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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
Structure of LICARBAZEPINE, (R)-

SMILES

NC(=O)N1C2=CC=CC=C2C[C@@H](O)C3=C1C=CC=C3

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

HIDE SMILES / InChI

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

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Enantioselective HPLC-UV method for determination of eslicarbazepine acetate (BIA 2-093) and its metabolites in human plasma.
2007 Nov
Binding of licarbazepine enantiomers to mouse and human plasma proteins.
2010 Jul
Patents

Sample Use Guides

Mice: 20 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:26:57 GMT 2023
Edited
by admin
on Sat Dec 16 09:26:57 GMT 2023
Record UNII
UQY83V0QWA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LICARBAZEPINE, (R)-
Common Name English
CGP-13698
Code English
(R)-(-)-10,11-DIHYDRO-10-HYDROXY-5H-DIBENZO(B,F)AZEPINE-5-CARBOXAMIDE
Systematic Name English
(R)-LICARBAZEPINE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE, 10,11-DIHYDRO-10-HYDROXY-, (10R)-
Systematic Name English
OXCARBAZEPINE METABOLITE, (R)-MHD
Common Name English
Code System Code Type Description
PUBCHEM
9816485
Created by admin on Sat Dec 16 09:26:57 GMT 2023 , Edited by admin on Sat Dec 16 09:26:57 GMT 2023
PRIMARY
CAS
104746-03-4
Created by admin on Sat Dec 16 09:26:57 GMT 2023 , Edited by admin on Sat Dec 16 09:26:57 GMT 2023
PRIMARY
DRUG BANK
DBMET01020
Created by admin on Sat Dec 16 09:26:57 GMT 2023 , Edited by admin on Sat Dec 16 09:26:57 GMT 2023
PRIMARY
FDA UNII
UQY83V0QWA
Created by admin on Sat Dec 16 09:26:57 GMT 2023 , Edited by admin on Sat Dec 16 09:26:57 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MINOR
PLASMA; URINE
PARENT -> METABOLITE