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Details

Stereochemistry RACEMIC
Molecular Formula C15H14N2O2
Molecular Weight 254.2844
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LICARBAZEPINE

SMILES

c1ccc2c(c1)CC(c3ccccc3N2C(=N)O)O

InChI

InChIKey=BMPDWHIDQYTSHX-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula C15H14N2O2
Molecular Weight 254.2844
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Licarbazepine is the pharmacologically active metabolite of oxcarbazepine, a drug indicated for the treatment of partial seizures and bipolar disorders. Phase III trials of licarbazepine were conducted in the US and Europe, and were initially delayed in November 2006. An isomer of licarbazepine, eslicarbazepine ((S)-(+)-licarbazepine), is an active metabolite of eslicarbazepine acetate.

Originator

Curator's Comment:: # Novartis

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Suppressive effects of oxcarbazepine on tooth pulp-evoked potentials recorded at the trigeminal spinal tract nucleus in cats.
2001 Mar
Oxcarbazepine final market image tablet formulation bioequivalence study after single administration and at steady state in healthy subjects.
2002 Nov
Assessment of the bioequivalence of two oxcarbazepine oral suspensions versus a film-coated tablet in healthy subjects.
2003 Jul
Overview of the clinical pharmacokinetics of oxcarbazepine.
2004
Safety, tolerability, and pharmacokinetic profile of BIA 2-093, a novel putative antiepileptic, in a rising multiple-dose study in young healthy humans.
2004 Aug
Simultaneous liquid chromatographic determination of lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in plasma of patients with epilepsy.
2005 Dec 15
A pilot study on brain-to-plasma partition of 10,11-dyhydro-10-hydroxy-5H-dibenzo(b,f)azepine-5-carboxamide and MDR1 brain expression in epilepsy patients not responding to oxcarbazepine.
2005 Oct
Drug monitoring and toxicology: a procedure for the monitoring of oxcarbazepine metabolite by HPLC-UV.
2006 Jan
Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection.
2007 Jul 16
A novel enantioselective microassay for the high-performance liquid chromatography determination of oxcarbazepine and its active metabolite monohydroxycarbazepine in human plasma.
2007 Jun
Stereoselective disposition of S- and R-licarbazepine in mice.
2008 Jun
Pharmacokinetics of licarbazepine in healthy volunteers: single and multiple oral doses and effect of food.
2008 May
Eyeblink conditioning anomalies in bipolar disorder suggest cerebellar dysfunction.
2009 Feb
Binding of licarbazepine enantiomers to mouse and human plasma proteins.
2010 Jul
Development and validation of an HPLC-UV method for the simultaneous quantification of carbamazepine, oxcarbazepine, eslicarbazepine acetate and their main metabolites in human plasma.
2010 Jun
Patents

Sample Use Guides

Bipolar I Disorder: 750- 2000 mg/day
Route of Administration: Oral
Free and bound fractions of S-licarbazepine (S-Lic) and R-licarbazepine (R-Lic) were separated by ultrafiltration after previous in vitro incubation of spiked plasma samples and protein solutions with each enantiomer at 10, 25 and 50 ug/ml.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:35:18 UTC 2021
Edited
by admin
on Sat Jun 26 15:35:18 UTC 2021
Record UNII
XFX1A5KJ3V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LICARBAZEPINE
INN   WHO-DD  
INN  
Official Name English
LICARBAZEPINE [INN]
Common Name English
LICARBAZEPINE [WHO-DD]
Common Name English
10,11-DIHYDRO-10-HYDROXY-5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
Code System Code Type Description
INN
7788
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
CAS
29331-92-8
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
NCI_THESAURUS
C81475
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL1067
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
EVMPD
SUB32907
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
FDA UNII
XFX1A5KJ3V
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
PUBCHEM
114709
Created by admin on Sat Jun 26 15:35:19 UTC 2021 , Edited by admin on Sat Jun 26 15:35:19 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY