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MedKoo Cat#: 584195 | Name: Eslicarbazepine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eslicarbazepine, also known as S(+)-Liscarbazepine, can be used for adjunctive therapy for adults with partial-onset seizures.

Chemical Structure

Eslicarbazepine
Eslicarbazepine
CAS#104746-04-5

Theoretical Analysis

MedKoo Cat#: 584195

Name: Eslicarbazepine

CAS#: 104746-04-5

Chemical Formula: C15H14N2O2

Exact Mass: 254.1055

Molecular Weight: 254.29

Elemental Analysis: C, 70.85; H, 5.55; N, 11.02; O, 12.58

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
BIA 2-194; BIA-2-194; BIA-2194; Erelib; Eslicarbazepine; Pazzul; Stedesa; Eslicarbazepine; S(+)-Liscarbazepine; (S)-Licarbazepine; S-licarbazepine
IUPAC/Chemical Name
(10S)-10,11-Dihydro-10-hydroxy-5H-dibenz(b,f)azepine-5-carboxamide
InChi Key
BMPDWHIDQYTSHX-AWEZNQCLSA-N
InChi Code
InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)/t14-/m0/s1
SMILES Code
O=C(N1C2=CC=CC=C2C[C@H](O)C3=CC=CC=C31)N
Appearance
Solid powder
Purity
>95% (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
More Info
Product Data
Product Data
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Eslicarbazepine is an oral anticonvulsant indicated for the adjunctive treatment of partial seizures.
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 250.0 983.13
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 254.29 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.

Recalculate based on batch purity %
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: Doeser A, Soares-da-Silva P, Beck H, Uebachs M. The effects of eslicarbazepine on persistent Na⁺ current and the role of the Na⁺ channel β subunits. Epilepsy Res. 2014 Feb;108(2):202-11. doi: 10.1016/j.eplepsyres.2013.11.022. Epub 2013 Dec 8. PubMed PMID: 24368131. 2: 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. Review. PubMed PMID: 24972948. 3: 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. Review. PubMed PMID: 24225327. 4: Elger C, Bialer M, Falcão A, Vaz-da-Silva M, Nunes T, Almeida L, Soares-da-Silva P. Pharmacokinetics and tolerability of eslicarbazepine acetate and oxcarbazepine at steady state in healthy volunteers. Epilepsia. 2013 Aug;54(8):1453-61. doi: 10.1111/epi.12242. Epub 2013 Jun 12. PubMed PMID: 23758485. 5: Potschka H, Soerensen J, Pekcec A, Loureiro A, Soares-da-Silva P. Effect of eslicarbazepine acetate in the corneal kindling progression and the amygdala kindling model of temporal lobe epilepsy. Epilepsy Res. 2014 Feb;108(2):212-22. doi: 10.1016/j.eplepsyres.2013.11.017. Epub 2013 Dec 1. PubMed PMID: 24345645. 6: Hussar DA, Dharsi N. Umeclidinium bromide/vilanterol trifenatate, perampanel, and eslicarbazepine acetate. J Am Pharm Assoc (2003). 2014 Jul-Aug;54(4):450-2, 454-5. doi: 10.1331/JAPhA.2014.14527. PubMed PMID: 25063267. 7: Shaikh S, Rizvi SM, Hameed N, Biswas D, Khan M, Shakil S, Kamal MA. Aptiom (eslicarbazepine acetate) as a dual inhibitor of β-secretase and voltage-gated sodium channel: advancement in Alzheimer's disease-epilepsy linkage via an enzoinformatics study. CNS Neurol Disord Drug Targets. 2014;13(7):1258-62. PubMed PMID: 25230222. 8: 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. PubMed PMID: 25242737. 9: Zaccara G, Giovannelli F, Maratea D, Fadda V, Verrotti A. Neurological adverse events of new generation sodium blocker antiepileptic drugs. Meta-analysis of randomized, double-blinded studies with eslicarbazepine acetate, lacosamide and oxcarbazepine. Seizure. 2013 Sep;22(7):528-36. doi: 10.1016/j.seizure.2013.03.016. Epub 2013 Apr 25. Review. PubMed PMID: 23623245. 10: Patsalos PN, Berry DJ. Pharmacotherapy of the third-generation AEDs: lacosamide, retigabine and eslicarbazepine acetate. Expert Opin Pharmacother. 2012 Apr;13(5):699-715. doi: 10.1517/14656566.2012.667803. Epub 2012 Mar 10. Review. PubMed PMID: 22404663. 11: Falcão A, Vaz-da-Silva M, Gama H, Nunes T, Almeida L, Soares-da-Silva P. Effect of eslicarbazepine acetate on the pharmacokinetics of a combined ethinylestradiol/levonorgestrel oral contraceptive in healthy women. Epilepsy Res. 2013 Aug;105(3):368-76. doi: 10.1016/j.eplepsyres.2013.02.020. Epub 2013 Apr 6. PubMed PMID: 23570863. 12: Sperling MR, Abou-Khalil B, Harvey J, Rogin JB, Biraben A, Galimberti CA, Kowacs PA, Hong SB, Cheng H, Blum D, Nunes T, Soares-da-Silva P; 304 Study Team. Eslicarbazepine acetate as adjunctive therapy in patients with uncontrolled partial-onset seizures: Results of a phase III, double-blind, randomized, placebo-controlled trial. Epilepsia. 2015 Feb;56(2):244-53. doi: 10.1111/epi.12894. Epub 2014 Dec 22. PubMed PMID: 25528898; PubMed Central PMCID: PMC4354260. 13: Nath K, Bhattacharya A, Praharaj SK. Eslicarbazepine acetate in the management of refractory bipolar disorder. Clin Neuropharmacol. 2012 Nov-Dec;35(6):295. doi: 10.1097/WNF.0b013e318271220b. PubMed PMID: 23151469. 14: Loureiro AI, Fernandes-Lopes C, Bonifácio MJ, Wright LC, Soares-da-Silva P. Hepatic UDP-glucuronosyltransferase is responsible for eslicarbazepine glucuronidation. Drug Metab Dispos. 2011 Sep;39(9):1486-94. doi: 10.1124/dmd.111.038620. Epub 2011 Jun 14. PubMed PMID: 21673130. 15: Correia FD, Freitas J, Magalhães R, Lopes J, Ramalheira J, Lopes-Lima J, Chaves J. Two-year follow-up with eslicarbazepine acetate: a consecutive, retrospective, observational study. Epilepsy Res. 2014 Oct;108(8):1399-405. doi: 10.1016/j.eplepsyres.2014.06.017. Epub 2014 Jul 6. PubMed PMID: 25060997. 16: Vaz-Da-Silva M, Nunes T, Almeida L, Gutierrez MJ, Litwin JS, Soares-Da-Silva P. Evaluation of Eslicarbazepine acetate on cardiac repolarization in a thorough QT/QTc study. J Clin Pharmacol. 2012 Feb;52(2):222-33. doi: 10.1177/0091270010391789. PubMed PMID: 21415284. 17: Nunes T, Rocha JF, Falcão A, Almeida L, Soares-da-Silva P. Steady-state plasma and cerebrospinal fluid pharmacokinetics and tolerability of eslicarbazepine acetate and oxcarbazepine in healthy volunteers. Epilepsia. 2013 Jan;54(1):108-16. doi: 10.1111/j.1528-1167.2012.03595.x. Epub 2012 Jul 19. PubMed PMID: 22812691. 18: 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. Review. PubMed PMID: 26038700; PubMed Central PMCID: PMC4448990. 19: Massot A, Gimenez-Arnau A. Cutaneous adverse drug reaction type erythema multiforme major induced by eslicarbazepine. J Pharmacol Pharmacother. 2014 Oct;5(4):271-4. doi: 10.4103/0976-500X.142456. PubMed PMID: 25422574; PubMed Central PMCID: PMC4231563. 20: Massot A, Vivanco R, Principe A, Roquer J, Rocamora R. Post-authorisation study of eslicarbazepine as treatment for drug-resistant epilepsy: preliminary results. Neurologia. 2014 Mar;29(2):94-101. doi: 10.1016/j.nrl.2013.02.013. Epub 2013 Apr 25. English, Spanish. PubMed PMID: 23623701.