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Mexiletine hydrochloride

Mexiletine hydrochloride structure

CAS No:
5370-01-4
Formula:
C11H18ClNO
Chemical Name:
Mexiletine hydrochloride
Synonyms:
1-(2,6-dimethylphenoxy)-2-aminopropanehydrochloride;1-(2,6-dimethylphenoxy)-2-propanaminhydrochloride;Ko 1173Cl;Mexilitene;1-(2,6-DIMETHYLPHENOXY)-2-PROPANANMINE HYDROCHLORIDE;MEXILETIN HYDROCHLORIDE;2-Propanamine, 1-(2,6-dimethylphenoxy)-, hydrochloride (9CI);Ethylamine, 1-methyl-2-(2,6-xylyloxy)-, hydrochloride (7CI, 8CI)
Categories:
Organic Chemistry > Amides

Description

Mexiletine hydrochloride is a non-selective voltage-gated sodium channel blocker; Class IB anti-arrhythmic compound.

Mexiletine Hydrochloride is the hydrochloride salt form of mexiletine, a local anesthetic and antiarrhythmic (Class IB) agent structurally related to lidocaine. Mexiletine exerts its antiarrhythmic effect by inhibiting the inward sodium current in cardiac cells, thereby reducing the rate of rise of the cardiac action potential (phase 0) and decreases automaticity in the Purkinje fibers. This slows nerve impulses in the heart and stabilizes the heartbeat. Mexiletine's anesthetic activity is due to its ability to block sodium influx in peripheral nerves, thereby reducing the rate and intensity of pain impulses reaching the central nervous system.|Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.

Mexiletine is a voltage-gated sodium channel blocker and class Ib antiarrhythmic agent that preferentially binds to open/inactive channels. It inhibits aconitine-induced dysrhythmias in mice with ED50values of 57 and 107 mg/kg for intraperitoneal and oral administration, respectively. Mexiletine decreases or inhibits conduction across the Purkinje fiber-muscle junction, shortens action potential duration, and decreases the refractory period when used at concentrations less than 5 μg/ml in isolated canine Purkinje fiber and ventricular muscle preparations.

White to Off-White Solid

ChEBI: A hydrochloride composed of equimolar amounts of mexiletine and hydrogen chloride.

Mexiletine hydrochloride Basic Attributes

Molecular Weight：

215.72

Exact Mass：

215.107697

EC Number：

226-362-1

NSC Number：

758639

DSSTox ID：

DTXSID2045783

NCI Thesaurus Code：

C652

Color/Form：

white

ATC Code：

C01BB02

HScode：

2922190900

Characteristics

λmax：

272nm(MeOH)(lit.)

PSA：

35.25000

Appearance：

white powder

Density：

1.12 g/cm3

Melting Point：

200-203°C

Boiling Point：

271.5ºC at 760 mmHg

Flash Point：

112.2ºC

Water Solubility：

ethanol: 50 mg/mL

Storage Conditions：

2-8°C

Toxicity：

LD50 in male, female rats, mice, rabbits (mg/kg): 350, 400, 310, 400, 180, 160 orally; in male, female rats, mice (mg/kg): 27, 30, 43, 50 i.v. (Kast)

PKA：

9.0(at 25℃)

Collision Cross Section：

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

Critical Temperature & Pressure：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

36-26

RTECS Number：

KR9300000

Marks：

Storage features：

Desiccate at +4°C

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

20/21/22-36/37/38-22

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 49 companies from 5 notifications to the ECHA C&L Inventory.

Drug Information

Drug Indication：

Namuscla is indicated for the symptomatic treatment of myotonia in adult patients with non-dystrophic myotonic disorders.|Treatment of myotonic disorders

MeSH：

A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)|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.)

MeSH Entry Terms：

KO 1173

Mexiletine hydrochloride Use and Manufacturing

Uses

Antiarrhythmic (class IB)

Mexiletine hydrochloride has been used as a sodium channel blocker:expressed in chinese hamster ovary cellsin human embryonic kidney (HEK) cells for whole cell patch-clamp studieselectrophysiology studies in HEK cells expressing Nav1.7 protein

antipsychotic

Use Classification：

Human drugs -> Orphan -> Namuscla -> EMA Drug Category|Cardiac therapy -> Human pharmacotherapeutic group|Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:215.72
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:215.1076919
Monoisotopic Mass:215.1076919
Topological Polar Surface Area:35.2
Heavy Atom Count:14
Complexity:139
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product belongs to Class Ib antiarrhythmic drugs. Its chemical structure and electrophysiological effects are similar to those of lidocaine, inhibiting the influx of sodium ions, shortening the action potential, relatively prolonging the effective refractory period, and reducing excitability. The therapeutic dose has little effect on the conduction of the sinoatrial node, atrium and atrioventricular node. In patients with normal conduction systems, it has no significant effect on the autonomy of the sinoatrial node, atrioventricular conduction, QRS wave and Q-T interval. The conduction effect on the atrioventricular bypass is still inconsistent. Its electrophysiological effects also vary depending on the dose and myocardial state (such as normal or ischemic, hypoxic, etc.). When the blood drug concentration is high, it can significantly prolong the refractory period of myocardial conduction fibers. This product has almost no inhibitory effect on the myocardium.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Mexiletine Hydrochloride Tablets
Ingredients	The main ingredient of this product is: Mexiletine 1-(2,6-dimethylphenoxy) 2-propylamine hydrochloride.
Indication	1 It may have synergistic effects with other antiarrhythmic drugs and can be used for refractory arrhythmias, but it should not be used in combination with Class Ib drugs. 2 In the early stages of acute myocardial infarction, morphine delays and reduces the absorption of this product, which may be related to delayed gastric emptying. 3 Hepatic enzyme inducers such as phenytoin sodium, phenobarbital, and rifampicin can accelerate the metabolism of this product and reduce blood drug concentrations. 4 Antacids can reduce the bioavailability of this product when taken orally, but the blood drug concentration may also increase due to increased urine pH. 5 Cimetidine can change the blood concentration of this product. Blood drug concentrations should be monitored. 6 Atropine can delay the absorption of this product. However, it does not affect the amount of this product absorbed, which may be due to slow gastric emptying. 7 Antiemetics such as metoclopramide increase gastric emptying and can increase the absorption rate of this product. 8 Others: This product does not increase the blood concentration of digoxin.
Specifications	50 mg
Manufacturer	Shanghai Sine Pharmaceutical Laboratories Co., Ltd.

Mexiletine Hydrochloride

Mexiletine Hydrochloride Injection
Ingredients	Mexiletine hydrochloride.
Indication	Clinical trials have reported that there is no mutual effect between mexiletine and commonly used anti-anginal, antihypertensive and antifibrinolytic drugs. If phenytoin sodium or other liver enzyme inducers such as rifampicin and phenobarbital are used in combination with mexiletine, the blood concentration of mexiletine can be reduced. It has been reported that benzodiazepines do not affect the blood concentration of mexiletine. The combination of mexiletine and digoxin, diuretics and propranolol does not affect the PR, QRS and QT intervals of the electrocardiogram.
Specifications	2ml:0.1g
Manufacturer	Shineway Pharmaceutical Group Ltd.

See More Related Drugs

Registered Holders

BIOPHORE INDIA PHARMACEUTICALS PVT LTD

United States
Active
ALEMBIC PHARMACEUTICALS LTD

United States
Active
COHANCE LIFESCIENCES LTD

United States
Active

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