Eslicarbazepine acetate

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Structural formula
Structural formula of eslicarbazepine acetate
General
Non-proprietary name Eslicarbazepine acetate
other names

( S ) -10-acetoxy-10,11-dihydro-5 H -dibenzo [ b , f ] azepine-5-carboxamide

Molecular formula C 17 H 16 N 2 O 3
External identifiers / databases
CAS number 236395-14-5
EC number 636-617-2
ECHA InfoCard 100.164.398
PubChem 179344
ChemSpider 156110
DrugBank DB09119
Wikidata Q410273
Drug information
ATC code

N03 AF04

Drug class

Anti-epileptic

Mechanism of action

Blockage of the sodium channels

properties
Molar mass 296.32 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Eslicarbazepine acetate is a chemical compound that is used as a drug for the long-term treatment of certain forms of epilepsy . Chemically, it is a derivative of carbamazepine , a carboxamide from the class of dibenzazepines . Eslicarbazepine was developed by the Portuguese pharmaceutical company BIAL in the 1990s and has been approved in Europe since 2009.

Pharmacokinetics

The prodrug eslicarbazepine acetate is rapidly absorbed after oral administration and 95% hydrolytically cleaved by liver esterases ( first-pass metabolism ) to the active metabolite eslicarbazepine [( S ) -licarbazepine, 10,11-dihydro-10-hydroxycarbamazepine]. Only small amounts of the (less effective) enantiomer R-licarbazepine are formed. This could result in a higher clinical efficacy for eslicarbazepine compared to the anti-epileptic oxcarbazepine , after which the S-licarbazepine to R-licarbazepine ratio is 4: 1 when metabolized . About 30% of eslicarbazepine is bound to plasma proteins. The half-life is 8 to 17 hours after a single dose and 20 to 24 hours with regular use. Almost all of the eslicarbazepine is excreted by the kidneys.

Mode of action

Eslicarbazepine basically has the same mode of action as the related carbamazepine. It inhibits voltage-dependent sodium channels in the axons of nerve cells , thus preventing the release of sodium-channel-dependent neurotransmitters . Eslicarbazepine stabilizes the inactive form of the sodium channels and in particular suppresses repetitive excitation.

Range of applications

In accordance with the spectrum of activity of carbamazepine and oxcarbazepine, eslicarbazepine is indicated in combination therapy for epilepsy with focal and secondary generalized seizures in adults.

unwanted effects

In placebo-controlled studies, 45.3% of subjects treated with eslicarbazepine acetate experienced adverse effects (compared with 24.4% of subjects treated with placebo). Adverse effects were mild to moderate in severity and occurred predominantly during the first few weeks. Eslicarbazepine in particular can make you dizzy and sleepy. Headaches, coordination and attention disorders may occur. Other undesirable effects are rash (1.1%), tremor, nausea, vomiting, diarrhea. A hyponatremia (reducing the content of sodium ions in the blood ) has been reported in less than 1% of users (as opposed to 23% - 73% oxcarbazepine)

Eslicarbazepine can make hormonal contraceptives less effective. Additional non-hormonal contraception is recommended when using eslicarbazepine.

Individual evidence

  1. ↑ a b data sheet BIA 2-093 from Sigma-Aldrich , accessed on March 30, 2011 ( PDF ).
  2. ↑ J. Maia, M. Vaz-da-Silva, L. Almeida, A. Falcao, P. Silveira, S. Guimaraes, P. Graziela, P. Soares-da-Silva: Effect of food on the pharmacokinetic profile of eslicarbazepine acetate (BIA 2-093). In: Drugs R D. 6, 2005, pp. 201-206.
  3. ↑ BJ Steinhoff, E. Trinka, AS Wendling: Abrupt replacement of slow-release oxcarbazepine against eslicarbazepine acetate. In: The neurologist. 2010.
  4. ↑ M. Bialer, SI Johannessen, HJ Kupferberg, RH Levy, E. Perucca, T. Tomson: Progress report on new antiepileptic drugs: a summary of the Eighth Eilat Conference (EILAT VIII). In: Epilepsy Res. 73, 2007, pp. 1-52. PMID 17158031
  5. ↑ L. Almeida, A. Falcao, J. Maia, D. Mazur, M. Gellert, P. Soares-da-Silva: Single-dose and steady-state pharmacokinetics of eslicarbazepine acetate (BIA 2-093) in healthy elderly and young subjects. In: J Clin Pharmacol . 45, 2005, pp. 1062-1066.
  6. ↑ L. Almeida, P. Soares-da-Silva: Eslicarbazepine acetate (BIA 2-093). In: Neurotherapeutics: the journal of the American Society for Experimental NeuroTherapeutics. Volume 4, number 1, January 2007, pp. 88-96, doi: 10.1016 / j.nurt.2006.10.005 . PMID 17199020 (Review).
  7. ↑ António Parada, Patrı́cio Soares-da-Silva: The novel anticonvulsant BIA 2-093 inhibits transmitter release during opening of voltage-gated sodium channels: a comparison with carbamazepine and oxcarbazepine . In: Neurochemistry International . tape 40 , no. 5 , April 2002, p. 435-440 , doi : 10.1016 / S0197-0186 (01) 00101-2 ( PDF ).

Trade names

Zebinix (EU), Exalief (EU, obsolete), Aptiom (USA), Stedesa (USA, obsolete)

Web links