Eslicarbazepine acetate

Base Information

• Chemical Name: Eslicarbazepine acetate
• CAS No.: 236395-14-5
• Molecular Formula: C₁₇H₁₆N₂O₃
• Molecular Weight: 296.326
• European Community (EC) Number: 636-617-2
• UNII: BEA68ZVB2K
• DSSTox Substance ID: DTXSID90178308
• Nikkaji Number: J1.143.147J
• Wikipedia: Eslicarbazepine_acetate
• Wikidata: Q410273
• NCI Thesaurus Code: C83697
• RXCUI: 1482501
• Pharos Ligand ID: SLH8AH6LDCA3
• Metabolomics Workbench ID: 152163
• ChEMBL ID: CHEMBL87992
• Mol file: 236395-14-5.mol

Synonyms:10-acetoxy-10,11-dihydro-5H-dibenz(b,f)azepine-5-carboxamide;Aptiom;BIA 2-093;BIA-2-093;eslicarbazepine acetate;Zebinix

Chemical Property of Eslicarbazepine acetate

Chemical Property:

• Appearance/Colour: White to Off-White Solid
• Vapor Pressure: 1.65E-07mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: 1.655
• Boiling Point: 427.377 °C at 760 mmHg
• PKA: 13.97±0.40(Predicted)
• Flash Point: 212.27 °C
• PSA: 72.63000
• Density: 1.326 g/cm³
• LogP: 3.82900
• Storage Temp.: 2-8°C
• Solubility.: H2O: insoluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 296.11609238
• Heavy Atom Count: 22
• Complexity: 440

Purity/Quality:

98% ^*data from raw suppliers

Eslicarbazepine Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1CC2=CC=CC=C2N(C3=CC=CC=C13)C(=O)N
• Isomeric SMILES: CC(=O)O[C@H]1CC2=CC=CC=C2N(C3=CC=CC=C13)C(=O)N
• Recent ClinicalTrials: A Study of a Drug to be Used in Addition With Another Drug to Treat Adults With Uncontrolled Partial-onset Seizures
• Recent EU Clinical Trials: prevention of epilepsy in stroke patients at high risk of developing unprovoked seizures: anti-epileptogenic effects of eslicarbazepine acetate
• Description: Although epilepsy is a neurological disorder with varying etiology and severity, the common feature is unprovoked, recurring seizures. Even when traditional AEDs, such as phenobarbital, phenytoin, carbamazepine, and valproate, control seizure activity, their effectiveness is hampered by considerable side effects and the tendency for drug-drug interactions. Designed for improved efficacy and safety, eslicarbazepine acetate is a third-generation AED that has been approved as adjunctive therapy for partial-onset seizures with or without secondary generalization. As a member of the carbamazepine family (first generation), it is the prodrug of eslicarbazepine and the active metabolite of oxcarbazepine (second generation). . Eslicarbazepine acetate is a sodium channel blocker (IC50 = 138 nM in a radioligand binding assay). It inhibits sodium uptake in a dose-dependent manner in rat cortical synaptosomes at concentrations ranging from 30-300 μM. In vivo, oral and i.p. administration of eslicarbazepine acetate is protective against seizures induced by maximal electroshock (MES) in mice with ED50 values of 4.7 and 6.3 mg/kg, respectively, which are well below the median toxic dose (TD50) values of 358.7 and 78.6 mg/kg for oral and i.p. administration respectively. High-dose administration (30 mg/kg) of eslicarbazepine acetate prevents picrotoxin-induced seizures in rats. Low-dose administration (10 mg/kg) does not suppress picrotoxin-induced seizures, however, it reduces seizure number and duration. Formulations containing eslicarbazepine acetate have been used for the treatment of partial-onset seizures.
• Uses: Eslicarbazepine acetate, (BIA 2-093), is a promising antiepileptic drug structurally related to Carbamazepine and Oxcarbazepine. Eslicarbazepine acetate, (BIA 2-093), is a promising antiepileptic drug structurally related to Carbamazepine and Oxcarbazepine. Neuroprotective & Neuroresearch product.

Technology Process of Eslicarbazepine acetate

There total 47 articles about Eslicarbazepine acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

acetyl chloride (75-36-5) + S-licarbazepine (104746-04-5) → eslicarbazepine acetate (186694-45-1,236395-14-5)

Guidance literature:

dmap; In dichloromethane; at 20 ℃;

Reference yield: 96.0%

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8) + acetic anhydride (108-24-7) → Licarbazepine acetate (186694-45-1,236395-14-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 0.5h;

Reference yield: 90.0%

potassium cyanate (590-28-3) + (S)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate (1431547-12-4) → eslicarbazepine acetate (186694-45-1,236395-14-5)

Guidance literature:

With perfluorosulfonic acid resin; In water; at 70 - 80 ℃; for 4h;

upstream raw materials:

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

acetyl chloride

oxcarbazepine

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one

Downstream raw materials:

R-licarbazepine

eslicarbazepine acetate

carbamazepine 10,11-epoxide

Refernces

• 1、 -. "Recrystallization purification process for precursor reactant of asymmetric catalytic hydrogenation reaction". Paragraph 0027; 0028; 0029; 0032-0038. . Retrieved 2018/12/13.
• 2、 -. "Preparation method of anti-epileptic drug eslicarbazepine acetate". Paragraph 0028; 0030. . Retrieved 2017/09/01.