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    Also known as: 104746-04-5, (s)-licarbazepine, (s)-10-hydroxy-10,11-dihydro-5h-dibenzo[b,f]azepine-5-carboxamide, Bia 2-194, S(+)-liscarbazepine, S-10-monohydroxy-dihydro-carbamazepin
    Molecular Formula
    C15H14N2O2
    Molecular Weight
    254.28  g/mol
    InChI Key
    BMPDWHIDQYTSHX-AWEZNQCLSA-N
    FDA UNII
    S5VXA428R4
    Eslicarbazepine
    Adjunctive Therapy for Adults with Partial-Onset Seizures
    The mechanism of action of eslicarbazepine is as a Cytochrome P450 3A4 Inducer, and Cytochrome P450 2C19 Inhibitor. The physiologic effect of eslicarbazepine is by means of Decreased Central Nervous System Disorganized Electrical Activity.
    1 2D Structure

    Eslicarbazepine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (5S)-5-hydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
    2.1.2 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)/t14-/m0/s1
    2.1.3 InChI Key
    BMPDWHIDQYTSHX-AWEZNQCLSA-N
    2.1.4 Canonical SMILES
    C1C(C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
    2.1.5 Isomeric SMILES
    C1[C@@H](C2=CC=CC=C2N(C3=CC=CC=C31)C(=O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    S5VXA428R4
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (10s)-10-hydroxy-10,11-dihydro-5h-dibenzo(b,f)azepin-5-carboxamide

    2.3.2 Depositor-Supplied Synonyms

    1. 104746-04-5

    2. (s)-licarbazepine

    3. (s)-10-hydroxy-10,11-dihydro-5h-dibenzo[b,f]azepine-5-carboxamide

    4. Bia 2-194

    5. S(+)-liscarbazepine

    6. S-10-monohydroxy-dihydro-carbamazepin

    7. Licarbazepine, (s)-

    8. (s)-mhd

    9. S5vxa428r4

    10. Ec 810-248-9

    11. (5s)-5-hydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide

    12. Bia-2-194

    13. Cgp-13751

    14. (10s)-10,11-dihydro-10-hydroxy-5h-dibenz(b,f)azepine-5-carboxamide

    15. (10s)-10,11-dihydro-10-hydroxy-5h-dibenz[b,f]azepine-5-carboxamide

    16. S-licarbazepine

    17. (10s)-10-hydroxy-10,11-dihydro-5h-dibenzo(b,f)azepin-5-carboxamide

    18. Eslicarbazepine [inn]

    19. Unii-s5vxa428r4

    20. (s)-(+)-10,11-dihydro-10-hydroxy-5h-dibenz[b,f]azepine-5-carboxamide

    21. (eslicarbazepine)

    22. (s)-(+)-10,11-dihydro-10-hydroxy-5h-dibenz(b,f)azepine-5-carboxamide

    23. Eslicarbazepine [usan:inn:ban]

    24. Monohydroxy Carbamazepine

    25. S-(+)-10,11-dihydro-10-hydroxy-5h-dibenz[b,f]azepine-5-carboxamide

    26. Eslicarbazepine [mi]

    27. Eslicarbazepine (usan/inn)

    28. Eslicarbazepine [usan]

    29. Schembl418933

    30. Eslicarbazepine [vandf]

    31. Chembl315985

    32. Gtpl7350

    33. Eslicarbazepine [mart.]

    34. Eslicarbazepine [who-dd]

    35. Eslicarbazepine (bia 2-194)

    36. Chebi:174358

    37. Dtxsid901316900

    38. Zinc896938

    39. Akos016844866

    40. Db14575

    41. Hy-114703

    42. Cs-0064132

    43. D09215

    44. (s)-10-monohydroxy-10,11-dihydro Carbamazepine

    45. J-001242

    46. Q27077226

    47. (10s)-10-hydroxy-10,11-dihydro-5h-dibenzo[b,f]azepine-5 Carboxamide

    48. (10s)-10-hydroxy-10,11-dihydro-5h-dibenzo[b,f]azepine-5-carboxamide

    49. (s)-(+)-10-hydroxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide

    50. 5h-dibenz[b,f]azepine-5-carboxamide,10,11-dihydro-10-hydroxy-,(10s)-

    51. 5h-dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10-hydroxy-, (10s)-

    52. (s)-licarbazepine; (10s)-10,11-dihydro-10-hydroxy-5h-dibenz[b,f]azepine-5-carboxamide; S-(+)-10,11-dihydro-10-hydroxy-5h-dibenz[b,f]azepine-5-carboxamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 254.28 g/mol
    Molecular Formula C15H14N2O2
    XLogP31.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass254.105527694 g/mol
    Monoisotopic Mass254.105527694 g/mol
    Topological Polar Surface Area66.6 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity347
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 FDA Pharmacological Classification
    4.1.1 Active Moiety
    ESLICARBAZEPINE
    4.1.2 FDA UNII
    S5VXA428R4
    4.1.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Cytochrome P450 2C19 Inhibitors
    4.2 ATC Code

    N - Nervous system

    N03 - Antiepileptics

    N03A - Antiepileptics

    N03AF - Carboxamide derivatives

    N03AF04 - Eslicarbazepine

    4.3 Mechanism of Action

    The precise mechanism(s) by which eslicarbazepine exerts anticonvulsant activity is unknown but is thought to involve inhibition of voltage-gated sodium channels.

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    05-Feb-2021
    31-Jul-2024
    KGS
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