Identification
- Summary
Gallamine triethiodide is a nondepolarizing nerve blocker used in addition to anesthesia to cause skeletal muscle relaxation.
- Generic Name
- Gallamine triethiodide
- DrugBank Accession Number
- DB00483
- Background
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)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gallamine triethiodide (DB00483)
- Weight
- Average: 891.5291
Monoisotopic: 891.176873061 - Chemical Formula
- C30H60I3N3O3
- Synonyms
- Gallamin triethiodid
- Gallamine triethiodide
- Gallamini Triethiodidum
- Triéthiodure de Gallamine
- Trietioduro de galamina
- External IDs
- F 2559
- HL 8583
- RP 3697
Pharmacology
- Indication
For use as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Gallamine 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 action
It 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.
Target Actions Organism AMuscarinic acetylcholine receptor M2 antagonistHumans AAcetylcholinesterase inhibitorHumans UNeuronal acetylcholine receptor subunit alpha-2 antagonistHumans UMuscarinic acetylcholine receptor M1 Not Available Humans UMuscarinic acetylcholine receptor M5 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Gallamine triethiodide is combined with 1,2-Benzodiazepine. Acebutolol Gallamine triethiodide may increase the bradycardic activities of Acebutolol. Acetazolamide The risk or severity of CNS depression can be increased when Gallamine triethiodide is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Gallamine triethiodide is combined with Acetophenazine. Acetylcholine The risk or severity of adverse effects can be increased when Gallamine triethiodide is combined with Acetylcholine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Flaxedil (Sanofi-Aventis) / Myraxan (Yoo Young) / Sincurarina (Carlo Erba) / Tricuran
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Flaxedil Inj 20mg/ml Liquid 20 mg / mL Intravenous Aventis Pharma Ltd. 1951-12-31 2003-07-22 Canada 
Categories
- Drug Categories
- Agents producing tachycardia
- Amines
- Anticholinergic Agents
- Central Nervous System Depressants
- Cholinergic Agents
- Cholinesterase Inhibitors
- Muscarinic Antagonists
- Neuromuscular Agents
- Neuromuscular Blocking Agents
- Neuromuscular-Blocking Agents (Nondepolarizing)
- Neurotransmitter Agents
- Nicotinic Antagonists
- Onium Compounds
- Peripheral Nervous System Agents
- Quaternary Ammonium Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Alkyl aryl ethers / Tetraalkylammonium salts / Organopnictogen compounds / Organic iodide salts / Hydrocarbon derivatives / Amines
- Substituents
- Alkyl aryl ether / Amine / Aromatic homomonocyclic compound / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic iodide salt / Organic nitrogen compound / Organic oxygen compound / Organic salt
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Q3254X40X2
- CAS number
- 65-29-2
- InChI Key
- REEUVFCVXKWOFE-UHFFFAOYSA-K
- InChI
- 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
- IUPAC Name
- (2-{2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy}ethyl)triethylazanium triiodide
- SMILES
- [I-].[I-].[I-].CC[N+](CC)(CC)CCOC1=CC=CC(OCC[N+](CC)(CC)CC)=C1OCC[N+](CC)(CC)CC
References
- Synthesis Reference
Fourneau, E.; U.S.Patent 2,544,076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014626
- PubChem Compound
- 6172
- PubChem Substance
- 46508651
- ChemSpider
- 5937
- 4639
- ChEMBL
- CHEMBL1200993
- Therapeutic Targets Database
- DAP001127
- PharmGKB
- PA164745088
- Wikipedia
- Gallamine_triethiodide
- MSDS
- Download (28.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Davis and geck div american cyanamid co
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Intravenous 20 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 152-153 Fourneau, E.; U.S.Patent 2,544,076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France. water solubility Soluble Not Available logP 3.5 Not Available - Predicted Properties
Property Value Source Water Solubility 4.65e-06 mg/mL ALOGPS logP -0.38 ALOGPS logP -7.7 Chemaxon logS -8.3 ALOGPS pKa (Strongest Basic) -4.5 Chemaxon Physiological Charge 3 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 27.69 Å2 Chemaxon Rotatable Bond Count 21 Chemaxon Refractivity 189.98 m3·mol-1 Chemaxon Polarizability 63.43 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8901 Blood Brain Barrier + 0.8616 Caco-2 permeable + 0.6256 P-glycoprotein substrate Substrate 0.6912 P-glycoprotein inhibitor I Non-inhibitor 0.8173 P-glycoprotein inhibitor II Non-inhibitor 0.8176 Renal organic cation transporter Non-inhibitor 0.6818 CYP450 2C9 substrate Non-substrate 0.8147 CYP450 2D6 substrate Non-substrate 0.6511 CYP450 3A4 substrate Substrate 0.5708 CYP450 1A2 substrate Non-inhibitor 0.8002 CYP450 2C9 inhibitor Non-inhibitor 0.8613 CYP450 2D6 inhibitor Non-inhibitor 0.8874 CYP450 2C19 inhibitor Non-inhibitor 0.8815 CYP450 3A4 inhibitor Non-inhibitor 0.9296 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6622 Ames test Non AMES toxic 0.6156 Carcinogenicity Non-carcinogens 0.5724 Biodegradation Not ready biodegradable 0.9841 Rat acute toxicity 2.8202 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7691 hERG inhibition (predictor II) Inhibitor 0.666
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01tm-1290013140-6f85bfa38f8c307bb580 - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.12082 predictedDeepCCS 1.0 (2019) [M+H]+ 229.51639 predictedDeepCCS 1.0 (2019) [M+Na]+ 235.42891 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- 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...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- 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. [Article]
- Radic Z, Taylor P: Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates. J Appl Toxicol. 2001 Dec;21 Suppl 1:S13-4. [Article]
- 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. [Article]
- Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
- CHRNA2
- Uniprot ID
- Q15822
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-2
- Molecular Weight
- 59764.82 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphatidylinositol phospholipase c 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...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Lazareno S, Popham A, Birdsall NJ: Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-(3)H]scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site. Mol Pharmacol. 2000 Jul;58(1):194-207. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphatidylinositol phospholipase c 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...
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Prilla S, Schrobang J, Ellis J, Holtje HD, Mohr K: Allosteric interactions with muscarinic acetylcholine receptors: complex role of the conserved tryptophan M2422Trp in a critical cluster of amino acids for baseline affinity, subtype selectivity, and cooperativity. Mol Pharmacol. 2006 Jul;70(1):181-93. Epub 2006 Apr 26. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:43