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
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
Molecular Formula | C17H16N2O3 |
Molecular Weight | 296.3205 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=11926264
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=17199020 | http://www.ncbi.nlm.nih.gov/pubmed/?term=18710399
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
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024. | 2002 Feb |
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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 |
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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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=15571507
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
Edited
Fri Dec 15 16:17:36 GMT 2023
by
admin
on
Fri Dec 15 16:17:36 GMT 2023
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Record UNII |
BEA68ZVB2K
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C264
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EMA ASSESSMENT REPORTS |
EXALIEF (WITHDRAWN: EPILEPSY)
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EMA ASSESSMENT REPORTS |
ZEBINIX (AUTHORIZED: EPILEPSY)
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100000093396
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m5024
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CHEMBL87992
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DTXSID90178308
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1482501
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BEA68ZVB2K
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C416835
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179344
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4303
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Eslicarbazepine acetate
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SUB30424
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236395-14-5
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WW-22
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DB09119
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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