Licarbazepine

Names

[ Name ]:
Licarbazepine

[Synonym ]:
10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide,Licarbazepine
Licarbazepine,10,11-Dihydro-10-hydroxy-5H-dibenz(Z)[b,f]azepin-5-carboxamide
10,11-Dihydro-10-hydroxy Carbamazepine
10,11-Dihydro-10-hydroxycarbamazepine
5H-Dibenz[b,f]azepine-5-carboxamide,10,11-dihydro-10-hydroxy-

Biological Activity

[Description]:

Licarbazepine (BIA 2-005; GP 47779) is a voltage-gated sodium channel blocker with anticonvulsant and mood-stabilizing effects[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Neurological Disease

[Target]

Sodium Channel[1]

[In Vivo]

Eslicarbazepine acetate (ESL) is an oral pro-drug that is rapidly and extensively metabolized by the liver via a hydrolytic first-pass metabolism into S-Licarbazepine, the biologically active drug. The plasma level of the prodrug remains below quantification[1]. ESL is a potent antiepileptic agent with a spectrum of action essentially limited to partial-onset and generalized tonic-clonic seizures. Its main mechanism of action is by blocking the voltage-gated sodium channel. ESL works by blocking the voltage-gated sodium channel, which play an essential role in the generation and propagation of the epileptic discharge. ESL is well absorbed after oral administration with a bio-availability about 16% higher than that observed after an equivalent dose of Oxcarbazepine (OXC)[1].

[References]

[1]. Rajinder P Singh, et al. A review of eslicarbazepine acetate for the adjunctive treatment of partial-onset epilepsy. J Cent Nerv Syst Dis. 2011 Jul 20;3:179-87.

Chemical & Physical Properties

[ Density]:
1.336g/cm3

[ Boiling Point ]:
431.3ºC at 760mmHg

[ Melting Point ]:
186-189ºC

[ Molecular Formula ]:
C₁₅H₁₄N₂O₂

[ Molecular Weight ]:
254.28400

[ Flash Point ]:
214.6ºC

[ Exact Mass ]:
254.10600

[ PSA ]:
66.56000

[ LogP ]:
3.25820

[ Vapour Pressure ]:
3.33E-08mmHg at 25°C

[ Index of Refraction ]:
1.677

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H332-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338

[ Hazard Codes ]:
N,Xn,F

[ Risk Phrases ]:
51/53-36-20/21/22-11

[ Safety Phrases ]:
61-36/37-26-16

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

First MEPS/HPLC assay for the simultaneous determination of venlafaxine and O-desmethylvenlafaxine in human plasma.

Bioanalysis 6(22) , 3025-38, (2014)

A new high-performance liquid chromatography-fluorescence detection assay based on microextraction by packed sorbent as sample preparation approach is described to quantify venlafaxine (VEN) and its m...

Evaluation of the matrix effect of different sample matrices for 33 pharmaceuticals by post-column infusion.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1000 , 84-94, (2015)

Matrix effects that occur during quantitative measurement by liquid chromatography mass spectrometry specifically when using electrospray ionization are a widely recognized phenomenon. Sample matrix c...