DECAMETHONIUM

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H38N2
Molecular Weight	258.4863
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	2

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C

InChI

InChIKey=MTCUAOILFDZKCO-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1279945/

Decamethylene disquaternary salts, with a ten-carbon (C10) chain between the quaternary groups, had the most potent curariform action in the series of polymethylene bisquaternaries. Decamethonium was used clinically as a neuromuscular blocking drug for a short time. Decamethonium was different from d-tubocurarine and that it produced a transient augmentation of contraction. C10 produces neuromuscular block by initiating some active response in the endplate or muscle fibre. Unlike d-tubocurare, decamethonium was not reversed by anticholinesterase agents.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7678947	Partial Agonist 290
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3729986 \| https://www.ncbi.nlm.nih.gov/pubmed/4154	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle spasm 40 Sources: http://www.minclinic.ru/drugs/drugs_eng/S/Syncurine.html	Preventing		Approved 8429	SYNCURINE Approved Use Syncurine is a short acting depolarizing muscle relaxant or neuromuscular blocking agent, and is used in anesthesia to induce paralysis.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3079779/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:41934	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41934
ChemicalBook	CB21343786	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB21343786
ZINC	ZINC000001532339	http://zinc15.docking.org/substances/ZINC000001532339

PubMed

Title	Date	PubMed
Sympathetic outflows from cervical spinal cord in the dog.	1966 Apr 15	17775175
The Effects of isoflurane on acetylcholine receptor channels: 3. Effects of conservative polar-to-nonpolar mutations within the channel pore.	2001 Sep	11502891
[Microbiological validation of the composition of "decaceol", an antiseptic prolonged-release drug].	2002	12587327
Effects of membranotropic agents on mono- and multilayer structures of dipalmitoylphosphatidylcholine.	2002 Dec	12602341
[3H]Epibatidine binding to bovine adrenal medulla: evidence for alpha3beta4* nicotinic receptors.	2002 Jan 25	11796195
Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice.	2002 Jun	12065623
Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.	2002 May	12010632
Structure of a complex of the potent and specific inhibitor BW284C51 with Torpedo californica acetylcholinesterase.	2002 Oct	12351819
Short-term rigid and flaccid paralyses diminish growth of embryonic chick limbs and abrogate joint cavity formation but differentially preserve pre-cavitated joints.	2002 Sep	15758413
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.	2003 Dec	14645658
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.	2003 Jun 12	12770692
GABAergic systems modulate nicotinic receptor-mediated seizures in mice.	2003 Sep	12829730
Expression of the alpha7 nicotinic acetylcholine receptor in human lung cells.	2005 Apr 4	15807899
Structural basis of acetylcholinesterase inhibition by triterpenoidal alkaloids.	2005 Jun 17	15959931
Dequalinium-induced protofibril formation of alpha-synuclein.	2006 Feb 10	16330551
Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts.	2006 Jan 26	16420066
Lymph heart in chick--somitic origin, development and embryonic oedema.	2007 Dec	18003736
Discovery of a novel nicotinic receptor antagonist for the treatment of nicotine addiction: 1-(3-Picolinium)-12-triethylammonium-dodecane dibromide (TMPD).	2007 Oct 15	17727820
Allergen uptake, activation, and IL-23 production by pulmonary myeloid DCs drives airway hyperresponsiveness in asthma-susceptible mice.	2008	19060952
Pharmacological evaluation of contractile activity of the dog heartworm Dirofilaria immitis.	2008 Mar	17899422
Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors.	2009 Dec 28	20038295
Single fiber electromyographic jitter and detection of acute changes in neuromuscular function in young and adult rats.	2009 Mar-Apr	19367692
[Dekasan application in treatment of infected pancreatic necrosis and its complications].	2010 Mar	20491259
Drug interaction: focusing on response surface models.	2010 May	20532049
Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes.	2010 May	20100906

Patents

Sample Use Guides

In Vivo Use Guide

The mean (SEM) dose of decamethonium producing 80% twitch tension depression (ED80) when administered alone was 37 (4.0) micrograms/kg.

Route of Administration: Parenteral

In Vitro Use Guide

1. In rat diaphragms immersed in solution containing 5 mm potassium the maximum uptake of labelled decamethonium was found at the end-plate region. In muscles depolarized in solution containing potassium methyl sulphate the uptake was reduced but a peak concentration at the end-plate region was still demonstrated. 2. The uptake of labelled decamethonium increased steadily with time and was interpreted in terms of the entry of decamethonium into the fibres. The permeability at 10-100 μm was similar to that of sodium. 3. The uptake of decamethonium at the end-plate region was dependent on the concentration. At low values the uptake in depolarized muscle was uniform along the fibres. Increase in concentration produced a peak at the end-plate region. This was interpreted as a change in permeability such that half the maximum effect was present at a concentration of approximately 5 μm.

Name

Type

Language

DECAMETHONIUM

Common Name

English

DECAMETHONIUM ION

Common Name

English

Decamethonium [WHO-DD]

Common Name

English

DECAMETHONIUM [HSDB]

Common Name

English

N,N,N,N',N',N'-HEXAMETHYLDECANE-1,10-DIAMINIUM

Systematic Name

English

1,10-DECANEDIAMINIUM, N,N,N,N',N',N'-HEXAMETHYL-

Systematic Name

English

DECAMETHONIUM CATION

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29696