Mexiletine

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Mexiletine
Mexiletine.svg
Systematic (IUPAC) name
(RS)-1-(2,6-dimethylphenoxy)propan-2-amine
OR
2-(2-aminopropoxy)-1,3-dimethylbenzene
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa607064
Legal status
RoutesOral, IV
Pharmacokinetic data
Bioavailability90%
Protein binding50-60%
MetabolismHepatic (CYP2D6 and 1A2- mediated)
Half-life10-12 hours
ExcretionRenal (10%)
Identifiers
CAS number31828-71-4 YesY
ATC codeC01BB02
PubChemCID 4178
IUPHAR ligand2629
DrugBankDB00379
ChemSpider4034 YesY
UNII1U511HHV4Z YesY
KEGGD08215 YesY
ChEBICHEBI:6916 YesY
ChEMBLCHEMBL558 YesY
Chemical data
FormulaC11H17NO 
Molecular mass179.259 g/mol
 YesY (what is this?)  (verify)
 
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Mexiletine
Mexiletine.svg
Systematic (IUPAC) name
(RS)-1-(2,6-dimethylphenoxy)propan-2-amine
OR
2-(2-aminopropoxy)-1,3-dimethylbenzene
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa607064
Legal status
RoutesOral, IV
Pharmacokinetic data
Bioavailability90%
Protein binding50-60%
MetabolismHepatic (CYP2D6 and 1A2- mediated)
Half-life10-12 hours
ExcretionRenal (10%)
Identifiers
CAS number31828-71-4 YesY
ATC codeC01BB02
PubChemCID 4178
IUPHAR ligand2629
DrugBankDB00379
ChemSpider4034 YesY
UNII1U511HHV4Z YesY
KEGGD08215 YesY
ChEBICHEBI:6916 YesY
ChEMBLCHEMBL558 YesY
Chemical data
FormulaC11H17NO 
Molecular mass179.259 g/mol
 YesY (what is this?)  (verify)

Mexiletine (INN, sold under the trade name Mexitil) 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.[1]

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[2] 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[edit]

Mexiletine synthesis:[3][4][5][6]

References[edit]

  1. ^ Mexiletine, RxList.com
  2. ^ Sweetman S (ed.) (2002). Martindale: The complete drug reference (33rd ed.). London: Pharmaceutical Press. ISBN 0-85369-499-0. 
  3. ^ H. Koppe, W. Kummer, U.S. Patent 3,954,872 (1976).
  4. ^ H. Koppe, W. Kummer, U.S. Patent 3,659,019 (1972).
  5. ^ C.H. Boehringer Sohns, Fr 1551055  (1968).
  6. ^ H. Koppe, W. Kummer, U.S. Patent 4,031,244 (1977).

Further reading[edit]

External links[edit]