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CAS 175481-36-4

Chemistry

Chemistry

Also known as: 175481-36-4, Erlosamide, Vimpat, (r)-2-acetamido-n-benzyl-3-methoxypropanamide, Harkoseride, Spm 927

Molecular Formula

C₁₃H₁₈N₂O₃

Molecular Weight

250.29 g/mol

InChI Key

VPPJLAIAVCUEMN-GFCCVEGCSA-N

FDA UNII

563KS2PQY5

Lacosamide is a functionalized amino acid compound specifically synthesized as an anticonvulsive drug to use as add-on therapy for partial-onset seizures with antinociceptive and neuroprotective activities. Lacosamide selectively enhances slow inactivation of voltage-gated sodium channels without affecting fast inactivation, thereby stabilizing hyperexcitabe neuronal membranes. Furthermore, this agent binds to collapsin response mediator protein 2 (CRMP2; DPYSL2), a cytosolic phosphoprotein expressed in most tissues. In the nervous system, CRMP2 acts as a mediator of growth cone collapse as well as modifies axon number, length, and neuronal polarity.

The physiologic effect of lacosamide is by means of Decreased Central Nervous System Disorganized Electrical Activity.

1 2D Structure

CAS 175481-36-4

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-acetamido-N-benzyl-3-methoxypropanamide

2.1.2 InChI

InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m1/s1

2.1.3 InChI Key

VPPJLAIAVCUEMN-GFCCVEGCSA-N

2.1.4 Canonical SMILES

CC(=O)NC(COC)C(=O)NCC1=CC=CC=C1

2.1.5 Isomeric SMILES

CC(=O)N[C@H](COC)C(=O)NCC1=CC=CC=C1

2.2 Other Identifiers

2.2.1 UNII

563KS2PQY5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(acetylamino)-3-methoxy-n-(phenylmethyl)-, (2r)-

2. Add-234037

3. Ertosamide

4. Harkoseride

5. Spm-927

2.3.2 Depositor-Supplied Synonyms

1. 175481-36-4

2. Erlosamide

3. Vimpat

4. (r)-2-acetamido-n-benzyl-3-methoxypropanamide

5. Harkoseride

6. Spm 927

7. Spm-927

8. (2r)-2-acetamido-n-benzyl-3-methoxypropanamide

9. (r)-lacosamide 1

10. Propanamide, 2-(acetylamino)-3-methoxy-n-(phenylmethyl)-, (2r)-

11. Add 243037

12. Add-234037

13. Chembl58323

14. 563ks2pqy5

15. Add-243037

16. Erlosamide [inn]

17. Ncgc00253740-01

18. (r)-2-acetamido-n-benzyl-3-methoxypropionamide.

19. (r)-2-acetylamino-n-benzyl-3-methoxy-propionamide

20. Lacosamide [usan]

21. (+)-(2r)-2-(acetylamino)-n-benzyl-3-methoxypropanamide

22. Ertosamide

23. Add 234037

24. Harkeroside

25. Unii-563ks2pqy5

26. Lacosamide [usan:inn:ban]

27. Lacosamide Cv

28. Spm-929

29. Lacosamide Racemate

30. Lacosamide- Bio-x

31. (2r)-2-(acetylamino)-n-benzyl-3-methoxypropanamide

32. Vimpat (tn)

33. Lacosamide [mi]

34. Lacosamide [inn]

35. Lacosamide [jan]

36. Lacosamide [vandf]

37. Lacosamide [mart.]

38. (r)-n-benzyl-2-acetamido-3-methoxypropionamide

39. Dsstox_cid_31455

40. Dsstox_rid_97341

41. Lacosamide [who-dd]

42. Dsstox_gsid_57666

43. Schembl35330

44. Lacosamide (jan/usan/inn)

45. Lacosamide [ema Epar]

46. Gtpl7472

47. Zinc7673

48. Dea No. 2746

49. Lacosamide Cv [usp-rs]

50. Dtxsid1057666

51. Lacosamide [orange Book]

52. Lacosamide [ep Monograph]

53. Chebi:135939

54. Lacosamide [usp Monograph]

55. Bcp02197

56. Tox21_113857

57. Bdbm50300204

58. Mfcd08272557

59. Akos005146274

60. Lacosamide 1.0 Mg/ml In Acetonitrile

61. Cs-0529

62. Db06218

63. Ks-1227

64. Ac-22750

65. Am808141

66. Bl164605

67. Hy-13015

68. A3897

69. Bb 0260890

70. Cas-175481-36-4

71. (r)-n-benzyl-2-acetamido-3-methoxypropanamide

72. D07299

73. (2r)-n-benzyl-2-acetamido-3-methoxypropanamide

74. (r)-2-acetamido-n-benzyl-3-methoxypropionamide

75. (r)-n-benzyl 2-acetamido-3-methoxypropionamide

76. (r)-n-benzyl 2-acetamido-3-methoxypropionamide,

77. Ab01559947-01

78. (2r)-2-acetylamino-n-benzyl-3-methoxypropanamide

79. (r)-2-acetylamino-n-benzyl-3-methoxypropionamide

80. 481l364

81. Ar-270/11402703

82. Q420077

83. Sr-01000942286

84. Sr-01000942286-1

85. (2r)-2-acetamido-3-methoxy-n-(phenylmethyl)propanamide

86. 2-(acetylamino)-3-methoxy-n-(phenylmethyl)-, (2r)-

87. Z1550648754

88. Lacosamide Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₈N₂O₃
Molecular Weight	250.29 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	250.13174244 g/mol
Monoisotopic Mass	250.13174244 g/mol
Topological Polar Surface Area	67.4 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	275
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 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	VIMPAT
Active Ingredient	LACOSAMIDE
Company	UCB INC (Application Number: N022253. Patent: RE38551); UCB INC (Application Number: N022254. Patent: RE38551); UCB INC (Application Number: N022255. Patent: RE38551)

4.2 Drug Indication

Lacosamide is indicated for adjunctive therapy for partial onset seizures in patients with epilepsy over 17 years old. Injection is indicated for short term use when oral therapy is not feasible.

FDA Label

Vimpat is indicated as monotherapy and adjunctive therapy in the treatment of partial-onset seizures with or without secondary generalisation in adults, adolescents and children from 4 years of age with epilepsy.

Lacosamide Accord is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in adults, adolescents and children from 4 years of age with epilepsy.

Lacosamide Accord is indicated as adjunctive therapy

in the treatment of partial-onset seizures with or without secondary generalisation in adults, adolescents and children from 4 years of age with epilepsy.

in the treatment of primary generalised tonic-clonic seizures in adults, adolescents and children from 4 years of age with idiopathic generalised epilepsy.

Lacosamide UCB is indicated as monotherapy and adjunctive therapy in the treatment of partial-onset seizures with or without secondary generalisation in adults, adolescents and children from 4 years of age with epilepsy.

Treatment of epilepsy with partial-onset seizures

Treatment of generalised epilepsy and epileptic syndromes

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lacosamide therapy is correlated with a decrease in seizure frequency. It should be noted that in group analyses, dosages above 400 mg/day do not appear to result in additional benefit.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

LACOSAMIDE

5.2.2 FDA UNII

563KS2PQY5

5.2.3 Pharmacological Classes

Decreased Central Nervous System Disorganized Electrical Activity [PE]; Anti-epileptic Agent [EPC]; Decreased Central Nervous System Disorganized Electrical Activity [PE]

5.3 ATC Code

N03AX18

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX18 - Lacosamide

5.4 Absorption, Distribution and Excretion

Absorption

Lacosamide has a negligible first pass effect with bioavailability of about 100%. The maximum Lacosamide plasma concentrations occur about 1-4 hours after oral administration, and the pharmacokinetics of Lacosamide are dose proportional. Food does not affect absorption.

Route of Elimination

Lacosamide is eliminated primarily from the systemic circulation by biotransformation and renal excretion.

Volume of Distribution

approximately 0.6 L/kg; thus close to the volume of total body water.

Clearance

95% recovered in the urine 0.5% in the feces

5.5 Metabolism/Metabolites

Lacosamide is a CYP2C19 substrate. The relative contribution of other CYP isoforms or non-CYP enzymes in the metabolism of lacosamide is not known. Primary compounds excreted were unchanged lacosamide (approximately 40% of the dose), its O-desmethyl metabolite (approximately 30%), and a structurally unknown polar fraction (~20%). The plasma exposure of the major human metabolite, O-desmethyl-lacosamide, is approximately 10% of that of lacosamide. This metabolite has no known pharmacological activity.

5.6 Biological Half-Life

13 Hours

5.7 Mechanism of Action

It is proposed that lacosamide's inhibition of sodium channels is responsible for analgesia. Lacosamide may be selective for inhibiting depolarized neurons rather than neurons with normal resting potentials. Pain and nociceptor hyperexcitability are associated with neural membrane depolarization. Lacosamide binds to collapsin response mediator protein-2 (CRMP-2), a phosphoprotein which is expressed primarily in the nervous system and is involved in neuronal differentiation and control of axonal outgrowth. The role CRMP-2 of binding in seizure control is hasn't been elucidated.