NAV

Gallamine triethiodide

Identification

Summary

Gallamine triethiodideis a nondepolarizing nerve blocker used in addition to anesthesia to cause skeletal muscle relaxation.

Generic Name
Gallamine triethiodide
DrugBank Accession Number
DB00483
Background

一种合成去极化屏蔽药物。该法案ions 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
MOL SDF PDB SMILES InChI
Similar Structures
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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Contraindications & Blackbox Warnings
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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
antagonist
 Humans
AAcetylcholinesterase
inhibitor
 Humans
UNeuronal acetylcholine receptor subunit alpha-2
antagonist
 Humans
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" 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
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interactions in your software
1,2-Benzodiazepine The risk or severity of adverse effects 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 adverse effects can be increased when Gallamine triethiodide is combined with Acetazolamide.
Acetophenazine The risk or severity of adverse effects 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.
Acetyldigitoxin The risk or severity of Cardiac Arrhythmia can be increased when Gallamine triethiodide is combined with Acetyldigitoxin.
Aclidinium The risk or severity of adverse effects can be increased when Gallamine triethiodide is combined with Aclidinium.
Adenosine The risk or severity of Tachycardia can be increased when Gallamine triethiodide is combined with Adenosine.
Agomelatine The risk or severity of adverse effects can be increased when Gallamine triethiodide is combined with Agomelatine.
Alfentanil The risk or severity of adverse effects can be increased when Gallamine triethiodide is combined with Alfentanil.
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食物相互作用
Not Available

Products

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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 flag

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
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大肠;专利2544年076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.
一般参考ences
Not Available
Human Metabolome Database
HMDB0014626
PubChem Compound
6172
PubChem Substance
46508651
ChemSpider
5937
RxNav
4639
ChEMBL
CHEMBL1200993
Therapeutic Targets Database
DAP001127
PharmGKB
PA164745088
Wikipedia
Gallamine_triethiodide
MSDS
Download (28.5 KB)

Clinical Trials

Clinical TrialsLearn More" title="" 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大肠;专利2544年076; March 6, 1951; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.
water solubility 可溶性 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
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Details 1.Muscarinic acetylcholine receptor M2
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
分子量
51714.605 Da
References
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details 2.Acetylcholinesterase
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
分子量
67795.525 Da
References
  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. [Article]
  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. [Article]
  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. [Article]
  4. Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. [Article]
  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. [Article]
  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. [Article]
Details 3.Neuronal acetylcholine receptor subunit alpha-2
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
分子量
59764.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  3. 井上Aoshima H, Y, Hori凯西:抑制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]
Details 4.Muscarinic acetylcholine receptor M1
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
分子量
51420.375 Da
References
  1. 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]
Details 5.Muscarinic acetylcholine receptor M5
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
分子量
60073.205 Da
References
  1. 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 February 03, 2023 08:09