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Identification
NameDecamethonium
Accession NumberDB01245  (APRD00696)
TypeSmall Molecule
GroupsApproved
DescriptionDecamethonium 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
Decamethonium
DECAMETHONIUM ion
Decamethonum
Decamethylenebis(trimethylammonium)
N,N,N,N',n',n'-hexamethyl-1,10-decanediaminium
External Identifiers
  • Lopac-D-1260
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SyncurineNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Decamethonium bromide
ThumbNot applicableDBSALT001347
Categories
UNIIC1CG1S3T2W
CAS number156-74-1
WeightAverage: 258.4863
Monoisotopic: 258.303499226
Chemical FormulaC16H38N2
InChI KeyInChIKey=MTCUAOILFDZKCO-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.
Related Articles
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 inhibitorNon-inhibitor0.9607
CYP450 2D6 inhibitorNon-inhibitor0.9633
CYP450 2C19 inhibitorNon-inhibitor0.9288
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (56.6 KB)
Interactions
Drug Interactions
Drug
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Decamethonium.
AcebutololDecamethonium may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Acetylcholine.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Decamethonium.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Decamethonium.
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Decamethonium.
AlprenololDecamethonium may increase the bradycardic activities of Alprenolol.
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Decamethonium.
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Decamethonium.
ArecolineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Arecoline.
ArotinololDecamethonium may increase the bradycardic activities of Arotinolol.
AtenololDecamethonium may increase the bradycardic activities of Atenolol.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Decamethonium.
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Decamethonium.
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Decamethonium.
BefunololDecamethonium may increase the bradycardic activities of Befunolol.
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Decamethonium.
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Decamethonium.
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Decamethonium.
BetaxololDecamethonium may increase the bradycardic activities of Betaxolol.
BethanecholThe risk or severity of adverse effects can be increased when Decamethonium is combined with Bethanechol.
BevantololDecamethonium may increase the bradycardic activities of Bevantolol.
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Decamethonium.
BisoprololDecamethonium may increase the bradycardic activities of Bisoprolol.
BopindololDecamethonium may increase the bradycardic activities of Bopindolol.
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Decamethonium.
BufuralolDecamethonium may increase the bradycardic activities of Bufuralol.
BupranololDecamethonium may increase the bradycardic activities of Bupranolol.
CarbacholThe risk or severity of adverse effects can be increased when Decamethonium is combined with Carbachol.
CarteololDecamethonium may increase the bradycardic activities of Carteolol.
CarvedilolDecamethonium may increase the bradycardic activities of Carvedilol.
CeliprololDecamethonium may increase the bradycardic activities of Celiprolol.
CevimelineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Cevimeline.
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Decamethonium.
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Decamethonium.
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Decamethonium.
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Decamethonium.
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Decamethonium.
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Decamethonium.
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Decamethonium.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Decamethonium.
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Decamethonium.
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Decamethonium.
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Decamethonium.
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Decamethonium.
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Decamethonium.
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Decamethonium.
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Decamethonium.
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Decamethonium.
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Decamethonium.
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Decamethonium.
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Decamethonium.
DipyridamoleThe therapeutic efficacy of Decamethonium can be decreased when used in combination with Dipyridamole.
EPIBATIDINEThe risk or severity of adverse effects can be increased when Decamethonium is combined with EPIBATIDINE.
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Decamethonium.
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Decamethonium.
EsmololDecamethonium may increase the bradycardic activities of Esmolol.
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Decamethonium.
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Decamethonium.
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Decamethonium.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Decamethonium.
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Decamethonium.
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Decamethonium.
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Decamethonium.
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Decamethonium.
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Decamethonium.
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Decamethonium.
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Decamethonium.
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Decamethonium.
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Decamethonium.
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Decamethonium.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Decamethonium.
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Decamethonium.
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Decamethonium.
GTS-21The risk or severity of adverse effects can be increased when Decamethonium is combined with GTS-21.
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Decamethonium.
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Decamethonium.
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Decamethonium.
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Decamethonium.
IndenololDecamethonium may increase the bradycardic activities of Indenolol.
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Decamethonium.
LabetalolDecamethonium may increase the bradycardic activities of Labetalol.
LobelineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Lobeline.
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Decamethonium.
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Decamethonium.
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Decamethonium.
MethacholineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Methacholine.
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Decamethonium.
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Decamethonium.
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Decamethonium.
MetoprololDecamethonium may increase the bradycardic activities of Metoprolol.
MivacuriumDecamethonium may decrease the neuromuscular blocking activities of Mivacurium.
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Decamethonium.
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Decamethonium.
NadololDecamethonium may increase the bradycardic activities of Nadolol.
NicotineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Nicotine.
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Decamethonium is combined with Nicotine bitartrate.
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Decamethonium.
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Decamethonium.
OxprenololDecamethonium may increase the bradycardic activities of Oxprenolol.
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Decamethonium.
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Decamethonium.
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Decamethonium.
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Decamethonium.
PenbutololDecamethonium may increase the bradycardic activities of Penbutolol.
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Decamethonium.
PilocarpineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Pilocarpine.
PindololDecamethonium may increase the bradycardic activities of Pindolol.
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Decamethonium.
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Decamethonium.
PractololDecamethonium may increase the bradycardic activities of Practolol.
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Decamethonium.
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Decamethonium.
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Decamethonium.
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Decamethonium.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Decamethonium.
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Decamethonium.
PropranololDecamethonium may increase the bradycardic activities of Propranolol.
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Decamethonium.
RapacuroniumDecamethonium may decrease the neuromuscular blocking activities of Rapacuronium.
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Decamethonium.
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Decamethonium.
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Decamethonium.
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Decamethonium.
SotalolDecamethonium may increase the bradycardic activities of Sotalol.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Decamethonium.
TimololDecamethonium may increase the bradycardic activities of Timolol.
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Decamethonium.
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Decamethonium.
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Decamethonium.
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Decamethonium.
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Decamethonium.
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Decamethonium.
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Decamethonium.
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Decamethonium.
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Decamethonium.
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Decamethonium.
VareniclineThe risk or severity of adverse effects can be increased when Decamethonium is combined with Varenicline.
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Decamethonium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
partial agonist
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
Molecular Weight:
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. [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. Lee C, Jones T: Molecular conformation-activity relationship of decamethonium congeners. Br J Anaesth. 2002 May;88(5):692-9. [PubMed:12067008 ]
  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:7848904 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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
Molecular Weight:
67795.525 Da
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:1207670 ]
  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:239236 ]
  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:2913485 ]
  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. 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:3345199 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Munoz-Delgado E, Vidal CJ: Kinetic behaviour of acetylcholinesterase from muscle microsomal membranes. Biochem Int. 1986 Oct;13(4):625-32. [PubMed:3801037 ]
  2. Danilov AF: [Inhibition of cholinesterase in the myoneural synapses by decamethonium and ditilin]. Farmakol Toksikol. 1967 Nov-Dec;30(6):664-9. [PubMed:5598433 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23