DECAMETHONIUM BROMIDE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H38N2.2Br
Molecular Weight	418.294
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C

InChI

InChIKey=HLXQFVXURMXRPU-UHFFFAOYSA-L

InChI=1S/C16H38N2.2BrH/c1-17(2,3)15-13-11-9-7-8-10-12-14-16-18(4,5)6;;/h7-16H2,1-6H3;2*1H/q+2;;/p-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
Effects of ganglion blocking agents on nicotine extensor convulsions and lethality in mice.	1969 Sep	4390479
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.	2000 Aug	10908297
Receptor protection studies to characterize neuronal nicotinic receptors: tubocurarine prevents alkylation of adrenal nicotinic receptors.	2001 Feb 9	11164821
Does "butyrylization" of acetylcholinesterase through substitution of the six divergent aromatic amino acids in the active center gorge generate an enzyme mimic of butyrylcholinesterase?	2001 Jun 26	11412096
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
Uptake of triiodothyronine and triiodothyroacetic acid in neonatal rat cardiomyocytes: effects of metabolites and analogs.	2002 May	12010632
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
beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies.	2003 Feb 1	12527333
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
Decamethonium bromide-mediated inhibition of embryonic muscle development.	2004 Apr	14997390
Mechanical modulation of cartilage structure and function during embryogenesis in the chick.	2004 Jan	14964718
Long-lasting activation of rhythmic neuronal activity by a novel mechanosensory system in the crustacean stomatogastric nervous system.	2004 Jan	14523066
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).	2004 Oct	15378568
[Application of the Decasan at the practice of urgent surgery].	2004 Sep	15560593
Expression of the alpha7 nicotinic acetylcholine receptor in human lung cells.	2005 Apr 4	15807899
Muscle relaxants--decamethonium.	2005 Dec	16398373
Structural basis of acetylcholinesterase inhibition by triterpenoidal alkaloids.	2005 Jun 17	15959931
The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction.	2005 May 13	15850600
Quaternary ammonium anticholinesterases have different effects on nicotinic receptors: is there a single binding site?	2006	17192677
Early effects of embryonic movement: 'a shot out of the dark'.	2006 Apr	16637868
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
Receptor protection studies comparing recombinant and native nicotinic receptors: Evidence for a subpopulation of mecamylamine-sensitive native alpha3beta4* nicotinic receptors.	2006 Jan 9	16198480
Diverse inhibitory actions of quaternary ammonium cholinesterase inhibitors on Torpedo nicotinic ACh receptors transplanted to Xenopus oocytes.	2007 Aug	17572698
The effect of some curarizing drugs in unanaesthetized man. I. d-Tubocurarine chloride, gallamonium iodide, decamethonium iodide, succinylcholine iodide and its bis-monoethyl-substituted derivative in single or repeated doses. Acta Anaesth. Scandinav. 1957, 1, 15-39.	2007 Sep	17697296
Allergen uptake, activation, and IL-23 production by pulmonary myeloid DCs drives airway hyperresponsiveness in asthma-susceptible mice.	2008	19060952
Identification of mechanosensitive genes during embryonic bone formation.	2008 Dec	19112485
Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors.	2009 Dec 28	20038295
Stabilization of Torpedo californica acetylcholinesterase by reversible inhibitors.	2009 Jan 27	19115961
Bone marrow cell derived arginase I is the major source of allergen-induced lung arginase but is not required for airway hyperresponsiveness, remodeling and lung inflammatory responses in mice.	2009 Jun 1	19486531
Single fiber electromyographic jitter and detection of acute changes in neuromuscular function in young and adult rats.	2009 Mar-Apr	19367692
[Application of antiseptic dekasan in urgent abdominal surgery].	2009 Nov-Dec	20458953
[Dekasan application in treatment of infected pancreatic necrosis and its complications].	2010 Mar	20491259
Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes.	2010 May	20100906
Mucosal sensitization to German cockroach involves protease-activated receptor-2.	2010 May 24	20497568

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 BROMIDE

Official Name

English

decamethonium bromide [INN]

Common Name

English

DECAMETHONIUM BROMIDE [ORANGE BOOK]

Common Name

English

SYNCURINE

Brand Name

English

Decamethylene bis[trimethylammonium] dibromide

Systematic Name

English

Decamethonium bromide [WHO-DD]

Common Name

English

NSC-23004

Code

English

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

Systematic Name

English

DECAMETHONIUM BROMIDE [MART.]

Common Name

English

DECAMETHONIUM BROMIDE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29696