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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 ESLICARBAZEPINE

SMILES

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

InChI

InChIKey=BMPDWHIDQYTSHX-AWEZNQCLSA-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-/m0/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

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=11926264

Eslicarbazepine acetate is a third generation antiepileptic drug indicated for the treatment of partial-onset seizures. Structurally, it belongs to the dibenzazepine family and is closely related to carbamazepine and oxcarbazepine. Eslicarbazepine acetate was developed by scientists in Portugal. Its main mechanism of action is by blocking the voltage-gated sodium channel. Eslicarbazepine acetate is a pro-drug that is rapidly metabolized almost exclusively into eslicarbazepine (S-licarbazepine), the biologically active drug. It has a favorable pharmacokinetic and drug-drug interaction profile. However, it may induce the metabolism of oral contraceptives and should be used with caution in females of child-bearing age.

CNS Activity

Curator's Comment: Eslicarbazepine acetate exerts its effect on CNS in human by blocking voltage-gated sodium channels. Its active metabolite was found to cross the blood-brain barrier in mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
APTIOM

Approved Use

APTIOM is indicated as adjunctive treatment of partial-onset seizures.

Launch Date

1.38386879E12
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

The recommended initial dosage is 400 mg once daily. For some patients, treatment may be initiated at 800 mg once daily if the need for seizure reduction outweighs an increased risk of adverse reactions during initiation. Dosage should be increased in weekly increments of 400 mg to 600 mg, based on clinical response and tolerability, to a recommended maintenance dosage of 800 mg to 1600 mg once daily. For patients on drug monotherapy, the 800 mg once daily maintenance dose should generally be considered in patients who are unable to tolerate a 1200 mg daily dose. For patients on adjunctive therapy, the 1600 mg daily dose should generally be considered in patients who did not achieve a satisfactory response with a 1200 mg daily dose.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: No degeneration and swelling of neurites or increased ROS production was observed indicating low toxicity of eslicarbazepine acetate to neuronal cells
Hippocampal neurons were treated for 24 h with 300 uM BIA 2-093 (eslicarbazepine acetate). No degeneration and swelling of neurites or increased ROS production was observed indicating low toxicity of eslicarbazepine acetate to neuronal cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:13:29 UTC 2023
Edited
by admin
on Fri Dec 15 17:13:29 UTC 2023
Record UNII
S5VXA428R4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESLICARBAZEPINE
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
(S)-LICARBAZEPINE
Common Name English
Eslicarbazepine [WHO-DD]
Common Name English
eslicarbazepine [INN]
Common Name English
BIA-2194
Code English
(10S)-10-Hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepin-5-carboxamide
Systematic Name English
LICARBAZEPINE, (S)-
Common Name English
CGP-13751
Code English
ESLICARBAZEPINE [VANDF]
Common Name English
ESLICARBAZEPINE [USAN]
Common Name English
BIA-2-194
Code English
ESLICARBAZEPINE [MI]
Common Name English
ESLICARBAZEPINE [MART.]
Common Name English
BIA 2-194
Code English
(S)-(+)-10,11-DIHYDRO-10-HYDROXY-5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE
Systematic Name English
5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE, 10,11-DIHYDRO-10-HYDROXY-, (10S)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC N03AF04
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
WHO-VATC QN03AF04
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
NCI_THESAURUS C264
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
Code System Code Type Description
MERCK INDEX
m5024
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81473
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
LACTMED
Eslicarbazepine
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
IUPHAR
7350
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL315985
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
FDA UNII
S5VXA428R4
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
PUBCHEM
9881504
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
DRUG BANK
DB14575
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
DAILYMED
S5VXA428R4
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
EVMPD
SUB27751
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
CAS
104746-04-5
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
USAN
WW-21
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
RXCUI
1482502
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY RxNorm
MESH
C571001
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
SMS_ID
100000091741
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
INN
8403
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY
NDF-RT
N0000185506
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY Cytochrome P450 3A4 Inducers [MoA]
NDF-RT
N0000182140
Created by admin on Fri Dec 15 17:13:29 UTC 2023 , Edited by admin on Fri Dec 15 17:13:29 UTC 2023
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
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