Bretylium
Basic information
- CAS
59-41-6- Standard SMILES
CC[N+](C)(C)Cc1ccccc1Br- InChIKey
AAQOQKQBGPPFNS-UHFFFAOYSA-N- Molecular formula
- C11H17BrN+
- Average molar mass
- 243.16 g/mol
- Monoisotopic mass
- 242.05444
Overview
Bretylium is a quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. It has a role as an antihypertensive agent, an adrenergic antagonist and an anti-arrhythmia drug.
Names & identifiers
- Preferred name
- Bretylium
- IUPAC
- (2-bromophenyl)methyl-ethyl-dimethylazanium
- English name
- Bretylium
- Molecular formula
- C11H17BrN
- Molecular weight
- 0
Names & synonyms
Bretylium59-41-6Bretylium ionBretylium cation(2-bromobenzyl)ethyldimethylaminium2-bromo-N-ethyl-N,N-dimethylbenzenemethanaminiumN-ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumRZR75EQ2KJBenzenemethanaminium, 2-bromo-N-ethyl-N,N-dimethyl-CHEBI:3172DTXSID3046958[(2-bromophenyl)methyl](ethyl)dimethylazanium
Show more names
Unii-rzr75eq2kj(2-bromophenyl)methyl-ethyl-dimethylazanium bromide
((2-bromophenyl)methyl)(ethyl)dimethylazaniumRefChem:570223DTXCID1026958BretylumBretylium tolsylate(2-bromophenyl)methyl-ethyl-dimethylazaniumBretylanBretylium tosylate(USAN)
Database identifiers
- CAS
59-41-6- PubChem CID
- 2431
- DTXSID
DTXSID3046958- ChEMBL
CHEMBL1199080- ChEBI
CHEBI:3172- UNII
- RZR75EQ2KJ
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 1
- Complexity
- 156
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility
Freely soluble
1.54e-04 g/L
Human Drugs
Breast Feeding; Lactation; Antiarrhythmics;
Pharmaceuticals
Physical DescriptionSolid
Physicochemical properties
- InChI
- InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
- InChIKey
- AAQOQKQBGPPFNS-UHFFFAOYSA-N
- SMILES
- CC[N+](C)(CC1C=CC=CC=1Br)C
- FDA UNII
- 75 EQ2KJ · RZR75EQ2KJ
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
Pharmacodynamics
Bretylium is a bromobenzyl quaternary ammonium compound which selectively accumulates in sympathetic ganglia and their postganglionic adrenergic neurons where it inhibits norepinephrine release by depressing adrenergic nerve terminal excitability. Bretylium also suppresses ventricular fibrillation and ventricular arrhythmias.
Mechanism of Action
Bretylium inhibits norepinephrine release by depressing adrenergic nerve terminal excitability. The mechanisms of the antifibrillatory and antiarrhythmic actions of bretylium are not established. In efforts to define these mechanisms, the following electrophysiologic actions of bretylium have been demonstrated in animal experiments: increase in ventricular fibrillation threshold, increase in action potential duration and effective refractory period without changes in heart rate, little effect on the rate of rise or amplitude of the cardiac action potential (Phase 0) or in resting membrane potential (Phase 4) in normal myocardium, decrease in the disparity in action potential duration between normal and infarcted regions, and increase in impulse formation and spontaneous firing rate of pacemaker tissue as well as increase ventricular conduction velocity.
Biological Half-LifeThe terminal half-life in four normal volunteers averaged 7.8±0.6 hours (range 6.9-8.1). During hemodialysis, this patient's arterial and venous bretylium concentrations declined rapidly, resulting in a half-life of 13 hours.
Metabolism/MetabolitesNo metabolites have been identified following administration in man and laboratory animals.
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
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