Mexiletine HCl | CAS#31828-71-4 | CAS#5370-01-4 | Non-Selective Voltage-Gated Sodium Channel Blocker

MedKoo Cat#: 318265 | Name: Mexiletine HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mexiletine is a non-selective voltage-gated sodium channel blocker which belongs to the Class IB anti-arrhythmic group of medicines. It is used to treat arrhythmias within the heart, or seriously irregular heartbeats. It slows conduction in the heart and makes the heart tissue less sensitive. Mexiletine may also be of use in patients experiencing refractory pain and is also effective for treating muscle stiffness resulting from myotonic dystrophy (Steinert's disease) or nondystrophic myotonias such as myotonia congenita (Thomsen disease).

Chemical Structure

Mexiletine HCl

CAS#5370-01-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 318265

Name: Mexiletine HCl

CAS#: 5370-01-4 (HCl)

Chemical Formula: C11H18ClNO

Exact Mass: 179.1310

Molecular Weight: 215.11

Elemental Analysis: C, 61.25; H, 8.41; Cl, 16.43; N, 6.49; O, 7.42

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 weeks
5g	USD 450.00	2 weeks
25g	USD 850.00	2 weeks

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Related CAS #

31828-71-4 (free) 5370-01-4 (HCl)

Synonym

Mexiletine, Mexitil, Mexiletene, KO-1173, KO 1173, KO1173

IUPAC/Chemical Name

1-(2,6-dimethylphenoxy)propan-2-amine hydrochloride

InChi Key

NFEIBWMZVIVJLQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H17NO.ClH/c1-8-5-4-6-9(2)11(8)13-7-10(3)12;/h4-6,10H,7,12H2,1-3H3;1H

SMILES Code

CC(N)COC1=C(C)C=CC=C1C.[H]Cl

Appearance

White to off-white crystalline powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mexiletine hydrochloride (KOE-1173 hydrochloride), a Class IB antianhythmic, is a non-selective voltage-gated sodium channel blocker.

In vitro activity:

Human wild-type and L858F-mutated NaV 1.7 channels were expressed in HEK293A cells. Whole-cell currents were recorded by voltage-clamp techniques to characterize the effect of mexiletine on channel gating properties. While the concentration-dependent tonic block of peak currents by mexiletine was similar in wild-type and L858F channels, phasic block was more pronounced in cells transfected with the L858F mutation. Moreover, mexiletine substantially shifted the pathologically-hyperpolarized voltage-dependence of steady-state activation in L858F-mutated channels towards wild-type values and the voltage-dependence of steady-state fast inactivation was shifted to more hyperpolarized potentials, leading to an overall reduction in window currents. Reference: Br J Pharmacol. 2014 Oct;171(19):4455-63. https://pubmed.ncbi.nlm.nih.gov/24866741/

In vivo activity:

In 15 isolated rabbit hearts, erythromycin (300 µM) was infused for simulation of long-QT-2-syndrome. In further 13 hearts, veratridine was administered to simulate long-QT-3-syndrome. Additional infusion of mexiletine (25 µM) resulted in a significant reduction of dispersion (erythromycin: -43 ms, P < 0.01; veratridine: -26 ms, P < 0.05). Reproducible induction of torsade de pointes was observed in 13 of 15 erythromycin-treated hearts (192 episodes) and 6 of 13 veratridine-treated hearts (36 episodes). Additional infusion of mexiletine significantly reduced ventricular tachycardia (VT) incidence. Mexiletine also increased atrial refractory period (+80 ms, P < 0.01) and thereby effectively suppressed atrial fibrillation. Reference: Europace. 2018 Aug 1;20(8):1375-1381. https://pubmed.ncbi.nlm.nih.gov/29016765/

	Solvent	mg/mL	mM
Solubility
	DMSO	35.2	163.59
	Ethanol	43.0	199.90
	Water	54.9	255.02

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 215.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cregg R, Cox JJ, Bennett DL, Wood JN, Werdehausen R. Mexiletine as a treatment for primary erythromelalgia: normalization of biophysical properties of mutant L858F NaV 1.7 sodium channels. Br J Pharmacol. 2014 Oct;171(19):4455-63. doi: 10.1111/bph.12788. Epub 2014 Aug 29. PMID: 24866741; PMCID: PMC4209151. 2. Tappenbeck K, Hoppe S, Hopster K, Kietzmann M, Feige K, Huber K. Lidocaine and structure-related mexiletine induce similar contractility-enhancing effects in ischaemia-reperfusion injured equine intestinal smooth muscle in vitro. Vet J. 2013 Jun;196(3):461-6. doi: 10.1016/j.tvjl.2012.11.011. Epub 2012 Dec 20. PMID: 23265867. 3. Frommeyer G, Garthmann J, Ellermann C, Dechering DG, Kochhäuser S, Reinke F, Köbe J, Wasmer K, Eckardt L. Broad antiarrhythmic effect of mexiletine in different arrhythmia models. Europace. 2018 Aug 1;20(8):1375-1381. doi: 10.1093/europace/eux221. PMID: 29016765. 4. Desaphy JF, Camerino DC, Tortorella V, De Luca A. Effect of mexiletine on sea anemone toxin-induced non-inactivating sodium channels of rat skeletal muscle: a model of sodium channel myotonia. Neuromuscul Disord. 1999 May;9(3):182-9. doi: 10.1016/s0960-8966(98)00115-1. PMID: 10382914.

In vitro protocol:

In vivo protocol:

1. Frommeyer G, Garthmann J, Ellermann C, Dechering DG, Kochhäuser S, Reinke F, Köbe J, Wasmer K, Eckardt L. Broad antiarrhythmic effect of mexiletine in different arrhythmia models. Europace. 2018 Aug 1;20(8):1375-1381. doi: 10.1093/europace/eux221. PMID: 29016765. 2. Desaphy JF, Camerino DC, Tortorella V, De Luca A. Effect of mexiletine on sea anemone toxin-induced non-inactivating sodium channels of rat skeletal muscle: a model of sodium channel myotonia. Neuromuscul Disord. 1999 May;9(3):182-9. doi: 10.1016/s0960-8966(98)00115-1. PMID: 10382914.

1: Catalano A, Carocci A, Sinicropi MS. Mexiletine metabolites: a review. Curr Med Chem. 2015;22(11):1400-13. Review. PubMed PMID: 25723511. 2: Gao Y, Xue X, Hu D, Liu W, Yuan Y, Sun H, Li L, Timothy KW, Zhang L, Li C, Yan GX. Inhibition of late sodium current by mexiletine: a novel pharmotherapeutical approach in timothy syndrome. Circ Arrhythm Electrophysiol. 2013 Jun;6(3):614-22. doi: 10.1161/CIRCEP.113.000092. Epub 2013 Apr 11. Review. PubMed PMID: 23580742. 3: Marmura MJ. Intravenous lidocaine and mexiletine in the management of trigeminal autonomic cephalalgias. Curr Pain Headache Rep. 2010 Apr;14(2):145-50. doi: 10.1007/s11916-010-0098-6. Review. PubMed PMID: 20425204. 4: Ebell MH. Systemic lidocaine or mexiletine for neuropathic pain. Am Fam Physician. 2006 Jul 1;74(1):79. Review. PubMed PMID: 16848381. 5: Jarvis B, Coukell AJ. Mexiletine. A review of its therapeutic use in painful diabetic neuropathy. Drugs. 1998 Oct;56(4):691-707. Review. PubMed PMID: 9806111. 6: Manolis AS, Deering TF, Cameron J, Estes NA 3rd. Mexiletine: pharmacology and therapeutic use. Clin Cardiol. 1990 May;13(5):349-59. Review. PubMed PMID: 2189614. 7: Denaro CP, Benowitz NL. Poisoning due to class 1B antiarrhythmic drugs. Lignocaine, mexiletine and tocainide. Med Toxicol Adverse Drug Exp. 1989 Nov-Dec;4(6):412-28. Review. PubMed PMID: 2513464. 8: Marinchak RA, Friehling TD, Kline RA, Stohler J, Kowey PR. Effect of antiarrhythmic drugs on defibrillation threshold: case report of an adverse effect of mexiletine and review of the literature. Pacing Clin Electrophysiol. 1988 Jan;11(1):7-12. Review. PubMed PMID: 2449675. 9: Campbell RW. Mexiletine. N Engl J Med. 1987 Jan 1;316(1):29-34. Review. PubMed PMID: 3537793. 10: Akhtar M. Practical considerations in the treatment of ventricular arrhythmias with mexiletine. Am Heart J. 1984 May;107(5 Pt 2):1086-90. Review. PubMed PMID: 6372424. 11: Shanks RG. Hemodynamic effects of mexiletine. Am Heart J. 1984 May;107(5 Pt 2):1065-71. Review. PubMed PMID: 6372422. 12: Pottage A. Clinical profiles of newer class I antiarrhythmic agents--tocainide, mexiletine, encainide, flecainide and lorcainide. Am J Cardiol. 1983 Sep 22;52(6):24C-31C. Review. PubMed PMID: 6414279. 13: Wulf BG. Mexiletine and tocainide: orally active congeners of lidocaine. Clin Pharm. 1983 Jul-Aug;2(4):340-6. Review. PubMed PMID: 6411416. 14: Touboul P, Kirkorian G, Atallah G, Moleur P. [New antiarrythmic drugs: mexiletine, tocainide, lorcainide, encainide, flecainide, propafenone, cipralan, sotalol]. Ann Cardiol Angeiol (Paris). 1982 Dec;31(7):531-7. Review. French. PubMed PMID: 6820620. 15: Witkowska M. [Clinical pharmacology of anti-arrhythymia agents. II. Lignocaine, mexiletine, tocainide, phenytoin]. Kardiol Pol. 1981;24(11-12):803-13. Review. Polish. PubMed PMID: 6804681. 16: Middleton D. Baseline pharmacology, electrophysiology and pharmacokinetics of mexiletine. Acta Cardiol Suppl. 1980;(25):45-53. Review. PubMed PMID: 6990666. 17: Chew CY, Collett J, Singh BN. Mexiletine: a review of its pharmacological properties and therapeutic efficacy in arrhythmias. Drugs. 1979 Mar;17(3):161-81. Review. PubMed PMID: 378646. 18: Labbé L, Turgeon J. Clinical pharmacokinetics of mexiletine. Clin Pharmacokinet. 1999 Nov;37(5):361-84. Review. PubMed PMID: 10589372. 19: Suzuki M. [Disopyramide, mexiletine, aprindine]. Nihon Rinsho. 1995 Feb;53 Su Pt 1:989-93. Review. Japanese. PubMed PMID: 8753606. 20: Duff HJ, Mitchell LB, Wyse DG, Gillis AM, Sheldon RS. Mexiletine/quinidine combination therapy: electrophysiologic correlates of anti-arrhythmic efficacy. Clin Invest Med. 1991 Oct;14(5):476-83. Review. PubMed PMID: 1660369.