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Identification
NameHexafluronium
Accession NumberDB00941  (APRD01013)
TypeSmall Molecule
GroupsApproved
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
Thumb
Synonyms
SynonymLanguageCode
HexafluoreniumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
MylaxenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Hexafluronium bromide
Thumb
  • InChI Key: WDEFPRUEZRUYNW-UHFFFAOYSA-L
  • Monoisotopic Mass: 660.171474648
  • Average Mass: 662.54
DBSALT000566
Categories
CAS number317-52-2
WeightAverage: 532.8011
Monoisotopic: 532.381749546
Chemical FormulaC38H48N2
InChI KeyUUNOBWWOFTYQRY-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;
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hexamethonium compounds. These are organic compounds containing a N,N,N,N',N',N'-hexamethylhexane-1,6-diaminium moiety.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassHexamethonium compounds
Direct ParentHexamethonium compounds
Alternative Parents
Substituents
  • Hexamethonium
  • Fluorene
  • Aralkylamine
  • Benzenoid
  • Hydrocarbon derivative
  • Amine
  • Hydrocarbon
  • Organic cation
  • Aromatic homopolycyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Pharmacology
IndicationUsed as an adjunct with succinylcholine (or suxamethonium chloride) to prolong muscle relaxation and to prevent succinylcholine-induced muscle fasciculations.
PharmacodynamicsHexafluronium 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 actionHexafluronium 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50 = 280 mg/kg (mouse, oral)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9105
Blood Brain Barrier+0.9722
Caco-2 permeable+0.6779
P-glycoprotein substrateSubstrate0.6897
P-glycoprotein inhibitor INon-inhibitor0.7472
P-glycoprotein inhibitor IIInhibitor0.7951
Renal organic cation transporterInhibitor0.6954
CYP450 2C9 substrateNon-substrate0.7536
CYP450 2D6 substrateSubstrate0.5964
CYP450 3A4 substrateSubstrate0.6599
CYP450 1A2 substrateNon-inhibitor0.7169
CYP450 2C9 substrateNon-inhibitor0.9223
CYP450 2D6 substrateNon-inhibitor0.6863
CYP450 2C19 substrateNon-inhibitor0.707
CYP450 3A4 substrateNon-inhibitor0.9637
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.85
Ames testNon AMES toxic0.7711
CarcinogenicityNon-carcinogens0.7479
BiodegradationNot ready biodegradable0.9234
Rat acute toxicity2.6334 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8767
hERG inhibition (predictor II)Inhibitor0.8131
Pharmacoeconomics
Manufacturers
  • Medpointe pharmaceuticals medpointe healthcare inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point153.5 °CPhysProp
logP-0.06Not Available
Predicted Properties
PropertyValueSource
logP-0.28ChemAxon
pKa (Strongest Acidic)16.64ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity184.49 m3·mol-1ChemAxon
Polarizability60.46 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesM03AC05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12