 Home > Encyclopedia > Bretylium tosylate

Bretylium tosylate

Bretylium tosylate structure

CAS No:
61-75-6
Formula:
C11H17BrN.C7H7O3S
Chemical Name:
Bretylium tosylate
Synonyms:
Benzenemethanaminium,2-bromo-N-ethyl-N,N-dimethyl-,4-methylbenzenesulfonate (1:1);(o-Bromobenzyl)ethyldimethylammonium p-toluenesulfonate;Ammonium,(o-bromobenzyl)ethyldimethyl-,p-toluenesulfonate;Benzenemethanaminium,2-bromo-N-ethyl-N,N-dimethyl-,salt with 4-methylbenzenesulfonic acid (1:1);Bretylium tosylate;Darenthin;Bretylium p-toluenesulfonate;N-Ethyl-N-(o-bromobenzyl)-N,N-dimethylammonium tosylate;Bretylan;Bretylate;Ornid;Bretylol;Bretylium tosilate;ASL 603;NSC 62164
Categories:
Organic Chemistry > Amides

Description

Bretylium (tosylate) is an inhibitor of the presynaptic release of vasoconstrictor neurotransmitters. It is the sympathetic nerve and adrenergic ganglion blocking agent .(1) Bretylium tosylate inhibits adrenergic function presynaptically only after an initial release in neurotransmitter substance.(2) The reference for administration dose is 15 mg/kg (I.P).

Bretylium tosylate is the tosylate salt of bretylium. 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 adrenergic antagonist, an anti-arrhythmia drug and an antihypertensive agent. It is a quaternary ammonium salt and an organosulfonate salt. It contains a bretylium.|Bretylium Tosylate is the tosylate salt form of bretylium, a quaternary ammonium salt and non-selective adrenergic neuronal blocking agent with anti-arrhythmic properties. Bretylium tosylate is selectively taken up into peripheral nerve terminals and initially causes a release of norepinephrine from sympathetic nerve endings, thereby causing a sympathomimetic effect. This is followed by a prolonged anti-adrenergic action which prevents further discharge of neurotransmitter from sympathetic nerve endings. Its myocardial effects include a prolongation of action potential as well as refractory period. This drug is used to treat and suppress ventricular arrhythmias, particularly ventricular fibrillation and ventricular tachycardia.|An agent that blocks the release of adrenergic transmitters and may have other actions. It was formerly used as an antihypertensive agent, but is now proposed as an anti-arrhythmic.

Bretylium tosylate Basic Attributes

Molecular Weight：

414.36

Exact Mass：

413.066010

EC Number：

200-516-8

UNII：

78ZP3YR353

NSC Number：

62164

DSSTox ID：

DTXSID1022685

NCI Thesaurus Code：

C47418

ATC Code：

C - Cardiovascular system

HScode：

2923900100

Characteristics

PSA：

65.6

Appearance：

white

Melting Point：

97-99 °C

Water Solubility：

H2O: soluble50mg/mL

Toxicity：

Peritoneal-rat LD50: 57 mg/kg; oral-mouse LD50: 400 mg/kg

Flammability characteristics：

Thermal decomposition releases toxic fumes of sulfur oxides, nitrogen oxides and ammonia

Collision Cross Section：

140.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

hazard class code：

20/21/22

safety instructions：

RTECS Number：

BO9450000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P261-P280-P301 + P312 + P330

Hazard Statements：

H302 + H312 + H332

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

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. (See all compounds classified as Anti-Arrhythmia Agents.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|Drugs that bind to but do not activate ADRENERGIC RECEPTORS. Adrenergic antagonists block the actions of the endogenous adrenergic transmitters EPINEPHRINE and NOREPINEPHRINE. (See all compounds classified as Adrenergic Antagonists.)

MeSH Entry Terms：

Bretylate

Bretylium tosylate Use and Manufacturing

Uses

Bretylium tosylate has a biphasic response, initially inducing norepinephrine release followed by sympathetic ganglionic blockade. Bretylium tosylate is a class III antiarrhythmic agent and a competitive inhibitor of acetylcholinesterase.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:414.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:413.06603
Monoisotopic Mass:413.06603
Topological Polar Surface Area:65.6
Heavy Atom Count:24
Complexity:349
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Material

o-Toluidine

Recommended Suppliers of Bretylium tosylate

HANGZHOU LEAP CHEM CO., LTD. Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives

Bretylium tosilate

CAS No.: 61-75-6

Content: 99.00%

Inquiry