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    Chemistry

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    Also known as: 236395-14-5, Bia 2-093, Zebinix, Exalief, Aptiom, Stedesa
    Molecular Formula
    C17H16N2O3
    Molecular Weight
    296.32  g/mol
    InChI Key
    QIALRBLEEWJACW-INIZCTEOSA-N
    FDA UNII
    BEA68ZVB2K
    Eslicarbazepine Acetate
    Eslicarbazepine acetate (ESL) is an anticonvulsant medication approved for use in Europe, the United States and Canada as an adjunctive therapy for partial-onset seizures that are not adequately controlled with conventional therapy. Eslicarbazepine acetate is a prodrug that is rapidly converted to eslicarbazepine, the primary active metabolite in the body. Eslicarbazepine's mechanism of action is not well understood, but it is known that it does exert anticonvulsant activity by inhibiting repeated neuronal firing and stabilizing the inactivated state of voltage-gated sodium channels, thus preventing their return to the activated state during which seizure activity can occur. Eslicarbazepine acetate is marketed as Aptiom in North America and Zebinix or Exalief in Europe. It is available in 200, 400, 600, or 800mg tablets that are taken once daily, with or without food. Eslicarbazepine acetate is associated with numerous side effects including dizziness, drowsiness, nausea, vomiting, diarrhea, headache, aphasia, lack of concentration, psychomotor retardation, speech disturbances, ataxia, depression and hyponatremia. It is recommended that patients taking eslicarbazepine acetate be monitored for suicidality.
    1 2D Structure

    Eslicarbazepine Acetate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(5S)-11-carbamoyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl] acetate
    2.1.2 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
    2.1.3 InChI Key
    QIALRBLEEWJACW-INIZCTEOSA-N
    2.1.4 Canonical SMILES
    CC(=O)OC1CC2=CC=CC=C2N(C3=CC=CC=C13)C(=O)N
    2.1.5 Isomeric SMILES
    CC(=O)O[C@H]1CC2=CC=CC=C2N(C3=CC=CC=C13)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    BEA68ZVB2K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 10-acetoxy-10,11-dihydro-5h-dibenz(b,f)azepine-5-carboxamide

    2. Aptiom

    3. Bia 2-093

    4. Bia-2-093

    5. Zebinix

    2.3.2 Depositor-Supplied Synonyms

    1. 236395-14-5

    2. Bia 2-093

    3. Zebinix

    4. Exalief

    5. Aptiom

    6. Stedesa

    7. Erelib

    8. Pazzul

    9. Bia-2-093

    10. Eslicarbazepine (acetate)

    11. (s)-5-carbamoyl-10,11-dihydro-5h-dibenzo[b,f]azepin-10-yl Acetate

    12. Sep-0002093

    13. Eslicarbazepine Acetate [usan]

    14. Bea68zvb2k

    15. Chembl87992

    16. Sep - 0002093

    17. Chebi:87016

    18. [(5s)-11-carbamoyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl] Acetate

    19. Bia-2093

    20. Exelief

    21. (s)-(-)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide

    22. S-(-)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide

    23. Eslicarbazepine Acetate (usan)

    24. (10s)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide

    25. (10s)-5-carbamoyl-10,11-dihydro-5h-dibenzo[b,f]azepin-10-yl Acetate

    26. (s)-10-acetoxy- 10,11-dihydro- 5h-dibenz[b,f]azepine- 5-carboxamide

    27. 5h-dibenz[b,f]azepine-5-carboxamide, 10-(acetyloxy)-10,11-dihydro-, (10s)-

    28. Sep 0002093

    29. Unii-bea68zvb2k

    30. (10s)-5-carbamoyl-10,11-dihydro-5h-dibenzo(b,f)azepin-10-yl Acetate

    31. 5h-dibenz(b,f)azepine-5-carboxamide, 10-(acetyloxy)-10,11-dihydro-, (10s)-

    32. Bia 2093

    33. Zebinix (tn)

    34. Aptiom (tn)

    35. Eslicarbazepine-acetate

    36. Eslicarbazapine Acetate

    37. Schembl250594

    38. Zinc7295

    39. Dtxsid90178308

    40. Hms3263m06

    41. Hms3885n14

    42. Hy-b0703

    43. Eslicarbazepine Acetate [mi]

    44. Tox21_501102

    45. Bdbm50240669

    46. Mfcd06798333

    47. S4657

    48. Akos005145781

    49. Ccg-222406

    50. Db09119

    51. Eslicarbazepine Acetate [mart.]

    52. Eslicarbazepine Acetate [vandf]

    53. Lp01102

    54. Sdccgsbi-0633789.p001

    55. Eslicarbazepine Acetate [who-dd]

    56. Ncgc00165752-01

    57. Ncgc00165752-02

    58. Ncgc00165752-04

    59. Ncgc00165752-06

    60. Ncgc00261787-01

    61. Ac-31734

    62. As-14058

    63. Eslicarbazepine Acetate [ema Epar]

    64. E1046

    65. Eslicarbazepine Acetate [orange Book]

    66. Bia 2-093, >=98% (hplc), Solid

    67. D09612

    68. H11471

    69. Ar-270/43507894

    70. Q410273

    71. J-015175

    72. (s)-10-acetoxy-10,11-dihydro-5hdibenz( B,f)azepine-5-carboxamide

    73. 10s)-5-carbamoyl-10,11-dihydro-5h-dibenzo[b,f]azepin-10-yl Acetate

    74. 5-(aminocarbonyl)-10,11-dihydro-5h-dibenzo[b,f]azepin-10-yl Acetate

    75. 5h-dibenz9b,f)azepine-5-carboxamide, 10-(acetyloxy)-10,11-dihydro-, (10s)-

    76. Acetic Acid (s)-5-carbamoyl-10,11-dihydro-5h-dibenzo[b,f]azepin-10-yl Ester

    77. Acetic Acid 5-carbamoyl-10,11-dihydro-5h-dibenzo[b,f]azepin-10(s)-yl Ester

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 296.32 g/mol
    Molecular Formula C17H16N2O3
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass296.11609238 g/mol
    Monoisotopic Mass296.11609238 g/mol
    Topological Polar Surface Area72.6 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity440
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAptiom
    PubMed HealthEslicarbazepine (By mouth)
    Drug ClassesAnticonvulsant, Central Nervous System Agent
    Drug LabelThe chemical name of APTIOM (eslicarbazepine acetate) is (S)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide. APTIOM is a dibenz[b,f]azepine-5-carboxamide derivative. Its molecular formula is C17H16N2O3 and its molecular weight is 296.32...
    Active IngredientEslicarbazepine acetate
    Dosage FormTablet
    RouteOral
    Strength200mg; 600mg; 800mg; 400mg
    Market StatusPrescription
    CompanySunovion Pharms

    2 of 2  
    Drug NameAptiom
    PubMed HealthEslicarbazepine (By mouth)
    Drug ClassesAnticonvulsant, Central Nervous System Agent
    Drug LabelThe chemical name of APTIOM (eslicarbazepine acetate) is (S)-10-Acetoxy-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide. APTIOM is a dibenz[b,f]azepine-5-carboxamide derivative. Its molecular formula is C17H16N2O3 and its molecular weight is 296.32...
    Active IngredientEslicarbazepine acetate
    Dosage FormTablet
    RouteOral
    Strength200mg; 600mg; 800mg; 400mg
    Market StatusPrescription
    CompanySunovion Pharms

    4.2 Drug Indication

    Eslicarbazepine acetate is indicated as adjunctive therapy in the treatment of partial-onset seizures that are not adequately controlled with conventional therapy in epileptic patients.

    FDA Label

    Zebinix is indicated as adjunctive therapy in adults, adolescents and children aged above 6 years, with partial-onset seizures with or without secondary generalisation.

    Exalief is indicated as adjunctive therapy in adults with partial-onset seizures with or without secondary generalisation.

    Treatment of epilepsy with partial-onset seizures

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Eslicarbazepine acetate is associated with a dose- and concentration-dependant increase in heart rate and prolongation of PR interval.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Voltage-Gated Sodium Channel Blockers

    A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Cytochrome P450 3A4 Inducers [MoA]; Decreased Central Nervous System Disorganized Electrical Activity [PE]; Cytochrome P450 2C19 Inhibitors [MoA]
    5.4 ATC Code

    N03AF04

    N03AF04

    5.5 Absorption, Distribution and Excretion

    Absorption

    Eslicarbazepine active metabolite has a high bioavailability and reaches peak serum concentration 1-4 hours after a given dose. Eslicarbazepine acetate absorption is not affected by food.

    Route of Elimination

    Eslicarbazepine acetate and its metabolites are eliminated primarily via renal excretion. Eslicarbazepine active metabolite is excreted two-thirds in the unchanged form and one-third as a glucuronide conjugate. This accounts for around 90% of total metabolites excreted, with the remaining 10% being minor metabolites. Renal tubular reabsorption is expected to occur with eslicarbazepine.

    Volume of Distribution

    The apparent volume of distribution of eslicarbazepine is 61.3 L for a body weight of 70 kg based on population PK analysis.

    Clearance

    Renal clearance of eslicarbazepine was found to be approximately 20 mL/min in healthy subjects with normal renal function.

    5.6 Metabolism/Metabolites

    Eslicarbazepine acetate is rapidly and extensively metabolized to its major active metabolite, eslicarbazepine, via hydrolytic first-pass metabolism. Eslicarbazepine corresponds to about 92% of systemic exposure. Minor active metabolites (R)-licarbazepine and oxcarbazepine consist of <5% of systemic exposure. Active metabolites are then metabolized to inactive glucuronides that correspond to about 3% of systemic exposure. Eslicarbazepine had a moderate inhibitory effect on CYP2C19 and a mild activation of UGT1A1-mediated glucuronidation when studied in human hepatic microsomes. It has been shown to induce CYP3A4 enzymes in vivo.

    5.7 Biological Half-Life

    The apparent plasma half-life of eslicarbazepine is 10-20 hours in healthy subjects and 13-20 hours in epilepsy patients. Steady-state plasma concentrations are attained after 4 to 5 days of once daily dosing.

    5.8 Mechanism of Action

    Eslicarbazepine acetate is converted to the active metabolite eslicarbazepine which carries out its anticonvulsant activity. The exact mechanism of action is unknown, but it is thought to involve the inhibition of voltage-gated sodium channels. In in vitro electrophysiological studies, eslicarbazepine was shown to inhibit repeated neuronal firing by stabilizing the inactivated state of voltage-gated sodium channels and preventing their return to the activated state. In vitro studies also showed eslicarbazepine inhibiting T-type calcium channels, which likely also has a role in anticonvulsant activity.

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    05-Feb-2021
    04-Sep-2024
    KGS
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