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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H16N2O3
Molecular Weight 296.3205
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESLICARBAZEPINE ACETATE

SMILES

CC(=O)O[C@H]1CC2=CC=CC=C2N(C(N)=O)C3=C1C=CC=C3

InChI

InChIKey=QIALRBLEEWJACW-INIZCTEOSA-N
InChI=1S/C17H16N2O3/c1-11(20)22-16-10-12-6-2-4-8-14(12)19(17(18)21)15-9-5-3-7-13(15)16/h2-9,16H,10H2,1H3,(H2,18,21)/t16-/m0/s1

HIDE SMILES / InChI

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
Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024.
2002 Feb
Neurotoxicity induced by antiepileptic drugs in cultured hippocampal neurons: a comparative study between carbamazepine, oxcarbazepine, and two new putative antiepileptic drugs, BIA 2-024 and BIA 2-093.
2004 Dec
Anticonvulsant effect of eslicarbazepine acetate (BIA 2-093) on seizures induced by microperfusion of picrotoxin in the hippocampus of freely moving rats.
2006 Dec
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.
Name Type Language
ESLICARBAZEPINE ACETATE
DASH   EMA EPAR   MART.   MI   USAN   VANDF   WHO-DD  
USAN  
Official Name English
ZEBINIX
Brand Name English
ERELIB
Brand Name English
ESLICARBAZEPINE ACETATE [MART.]
Common Name English
(10S)-5-Carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate
Systematic Name English
BIA-2093
Code English
ESLICARBAZEPINE ACETATE [VANDF]
Common Name English
EXALIEF
Brand Name English
ESLICARBAZEPINE ACETATE [ORANGE BOOK]
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-CARBOXAMIDE, 10-(ACETYLOXY)-10,11-DIHYDRO-, (10S)-
Systematic Name English
ESLICARBAZEPINE ACETATE [USAN]
Common Name English
STEDESA
Brand Name English
BIA 2-093
Code English
Eslicarbazepine acetate [WHO-DD]
Common Name English
SEP-0002093
Code English
ESLICARBAZEPINE ACETATE [MI]
Common Name English
ESLICARBAZEPINE ACETATE [EMA EPAR]
Common Name English
APTIOM
Brand Name English
(S)-10-ACETOXY-10,11-DIHYDRO-5HDIBENZ( B,F)AZEPINE-5-CARBOXAMIDE
Systematic Name English
BIA-2-093
Code English
PAZZUL
Brand Name English
SEP0002093
Code English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
EMA ASSESSMENT REPORTS EXALIEF (WITHDRAWN: EPILEPSY)
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
EMA ASSESSMENT REPORTS ZEBINIX (AUTHORIZED: EPILEPSY)
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
Code System Code Type Description
SMS_ID
100000093396
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
MERCK INDEX
m5024
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL87992
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID90178308
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
RXCUI
1482501
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY RxNorm
DAILYMED
BEA68ZVB2K
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
MESH
C416835
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
PUBCHEM
179344
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
NCI_THESAURUS
C83697
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
FDA UNII
BEA68ZVB2K
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
DRUG CENTRAL
4303
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
WIKIPEDIA
Eslicarbazepine acetate
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
EVMPD
SUB30424
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
CAS
236395-14-5
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
USAN
WW-22
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY
DRUG BANK
DB09119
Created by admin on Fri Dec 15 16:17:36 UTC 2023 , Edited by admin on Fri Dec 15 16:17:36 UTC 2023
PRIMARY