DrugBank: Hexafluronium (DB00941)

targets (1)

Identification

Name

Hexafluronium

Accession Number

DB00941 (APRD01013)

Type

small molecule

Groups

approved

Description

Hexafluronium bromide is a neuromuscular blocking agent used in anesthesiology to prolong and potentiate the skeletal muscle relaxing action of suxamethonium during surgery. It is known to bind and block the activity of plasma cholinesterases.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Hexafluorenium
Hexafluorenium bromide
Hexafluronium bromide

Salts

Not Available

Brand names

Name	Company
Milaxen
Mylaxen

Brand mixtures

Not Available

Categories

Muscle Relaxants

CAS number

317-52-2

Weight

Average: 532.8011
Monoisotopic: 532.381749546

Chemical Formula

C₃₈H₄₈N₂

InChI Key

InChIKey=UUNOBWWOFTYQRY-UHFFFAOYSA-N

InChI

InChI=1S/C36H42N2.C2H6/c1-37(2,35-31-21-11-7-17-27(31)28-18-8-12-22-32(28)35)25-15-5-6-16-26-38(3,4)36-33-23-13-9-19-29(33)30-20-10-14-24-34(30)36;1-2/h7-14,17-24,35-36H,5-6,15-16,25-26H2,1-4H3;1-2H3/q+2;

Plain Text

IUPAC Name

N-{6-[(9H-fluoren-9-yl)dimethylazaniumyl]hexyl}-N,N-dimethyl-9H-fluoren-9-aminium; ethane

SMILES

CC.C[N+](C)(CCCCCC[N+](C)(C)C1C2=C(C=CC=C2)C2=C1C=CC=C2)C1C2=C(C=CC=C2)C2=C1C=CC=C2

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Used as an adjunct with succinylcholine (or suxamethonium chloride) to prolong muscle relaxation and to prevent succinylcholine-induced muscle fasciculations.

Pharmacodynamics

Hexafluronium bromide is a cholinesterase antagonist that can be used to prolong the relaxation effects of succinylcholine or suxamethonium chloride. Suxamethonium acts as a depolarizing muscle relaxant. It imitates the action of acetylcholine at the neuromuscular junction and is degraded by pseudocholinesterase, a plasma cholinesterase. The prolonged stimulation of the acetylcholine receptor results first in disorganized muscle contractions, then in profound relaxation. Cholinesterases catalyze the hydrolysis of the neurotransmitter acetylcholine into choline and acetic acid, a reaction necessary to allow a cholinergic neuron to return to its resting state after activation. There are two types of cholinesterase acetylcholinesterase and pseuodocholinesterase. The first hydrolyses acetylcholine more quickly; the latter hydrolyses butyrylcholine and succinylcholine more quickly. An absence or mutation of the pseudocholinesterase enzyme leads to a medical condition known simply as pseudocholinesterase deficiency. This is a silent condition that only manifests itself when people who have the deficiency receive the muscle relaxants succinylcholine or mivacurium during a surgery.

Mechanism of action

Hexafluronium bromide is a non-competitive reversible inhibitor of human plasma cholinesterase or pseudocholinesterase. Hexafluornium probably binds to anionic side receptors near the active center, causing a conformational change in the enzyme, preventing acylation of the esteratic site. The esteratic site on cholistereases is where acetylcholine is hydrolyzed to acetic acid and choline.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

LD₅₀ = 280 mg/kg (mouse, oral)

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Medpointe pharmaceuticals medpointe healthcare inc

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	153.5 °C	PhysProp
logP	-0.06	Not Available

Predicted Properties

Property	Value	Source
logP	-0.28	ChemAxon
pKa (strongest acidic)	16.64	ChemAxon
physiological charge	2	ChemAxon
hydrogen acceptor count	0	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	0	ChemAxon
rotatable bond count	9	ChemAxon
refractivity	184.49	ChemAxon
polarizability	60.46	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D04435
PubChem Compound	9434
PubChem Substance	46507171
Therapeutic Targets Database	DAP000963
PharmGKB	PA164743020
Wikipedia	http://en.wikipedia.org/wiki/Hexafluronium_bromide

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Cholinesterase Pharmacological action: yes Actions: inhibitor An acylcholine + H(2)O = choline + a carboxylate Organism class: human UniProt ID: P06276 Gene: BCHE Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Schuh FR: Interaction of hexafluorenium with human plasma cholinesterase in comparison with hexamethonium. Naunyn Schmiedebergs Arch Pharmacol. 1976;293(1):11-3. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Cholinesterase

Pharmacological action: yes
Actions: inhibitor

An acylcholine + H(2)O = choline + a carboxylate

Organism class: human
UniProt ID: P06276 Link_out

Gene: BCHE Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Schuh FR: Interaction of hexafluorenium with human plasma cholinesterase in comparison with hexamethonium. Naunyn Schmiedebergs Arch Pharmacol. 1976;293(1):11-3. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19