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

Molecular Formula	C16H38N2
Molecular Weight	258.4863
Charge	2
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Effects of ganglion blocking agents on nicotine extensor convulsions and lethality in mice.	1969 Sep	4390479
[Microbiological validation of the composition of "decaceol", an antiseptic prolonged-release drug].	2002	12587327
Ocular tolerance of absorption enhancers in ophthalmic preparations.	2002	12049486
[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
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
beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies.	2003 Feb 1	12527333
Mechanical modulation of cartilage structure and function during embryogenesis in the chick.	2004 Jan	14964718
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
Muscle relaxants--decamethonium.	2005 Dec	16398373
Structural basis of acetylcholinesterase inhibition by triterpenoidal alkaloids.	2005 Jun 17	15959931
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
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
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
[Application of antiseptic dekasan in urgent abdominal surgery].	2009 Nov-Dec	20458953
Role of phospholipases in fungal fitness, pathogenicity, and drug development - lessons from cryptococcus neoformans.	2010	21687772
[Dekasan application in treatment of infected pancreatic necrosis and its complications].	2010 Mar	20491259
Drug interaction: focusing on response surface models.	2010 May	20532049

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:24 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:24 GMT 2023`
Record UNII	C1CG1S3T2W
Record Status	`Validated (UNII)`
Record Version

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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