Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H14N2O2 |
| Molecular Weight | 254.2839 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)N1C2=CC=CC=C2C[C@@H](O)C3=CC=CC=C13
InChI
InChIKey=BMPDWHIDQYTSHX-CQSZACIVSA-N
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)/t14-/m1/s1
| Molecular Formula | C15H14N2O2 |
| Molecular Weight | 254.2839 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Licarbazepine, (R)- is a hydroxy derivative of R-licarbazepine acetate. Eslicarbazepine acetate (ESL), or S-licarbazepine acetate (ESL), Licarbazepine, (R)- acetate and their racemic mixture, as well as other related compounds, were orally assessed in rats for anticonvulsant activity and compared with carbamazepine (CBZ) and oxcarbazepine (OXC). Metabolism of OXC and its derivatives varies considerably between species. Rats metabolize ESL to OXC with minimal (S)-licarbazepine or Licarbazepine, (R)- metabolites. Licarbazepine, (R)- undergoes a further oxidation to the trans-diol metabolite, demonstrating an increased predisposition to earlier inactivation. Administration of ESL and of eslicarbazepine significantly protected mice against Maximal electroshocks-induced seizures, whereas that of Licarbazepine, (R)- failed to provide protection. This finding raises doubts on the contribution of Licarbazepine, (R)- as an active anticonvulsant.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21557472 | https://www.ncbi.nlm.nih.gov/pubmed/18306292
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Binding of licarbazepine enantiomers to mouse and human plasma proteins. | 2010-07 |
|
| Dosage form proportionality and food effect of the final tablet formulation of eslicarbazepine acetate: randomized, open-label, crossover, single-centre study in healthy volunteers. | 2008 |
|
| Enantioselective HPLC-UV method for determination of eslicarbazepine acetate (BIA 2-093) and its metabolites in human plasma. | 2007-11 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25489632
Mice: 20 mg/kg
Route of Administration:
Intraperitoneal
| Substance Class |
Chemical
Created
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Validated (UNII)
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PARENT -> METABOLITE |
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PARENT -> METABOLITE ACTIVE |