Identification
- Generic Name
- Decamethonium
- DrugBank Accession Number
- DB01245
- Background
Decamethonium is used in anesthesia to cause paralysis. It is a short acting depolarizing muscle relaxant. It is similar to acetylcholine and acts as a partial agonist of the nicotinic acetylcholine receptor.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Decamethonium (DB01245)
- Weight
- Average: 258.4863
Monoisotopic: 258.303499226 - Chemical Formula
- C16H38N2
- Synonyms
- Decamethonium
- Decamethonium cation
- Decamethonium ion
- Decamethonum
- Decamethylenebis(trimethylammonium)
- N,N,N,N',N',N'-hexamethyl-1,10-decanediaminium
- External IDs
- Lopac-D-1260
Pharmacology
- Indication
For use as a skeletal muscle relaxant
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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
Decamethonium 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 action
Binds 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.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 partial agonistHumans UNeuronal acetylcholine receptor subunit alpha-4 Not Available Humans UNeuronal acetylcholine receptor subunit beta-2 Not Available Humans UAcetylcholinesterase inhibitorHumans - Absorption
Rapidly absorbed.
- 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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LD50=190 mg/kg (orally in mice). Prolonged apnoea, neuromuscular paralysis and cardiac arrest may occur.
- 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 Decamethonium is combined with 1,2-Benzodiazepine. Acebutolol Decamethonium may increase the bradycardic activities of Acebutolol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Decamethonium. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Decamethonium. Acetylcholine The risk or severity of adverse effects can be increased when Decamethonium 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.- Product Ingredients
Ingredient UNII CAS InChI Key Decamethonium bromide 55C6RK944K 541-22-0 HLXQFVXURMXRPU-UHFFFAOYSA-L - International/Other Brands
- Syncurine
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as decamethonium compounds. These are quaternary ammonium compounds containing a trimethyl-(10-trimethylammoniodecyl)ammonium moiety.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Quaternary ammonium salts
- Direct Parent
- Decamethonium compounds
- Alternative Parents
- Tetraalkylammonium salts / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations
- Substituents
- Aliphatic acyclic compound / Amine / Decamethonium / Hydrocarbon derivative / Organic cation / Organic salt / Organopnictogen compound / Tetraalkylammonium salt
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- quaternary ammonium ion (CHEBI:41934)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- C1CG1S3T2W
- CAS number
- 156-74-1
- InChI Key
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015375
- KEGG Compound
- C11733
- PubChem Compound
- 2968
- PubChem Substance
- 46507737
- ChemSpider
- 2862
- BindingDB
- 50060582
- ChEBI
- 41934
- ChEMBL
- CHEMBL1190
- ZINC
- ZINC000001532339
- Therapeutic Targets Database
- DAP000378
- PharmGKB
- PA164747980
- PDBe Ligand
- DME
- Wikipedia
- Decamethonium
- PDB Entries
- 1acl / 1maa / 2xud / 5e2i / 5e4j / 6ep4
- MSDS
- Download (56.6 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
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 268-270 °C Not Available water solubility Substantial Not Available - Predicted Properties
Property Value Source Water Solubility 7.04e-06 mg/mL ALOGPS logP -2.8 ALOGPS logP -4.9 Chemaxon logS -7.7 ALOGPS Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 0 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 0 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 106.95 m3·mol-1 Chemaxon Polarizability 35.94 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9862 Blood Brain Barrier + 0.9444 Caco-2 permeable + 0.7036 P-glycoprotein substrate Substrate 0.5439 P-glycoprotein inhibitor I Non-inhibitor 0.9679 P-glycoprotein inhibitor II Non-inhibitor 0.7809 Renal organic cation transporter Non-inhibitor 0.5386 CYP450 2C9 substrate Non-substrate 0.8398 CYP450 2D6 substrate Non-substrate 0.661 CYP450 3A4 substrate Non-substrate 0.5423 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9607 CYP450 2D6 inhibitor Non-inhibitor 0.9633 CYP450 2C19 inhibitor Non-inhibitor 0.9288 CYP450 3A4 inhibitor Non-inhibitor 0.9882 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9899 Ames test Non AMES toxic 0.9423 Carcinogenicity Carcinogens 0.6778 Biodegradation Not ready biodegradable 0.5263 Rat acute toxicity 2.6822 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7991 hERG inhibition (predictor II) Non-inhibitor 0.6249
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 166.1781 predictedDeepCCS 1.0 (2019) [M+H]+ 168.53633 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.62949 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- Lee C, Jones T: Molecular conformation-activity relationship of decamethonium congeners. Br J Anaesth. 2002 May;88(5):692-9. [Article]
- Maneckjee R, Minna JD: Opioids induce while nicotine suppresses apoptosis in human lung cancer cells. Cell Growth Differ. 1994 Oct;5(10):1033-40. [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
- Unknown
- Curator comments
- competitive antagonist
- General Function
- 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 permeabl...
- Gene Name
- CHRNA4
- Uniprot ID
- P43681
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-4
- Molecular Weight
- 69956.47 Da
References
- Eaton JB, Peng JH, Schroeder KM, George AA, Fryer JD, Krishnan C, Buhlman L, Kuo YP, Steinlein O, Lukas RJ: Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. Mol Pharmacol. 2003 Dec;64(6):1283-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- competitive antagonist
- General Function
- 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 permeabl...
- Gene Name
- CHRNB2
- Uniprot ID
- P17787
- Uniprot Name
- Neuronal acetylcholine receptor subunit beta-2
- Molecular Weight
- 57018.575 Da
References
- Eaton JB, Peng JH, Schroeder KM, George AA, Fryer JD, Krishnan C, Buhlman L, Kuo YP, Steinlein O, Lukas RJ: Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. Mol Pharmacol. 2003 Dec;64(6):1283-94. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- 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]
- 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. [Article]
- Wu CS, Yang JT: Tacrine protection of acetylcholinesterase from inactivation by diisopropylfluorophosphate: a circular dichroism study. Mol Pharmacol. 1989 Jan;35(1):85-92. [Article]
- Seto Y, Shinohara T: Structure-activity relationship of reversible cholinesterase inhibitors including paraquat. Arch Toxicol. 1988 Aug;62(1):37-40. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Munoz-Delgado E, Vidal CJ: Kinetic behaviour of acetylcholinesterase from muscle microsomal membranes. Biochem Int. 1986 Oct;13(4):625-32. [Article]
- Danilov AF: [Inhibition of cholinesterase in the myoneural synapses by decamethonium and ditilin]. Farmakol Toksikol. 1967 Nov-Dec;30(6):664-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:53