Aptiom

Eslicarbazepine acetate

Clinical data
Trade names	Aptiom, Zebinix, Exalief
AHFS/Drugs.com	Aptiom
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	By mouth (tablets)
ATC code	N03AF04 (WHO)
Legal status
Legal status	US: ℞-only ℞ (Prescription only)
Pharmacokinetic data
Protein binding	~30%
Metabolism	UGT (?)
Metabolites	Eslicarbazepine (active), glucuronides (inactive), etc.
Biological half-life	10–20 hours
Excretion	~90% renal
Identifiers
IUPAC name (S)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide
CAS Number	236395-14-5
PubChem (CID)	179344
DrugBank	DB09119
ChemSpider	156110
UNII	BEA68ZVB2K
KEGG	D09612
ChEBI	CHEBI:87016
ChEMBL	CHEMBL87992 Y
ECHA InfoCard	100.164.398
Chemical and physical data
Formula	C17H16N2O3
Molar mass	296.320 g/mol
3D model (Jmol)	Interactive image
SMILES CC(=O)OC2Cc1ccccc1N(C(N)=O)c3c2cccc3
InChI 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-/m0/s1 Key:QIALRBLEEWJACW-INIZCTEOSA-N

Eslicarbazepine acetate (trade names Aptiom in the US, Zebinix in Europe, Exalief in Russia), abbreviated as ESL, is an anticonvulsant medication approved for use in Europe and the United States as monotherapy or adjunctive therapy (additional therapy) for partial-onset seizures epilepsy.

Similarly to oxcarbazepine, ESL behaves as a prodrug to (S)-(+)-licarbazepine. As such, their mechanisms of action are identical.

Eslicarbazepine acetate is contraindicated in people with second- or third-degree atrioventricular block, a type of heart block, and in people who are hypersensitive to eslicarbazepine, oxcarbazepine or carbazepine.

Adverse effects are similar to oxcarbazepine. The most common ones (more than 10% of patients) are tiredness and dizziness. Other fairly common side effects (1 to 10%) include impaired coordination, gastrointestinal disorders such as diarrhoea, nausea and vomiting, rash (1.1%), and hyponatraemia (low sodium blood levels, 1.2%).

Symptoms of overdosing are similar to adverse effects of standard doses. They include (severe) hyponatraemia, somnolence, walking difficulties, hemiparesis (weakness of one side of the body), diplopia, and gastrointestinal disorders. No specific antidote is available. Eslicarbazepine and metabolites can be dialyzed.

Like oxcarbazepine, eslicarbazepine can reduce plasma levels of drugs that are metabolized by the liver enzymes CYP3A4 (verified in studies for simvastatin and the oral contraceptive levonorgestrel/ethinylestradiol) and UDP-glucuronosyltransferase, and increase plasma levels of drugs metabolized by CYP2C19.