Identification

Name
Bretylium
Accession Number
DB01158  (APRD00830)
Type
Small Molecule
Groups
Approved
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 ventricular tachycardia and ventricular 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 extracellular K-site.

Structure
Thumb
Synonyms
  • (2-Bromobenzyl)ethyldimethylaminium
  • 2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminium
  • N-Ethyl-N,N-dimethyl-2-bromobenzenemethanaminium
Product Ingredients
IngredientUNIICASInChI Key
Bretylium tosylate78ZP3YR35361-75-6KVWNWTZZBKCOPM-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bretylate Inj 50mg/mlLiquid50 mgIntramuscular; IntravenousGlaxo Wellcome1980-12-312000-01-19Canada
Bretylium Tosylate Inj 50mg/mlSolution50 mgIntramuscular; IntravenousAbbott1991-12-312007-07-31Canada
Bretylium Tosylate Injection USPSolution50 mgIntramuscular; IntravenousSandoz Canada Incorporated1995-12-31Not applicableCanada
International/Other Brands
Anxyrex (Sanofi-Aventis) / Bretylol (ICI) / Bromidem (Nycomed) / Creosedin (AstraZeneca) / Darenthin (Burroughs Wellcome) / Lexotan (Roche) / Xionil (Novartis)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bretylium Tosylate 0.2% and Dextrose 5% InjBretylium tosylate (2 mg) + Glucose (50 mg)SolutionIntravenousAbbott1988-12-312007-07-31Canada
Bretylium Tosylate 0.4% and Dextrose 5% InjBretylium tosylate (4 mg) + Glucose (50 mg)SolutionIntravenousAbbott1988-12-312007-07-31Canada
Categories
UNII
RZR75EQ2KJ
CAS number
59-41-6
Weight
Average: 243.163
Monoisotopic: 242.054437196
Chemical Formula
C11H17BrN
InChI Key
AAQOQKQBGPPFNS-UHFFFAOYSA-N
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
IUPAC Name
[(2-bromophenyl)methyl](ethyl)dimethylazanium
SMILES
CC[N+](C)(C)CC1=CC=CC=C1Br

Pharmacology

Indication

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.

Structured Indications
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.

TargetActionsOrganism
ASodium/potassium-transporting ATPase subunit alpha-1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

No metabolites have been identified following administration in man and laboratory animals.

Route of elimination
Not Available
Half life

The 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.

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 400 mg/kg. In the presence of life-threatening arrhythmias, underdosing with bretylium probably presents a greater risk to the patient than potential overdosage. However, one case of accidental overdose has been reported in which a rapidly injected intravenous bolus of 30 mg/kg was given instead of an intended 10 mg/kg dose during an episode of ventricular tachycardia. Marked hypertension resulted, followed by protracted refractory hypotension. The patient expired 18 hours later in asystole, complicated by renal failure and aspiration pneumonitis. Bretylium serum levels were 8000 ng/mL.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Bretylium.Experimental
AcebutololBretylium may increase the hypotensive activities of Acebutolol.Approved
AcemetacinThe therapeutic efficacy of Bretylium can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
AlfuzosinAlfuzosin may increase the hypotensive activities of Bretylium.Approved, Investigational
AliskirenBretylium may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Bretylium.Approved, Withdrawn
AmbrisentanBretylium may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineBretylium may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Bretylium.Approved
AmphetamineAmphetamine may increase the hypotensive activities of Bretylium.Approved, Illicit
AtenololAtenolol may increase the hypotensive activities of Bretylium.Approved
AvanafilAvanafil may increase the antihypertensive activities of Bretylium.Approved
BarnidipineBretylium may increase the antihypertensive activities of Barnidipine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Bretylium.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Bretylium.Approved
BepridilBretylium may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Bretylium.Approved
BethanidineBethanidine may increase the hypotensive activities of Bretylium.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Bretylium.Experimental
BimatoprostBimatoprost may increase the hypotensive activities of Bretylium.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Bretylium.Approved
BosentanBosentan may increase the hypotensive activities of Bretylium.Approved, Investigational
BQ-123Bretylium may increase the hypotensive activities of BQ-123.Investigational
BrimonidineBrimonidine may increase the antihypertensive activities of Bretylium.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Bretylium.Experimental
BupranololBretylium may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Bretylium.Experimental
CafedrineBretylium may increase the hypotensive activities of Cafedrine.Investigational
CandesartanBretylium may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Bretylium.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Bretylium.Experimental
CaptoprilBretylium may increase the hypotensive activities of Captopril.Approved
CarteololCarteolol may increase the hypotensive activities of Bretylium.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Bretylium.Approved, Investigational
CeliprololBretylium may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideChlorothiazide may increase the hypotensive activities of Bretylium.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Bretylium.Approved
CicletanineBretylium may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilBretylium may increase the hypotensive activities of Cilazapril.Approved
ClonidineClonidine may increase the hypotensive activities of Bretylium.Approved
CloranololBretylium may increase the hypotensive activities of Cloranolol.Experimental
CryptenamineCryptenamine may increase the hypotensive activities of Bretylium.Approved
CyclopenthiazideBretylium may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideCyclothiazide may increase the hypotensive activities of Bretylium.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Bretylium.Approved, Investigational
DelaprilBretylium may increase the hypotensive activities of Delapril.Experimental
DeserpidineBretylium may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Bretylium.Approved
DiethylnorspermineBretylium may increase the hypotensive activities of Diethylnorspermine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Bretylium.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Bretylium.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Bretylium.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Bretylium.Approved
EfonidipineBretylium may increase the hypotensive activities of Efonidipine.Approved, Investigational
EnalaprilEnalapril may increase the hypotensive activities of Bretylium.Approved, Vet Approved
EnalaprilatBretylium may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Bretylium.Experimental
EpanololBretylium may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolBretylium may increase the hypotensive activities of Epoprostenol.Approved
EprosartanEprosartan may increase the hypotensive activities of Bretylium.Approved
FelodipineFelodipine may increase the hypotensive activities of Bretylium.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Bretylium.Approved
Ferulic acidBretylium may increase the hypotensive activities of Ferulic acid.Experimental
FosinoprilFosinopril may increase the hypotensive activities of Bretylium.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Bretylium.Approved, Investigational, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Bretylium.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Bretylium.Approved
GuanazodineBretylium may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineBretylium may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Bretylium.Approved, Investigational
GuanoclorBretylium may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzBretylium may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanBretylium may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Bretylium.Experimental
HexamethoniumBretylium may increase the hypotensive activities of Hexamethonium.Experimental
HydralazineHydralazine may increase the hypotensive activities of Bretylium.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Bretylium.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Bretylium.Approved, Investigational
ImidaprilBretylium may increase the hypotensive activities of Imidapril.Investigational
IndapamideIndapamide may increase the hypotensive activities of Bretylium.Approved
IndenololBretylium may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Bretylium.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Bretylium.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Bretylium.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Bretylium.Approved
IsradipineIsradipine may increase the hypotensive activities of Bretylium.Approved
KetanserinKetanserin may increase the hypotensive activities of Bretylium.Investigational
LabetalolLabetalol may increase the hypotensive activities of Bretylium.Approved
LacidipineBretylium may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Bretylium.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Bretylium.Approved, Investigational
LinsidomineBretylium may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Bretylium.Approved, Investigational
LofexidineBretylium may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Bretylium.Approved
MacitentanBretylium may increase the hypotensive activities of Macitentan.Approved
ManidipineBretylium may increase the hypotensive activities of Manidipine.Approved, Investigational
MecamylamineMecamylamine may increase the hypotensive activities of Bretylium.Approved
MethoserpidineBretylium may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaMethyldopa may increase the hypotensive activities of Bretylium.Approved
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Bretylium.Approved, Investigational
MetipranololBretylium may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Bretylium.Approved
MetoprololMetoprolol may increase the hypotensive activities of Bretylium.Approved, Investigational
MetyrosineBretylium may increase the hypotensive activities of Metyrosine.Approved
MibefradilBretylium may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Bretylium.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Bretylium.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Bretylium.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Bretylium.Approved
MoexiprilMoexipril may increase the hypotensive activities of Bretylium.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Bretylium.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Bretylium.Approved, Investigational
MuzolimineBretylium may increase the hypotensive activities of Muzolimine.Experimental
NadololBretylium may increase the hypotensive activities of Nadolol.Approved
NaftopidilBretylium may increase the hypotensive activities of Naftopidil.Investigational
NebivololBretylium may increase the hypotensive activities of Nebivolol.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Bretylium.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Bretylium.Approved
NicorandilBretylium may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineBretylium may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineBretylium may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Bretylium.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Bretylium.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Bretylium.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Bretylium.Approved
ObinutuzumabBretylium may increase the hypotensive activities of Obinutuzumab.Approved
OlmesartanOlmesartan may increase the hypotensive activities of Bretylium.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Bretylium.Investigational
OxprenololBretylium may increase the hypotensive activities of Oxprenolol.Approved
PargylinePargyline may increase the hypotensive activities of Bretylium.Approved
PenbutololBretylium may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumPentolinium may increase the hypotensive activities of Bretylium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Bretylium.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Bretylium.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Bretylium.Approved
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Bretylium.Approved
PhentolaminePhentolamine may increase the hypotensive activities of Bretylium.Approved
PinacidilPinacidil may increase the hypotensive activities of Bretylium.Withdrawn
PindololPindolol may increase the hypotensive activities of Bretylium.Approved
PirlindolePirlindole may increase the hypotensive activities of Bretylium.Approved
Platelet Activating FactorBretylium may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazideBretylium may increase the hypotensive activities of Polythiazide.Approved
PrazosinPrazosin may increase the hypotensive activities of Bretylium.Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Bretylium.Approved
PropranololPropranolol may increase the hypotensive activities of Bretylium.Approved, Investigational
QuinaprilQuinapril may increase the hypotensive activities of Bretylium.Approved, Investigational
RamiprilRamipril may increase the hypotensive activities of Bretylium.Approved
RasagilineRasagiline may increase the hypotensive activities of Bretylium.Approved
RemikirenRemikiren may increase the hypotensive activities of Bretylium.Approved
RescinnamineBretylium may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Bretylium.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Bretylium.Investigational
RiociguatBretylium may increase the hypotensive activities of Riociguat.Approved
RituximabBretylium may increase the hypotensive activities of Rituximab.Approved
SaprisartanBretylium may increase the hypotensive activities of Saprisartan.Experimental
SelegilineSelegiline may increase the hypotensive activities of Bretylium.Approved, Investigational, Vet Approved
SelexipagBretylium may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Bretylium.Approved, Investigational
SitaxentanBretylium may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilBretylium may increase the hypotensive activities of Spirapril.Approved
TadalafilTadalafil may increase the antihypertensive activities of Bretylium.Approved, Investigational
TalinololBretylium may increase the hypotensive activities of Talinolol.Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Bretylium.Approved, Investigational
TemocaprilBretylium may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinBretylium may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineBretylium may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineBretylium may increase the hypotensive activities of Theodrenaline.Investigational
TiboloneBretylium may increase the hypotensive activities of Tibolone.Approved, Investigational
TicrynafenBretylium may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Bretylium.Approved
TolazolineTolazoline may increase the hypotensive activities of Bretylium.Approved, Vet Approved
TolonidineBretylium may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Bretylium.Approved
TorasemideTorasemide may increase the hypotensive activities of Bretylium.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Bretylium.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Bretylium.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Bretylium.Approved
TravoprostTravoprost may increase the hypotensive activities of Bretylium.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Bretylium.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Bretylium.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Bretylium.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Bretylium.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Bretylium.Approved, Investigational
UnoprostoneBretylium may increase the hypotensive activities of Unoprostone.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Bretylium.Investigational
ValsartanValsartan may increase the hypotensive activities of Bretylium.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Bretylium.Approved
VincamineBretylium may increase the hypotensive activities of Vincamine.Experimental
VinpocetineBretylium may increase the hypotensive activities of Vinpocetine.Investigational
XipamideBretylium may increase the hypotensive activities of Xipamide.Experimental
XylometazolineBretylium may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Bretylium.Approved, Vet Approved
ZofenoprilBretylium may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Copp, F.C. and Stephenson, D.; US. Patent 3,038,004; June 5, 1962; assigned to Burroughs Wellcome & Co.

US3038004
General References
Not Available
External Links
Human Metabolome Database
HMDB0015289
KEGG Drug
D00645
KEGG Compound
C06855
PubChem Compound
2431
PubChem Substance
46505320
ChemSpider
2337
ChEBI
3172
ChEMBL
CHEMBL1199080
Therapeutic Targets Database
DAP000939
PharmGKB
PA448662
RxList
RxList Drug Page
Wikipedia
Bretylium
AHFS Codes
  • 24:04.04.20 — Class III Antiarrythmics
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous50 mg
SolutionIntravenous
SolutionIntramuscular; Intravenous50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)238Fryer, R.I., Schmidt, R.A. and Sternbach, L.H.; U.S. Patent 3,100,770; August 13, 1963; assigned to Hoffmann-LaRoche Inc. Fryer, R.I., Schmidt, R.A. and Sternbach, L.H.; U.S. Patent 3,182,065; May 4, 1965; assigned to Hoffmann-LaRoche Inc. Fryer, R.I., Schmidt, R.A. and Sternbach, L.H.; US. Patent 3,182,067; May 4, 1965; assigned to Hoffmann-LaRoche Inc.
water solubilityFreely solubleNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier+0.9484
Caco-2 permeable+0.6831
P-glycoprotein substrateSubstrate0.5105
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.8742
Renal organic cation transporterNon-inhibitor0.6279
CYP450 2C9 substrateNon-substrate0.861
CYP450 2D6 substrateNon-substrate0.6999
CYP450 3A4 substrateSubstrate0.5132
CYP450 1A2 substrateNon-inhibitor0.6973
CYP450 2C9 inhibitorNon-inhibitor0.8505
CYP450 2D6 inhibitorNon-inhibitor0.8475
CYP450 2C19 inhibitorNon-inhibitor0.8038
CYP450 3A4 inhibitorNon-inhibitor0.9752
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6854
Ames testNon AMES toxic0.9045
CarcinogenicityCarcinogens 0.5905
BiodegradationNot ready biodegradable0.9157
Rat acute toxicity2.6214 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9291
hERG inhibition (predictor II)Inhibitor0.6322
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
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
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:3172)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid hormone 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 th...
Gene Name
ATP1A1
Uniprot ID
P05023
Uniprot Name
Sodium/potassium-transporting ATPase subunit alpha-1
Molecular Weight
112895.01 Da
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]

Drug created on June 13, 2005 07:24 / Updated on January 23, 2018 12:16