| Common Name |
Bretylium
| Description |
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 ventricliar tachycardia and ventricliar fibrillation. 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 extracellliar K-site.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(2-Bromobenzyl)ethyldimethylaminiumChEBI
2-bromo-N-Ethyl-N,N-dimethylbenzenemethanaminiumChEBI
N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminiumChEBI
BretylateHMDB
Bretylium tolsylateHMDB
Bretylium tosylateHMDB
BretylumHMDB
Bretylium bromideMeSH
Bretylium chlorideMeSH
Bretylium iodideMeSH
| Chemical Formlia |
C11H17BrN
| Average Molecliar Weight |
243.163
| Monoisotopic Molecliar Weight |
242.054437196
| IUPAC Name |
[(2-bromophenyl)methyl](ethyl)dimethylazanium
| Traditional Name |
bretylium
| CAS Registry Number |
59-41-6
| 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 Key |
AAQOQKQBGPPFNS-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Benzene and substituted derivatives
| Direct Parent |
Phenylmethylamines
| Alternative Parents |
Benzylamines
Bromobenzenes
Aralkylamines
Aryl bromides
Tetraalkylammonium salts
Organopnictogen compounds
Organobromides
Organic salts
Hydrocarbon derivatives
Organic cations
| 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
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
quaternary ammonium ion (CHEBI:3172 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Adrenergic Antagonists
Anti-Arrhythmia Agents
Antihypertensive Agents
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.54e-04 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.000154 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.89 m3·mol-1ChemAxon
Polarizability23.24 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01158
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01158
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01158
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
2337
| KEGG Compound ID |
C06855
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Bretylium
| NuGOwiki Link |
HMDB15289
| Metagene Link |
HMDB15289
| METLIN ID |
Not Available
| PubChem Compound |
2431
| PDB ID |
Not Available
| ChEBI ID |
3172
Product: 6-BrdU
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not 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
- 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 ]
- 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 ]
- Dzimiri N, Almotrefi AA: Interaction of bretylium tosylate with guinea-pig myocardial Na(+)-K(+)-ATPase. Gen Pharmacol. 1991;22(5):935-8. [PubMed:1662173 ]
- 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 ]
PMID: 22292739
