Eslicarbazepine Acetate

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 Search

SMILES

CC(=O)O[C@H]1CC2=CC=CC=C2N(C(N)=O)C3=CC=CC=C13

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022416s000lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022416s000lbl.pdf	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Partial-onset seizures 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022416s000lbl.pdf	Primary		Approved 8583	APTIOM Approved Use APTIOM is indicated as adjunctive treatment of partial-onset seizures. Launch Date 2013

C_max

Value	Dose	Co-administered	Analyte	Population
9.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21680153/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ESLICARBAZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
132.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21680153/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ESLICARBAZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21680153/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ESLICARBAZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022416s009lbl.pdf	1 times / day unknown, oral		ESLICARBAZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
60% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022416s009lbl.pdf	1 times / day unknown, oral		ESLICARBAZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0037YY	https://www.aablocks.com/goods/Goods/detail?id=AA0037YY
AK Scientific, Inc. (AKSCI)	V0814	http://www.aksci.com/item_detail.php?cat=V0814
Alfa Chemistry	104746-04-5	https://www.alfa-chemistry.com/cas_104746-04-5.htm
Alichem	19096134	http://www.alichem.com/en/products/104746-04-5.html
Angene	AGN-PC-0OTSW1	http://www.angenechemical.com/productshow/AGN-PC-0OTSW1.html
BioSynth	J-001242	https://www.biosynth.com/en/products/all-products/products/J-001242.html
BLD Pharm	BD254896	http://www.bldpharm.com/products/104746-04-5.html
Chem Scene	CS-0064132	http://www.chemscene.com/104746-04-5.html
ChemMol	49401415	http://www.chemmol.com/chemmol/49401415.html
Chemspace	CSSB00020633427	https://chem-space.com/CSSB00020633427
DC Chemicals	DC12325	http://www.dcchemicals.com/product_show-Eslicarbazepine.html
eNovation Chemicals	D671189	https://www.enovationchem.com/ProductDetails.asp?ProductID=D671189
iChemical	EBD937708	http://www.ichemical.com/products/104746-04-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
MedChem Express	HY-114703	https://www.medchemexpress.com/Eslicarbazepine.html
MuseChem	R005604	https://www.musechem.com/product/R005604.html
Smolecule	S527428	http://www.smolecule.com/products/s527428
Synthink Research Chemicals	SA28800	https://synthinkchemicals.com/product/monohydroxy-carbamazepine/
THE BioTek	bt-267741	https://www.thebiotek.com/product/inhibitors/bt-267741

PubMed

Title	Date	PubMed
Anticonvulsant effect of eslicarbazepine acetate (BIA 2-093) on seizures induced by microperfusion of picrotoxin in the hippocampus of freely moving rats.	2006-12	16920333
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.	2004-12	15571507
Mechanisms of action of carbamazepine and its derivatives, oxcarbazepine, BIA 2-093, and BIA 2-024.	2002-02	11926264

Patents

Sample Use Guides

In Vivo Use Guide

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

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

Official Name

English

APTIOM

Preferred 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

(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