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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:20 UTC
HMDB IDHMDB0015289
Secondary Accession Numbers
  • HMDB15289
Metabolite Identification
Common NameBretylium
DescriptionBretylium, also known as bretylate or bretylium bromide, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. Bretylium is a drug which is used for use in the prophylaxis and therapy of ventricular fibrillation. also used in the treatment of life-threatening ventricular arrhythmias, such as ventricular tachycardia, that have failed to respond to adequate doses of a first-line antiarrhythmic agent, such as lidocaine. The primary mode of action for bretylium is thought to be inhibition of voltage-gated K(+) channels. Recent evidence has shown that bretylium may also inhibit the Na,K-ATPase by binding to the extracellular K-site. Bretylium is an extremely weak acidic (essentially neutral) compound (based on its pKa). 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. 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 blocks the release of noradrenaline 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. Marked hypertension resulted, followed by protracted refractory hypotension. In the presence of life-threatening arrhythmias, underdosing with bretylium probably presents a greater risk to the patient than potential overdosage. Bretylium also suppresses ventricular fibrillation and ventricular arrhythmias. Bretylium serum levels were 8000 ng/mL. Bretylium inhibits norepinephrine release by depressing adrenergic nerve terminal excitability.
Structure
Data?1582753280
Synonyms
ValueSource
(2-Bromobenzyl)ethyldimethylaminiumChEBI
2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminiumChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumChEBI
BretylateHMDB
Bretylium tolsylateHMDB
Bretylium tosylateHMDB
BretylumHMDB
Bretylium bromideHMDB
Bretylium chlorideHMDB
Bretylium iodideHMDB
Chemical FormulaC11H17BrN
Average Molecular Weight243.163
Monoisotopic Molecular Weight242.054437196
IUPAC Name[(2-bromophenyl)methyl](ethyl)dimethylazanium
Traditional Namebretylium
CAS Registry Number59-41-6
SMILES
CC[N+](C)(C)CC1=CC=CC=C1Br
InChI Identifier
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
InChI KeyAAQOQKQBGPPFNS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Benzylamine
  • Phenylmethylamine
  • Aralkylamine
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00015 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)17.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.89 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-9660000000-f1a790c5dc75745515bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4aeb2988fef6edbee36eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0390000000-a00c3f0ed8c3aa8c892aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2910000000-431fec477d416b1fea58Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01158 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01158 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01158
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2337
KEGG Compound IDC06855
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBretylium
METLIN IDNot Available
PubChem Compound2431
PDB IDNot Available
ChEBI ID3172
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
References
  1. Dzimiri N, Almotrefi AA: Inhibition of myocardial Na(+)-K(+)-ATPase activity by bretylium: role of potassium. Arch Int Pharmacodyn Ther. 1992 Jul-Aug;318:76-85. [PubMed:1334399 ]
  2. Helms JB, Arnett KL, Gatto C, Milanick MA: Bretylium, an organic quaternary amine, inhibits the Na,K-ATPase by binding to the extracellular K-site. Blood Cells Mol Dis. 2004 May-Jun;32(3):394-400. [PubMed:15121098 ]
  3. Dzimiri N, Almotrefi AA: Interaction of bretylium tosylate with guinea-pig myocardial Na(+)-K(+)-ATPase. Gen Pharmacol. 1991;22(5):935-8. [PubMed:1662173 ]
  4. Tiku PE, Nowell PT: Selective inhibition of K(+)-stimulation of Na,K-ATPase by bretylium. Br J Pharmacol. 1991 Dec;104(4):895-900. [PubMed:1667290 ]