Licarbazepine

Licarbazepine is a voltage-gated sodium channel blocker with anticonvulsant and mood-stabilizing effects that is related to oxcarbazepine.[1] It is an active metabolite of oxcarbazepine.[1][2] In addition, an enantiomer of licarbazepine, eslicarbazepine ((S)-(+)-licarbazepine), is an active metabolite of eslicarbazepine acetate.[1][2] Oxcarbazepine and eslicarbazepine acetate are inactive on their own, and behave instead as prodrugs to licarbazepine and eslicarbazepine, respectively, to produce their therapeutic effects.[1][2]

Licarbazepine
Top: (R)-(−)-licarbazepine
Bottom: (S)-(+)-licarbazepine
Clinical data
ATC code
  • None
Pharmacokinetic data
Protein binding<40%
MetabolitesGlucuronides
ExcretionMainly renal
Identifiers
IUPAC name
  • (RS)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.122.427
Chemical and physical data
FormulaC15H14N2O2
Molar mass254.289 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • NC(=O)N1c2ccccc2CC(O)c3ccccc13
InChI
  • InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)
  • Key:BMPDWHIDQYTSHX-UHFFFAOYSA-N

References
  1. Singh RP, Asconapé JJ (2011). "A review of eslicarbazepine acetate for the adjunctive treatment of partial-onset epilepsy". Journal of Central Nervous System Disease. 3: 179–87. doi:10.4137/JCNSD.S4888. PMC 3663619. PMID 23861647.
  2. Bialer M, Soares-da-Silva P (June 2012). "Pharmacokinetics and drug interactions of eslicarbazepine acetate". Epilepsia. 53 (6): 935–46. doi:10.1111/j.1528-1167.2012.03519.x. PMID 22612290. S2CID 21233948.
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