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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:29:16 UTC
HMDB IDHMDB14626
Secondary Accession NumbersNone
Metabolite Identification
Common NameGallamine Triethiodide
DescriptionA 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)
Structure
Thumb
Synonyms
ValueSource
FlaxedilKegg
Benzcurine iodideHMDB
BenzkurinHMDB
Gallamin triethiodideHMDB
Gallamine iodideHMDB
Gallamine triethiiodideHMDB
Gallamine triiodoethylateHMDB
Gallamone triethiodideHMDB
GallamonumHMDB
Triiodoethylate de gallamineHMDB
Chemical FormulaC30H60I3N3O3
Average Molecular Weight891.5291
Monoisotopic Molecular Weight891.176873061
IUPAC Name(2-{2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy}ethyl)triethylazanium triiodide
Traditional Name(2-{2,3-bis[2-(triethylammonio)ethoxy]phenoxy}ethyl)triethylazanium triiodide
CAS Registry Number65-29-2
SMILES
[I-].[I-].[I-].CC[N+](CC)(CC)CCOC1=CC=CC(OCC[N+](CC)(CC)CC)=C1OCC[N+](CC)(CC)CC
InChI Identifier
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
InChI KeyInChIKey=REEUVFCVXKWOFE-UHFFFAOYSA-K
Chemical Taxonomy
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
Substituents
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Neuromuscular Nondepolarizing Agents
  • Nicotinic Antagonists
  • Skeletal Muscle Relaxants
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.65e-06 g/LNot Available
LogP3.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.65e-06 mg/mLALOGPS
logP-0.38ALOGPS
logP-7.7ChemAxon
logS-8.3ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00483
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00483
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00483
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5937
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGallamine_triethiodide
NuGOwiki LinkHMDB14626
Metagene LinkHMDB14626
METLIN IDNot Available
PubChem Compound6172
PDB IDNot Available
ChEBI ID774944
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase 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
Molecular weight:
67795.525
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. [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. [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. [1207670 ]
  4. Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. [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. [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. [17944454 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
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. [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. [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. [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. [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. [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. Epub 2008 Jun 13. [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. Epub 2010 Jan 18. [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. Epub 2008 Feb 27. [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. [17944454 ]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in extracellular ligand-gated ion channel activity
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
Molecular weight:
59764.8
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. [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. [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. [1337082 ]