyelids) being most sensitive, followed by the muscles of the neck, jaw, limbs and then abdomen. The diaphragm is the least sensitive muscle to NDMRDs. Although the nondepolarizing neuromuscular blocking drugs do not have the same adverse effects as succinylcholine, their onset of action is slower. They also have a longer duration of action, making them more suitable for maintaining neuromuscular relaxation during major surgical procedures.
Mechanism of actionIt competes with acetylcholine (ACh) molecules and binds to muscarinic acetylcholine receptors on the post-synaptic membrane of the motor endplate. It acts by combining with the cholinergic receptor sites in muscle and competitively blocking the transmitter action of acetylcholine. It blocks the action of ACh and prevents activation of the muscle contraction process. It can also act on nicotinic presynaptic acetylcholine receptors which inhibits the release of ACh.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption-0.8901
Blood Brain Barrier+0.8616
Caco-2 permeable+0.6256
P-glycoprotein substrateSubstrate0.6912
P-glycoprotein inhibitor INon-inhibitor0.8173
P-glycoprotein inhibitor IINon-inhibitor0.8176
Renal organic cation transporterNon-inhibitor0.6818
CYP450 2C9 substrateNon-substrate0.8147
CYP450 2D6 substrateNon-substrate0.6511
CYP450 3A4 substrateSubstrate0.5708
CYP450 1A2 substrateNon-inhibitor0.8002
CYP450 2C9 inhibitorNon-inhibitor0.8613
CYP450 2D6 inhibitorNon-inhibitor0.8874
CYP450 2C19 inhibitorNon-inhibitor0.8815
CYP450 3A4 inhibitorNon-inhibitor0.9296
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6622
Ames testNon AMES toxic0.6156
BiodegradationNot ready biodegradable0.9841
Rat acute toxicity2.8202 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7691
hERG inhibition (predictor II)Inhibitor0.666
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
  • Davis and geck div american cyanamid co
PackagersNot Available
Dosage forms
Liquidintravenous20 mg
PricesNot Available
PatentsNot Available
Experimental Properties
melting point152-153Fourneau, E.; U.S.Patent 2,544,076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.
water solubilitySolubleNot Available
logP3.5Not Available
Predicted Properties
Water Solubility4.65e-06 mg/mLALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity189.98 m3·mol-1ChemAxon
Polarizability63.43 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Fourneau, E.; U.S.Patent 2,544,076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (28.5 KB)
Drug InteractionsNo interactions found.
Food InteractionsNot Available


Pharmacological action
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
Uniprot ID:
Molecular Weight:
51714.605 Da
  1. Huang XP, Prilla S, Mohr K, Ellis J: Critical amino acid residues of the common allosteric site on the M2 muscarinic acetylcholine receptor: more similarities than differences between the structurally divergent agents gallamine and bis(ammonio)alkane-type hexamethylene-bis-[dimethyl-(3-phthalimidopropyl)ammonium]dibromide. Mol Pharmacol. 2005 Sep;68(3):769-78. Epub 2005 Jun 3. [PubMed:15937215 ]
  2. De Vries B, Roffel AF, Kooistra JM, Meurs H, Zaagsma J: Effects of fenoterol on beta-adrenoceptor and muscarinic M2 receptor function in bovine tracheal smooth muscle. Eur J Pharmacol. 2001 May 11;419(2-3):253-9. [PubMed:11426849 ]
  3. Cembala TM, Forde SC, Appadu BL, Lambert DG: Allosteric interaction of the neuromuscular blockers vecuronium and pancuronium with recombinant human muscarinic M2 receptors. Eur J Pharmacol. 2007 Aug 13;569(1-2):37-40. Epub 2007 May 22. [PubMed:17588565 ]
  4. Ten Berge RE, Krikke M, Teisman AC, Roffel AF, Zaagsma J: Dysfunctional muscarinic M2 autoreceptors in vagally induced bronchoconstriction of conscious guinea pigs after the early allergic reaction. Eur J Pharmacol. 1996 Dec 27;318(1):131-9. [PubMed:9007524 ]
  5. Spina D, Minshall E, Goldie RG, Page CP: The effect of allosteric antagonists in modulating muscarinic M2-receptor function in guinea-pig isolated trachea. Br J Pharmacol. 1994 Jul;112(3):901-5. [PubMed:7522861 ]
  6. Redka DS, Pisterzi LF, Wells JW: Binding of orthosteric ligands to the allosteric site of the M(2) muscarinic cholinergic receptor. Mol Pharmacol. 2008 Sep;74(3):834-43. doi: 10.1124/mol.108.048074. Epub 2008 Jun 13. [PubMed:18552124 ]
  7. Maier-Peuschel M, Frolich N, Dees C, Hommers LG, Hoffmann C, Nikolaev VO, Lohse MJ: A fluorescence resonance energy transfer-based M2 muscarinic receptor sensor reveals rapid kinetics of allosteric modulation. J Biol Chem. 2010 Mar 19;285(12):8793-800. doi: 10.1074/jbc.M109.098517. Epub 2010 Jan 18. [PubMed:20083608 ]
  8. Ehlert FJ, Griffin MT: Two-state models and the analysis of the allosteric effect of gallamine at the M2 muscarinic receptor. J Pharmacol Exp Ther. 2008 Jun;325(3):1039-60. doi: 10.1124/jpet.108.136960. Epub 2008 Feb 27. [PubMed:18305010 ]
  9. Elsinghorst PW, Cieslik JS, Mohr K, Trankle C, Gutschow M: First gallamine-tacrine hybrid: design and characterization at cholinesterases and the M2 muscarinic receptor. J Med Chem. 2007 Nov 15;50(23):5685-95. Epub 2007 Oct 18. [PubMed:17944454 ]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Pharmacological action
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
Uniprot ID:
Molecular Weight:
67795.525 Da
  1. Radic Z, Taylor P: The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases. Chem Biol Interact. 1999 May 14;119-120:111-7. [PubMed:10421444 ]
  2. Radic Z, Taylor P: Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates. J Appl Toxicol. 2001 Dec;21 Suppl 1:S13-4. [PubMed:11920914 ]
  3. Robaire B, Kato G: Effects of edrophonium, eserine, decamethonium, d-tubocurarine, and gallamine on the kinetics of membrane-bound and solubilized eel acetylcholinesterase. Mol Pharmacol. 1975 Nov;11(6):722-34. [PubMed:1207670 ]
  4. Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. [PubMed:3190453 ]
  5. Bourgeois JP, Betz H, Changuex JP: [Effects of chronic paralysis of chick embryo by flaxedil on the development of the neuromuscular junction]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Mar 13;286(10):773-6. [PubMed:417864 ]
  6. Elsinghorst PW, Cieslik JS, Mohr K, Trankle C, Gutschow M: First gallamine-tacrine hybrid: design and characterization at cholinesterases and the M2 muscarinic receptor. J Med Chem. 2007 Nov 15;50(23):5685-95. Epub 2007 Oct 18. [PubMed:17944454 ]
Pharmacological action
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
Uniprot ID:
Molecular Weight:
59764.82 Da
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Aoshima H, Inoue Y, Hori K: Inhibition of ionotropic neurotransmitter receptors by antagonists: strategy to estimate the association and the dissociation rate constant of antagonists with very strong affinity to the receptors. J Biochem. 1992 Oct;112(4):495-502. [PubMed:1337082 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23