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HCID 4178Erstellt: 3. November 2026

Mexiletin

Mexiletine · MEXILETIN · C07220 · Mexilux · Mexilitine · Mexiletene · Mexilitine R · dl-Mexiletine

Identifikatoren & physikalische Daten

CAS No.	31828-71-4
Summenformel	C11H17NO
Durchschnittliche Molmasse	179,26 g/mol
Monoisotopische Masse	179,13101417 g/mol
SMILES	Cc1cccc(C)c1OCC(C)N
InChIKey	VLPIATFUUWWMKC-UHFFFAOYSA-N
PubChem CID	4178
ChEMBL	CHEMBL558
ChEBI	CHEBI:6916
EC No.	250-825-7
DTXSID	DTXSID8048446
Lokaler Name	Mexiletin

Chemische & physikalische Eigenschaften

XLogP	2,1
Polarare Oberfläche (TPSA)	35,3
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	3
Schwere Atome	13
Formalladung	0
Komplexität	139
Arzneimittel	Pharmaceuticals
LogP (Verteilungskoeffizient)	2.12.15
Löslichkeit	5.38e-01 g/Lethanol: 50 mg/mL
Human Drugs	Breast FeedingLactationMilk, HumanAntiarrhythmicsEMA approved medicines: Human medicine (Orphan designations)
Schmelzpunkt	203-205 °C203 - 205 °C
Physical Description	Solid
Dissociation Constants	9.149.159.2
Collision Cross Section	145.11 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Siedepunkt	271.5±28.0 °C(Predicted)
Dichte	0.979±0.06 g/cm3(Predicted)
Lagerbedingungen	2-8°C
pKa (Säurekonstante)	pKa 9.14± 0.01(H2O,t =25±0.2,I=0.01(NaCl))(Approximate)
Aggregatzustand	powder
Farbe	white
BCS Class	1
CAS Datenbank	31828-71-4(CAS DataBase Reference)
NIST chemische Informationen	Mexiletine(31828-71-4)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Regulatorische Informationen	REACH registered substance: Mexiletine (EC: 250-825-7)
Hazard Classes and Categories	Acute Tox. 4 (100%)
Hepatotoxicity	In clinical trials, mexiletine was associated with a low rate of serum aminotransferase and alkaline phosphatase elevations (~0.5%). Despite wide scale use, mexiletine has only rarely been linked to cases of clinically apparent liver injury. Most cases are associated with a hypersensitivity reaction. Typically, patients present with fever, rash, eosinophilia and systemic systemics (DRESS syndrome) after 2 to 6 weeks of mexiletine therapy. Eosinophilia or atypical lymphocytosis usually accompany the liver test abnormalities but may arise or continue to worsen days or weeks after onset. The pattern of serum enzyme elevations ranges from cholestatic to hepatocellular, but jaundice is usually mild or absent. Autoimmune features are uncommon. Cases of Stevens Johnson and DRESS syndrome due to mexiletine have also been reported. Corticosteroids were often used, but largely for the fever and skin rash rather than the liver disease which was typically mild. Rare instances of cholestatic hepatitis with mexiletine therapy have also been reported and may represent a different form of liver injury.
Unerwünschte Wirkungen	The adverse effect profile of mexiletine is extensive and limits its use. It affects nearly every organ systemmost notably, it has significant cardiovascular and central nervous system (CNS) side effects and affecting the gastrointestinal (GI), musculoskeletal, dermatologic systems.
Toxizitätsübersicht	Toxicity is common with mexiletine and can manifest in several organ systems. Cardiovascular, CNS, and GI-related symptoms most commonly occur. Cardiovascular toxicity can present as varying degrees of heart block, heart failure, exacerbation of cardiac arrhythmias, and cardiac arrest. Central nervous system-related symptoms include lightheadedness, fatigue, confusion, the presence of tremors, and seizures. Gastrointestinal symptoms are highly variable but can include xerostomia, nausea/vomiting, and diarrhea. Mexiletine has a half-life of 10 to 12 hours and is metabolized by the liver with small amounts, about 10% of the administered dose, of excretion in the urine. Thus, toxicity is much more prevalent in the setting of liver failure as metabolism is largely impaired.

Anwendungen & Verwendung

Verwenden

Cardiac depressant (anti-arrhythmic).

CAS No.

31828-71-4

Summenformel

C11H17NO

Durchschnittliche Molmasse

179,26 g/mol

Monoisotopische Masse

179,13101417 g/mol

SMILES

Cc1cccc(C)c1OCC(C)N

InChIKey

VLPIATFUUWWMKC-UHFFFAOYSA-N

PubChem CID

4178

ChEMBL

CHEMBL558

ChEBI

CHEBI:6916

EC No.

250-825-7

DTXSID

DTXSID8048446

Lokaler Name

Mexiletin

Chemische & physikalische Eigenschaften

XLogP

2,1

Polarare Oberfläche (TPSA)

35,3

H-Brücken-Donoren

H-Brücken-Akzeptoren

Frei drehbare Bindungen

Schwere Atome

Formalladung

Komplexität

139

Arzneimittel

Pharmaceuticals

LogP (Verteilungskoeffizient)

2.12.15

Löslichkeit

5.38e-01 g/Lethanol: 50 mg/mL

Human Drugs

Breast FeedingLactationMilk, HumanAntiarrhythmicsEMA approved medicines: Human medicine (Orphan designations)

Schmelzpunkt

203-205 °C203 - 205 °C

Physical Description

Solid

Dissociation Constants

9.149.159.2

Collision Cross Section

145.11 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]

Siedepunkt

271.5±28.0 °C(Predicted)

Dichte

0.979±0.06 g/cm3(Predicted)

Lagerbedingungen

2-8°C

pKa (Säurekonstante)

pKa 9.14± 0.01(H2O,t =25±0.2,I=0.01(NaCl))(Approximate)

Aggregatzustand

powder

Farbe

white

BCS Class

CAS Datenbank

31828-71-4(CAS DataBase Reference)

NIST chemische Informationen

Mexiletine(31828-71-4)

Sicherheit & Vorschriften

GHS-Einstufung

WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Regulatorische Informationen

REACH registered substance: Mexiletine (EC: 250-825-7)

Hazard Classes and Categories

Acute Tox. 4 (100%)

Hepatotoxicity

In clinical trials, mexiletine was associated with a low rate of serum aminotransferase and alkaline phosphatase elevations (~0.5%). Despite wide scale use, mexiletine has only rarely been linked to cases of clinically apparent liver injury. Most cases are associated with a hypersensitivity reaction. Typically, patients present with fever, rash, eosinophilia and systemic systemics (DRESS syndrome) after 2 to 6 weeks of mexiletine therapy. Eosinophilia or atypical lymphocytosis usually accompany the liver test abnormalities but may arise or continue to worsen days or weeks after onset. The pattern of serum enzyme elevations ranges from cholestatic to hepatocellular, but jaundice is usually mild or absent. Autoimmune features are uncommon. Cases of Stevens Johnson and DRESS syndrome due to mexiletine have also been reported. Corticosteroids were often used, but largely for the fever and skin rash rather than the liver disease which was typically mild. Rare instances of cholestatic hepatitis with mexiletine therapy have also been reported and may represent a different form of liver injury.

Unerwünschte Wirkungen

The adverse effect profile of mexiletine is extensive and limits its use. It affects nearly every organ systemmost notably, it has significant cardiovascular and central nervous system (CNS) side effects and affecting the gastrointestinal (GI), musculoskeletal, dermatologic systems.

Toxizitätsübersicht

Toxicity is common with mexiletine and can manifest in several organ systems. Cardiovascular, CNS, and GI-related symptoms most commonly occur. Cardiovascular toxicity can present as varying degrees of heart block, heart failure, exacerbation of cardiac arrhythmias, and cardiac arrest. Central nervous system-related symptoms include lightheadedness, fatigue, confusion, the presence of tremors, and seizures. Gastrointestinal symptoms are highly variable but can include xerostomia, nausea/vomiting, and diarrhea. Mexiletine has a half-life of 10 to 12 hours and is metabolized by the liver with small amounts, about 10% of the administered dose, of excretion in the urine. Thus, toxicity is much more prevalent in the setting of liver failure as metabolism is largely impaired.