Licarbazepine | BIA-2-005 | GP-47779 | CAS#29331-92-8 | sodium channel blocker

MedKoo Cat#: 326960 | Name: Licarbazepine

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Description:

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

Licarbazepine, also known as BIA-2-005; GP-47779; LIC-477; LIC-477D; TRI-477, is a voltage-gated sodium channel blocker with anticonvulsant and mood-stabilizing effects that is related to oxcarbazepine. It is an active metabolite of oxcarbazepine. In addition, an isomer of licarbazepine, eslicarbazepine ((S)-(+)-licarbazepine), is an active metabolite of eslicarbazepine acetate. Oxcarbazepine and eslicarbazepine acetate are inactive on their own, and behave instead as prodrugs to licarbazepine and eslicarbazepine, respectively, to produce their therapeutic effects.

Chemical Structure

Licarbazepine

CAS#29331-92-8

Theoretical Analysis

MedKoo Cat#: 326960

Name: Licarbazepine

CAS#: 29331-92-8

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
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
500mg	USD 750.00	2 Weeks
1g	USD 1,150.00	2 Weeks

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Synonym

Licarbazepine; BIA-2-005; GP-47779; LIC-477; LIC-477D; TRI-477; BIA2-005; GP47779; LIC477; LIC477D; TRI477.

IUPAC/Chemical Name

10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

InChi Key

BMPDWHIDQYTSHX-UHFFFAOYSA-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)

SMILES Code

O=C(N1C2=CC=CC=C2CC(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

>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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Licarbazepine (BIA 2-005; GP 47779) is a voltage-gated sodium channel blocker with anticonvulsant and mood-stabilizing effects.

In vitro activity:

This study characterized the electrophysiological effects of GP 47779 on striatal neurons by making intracellular recordings from corticostriatal slices. GP 47779 (3-100 microM) produced a dose-dependent inhibition of glutamatergic excitatory postsynaptic potentials (EPSPs). GP 47779 reduced the current-evoked firing discharge only at concentrations > 100 microM. Reference: Epilepsia. 1995 Oct;36(10):990-6. https://pubmed.ncbi.nlm.nih.gov/7555963/

In vivo activity:

This study studied the action of the new antiepileptic drugs lamotrigine (LTG), GP 47779 (the active metabolite of oxcarbazepine), and felbamate (FBM) on stimulus-evoked field potentials recorded from rat prefrontal and frontal cortical slices. LTG and GP 47779 decreased, in a dose-dependent manner, the field potential amplitude under both experimental conditions. Reference: Neurology. 1996 Aug;47(2):557-62. https://pubmed.ncbi.nlm.nih.gov/8757038/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	98.31
	DMSO	50.1	197.19
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.97
	Ethanol	7.9	30.89

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.

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. Bayraktar E, Liu Y, Sonnenberg L, Hedrich UBS, Sara Y, Eltokhi A, Lyu H, Lerche H, Wuttke TV, Lauxmann S. In vitro effects of eslicarbazepine (S-licarbazepine) as a potential precision therapy on SCN8A variants causing neuropsychiatric disorders. Br J Pharmacol. 2022 Nov 2. doi: 10.1111/bph.15981. Epub ahead of print. PMID: 36321697. 2. Calabresi P, De Murtas M, Stefani A, Pisani A, Sancesario G, Mercuri NB, Bernardi G. Action of GP 47779, the active metabolite of oxcarbazepine, on the corticostriatal system. I. Modulation of corticostriatal synaptic transmission. Epilepsia. 1995 Oct;36(10):990-6. doi: 10.1111/j.1528-1157.1995.tb00957.x. PMID: 7555963. 3. Calabresi P, Siniscalchi A, Pisani A, Stefani A, Mercuri NB, Bernardi G. A field potential analysis on the effects of lamotrigine, GP 47779, and felbamate in neocortical slices. Neurology. 1996 Aug;47(2):557-62. doi: 10.1212/wnl.47.2.557. PMID: 8757038.

In vitro protocol:

In vivo protocol:

1. Calabresi P, Siniscalchi A, Pisani A, Stefani A, Mercuri NB, Bernardi G. A field potential analysis on the effects of lamotrigine, GP 47779, and felbamate in neocortical slices. Neurology. 1996 Aug;47(2):557-62. doi: 10.1212/wnl.47.2.557. PMID: 8757038.

1: 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. 2: Ferreira A, Rodrigues M, Oliveira P, Francisco J, Fortuna A, Rosado L, Rosado P, Falcão A, Alves G. Liquid chromatographic assay based on microextraction by packed sorbent for therapeutic drug monitoring of carbamazepine, lamotrigine, oxcarbazepine, phenobarbital, phenytoin and the active metabolites carbamazepine-10,11-epoxide and licarbazepine. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Nov 15;971:20-9. doi: 10.1016/j.jchromb.2014.09.010. Epub 2014 Sep 16. PubMed PMID: 25261836. 3: Bocato MZ, Bortoleto MA, Pupo MT, de Oliveira AR. A new enantioselective CE method for determination of oxcarbazepine and licarbazepine after fungal biotransformation. Electrophoresis. 2014 Oct;35(19):2877-84. doi: 10.1002/elps.201400137. Epub 2014 Aug 18. PubMed PMID: 24981999. 4: Serralheiro A, Alves G, Fortuna A, Rocha M, Falcão A. First HPLC-UV method for rapid and simultaneous quantification of phenobarbital, primidone, phenytoin, carbamazepine, carbamazepine-10,11-epoxide, 10,11-trans-dihydroxy-10,11-dihydrocarbamazepine, lamotrigine, oxcarbazepine and licarbazepine in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:1-9. doi: 10.1016/j.jchromb.2013.02.026. Epub 2013 Feb 27. PubMed PMID: 23507454. 5: 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. 6: Fortuna A, Alves G, Almeida A, Lopes B, Falcão A, Soares-da-Silva P. A chiral liquid chromatography method for the simultaneous determination of oxcarbazepine, eslicarbazepine, R-licarbazepine and other new chemical derivatives BIA 2-024, BIA 2-059 and BIA 2-265, in mouse plasma and brain. Biomed Chromatogr. 2012 Mar;26(3):384-92. doi: 10.1002/bmc.1670. Epub 2011 Jul 21. PubMed PMID: 21780155. 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: Alves G, Figueiredo I, Falcão A, Castel-Branco M, Caramona M, Soares-Da-Silva P. Stereoselective disposition of S- and R-licarbazepine in mice. Chirality. 2008 Jun;20(6):796-804. doi: 10.1002/chir.20546. PubMed PMID: 18306292. 9: Souppart C, Gardin A, Greig G, Balez S, Batard Y, Krebs-Brown A, Appel-Dingemanse S. Pharmacokinetics of licarbazepine in healthy volunteers: single and multiple oral doses and effect of food. J Clin Pharmacol. 2008 May;48(5):563-9. doi: 10.1177/0091270007313323. Epub 2008 Feb 7. PubMed PMID: 18258749. 10: 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.