Eslicarbazepine

Base Information

• Chemical Name: Eslicarbazepine
• CAS No.: 104746-04-5
• Molecular Formula: C15H14N2O2
• Molecular Weight: 254.288
• Hs Code.: 2933990090
• European Community (EC) Number: 810-248-9
• UNII: S5VXA428R4
• DSSTox Substance ID: DTXSID901316900
• Nikkaji Number: J514.997E
• Wikidata: Q27077226
• NCI Thesaurus Code: C81473
• RXCUI: 1482502
• Metabolomics Workbench ID: 154969
• ChEMBL ID: CHEMBL315985
• Mol file: 104746-04-5.mol

Synonyms:(10S)-10-hydroxy-10,11-dihydro-5H-dibenzo(b,f)azepin-5-carboxamide;eslicarbazepine

Chemical Property of Eslicarbazepine

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 188-190°C
• Refractive Index: 1.677
• Boiling Point: 431.275 °C at 760 mmHg
• PKA: 13.75±0.20(Predicted)
• Flash Point: 214.628 °C
• PSA: 66.56000
• Density: 1.336 g/cm³
• LogP: 3.25820
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.105527694
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-10-Monohydroxy-10,11-dihydroCarbamazepine(Eslicarbazepine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1C(C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
• Isomeric SMILES: C1[C@@H](C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
• Recent ClinicalTrials: Comparison of the Cognitive and Behavioral Effects of Eslicarbazepine Acetate and Carbamazepine in Healthy Adults
• Uses: An optically active metabolite of carbamazepine (S)-10-Monohydroxy-10,11-dihydro Carbamazepine is the metabolite of Eslicarbazepine acetate, (BIA 2-093), (E659000) a novel central nervous system drug.

Technology Process of Eslicarbazepine

There total 34 articles about Eslicarbazepine 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%

oxcarbazepine (28721-07-5) → S-licarbazepine (104746-04-5)

Guidance literature:

With C₃₂H₃₉BrMnN₂O₂P; potassium tert-butylate; hydrogen; In methanol; at 20 ℃; for 16h; under 22502.3 Torr; enantioselective reaction; Glovebox; Autoclave;

DOI:10.1002/anie.201814751

Reference yield: 96.0%

5-Carbamoyl-5H-dibenz[b,f]azepinEN5-Cyano-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine (356760-08-2) → S-licarbazepine (104746-04-5)

Guidance literature:

5-Carbamoyl-5H-dibenz[b,f]azepinEN₅-Cyano-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine; With ethanol; water; dihydrogen peroxide; potassium carbonate; at 0 - 20 ℃; for 0.5h; Heating / reflux;

With sodium hydroxide; In ethanol; water; at 20 ℃; for 2h; pH=14;

Reference yield: 85.4%

C23H22N2O9 (475674-43-2) → S-licarbazepine (104746-04-5)

Guidance literature:

With water; sodium hydroxide; In methanol; at 25 - 30 ℃; for 0.75h;

upstream raw materials:

oxcarbazepine

5-Carbamoyl-5H-dibenz[b,f]azepinEN₅-Cyano-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine

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

C₁₈H₁₈N₂O₄

Downstream raw materials:

eslicarbazepine acetate

(+)-Licarbazepine acetate

Refernces

• 1、 Modukuru, Naga K.,Sukumaran, Joly,Collier, Steven J.,Chan, Ann Shu,Gohel, Anupam,Huisman, Gjalt W.,Keledjian, Raquel,Narayanaswamy, Karthik,Novick, Scott J.,Palanivel,Smith, Derek,Wei, Zhang,Wong, Brian,Yeo, Wan Lin,Entwistle, David A.. "Development of a practical, biocatalytic reduction for the manufacture of (s)-licarbazepine using an evolved ketoreductase". . p. 810 - 815. Retrieved 2014.
• 2、 Jothi, Saravanan,Vuppu, Suneetha. "An industrial perspective fermentative bioreduction of aromatic ketones by Penicillium rubens VIT SS1 and Penicillium citrinum VIT SS2". . . Retrieved 2021/08/18.
• 3、 Zhang, Linli,Tang, Yitian,Han, Zhaobin,Ding, Kuiling. "Lutidine-Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones". supporting information. p. 4973 - 4977. Retrieved 2019/03/17.