Details of the Drug

General Information of Drug (ID: DM1FX74)

Drug Name

Bretylium

Synonyms

Bretylum; Bretylium tolsylate; Bretylium tosylate(USAN); N-(2-bromobenzyl)-N,N-dimethylethanaminium; N-ethyl-N,N-dimethyl-2-bromobenzenemethanaminium; Benzenemethanaminium, 2-bromo-N-ethyl-N,N-dimethyl-, salt with 4-methylbenzenesulfonic acid (1:1); (2-bromobenzyl)ethyldimethylaminium; (2-bromophenyl)methyl-ethyl-dimethylazanium; (o-Bromobenzyl)ethyldimethylammonium p-toluenesulfonate; 2-bromo-N-ethyl-N,N-dimethylbenzenemethanaminium

Indication

Disease Entry	ICD 11	Status	REF
Long QT syndrome	BC65.0	Approved	[1]
Ventricular fibrillation	BC71.1	Approved	[2]
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Therapeutic Class

Antiarrhythmic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

243.16

Logarithm of the Partition Coefficient (xlogp)

2.8

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

0

Hydrogen Bond Acceptor Count (hbondacc)

0

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Elimination: 77% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 7.8 +/- 0.6 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 12.0668 micromolar/kg/day [5]
Water Solubility: The ability of drug to dissolve in water is measured as 50 mg/mL [3]

Chemical Identifiers

Formula: C11H17BrN+
IUPAC Name: (2-bromophenyl)methyl-ethyl-dimethylazanium
Canonical SMILES: CC[N+](C)(C)CC1=CC=CC=C1Br
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

Cross-matching ID

PubChem CID: 2431
ChEBI ID: CHEBI:3172
CAS Number: 59-41-6
DrugBank ID: DB01158
TTD ID: D02YYF
VARIDT ID: DR01325
ACDINA ID: D00890

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor beta-1 (ADRB1)	TTR6W5O	ADRB1_HUMAN	Antagonist	[6]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Sodium-dependent dopamine transporter (SLC6A3)	DT3BA8L	SC6A3_HUMAN	Substrate	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Bretylium

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Propafenone	DMPIBJK	Major	Increased risk of prolong QT interval by the combination of Bretylium and Propafenone.	Ventricular tachyarrhythmia [BC71]	[8]
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Coadministration of a Drug Treating the Disease Different from Bretylium (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Amisulpride	DMSJVAM	Major	Increased risk of prolong QT interval by the combination of Bretylium and Amisulpride.	Schizophrenia [6A20]	[9]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Hydrochloric acid	E00015	313	Acidulant
Sodium hydroxide	E00234	14798	Alkalizing agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Bretylium 50mg/ml injectable	50mg/ml	Injectable	Injection

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References

1	Bretylium FDA Label
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Components of functional sympathetic control of heart rate in neonatal rats. Am J Physiol. 1985 May;248(5 Pt 2):R601-10.
7	Which form of dopamine is the substrate for the human dopamine transporter: the cationic or the uncharged species? J Biol Chem. 1999 Feb 19;274(8):4876-82.
8	Buss J, Neuss H, Bilgin Y, Schlepper M "Malignant ventricular tachyarrhythmias in association with propafenone treatment." Eur Heart J 6 (1985): 424-8. [PMID: 4043097]
9	Cerner Multum, Inc. "Australian Product Information.".