Licarbazepine

Licarbazepine
	Top: (R)-(−)-licarbazepine; Bottom: (S)-(+)-licarbazepine
Clinical data
ATC code	None;
Pharmacokinetic data
Protein binding	<40%
Metabolites	Glucuronides
Excretion	Mainly renal
Identifiers
	IUPAC name (RS)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide;
CAS Number	29331-92-8;
PubChem CID	114709;
ChemSpider	102704;
UNII	XFX1A5KJ3V;
KEGG	D09215;
ChEMBL	ChEMBL1067;
CompTox Dashboard (EPA)	DTXSID50865484 ;
ECHA InfoCard	100.122.427
Chemical and physical data
Formula	C15H14N2O2
Molar mass	254.289 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES NC(=O)N1c2ccccc2CC(O)c3ccccc13;
	InChI 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); Key:BMPDWHIDQYTSHX-UHFFFAOYSA-N;

Licarbazepine is a voltage-gated sodium channel blocker with anticonvulsant and mood-stabilizing effects that is related to oxcarbazepine.^[1] It is an active metabolite of oxcarbazepine.^[1]^[2] In addition, an enantiomer of licarbazepine, eslicarbazepine ((S)-(+)-licarbazepine), is an active metabolite of eslicarbazepine acetate.^[1]^[2] Oxcarbazepine and eslicarbazepine acetate are inactive on their own, and behave instead as prodrugs to licarbazepine and eslicarbazepine, respectively, to produce their therapeutic effects.^[1]^[2]

References[]

^ ^a ^b ^c ^d Singh RP, Asconapé JJ (2011). "A review of eslicarbazepine acetate for the adjunctive treatment of partial-onset epilepsy". Journal of Central Nervous System Disease. 3: 179–87. doi:10.4137/JCNSD.S4888. PMC 3663619. PMID 23861647.
^ ^a ^b ^c Bialer M, Soares-da-Silva P (June 2012). "Pharmacokinetics and drug interactions of eslicarbazepine acetate". Epilepsia. 53 (6): 935–46. doi:10.1111/j.1528-1167.2012.03519.x. PMID 22612290. S2CID 21233948.

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[pmid23861647-1] Singh RP, Asconapé JJ (2011). "A review of eslicarbazepine acetate for the adjunctive treatment of partial-onset epilepsy". Journal of Central Nervous System Disease. 3: 179–87. doi:10.4137/JCNSD.S4888. PMC 3663619. PMID 23861647.

[pmid22612290-2] Bialer M, Soares-da-Silva P (June 2012). "Pharmacokinetics and drug interactions of eslicarbazepine acetate". Epilepsia. 53 (6): 935–46. doi:10.1111/j.1528-1167.2012.03519.x. PMID 22612290. S2CID 21233948.

[1]

[2]

v t Mood stabilizers
Anticonvulsants	Carbamazepine Lamotrigine Oxcarbazepine Valproate Valnoctamide Valproate pivoxil Valpromide
Atypical antipsychotics	Aripiprazole Asenapine Cariprazine Clozapine Lurasidone Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Ziprasidone
Others	Ketamine Lithium (lithium acetate, lithium carbonate, lithium chloride, lithium citrate, lithium hydroxide, lithium orotate) Omega-3 fatty acids (docosahexaenoic acid, eicosapentaenoic acid)

v t Neuropathic pain and fibromyalgia pharmacotherapies
Monoaminergics	SNRIs (e.g., duloxetine, milnacipran) TCAs (e.g., amitriptyline, nortriptyline, dosulepin) Opioid MRIs (e.g., tapentadol, tramadol)
Ion channel blockers	Anticonvulsants (e.g., gabapentin, pregabalin, mirogabalin, carbamazepine, oxcarbazepine, lacosamide, lamotrigine) Local anesthetics (e.g., lidocaine) Mexiletine TCAs (e.g., amitriptyline, nortriptyline, desipramine) Ziconotide
Others	Alpha lipoic acid Benfotiamine Botulinum toxin A Bupropion Cannabinoids (e.g., cannabis, dronabinol, nabilone) NMDA receptor antagonists (e.g., ketamine, dextromethorphan, methadone) Opioids (e.g., hydrocodone, morphine, oxycodone, methadone, buprenorphine, tramadol, tapentadol) Sodium oxybate (GHB)

v t Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Esmirtazapine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Naranol Nitroxazepine Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline (teciptiline) Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Clocapramine Clorotepine Clotiapine Clozapine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Levomepromazine/Methotrimeprazine Loxapine Lurasidone Mesoridazine Metiapine Metitepine Mosapramine Naranol Olanzapine Oxyprothepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Trifluoperazine Triflupromazine Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Others	Adosopine Atiprosin Benzoctamine Carvedilol Cidoxepin Cyclobenzaprine Methylene blue Monatepil Oxetorone Perlapine Pipazethate P7C3 Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Telenzepine Tropatepine

Clinical data
Top: (R)-(−)-licarbazepine Bottom: (S)-(+)-licarbazepine
ATC code	None
Pharmacokinetic data
Protein binding	<40%
Metabolites	Glucuronides
Excretion	Mainly renal
Identifiers
IUPAC name (RS)-10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide
CAS Number	29331-92-8
PubChem CID	114709
ChemSpider	102704
UNII	XFX1A5KJ3V
KEGG	D09215
ChEMBL	ChEMBL1067
CompTox Dashboard (EPA)	DTXSID50865484
ECHA InfoCard	100.122.427
Chemical and physical data
Formula	C₁₅H₁₄N₂O₂
Molar mass	254.289 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES NC(=O)N1c2ccccc2CC(O)c3ccccc13
InChI 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) Key:BMPDWHIDQYTSHX-UHFFFAOYSA-N