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CAS 175481-36-4
PharmaCompass
  • Chemistry
CAS 175481-36-4
Also known as: 175481-36-4, Erlosamide, (r)-2-acetamido-n-benzyl-3-methoxypropanamide, Harkoseride, Vimpat, Erlosamide [inn]
Molecular Formula
C13H18N2O3
Molecular Weight
250.298  g/mol
InChI Key
VPPJLAIAVCUEMN-GFCCVEGCSA-N
FDA UNII
563KS2PQY5

Lacosamide is a functionalized amino acid that has activity in the maximal electroshock seizure test, and is indicated for the adjunctive treatment of partial-onset seizures and diabetic neuropathic pain. Recent studies indicate that Lacosamide only affects those neurons which are depolarized or active for long periods of time, typical of neurons at the focus of an epileptic seizure, as opposed to other antiepileptic drugs such as carbamazepine or lamotrigine which slow the recovery from inactivation and reduce the ability of neurons to fire action potentials.
Lacosamide is an Anti-epileptic Agent. 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 Depositor-Supplied Synonyms

1. 175481-36-4

2. Erlosamide

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

4. Harkoseride

5. Vimpat

6. Erlosamide [inn]

7. Spm 927

8. Spm-927

9. Unii-563ks2pqy5

10. Add 234037

11. Chembl58323

12. Spm-929

13. (2r)-2-acetamido-n-benzyl-3-methoxypropanamide

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

15. (2r)-2-(acetylamino)-n-benzyl-3-methoxypropanamide

16. Add-234037

17. Ncgc00253740-01

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

19. Lacosamide [usan]

20. Ertosamide

21. Harkeroside

22. Lacosamide [usan:inn:ban]

23. Add 243037

24. Ks-1227

25. Lacosamide Racemate

26. Vimpat (tn)

27. Lacosamide (usan/inn)

28. D05ofx

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

30. Dsstox_cid_31455

31. Dsstox_rid_97341

32. Dsstox_gsid_57666

33. Schembl35330

34. Lacosamide (jan/usan/inn)

35. Erlosamide, Vimpat, Lacosamide

36. 563ks2pqy5

37. Ac1l560m

38. Gtpl7472

39. Zinc7673

40. Dea No. 2746

41. Dtxsid1057666

42. Ctk8b7781

43. Ks-00000xoq

44. Chebi:135939

45. Molport-006-170-142

46. Vppjlaiavcuemn-gfccvegcsa-n

47. Ebd27785

48. Tox21_113857

49. Anw-58547

50. Bdbm50300204

51. Mfcd08272557

52. Akos005146274

53. Add-243037

54. An-5196

55. Cs-0529

56. Db06218

57. Rl02246

58. Ac-22750

59. Aj-08306

60. Ak-80442

61. Am808141

62. Cj-00115

63. Hy-13015

64. Or059448

65. Or231753

66. Ab0020074

67. Ab1011880

68. Ls-185541

69. Tc-064381

70. Bb 0260890

71. Cas-175481-36-4

72. Ft-0650739

73. St24026403

74. V0815

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

76. D07299

77. M-1600

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

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

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

81. Ab01559947-01

82. (2r)-2-acetamido-n-benzyl-3-methoxy-propanamide

83. (2r)-2-acetylamino-n-benzyl-3-methoxypropanamide

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

85. 481l364

86. Sr-01000942286

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

88. I01-7424

89. Sr-01000942286-1

90. I14-32137

91. (2r)-2-acetamido-3-methoxy-n-(phenylmethyl)propanamide

92. Z1550648754

93. ( )-(2r)-2-(acetylamino)-n-benzyl-3-methoxypropanamide

94. (2r)-2-(acetylamino)-n-benzyl-3-methoxypropanamide;lacosamide

95. 2-(acetylamino)-3-methoxy-n-(phenylmethyl)propanamide, (2r)-

96. Lacosamide; Propanamide,2-(acetylamino)-3-methoxy-n-(phenylmethyl)-, (r)-

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

98. 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 Weight 250.298 g/mol
Molecular Formula C13H18N2O3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass250.132 g/mol
Monoisotopic Mass250.132 g/mol
Topological Polar Surface Area67.4 A^2
Heavy Atom Count18
Formal Charge0
Complexity275
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 1  
Drug NameVIMPAT
Active IngredientLACOSAMIDE
CompanyUCB 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


Adjunctive therapy in the treatment of partial-onset seizures with or without secondary generalisation in adult and adolescent (16-18 years) patients with epilepsy.


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.


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.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety

LACOSAMIDE


5.2.2 FDA UNII

563KS2PQY5


5.2.3 Pharmacological Classes

Established Pharmacologic Class [EPC]

Anti-epileptic Agent


Physiologic Effects [PE]

Decreased Central Nervous System Disorganized Electrical Activity


5.3 ATC Code

Anatomical main group: N - Nervous system
Therapeutic subgroup: N03 - Antiepileptics
Pharmacological subgroup: N03A - Antiepileptics
Chemical subgroup: N03AX - Other antiepileptics
Chemical substance: N03AX18 - lacosamide


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

Metabolism

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.


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