Mexiletine

Mexiletine
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a607064
Pregnancy
category
  • AU: B1
  • US: C (Risk not ruled out)
Routes of
administration		 Oral, IV
ATC code C01BB02 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
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 YesY
PubChem (CID) 4178
IUPHAR/BPS 2629
DrugBank DB00379 YesY
ChemSpider 4034 YesY
UNII 1U511HHV4Z YesY
KEGG D08215 YesY
ChEBI CHEBI:6916 YesY
ChEMBL CHEMBL558 YesY
ECHA InfoCard 100.046.190
Chemical and physical data
Formula C11H17NO
Molar mass 179.259 g/mol
3D model (Jmol) Interactive image
Chirality Racemic mixture
  (verify)

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.[1] 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.[2]

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[3] 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:[4][5][6][7]

References

  1. ↑ Sergio Canavero; Vincenzo Bonicalzi (13 October 2011). Central Pain Syndrome: Pathophysiology, Diagnosis and Management. Cambridge University Press. pp. 286–. ISBN 978-1-107-01021-5.
  2. ↑ Mexiletine, RxList.com
  3. ↑ Sweetman S (ed.) (2002). Martindale: The complete drug reference (33rd ed.). London: Pharmaceutical Press. ISBN 0-85369-499-0.
  4. ↑ H. Koppe, W. Kummer, U.S. Patent 3,954,872 (1976).
  5. ↑ H. Koppe, W. Kummer, U.S. Patent 3,659,019 (1972).
  6. ↑ C.H. Boehringer Sohns, Fr 1551055 (1968).
  7. ↑ H. Koppe, W. Kummer, U.S. Patent 4,031,244 (1977).

Further reading



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