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Identification
NameDecamethonium
Accession NumberDB01245  (APRD00696)
TypeSmall Molecule
GroupsApproved
Description

Decamethonium is a short acting depolarizing muscle relaxant or neuromuscular blocking agent, and is used in anesthesia to induce paralysis. It is similar to acetylcholine and acts as a partial agonist of the nicotinic acetylcholine receptor.

Structure
Thumb
Synonyms
SynonymLanguageCode
DecamethoniumNot AvailableNot Available
DECAMETHONIUM ionNot AvailableNot Available
DecamethonumNot AvailableNot Available
Decamethylenebis(trimethylammonium)Not AvailableNot Available
N,N,N,N',n',n'-hexamethyl-1,10-decanediaminiumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
SyncurineNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number156-74-1
WeightAverage: 258.4863
Monoisotopic: 258.303499226
Chemical FormulaC16H38N2
InChI KeyMTCUAOILFDZKCO-UHFFFAOYSA-N
InChI
InChI=1S/C16H38N2/c1-17(2,3)15-13-11-9-7-8-10-12-14-16-18(4,5)6/h7-16H2,1-6H3/q+2
IUPAC Name
trimethyl[10-(trimethylazaniumyl)decyl]azanium
SMILES
C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as decamethonium compounds. These are quaternary ammonium compounds containing a trimethyl-(10-trimethylammoniodecyl)ammonium moiety.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassDecamethonium compounds
Direct ParentDecamethonium compounds
Alternative Parents
Substituents
  • Decamethonium
  • Hydrocarbon derivative
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor use as a skeletal muscle relaxant
PharmacodynamicsDecamethonium acts as a depolarizing muscle relaxant or neuromuscular blocking agent. It acts as an agonist of nicotinic acetycholine receptors in the motor endplate and causes depolarization. This class of drugs has its effect at the neuromuscular junction by preventing the effects of acetylcholine. Normally, when a nerve stimulus acts to contract a muscle, it releases acetylcholine. The binding of this acetylcholine to receptors causes the muscle to contract. Muscle relaxants play an important role in anesthesia even though they don't provide any pain relief or produce unconsciousness.
Mechanism of actionBinds to the nicotinic acetycholine receptors (by virtue of its similarity to acetylcholine) in the motor endplate and blocks access to the receptors. In the process of binding, the receptor is actually activated - causing a process known as depolarization. Since it is not degraded in the neuromuscular junction, the depolarized membrance remains depolarized and unresponsive to any other impulse, causing muscle paralysis.
AbsorptionRapidly absorbed.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=190 mg/kg (orally in mice). Prolonged apnoea, neuromuscular paralysis and cardiac arrest may occur.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9862
Blood Brain Barrier+0.9444
Caco-2 permeable+0.7036
P-glycoprotein substrateSubstrate0.5439
P-glycoprotein inhibitor INon-inhibitor0.9679
P-glycoprotein inhibitor IINon-inhibitor0.7809
Renal organic cation transporterNon-inhibitor0.5386
CYP450 2C9 substrateNon-substrate0.8398
CYP450 2D6 substrateNon-substrate0.661
CYP450 3A4 substrateNon-substrate0.5423
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9607
CYP450 2D6 substrateNon-inhibitor0.9633
CYP450 2C19 substrateNon-inhibitor0.9288
CYP450 3A4 substrateNon-inhibitor0.9882
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9899
Ames testNon AMES toxic0.9423
CarcinogenicityCarcinogens 0.6778
BiodegradationNot ready biodegradable0.5263
Rat acute toxicity2.6822 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7991
hERG inhibition (predictor II)Non-inhibitor0.6249
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point268-270 °CNot Available
water solubilitySubstantialNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.04e-06 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.9ChemAxon
logS-7.7ALOGPS
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity106.95 m3·mol-1ChemAxon
Polarizability35.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (56.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: partial agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

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. Pubmed
  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
  3. Lee C, Jones T: Molecular conformation-activity relationship of decamethonium congeners. Br J Anaesth. 2002 May;88(5):692-9. Pubmed
  4. Maneckjee R, Minna JD: Opioids induce while nicotine suppresses apoptosis in human lung cancer cells. Cell Growth Differ. 1994 Oct;5(10):1033-40. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Acetylcholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Acetylcholinesterase P22303 Details

References:

  1. 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
  2. Sinha BK, Chignell CF: Synthesis and biological activity of spin-labeled analogs of biotin, hexamethonium, decamethonium, dichlorisoproterenol, and propranolol. J Med Chem. 1975 Jul;18(7):669-73. Pubmed
  3. Wu CS, Yang JT: Tacrine protection of acetylcholinesterase from inactivation by diisopropylfluorophosphate: a circular dichroism study. Mol Pharmacol. 1989 Jan;35(1):85-92. Pubmed
  4. Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. Pubmed
  5. Hallek M, Szinicz L: Effects of some mono- and bisquaternary ammonium compounds on the reactivatability of soman-inhibited human acetylcholinesterase in vitro. Biochem Pharmacol. 1988 Mar 1;37(5):819-25. Pubmed

Enzymes

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

  1. Munoz-Delgado E, Vidal CJ: Kinetic behaviour of acetylcholinesterase from muscle microsomal membranes. Biochem Int. 1986 Oct;13(4):625-32. Pubmed
  2. Danilov AF: [Inhibition of cholinesterase in the myoneural synapses by decamethonium and ditilin]. Farmakol Toksikol. 1967 Nov-Dec;30(6):664-9. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13