Mexiletine

Mexiletine

Systematic (IUPAC) name
(RS)-1-(2,6-dimethylphenoxy)propan-2-amine OR 2-(2-aminopropoxy)-1,3-dimethylbenzene
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a607064
Pregnancy category	AU: B1 US: C (Risk not ruled out)
Legal status	UK: POM (Prescription only)
Routes of administration	Oral, IV
Pharmacokinetic data
Bioavailability	90%
Protein binding	50-60%
Metabolism	Hepatic (CYP2D6 and 1A2- mediated)
Biological half-life	10-12 hours
Excretion	Renal (10%)
Identifiers
CAS Number	31828-71-4 Y
ATC code	C01BB02 (WHO)
PubChem	CID: 4178
IUPHAR/BPS	2629
DrugBank	DB00379 Y
ChemSpider	4034 Y
UNII	1U511HHV4Z Y
KEGG	D08215 Y
ChEBI	CHEBI:6916 Y
ChEMBL	CHEMBL558 Y
Chemical data
Formula	C11H17NO
Molecular mass	179.259 g/mol
SMILES O(c1c(cccc1C)C)CC(N)C
InChI InChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3 Y Key:VLPIATFUUWWMKC-UHFFFAOYSA-N Y
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Mexiletine (INN) (sold under the trade name Mexitil) 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. Dizziness, heartburn, nausea, nervousness, trembling, unsteadiness are common side effects. It is available in injection and capsule form.

Class IB antiarrhythmics decrease action potential frequency by lengthening the repolarization phase. This is achieved by blocking sodium channels.

This drug is now no longer freely available as a licensed product in either the US or the UK. It can be imported to the UK as an unlicensed, 'named-patient' drug. Its use in arrhythmias is restricted to use in life-threatening conditions only.

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).

Synthesis

Mexiletine synthesis:

External links

• MedlinePlus Drug Information: Mexiletine