Synonym
BIA 2093; BIA-2093; BIA 2-093; BIA-2-093; Zebinix; Exalief; Stedesa; Aptiom; Eslicarbazepine acetate
IUPAC/Chemical Name
(S)-10-Acetoxy- 10,11-dihydro- 5H-dibenz[b,f]azepine- 5-carboxamide
InChi Key
QIALRBLEEWJACW-INIZCTEOSA-N
InChi Code
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
SMILES Code
O=C(N1C2=CC=CC=C2C[C@H](OC(C)=O)C3=CC=CC=C31)N
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Eslicarbazepine acetate (BIA 2-093), an antiepileptic drug, is a dual a dual Inhibitor of β-Secretase and voltage-gated sodium channel.
In vitro activity:
CBZ and eslicarbazepine exhibit similar concentration dependent suppression of epileptiform activity in hippocampal slices. Eslicarbazepine- and LCM-treated fast-inactivated channels recovered similarly to control conditions, whereas CBZ- and OXC-treated channels required longer pulses to recover.
Reference: Neuropharmacology. 2015 Feb;89:122-35. https://pubmed.ncbi.nlm.nih.gov/25242737/
In vivo activity:
The antinociceptive effects of orally administered ESL (eslicarbazepine), standard/alternative analgesics, and two-drug ESL-analgesic combinations were examined in the orofacial formalin test in mice. ESL, analgesics, and two-drug ESL-analgesic combinations significantly and dose-dependently reduced nociceptive behaviour in the second, inflammatory phase of the test.
Reference: Psychopharmacology (Berl). 2020 May;237(5):1435-1446. https://pubmed.ncbi.nlm.nih.gov/32025776/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
79.5 |
268.29 |
| Ethanol |
11.0 |
37.12 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
296.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hebeisen S, Pires N, Loureiro AI, Bonifácio MJ, Palma N, Whyment A, Spanswick D, Soares-da-Silva P. Eslicarbazepine and the enhancement of slow inactivation of voltage-gated sodium channels: a comparison with carbamazepine, oxcarbazepine and lacosamide. Neuropharmacology. 2015 Feb;89:122-35. doi: 10.1016/j.neuropharm.2014.09.008. Epub 2014 Sep 19. PMID: 25242737.
2. Pecikoza U, Tomić M, Micov A, Vuković M, Stepanović-Petrović R. Eslicarbazepine acetate interacts in a beneficial manner with standard and alternative analgesics to reduce trigeminal nociception. Psychopharmacology (Berl). 2020 May;237(5):1435-1446. doi: 10.1007/s00213-020-05470-7. Epub 2020 Feb 5. PMID: 32025776.
3. Pecikoza U, Micov A, Tomić M, Stepanović-Petrović R. Eslicarbazepine acetate reduces trigeminal nociception: Possible role of adrenergic, cholinergic and opioid receptors. Life Sci. 2018 Dec 1;214:167-175. doi: 10.1016/j.lfs.2018.10.059. Epub 2018 Oct 27. PMID: 30393024.
In vitro protocol:
1. Hebeisen S, Pires N, Loureiro AI, Bonifácio MJ, Palma N, Whyment A, Spanswick D, Soares-da-Silva P. Eslicarbazepine and the enhancement of slow inactivation of voltage-gated sodium channels: a comparison with carbamazepine, oxcarbazepine and lacosamide. Neuropharmacology. 2015 Feb;89:122-35. doi: 10.1016/j.neuropharm.2014.09.008. Epub 2014 Sep 19. PMID: 25242737.
In vivo protocol:
1. Pecikoza U, Tomić M, Micov A, Vuković M, Stepanović-Petrović R. Eslicarbazepine acetate interacts in a beneficial manner with standard and alternative analgesics to reduce trigeminal nociception. Psychopharmacology (Berl). 2020 May;237(5):1435-1446. doi: 10.1007/s00213-020-05470-7. Epub 2020 Feb 5. PMID: 32025776.
2. Pecikoza U, Micov A, Tomić M, Stepanović-Petrović R. Eslicarbazepine acetate reduces trigeminal nociception: Possible role of adrenergic, cholinergic and opioid receptors. Life Sci. 2018 Dec 1;214:167-175. doi: 10.1016/j.lfs.2018.10.059. Epub 2018 Oct 27. PMID: 30393024.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Eslicarbazepine. 2020 Sep 21. PMID: 29999698.
2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Eslicarbazepine. 2018 Feb 14. PMID: 31644244.
3: Heo YA. Eslicarbazepine Acetate: A Review in Focal-Onset Seizures. CNS Drugs. 2020 Sep;34(9):989-1000. doi: 10.1007/s40263-020-00751-3. PMID: 32737793.
4: McCormack PL, Robinson DM. Eslicarbazepine acetate. CNS Drugs. 2009;23(1):71-9. doi: 10.2165/0023210-200923010-00005. PMID: 19062776.
5: Rissardo JP, Caprara ALF. Carbamazepine-, Oxcarbazepine-, Eslicarbazepine- Associated Movement Disorder: A Literature Review. Clin Neuropharmacol. 2020 May/Jun;43(3):66-80. doi: 10.1097/WNF.0000000000000387. PMID: 32384309.
6: Shirley M, Dhillon S. Eslicarbazepine Acetate Monotherapy: A Review in Partial-Onset Seizures. Drugs. 2016 Apr;76(6):707-17. doi: 10.1007/s40265-016-0570-7. PMID: 27055527.
7: Eslicarbazepine acetate (aptiom) for epilepsy. Med Lett Drugs Ther. 2014 May 26;56(1443):42-3. PMID: 24869714.
8: Alcántara Montero A, Sánchez Carnerero CI. Eslicarbazepine acetate for neuropathic pain, headache, and cranial neuralgia: Evidence and experience. Neurologia (Engl Ed). 2019 Jul-Aug;34(6):386-395. English, Spanish. doi: 10.1016/j.nrl.2016.11.009. Epub 2017 Feb 16. PMID: 28215909.
9: Chang XC, Yuan H, Wang Y, Xu HQ, Hong WK, Zheng RY. Eslicarbazepine acetate add-on for drug-resistant partial epilepsy. Cochrane Database Syst Rev. 2017 Oct 25;10(10):CD008907. doi: 10.1002/14651858.CD008907.pub3. Update in: Cochrane Database Syst Rev. 2021 Jun 22;6:CD008907. PMID: 29067682; PMCID: PMC6485774.
10: Soares-da-Silva P, Pires N, Bonifácio MJ, Loureiro AI, Palma N, Wright LC. Eslicarbazepine acetate for the treatment of focal epilepsy: an update on its proposed mechanisms of action. Pharmacol Res Perspect. 2015 Mar;3(2):e00124. doi: 10.1002/prp2.124. Epub 2015 Mar 30. PMID: 26038700; PMCID: PMC4448990.
11: Abou-Khalil BW. Update on Antiseizure Medications 2022. Continuum (Minneap Minn). 2022 Apr 1;28(2):500-535. doi: 10.1212/CON.0000000000001104. Erratum in: Continuum (Minneap Minn). 2023 Jun 1;29(3):995. PMID: 35393968.
12: Rauchenzauner M, Luef G. Eslicarbazepine acetate for partial-onset seizures. Expert Rev Neurother. 2011 Dec;11(12):1673-81. doi: 10.1586/ern.11.158. PMID: 22091592.
13: Vidaurre J, Herbst J. Nuevos fármacos antiepilépticos [New antiepileptic drugs]. Medicina (B Aires). 2019;79 Suppl 3:48-53. Spanish. PMID: 31603844.
14: Verrotti A, Loiacono G, Rossi A, Zaccara G. Eslicarbazepine acetate: an update on efficacy and safety in epilepsy. Epilepsy Res. 2014 Jan;108(1):1-10. doi: 10.1016/j.eplepsyres.2013.10.005. Epub 2013 Oct 23. PMID: 24225327.
15: Costa R, Magalhães LM, Graça J, Vieira M, Gama H, Moreira J, Rocha JF, Soares-da-Silva P. Eslicarbazepine acetate exposure in pregnant women with epilepsy. Seizure. 2018 May;58:72-74. doi: 10.1016/j.seizure.2018.04.007. Epub 2018 Apr 10. PMID: 29674237.
16: Galiana GL, Gauthier AC, Mattson RH. Eslicarbazepine Acetate: A New Improvement on a Classic Drug Family for the Treatment of Partial-Onset Seizures. Drugs R D. 2017 Sep;17(3):329-339. doi: 10.1007/s40268-017-0197-5. PMID: 28741150; PMCID: PMC5629137.
17: Almeida L, Soares-da-Silva P. Eslicarbazepine acetate (BIA 2-093). Neurotherapeutics. 2007 Jan;4(1):88-96. doi: 10.1016/j.nurt.2006.10.005. PMID: 17199020; PMCID: PMC7479690.
18: Keating GM. Eslicarbazepine acetate: a review of its use as adjunctive therapy in refractory partial-onset seizures. CNS Drugs. 2014 Jul;28(7):583-600. doi: 10.1007/s40263-014-0182-2. PMID: 24972948.
19: Gambeta E, Chichorro JG, Zamponi GW. Trigeminal neuralgia: An overview from pathophysiology to pharmacological treatments. Mol Pain. 2020 Jan- Dec;16:1744806920901890. doi: 10.1177/1744806920901890. PMID: 31908187; PMCID: PMC6985973.
20: Shorvon SD, Trinka E, Steinhoff BJ, Holtkamp M, Villanueva V, Peltola J, Ben-Menachem E. Eslicarbazepine acetate: its effectiveness as adjunctive therapy in clinical trials and open studies. J Neurol. 2017 Mar;264(3):421-431. doi: 10.1007/s00415-016-8338-2. Epub 2017 Jan 18. PMID: 28101651; PMCID: PMC5336540.
