Licarbazepine

Base Information

• Chemical Name: Licarbazepine
• CAS No.: 29331-92-8
• Molecular Formula: C15H14 N2 O2
• Molecular Weight: 254.288
• Hs Code.: 2933990090
• European Community (EC) Number: 608-350-1
• UNII: XFX1A5KJ3V
• DSSTox Substance ID: DTXSID50865484
• Nikkaji Number: J394.865J
• Wikipedia: Licarbazepine
• Wikidata: Q6542996
• NCI Thesaurus Code: C81475
• Metabolomics Workbench ID: 68105
• ChEMBL ID: CHEMBL1067
• Mol file: 29331-92-8.mol

Synonyms:10,11-dihydro-10-hydroxy-5H-dibenz(b,f)azepine-5-carboxamide;10,11-MHD;Licarbazepine

Chemical Property of Licarbazepine

Chemical Property:

• Vapor Pressure: 3.33E-08mmHg at 25°C
• Melting Point: 186-189°C
• Boiling Point: 431.3°Cat760mmHg
• PKA: 13.75±0.20(Predicted)
• Flash Point: 214.6°C
• PSA: 66.56000
• Density: 1.336g/cm³
• LogP: 3.25820
• Storage Temp.: Store at RT
• 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%, ^*data from raw suppliers

Licarbazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N,Xn,F
• Hazard Codes: N,Xn,F
• Statements: 51/53-36-20/21/22-11
• Safety Statements: 61-36/37-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
• Recent ClinicalTrials: Open Label Extension Study of Licarbazepine in the Treatment of Manic Episodes of Bipolar I Disorder
• Recent EU Clinical Trials: A 52-week open-label extension study to evaluate the safety and tolerability of licarbazepine 750-2000 mg/d in the treatment of manic episodes of bipolar I disorder
• Uses: A metabolite of Oxcarbazepine A labelled metabolite of Oxcarbazepine 10,11-dihydro-10-hydroxy Carbamazepinee is the active metabolite of oxcarbazepine . Oxcarbazepine is rapidly and almost completely converted to 10,11-dihydro-10-hydroxycarbamazepine, which then demonstrates anticonvulsant efficacy by modulating several ion channels and receptors. ?10,11-dihydro-10-hydroxy Carbamazepine is reported to inhibit both voltage-gated Na+ and Ca2+ channels, to potentiate voltage-gated K+ channels, to antagonize adenosine A1 receptors, to increase dopaminergic transmission, and to inhibit glutamate release.

Technology Process of Licarbazepine

There total 9 articles about Licarbazepine 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: 97.3%

oxcarbazepine (28721-07-5) → 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 20 - 45 ℃; for 1.5h;

Reference yield: 93.0%

carbamazepine 10,11-epoxide (36507-30-9) → 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; dichloromethane; water; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 90.0%

10-chloro-10,11-dihydro-5H-dibenz/b,f/azepine-5-carboxamide (791633-38-0) → 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide (29331-92-8)

Guidance literature:

With water; at 20 ℃; for 48h;

upstream raw materials:

10,11-Dihydrocarbamazepin

oxcarbazepine

10-chloro-10,11-dihydro-5H-dibenz/b,f/azepine-5-carboxamide

carbamazepine 10,11-epoxide

Downstream raw materials:

R-licarbazepine

S-licarbazepine

Licarbazepine acetate

eslicarbazepine acetate

Refernces

• 1、 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.
• 2、 -. "Preparation method of anti-epileptic drug eslicarbazepine acetate". Paragraph 0028; 0029; 0034; 0035; 0036. . Retrieved 2017/09/01.