WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326960
CAS#: 29331-92-8
Description: 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.
Hodoodo Cat#: H326960
Name: Licarbazepine
CAS#: 29331-92-8
Chemical Formula: C15H14N2O2
Exact Mass: 254.11
Molecular Weight: 254.289
Elemental Analysis: C, 70.85; H, 5.55; N, 11.02; O, 12.58
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
More Info:
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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: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
