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MedKoo Cat#: 598830 | Name: (R)-Licarbazepine Acetate
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Description:

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

(R)-Licarbazepine Acetate is a promising antiepileptic drug structurally related to Carbamazepine and Oxcarbazepine.

Chemical Structure

(R)-Licarbazepine Acetate
(R)-Licarbazepine Acetate
CAS#186694-45-1

Theoretical Analysis

MedKoo Cat#: 598830

Name: (R)-Licarbazepine Acetate

CAS#: 186694-45-1

Chemical Formula: C17H16N2O3

Exact Mass: 296.1161

Molecular Weight: 296.32

Elemental Analysis: C, 68.91; H, 5.44; N, 9.45; O, 16.20

Price and Availability

Size Price Availability Quantity
5mg USD 450.00
50mg USD 1,600.00
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Synonym
(R)-Licarbazepine Acetate; BIA 2-059; Licarbazepine acetate, (R)-; BIA-2-059; BIA2-059;
IUPAC/Chemical Name
(R)-5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate
InChi Key
QIALRBLEEWJACW-MRXNPFEDSA-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-/m1/s1
SMILES Code
O=C(N1C2=CC=CC=C2C[C@@H](OC(C)=O)C3=CC=CC=C31)N
Appearance
Solid powder
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
>3 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
2934.99.03.00
More Info

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.

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
1: 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. 2: Loureiro AI, Fernandes-Lopes C, Wright LC, Soares-da-Silva P. Development and validation of an enantioselective liquid-chromatography/tandem mass spectrometry method for the separation and quantification of eslicarbazepine acetate, eslicarbazepine, R-licarbazepine and oxcarbazepine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Sep 1;879(25):2611-8. doi: 10.1016/j.jchromb.2011.07.019. Epub 2011 Jul 20. PubMed PMID: 21816689. 3: Perucca E, Elger C, Halász P, Falcão A, Almeida L, Soares-da-Silva P. Pharmacokinetics of eslicarbazepine acetate at steady-state in adults with partial-onset seizures. Epilepsy Res. 2011 Sep;96(1-2):132-9. doi: 10.1016/j.eplepsyres.2011.05.013. Epub 2011 Jun 15. PubMed PMID: 21680153. 4: 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. 5: Bialer M, Soares-da-Silva P. Pharmacokinetics and drug interactions of eslicarbazepine acetate. Epilepsia. 2012 Jun;53(6):935-46. doi: 10.1111/j.1528-1167.2012.03519.x. Epub 2012 May 21. Review. PubMed PMID: 22612290. 6: Alves G, Figueiredo I, Castel-Branco M, Loureiro A, Falcão A, Caramona M. Simultaneous and enantioselective liquid chromatographic determination of eslicarbazepine acetate, S-licarbazepine, R-licarbazepine and oxcarbazepine in mouse tissue samples using ultraviolet detection. Anal Chim Acta. 2007 Jul 16;596(1):132-40. Epub 2007 Jun 3. PubMed PMID: 17616250. 7: Fortuna A, Alves G, Falcão A, Soares-da-Silva P. Binding of licarbazepine enantiomers to mouse and human plasma proteins. Biopharm Drug Dispos. 2010 Jul;31(5-6):362-6. doi: 10.1002/bdd.716. PubMed PMID: 20578208. 8: 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. 9: Mone MK, Chandrasekhar KB. Development of liquid chromatographic enantiomer separation methods and validation for the estimation of (R)-enantiomer in eslicarbazepine acetate. J Pharm Biomed Anal. 2011 Jan 5;54(1):248-51. doi: 10.1016/j.jpba.2010.08.015. Epub 2010 Aug 19. PubMed PMID: 20832962. 10: Servais AC, Janicot B, Takam A, Crommen J, Fillet M. Liquid chromatography separation of the chiral prodrug eslicarbazepine acetate and its main metabolites in polar organic mode. Application to their analysis after in vitro metabolism. J Chromatogr A. 2016 Oct 7;1467:306-311. doi: 10.1016/j.chroma.2016.07.022. Epub 2016 Jul 9. PubMed PMID: 27439356. 11: Sunkaraneni S, Kharidia J, Schutz R, Blum D, Cheng H. A Pharmacokinetic Study Comparing Eslicarbazepine Acetate Administered Orally as a Crushed or Intact Tablet in Healthy Volunteers. Clin Pharmacol Drug Dev. 2016 Jul;5(4):278-84. doi: 10.1002/cpdd.242. Epub 2016 Feb 8. PubMed PMID: 27249205. 12: Alves G, Figueiredo I, Castel-Branco M, Lourenço N, Falcão A, Caramona M, Soares-da-Silva P. Disposition of eslicarbazepine acetate in the mouse after oral administration. Fundam Clin Pharmacol. 2008 Oct;22(5):529-36. doi: 10.1111/j.1472-8206.2008.00617.x. Epub 2008 Aug 15. PubMed PMID: 18710399. 13: Fortuna A, Sousa J, Alves G, Falcão A, Soares-da-Silva P. Development and validation of an HPLC-UV method for the simultaneous quantification of carbamazepine, oxcarbazepine, eslicarbazepine acetate and their main metabolites in human plasma. Anal Bioanal Chem. 2010 Jun;397(4):1605-15. doi: 10.1007/s00216-010-3673-0. Epub 2010 Apr 18. PubMed PMID: 20401721. 14: Fortuna A, Bicker J, Alves G, Falcão A, Soares-da-Silva P. A chiral HPLC-UV method for the quantification of dibenz[b,f]azepine-5-carboxamide derivatives in mouse plasma and brain tissue: eslicarbazepine acetate, carbamazepine and main metabolites. J Sep Sci. 2011 Jun;34(12):1391-401. doi: 10.1002/jssc.201100099. Epub 2011 May 9. PubMed PMID: 21557472. 15: Alves G, Fortuna A, Sousa J, Direito R, Almeida A, Rocha M, Falcão A, Soares-da-Silva P. Enantioselective assay for therapeutic drug monitoring of eslicarbazepine acetate: no interference with carbamazepine and its metabolites. Ther Drug Monit. 2010 Aug;32(4):512-6. doi: 10.1097/FTD.0b013e3181e5c855. PubMed PMID: 20592643. 16: Alves G, Figueiredo I, Castel-Branco M, Loureiro A, Fortuna A, Falcão A, Caramona M. Enantioselective HPLC-UV method for determination of eslicarbazepine acetate (BIA 2-093) and its metabolites in human plasma. Biomed Chromatogr. 2007 Nov;21(11):1127-34. PubMed PMID: 17594694. 17: Kim TH, Reid CA, Petrou S. Oxcarbazepine and its active metabolite, (S)-licarbazepine, exacerbate seizures in a mouse model of genetic generalized epilepsy. Epilepsia. 2015 Jan;56(1):e6-9. doi: 10.1111/epi.12866. Epub 2014 Dec 8. PubMed PMID: 25489632. 18: Mauri-Llerda JA. [Eslicarbazepine acetate: a novel therapeutic alternative in the treatment of focal seizures]. Rev Neurol. 2012 May 1;54(9):551-5. Review. Spanish. PubMed PMID: 22532219. 19: Nunes T, Sicard E, Almeida L, Falcão A, Rocha JF, Brunet JS, Lefebvre M, Soares-da-Silva P. Pharmacokinetic interaction study between eslicarbazepine acetate and topiramate in healthy subjects. Curr Med Res Opin. 2010 Jun;26(6):1355-62. doi: 10.1185/03007991003740861. PubMed PMID: 20377319. 20: Morte MI, Carreira BP, Falcão MJ, Ambrósio AF, Soares-da-Silva P, Araújo IM, Carvalho CM. Evaluation of neurotoxic and neuroprotective pathways affected by antiepileptic drugs in cultured hippocampal neurons. Toxicol In Vitro. 2013 Dec;27(8):2193-202. doi: 10.1016/j.tiv.2013.09.008. Epub 2013 Sep 19. PubMed PMID: 24055897.

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