Mexiletine

Mexiletine
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a607064
Pregnancy; category	AU: B1; ;
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)
Elimination half-life	10-12 hours
Excretion	Renal (10%)
Identifiers
	IUPAC name (RS)-1-(2,6-dimethylphenoxy)propan-2-amine; OR; 2-(2-aminopropoxy)-1,3-dimethylbenzene;
CAS Number	31828-71-4 ;
PubChem CID	4178;
IUPHAR/BPS	2629;
DrugBank	DB00379 ;
ChemSpider	4034 ;
UNII	1U511HHV4Z;
KEGG	D08215 ;
ChEBI	CHEBI:6916 ;
ChEMBL	ChEMBL558 ;
CompTox Dashboard (EPA)	DTXSID8048446 ;
ECHA InfoCard	100.046.190
Chemical and physical data
Formula	C11H17NO
Molar mass	179.259 g/mol g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	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 ; Key:VLPIATFUUWWMKC-UHFFFAOYSA-N ;
	(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

References

^ 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.
^ Mexiletine, RxList.com
^ Sweetman S (ed.) (2002). Martindale: The complete drug reference (33rd ed.). London: Pharmaceutical Press. ISBN 0-85369-499-0. {{cite book}}: |author= has generic name (help)
^ H. Koppe, W. Kummer, U.S. patent 3,954,872 (1976).
^ H. Koppe, W. Kummer, U.S. patent 3,659,019 (1972).
^ C.H. Boehringer Sohns, Fr 1551055 (1968).
^ H. Koppe, W. Kummer, U.S. patent 4,031,244 (1977).

External links

MedlinePlus Drug Information: Mexiletine

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[CanaveroBonicalzi2011-1] 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. {{cite book}}: |author= has generic name (help)

[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).

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v t e Neuropathic pain and fibromyalgia pharmacotherapies
Monoaminergics	SNRIsTooltip Serotonin–norepinephrine reuptake inhibitor (e.g., duloxetine, milnacipran) TCAsTooltip Tricyclic antidepressants (e.g., amitriptyline, nortriptyline, dosulepin) Opioid MRIsTooltip monoamine reuptake inhibitors (e.g., tapentadol, tramadol)
Ion channel blockers	Anticonvulsants (e.g., gabapentin, pregabalin, mirogabalin, carbamazepine, oxcarbazepine, lacosamide, lamotrigine) Local anesthetics (e.g., lidocaine) Mexiletine TCAsTooltip Tricyclic antidepressants (e.g., amitriptyline, nortriptyline, desipramine) Ziconotide
Others	Alpha lipoic acid Benfotiamine Botulinum toxin A Bupropion Cannabinoids (e.g., cannabis, dronabinol, nabilone) NMDA receptor antagonists (e.g., ketamine, dextromethorphan, methadone) Opioids (e.g., hydrocodone, morphine, oxycodone, methadone, buprenorphine, tramadol, tapentadol) Sodium oxybate (GHB)

Synthesis

References

Further reading

External links