2-(2-aminopropoxy)-1,3-dimethylbenzene

• ChemBase ID: 263
• Molecular Formular: C11H17NO
• Molecular Mass: 179.25878
• Monoisotopic Mass: 179.13101417
• SMILES: O(CC(N)C)c1c(cccc1C)C
• Canonical SMILES: CC(COc1c(C)cccc1C)N
• 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
• InChIKey: VLPIATFUUWWMKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-aminopropoxy)-1,3-dimethylbenzene
• IUPAC Traditional name: mexiletine
• Brand Name: Mexitil
• Synonyms: 2-(2-aminopropoxy)-1,3-dimethylbenzene; Mexiletina [INN-Spanish]; Mexiletine HCL; Mexiletinum [INN-Latin]; Mexilitine; Mexiletine

Database IDs

• CAS Number: 31828-71-4
• MDL Number: MFCD00792471
• PubChem SID: 46505491; 160963726
• PubChem CID: 4178
• CHEBI ID: 6916
• ATC CODE: C01BB02
• CHEMBL: 558
• Chemspider ID: 4034
• DrugBank ID: DB00379
• IUPHAR ligand ID: 2629
• KEGG ID: D08215
• Unique Ingredient Identifier: 1U511HHV4Z
• Wikipedia Title: Mexiletine
• Medline Plus: a607064

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.52837545
• LogD (pH = 7.4): 0.39041123
• Log P: 2.4620085
• Molar Refractivity: 54.9722 cm^3
• Polarizability: 21.605932 Å^3
• Polar Surface Area: 35.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.17
• LOG S: -2.52
• Solubility (Water): 5.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: 8.25 mg/mL
• Hydrophobicity(logP): 2.1; 2.569

Pharmacology Properties

• Admin Routes: Oral, IV
• Bioavailability: 90%
• Excretion: Renal (10%)
• Half Life: 10-12 hours
• Metabolism: Hepatic (CYP2D6 and 1A2- mediated)
• Protein Bound: 50-60%
• Legal Status: POM (UK)
• Pregnancy Category: B1 (Australia); C (US)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00379

• Drug Groups: approved
• Description: Antiarrhythmic agent pharmacologically similar to lidocaine. It may have some anticonvulsant properties. [PubChem]
• Indication: For the treatment of ventricular tachycardia and symptomatic premature ventricular beats, and prevention of ventricular fibrillation.
• Pharmacology: Mexiletine is a local anesthetic, antiarrhythmic agent (Class Ib), structurally similar to lidocaine, but orally active. Mexiletine has fast onset and offset kinetics, meaning that they have little or no effect at slower heart rates, and more effects at faster heart rates. It shortens the action potential duration, reduces refractoriness, and decreases Vmax in partially depolarized cells with fast response action potentials. Mexiletine either does not change the action potential duration, or decreases the action potential duration.
• Toxicity: Symptoms of overdose include nausea, hypotension, sinus bradycardia, paresthesia, seizures, bundle branch block, AV heart block, asystole, ventricular tachyarrythmia, including ventricular fibrillation, cardiovascular collapse, and coma.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic (85%) via CYP2D6 and CYP1A2 (primarily CYP2D6).
• Absorption: Well absorbed (bioavailability 90%) from the gastrointenstinal tract.
• Half Life: 10-12 hours
• Protein Binding: 50-60%
• Elimination: Approximately 10% is excreted unchanged by the kidney. The urinary excretion of N-methylmexiletine in man is less than 0.5%.
• Distribution: * 5 to 7 L/lg
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com