| Identification | Back Directory | [Name]
BIA 2-093 | [CAS]
236395-14-5 | [Synonyms]
Aptiom
Exalief
Stedesa
Zebinix
Sep 0002093
BIA 2-093;APTIOM
S-Licarbazepine Acetate
EslicarbazepineAcetate>
Licarbazepine Acetate S-Isomer
Eslicarbazepine acetate Impurity
Eslicarbazepine Acetate BIA 2-093
Eslicarbazepine acetate (racemate)
Licarbazepine Impurity 4(Licarbazepine Acetate S-Isomer)
(S)-5-CarbaMoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate
S(+)-10-acetoxy-10,11-Dihydro-10-5H-dibenz[b,f]azepine-5-carboxamide
(S)-(-)-10-ACETOXY-10,11-DIHYDRO-5H-DIBENZO/B,F/AZEPINE-5-CARBOXAMIDE-
(10S)-10-(Acetyloxy)-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxaMide
Acetic acid 5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl ester
5H-Dibenz[b,f]azepine-5-carboxaMide, 10-(acetyloxy)-10,11-dihydro-, (10S)-
Acetic acid 5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10(S)-yl ester | [EINECS(EC#)]
636-617-2 | [Molecular Formula]
C17H16N2O3 | [MDL Number]
MFCD06798333 | [MOL File]
236395-14-5.mol | [Molecular Weight]
296.324 |
| Chemical Properties | Back Directory | [Melting point ]
183-185°C | [Boiling point ]
427.4±55.0 °C(Predicted) | [density ]
1.32 | [storage temp. ]
2-8°C
| [solubility ]
H2O: insoluble
| [form ]
solid
| [pka]
13.97±0.40(Predicted) | [color ]
white
| [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 | [InChIKey]
QIALRBLEEWJACW-INIZCTEOSA-N | [SMILES]
CC(=O)O[C@H]1Cc2ccccc2N(C(N)=O)c3ccccc13 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [HS Code ]
2934.99.3000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
Although epilepsy is a neurological disorder with varying etiology
and severity, the common feature is unprovoked, recurring seizures.
Even when traditional AEDs, such as phenobarbital,
phenytoin, carbamazepine, and valproate, control seizure activity, their
effectiveness is hampered by considerable side effects and the tendency
for drug-drug interactions. Designed for improved efficacy and safety,
eslicarbazepine acetate is a third-generation AED that has been approved
as adjunctive therapy for partial-onset seizures with or without secondary generalization. As a member of the carbamazepine family (first generation), it is the prodrug of eslicarbazepine and the active metabolite of
oxcarbazepine (second generation).
. | [Chemical Properties]
White to Off-White Solid | [Originator]
BIAL Group (Spain) | [Uses]
Eslicarbazepine acetate, (BIA 2-093), is a promising antiepileptic drug structurally related to Carbamazepine and Oxcarbazepine. | [Definition]
ChEBI: The acetate ester, with S configuration, of licarbazepine. An anticonvulsant, it is approved for use in Europe and the United States as an adjunctive therapy for epilepsy. | [Brand name]
Zebinix; Exalief, Stedesa | [Side effects]
The most
common adverse events occurring with an incidence of >2% were dizziness, somnolence, nausea, diplopia, headache, vomiting, abnormal coordination, blurred vision, vertigo, and fatigue. While most of these side effects appeared to be mild to moderate, they did display a dose dependency. Although eslicarbazepine acetate is only contraindicated in patients with a known hypersensitivity to the carbamazepine family of AEDs, caution should be exercised in patients with cardiac conduction abnormalities (potential for prolongations in PR intervals), renal impairment, and in patients of Han Chinese and Thai origin since the presence of HLA-B*1502 allele in these individuals has been shown to be strongly associated with the risk of developing Stevens-Johnson syndrome. Regarding drug interactions, eslicarbazepine acetate may decrease the effectiveness of hormonal contraceptives, so alternative or additional methods of contraception should be considered. | [References]
[1] JAN BENES. Anticonvulsant and Sodium Channel-Blocking Properties of Novel 10,11-Dihydro-5H-dibenz[b,f]azepine-5-carboxamide Derivatives[J]. Journal of Medicinal Chemistry, 1999, 42 14: 2582-2587. DOI: 10.1021/jm980627g
[2] GERMáN SIERRA-PAREDES. Anticonvulsant effect of eslicarbazepine acetate (BIA 2-093) on seizures induced by microperfusion of picrotoxin in the hippocampus of freely moving rats[J]. Epilepsy Research, 2006, 72 2: Pages 140-146. DOI: 10.1016/j.eplepsyres.2006.07.010
[3] RAFAEL TOLEDANO . Efficacy and safety of eslicarbazepine acetate monotherapy for partial-onset seizures: Experience from a multicenter, observational study[J]. Epilepsy & Behavior, 2017, 73: Pages 173-179. DOI: 10.1016/j.yebeh.2017.02.028 |
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