CAS 104746-04-5

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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

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

CAS 104746-04-5

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 Formula	C₁₅H₁₄N₂O₂
Molecular Weight	254.28 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	254.105527694 g/mol
Monoisotopic Mass	254.105527694 g/mol
Topological Polar Surface Area	66.6 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	347
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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