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Chemistry

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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
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

Lacosamide

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 Weight 250.29 g/mol
Molecular Formula C13H18N2O3
XLogP30.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass250.13174244 g/mol
Monoisotopic Mass250.13174244 g/mol
Topological Polar Surface Area67.4 Ų
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 2  
Drug NameVimpat
PubMed HealthLacosamide
Drug ClassesAnticonvulsant
Active IngredientLacosamide
Dosage FormTablet; Solution
RouteOral; Intravenous
Strength200mg/20ml (10mg/ml); 200mg; 150mg; 10mg/ml; 100mg; 50mg
Market StatusPrescription
CompanyUcb

2 of 2  
Drug NameVimpat
PubMed HealthLacosamide
Drug ClassesAnticonvulsant
Active IngredientLacosamide
Dosage FormTablet; Solution
RouteOral; Intravenous
Strength200mg/20ml (10mg/ml); 200mg; 150mg; 10mg/ml; 100mg; 50mg
Market StatusPrescription
CompanyUcb

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


N03AX18


N03AX18


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.


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07-Jan-2022
29-May-2025
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DOSAGE - TABLET;ORAL - 100MG

USFDA APPLICATION NUMBER - 22253

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DOSAGE - TABLET;ORAL - 150MG

USFDA APPLICATION NUMBER - 22253

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DOSAGE - TABLET;ORAL - 200MG

USFDA APPLICATION NUMBER - 22253

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ABOUT THIS PAGE

Looking for 175481-36-4 / Lacosamide API manufacturers, exporters & distributors?

Lacosamide manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Lacosamide API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Lacosamide manufacturer or Lacosamide supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Lacosamide manufacturer or Lacosamide supplier.

PharmaCompass also assists you with knowing the Lacosamide API Price utilized in the formulation of products. Lacosamide API Price is not always fixed or binding as the Lacosamide Price is obtained through a variety of data sources. The Lacosamide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Lacosamide

Synonyms

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

Cas Number

175481-36-4

Unique Ingredient Identifier (UNII)

563KS2PQY5

About Lacosamide

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.

Lacosamide Manufacturers

A Lacosamide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Lacosamide, including repackagers and relabelers. The FDA regulates Lacosamide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Lacosamide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Lacosamide manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Lacosamide Suppliers

A Lacosamide supplier is an individual or a company that provides Lacosamide active pharmaceutical ingredient (API) or Lacosamide finished formulations upon request. The Lacosamide suppliers may include Lacosamide API manufacturers, exporters, distributors and traders.

click here to find a list of Lacosamide suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Lacosamide USDMF

A Lacosamide DMF (Drug Master File) is a document detailing the whole manufacturing process of Lacosamide active pharmaceutical ingredient (API) in detail. Different forms of Lacosamide DMFs exist exist since differing nations have different regulations, such as Lacosamide USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Lacosamide DMF submitted to regulatory agencies in the US is known as a USDMF. Lacosamide USDMF includes data on Lacosamide's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Lacosamide USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Lacosamide suppliers with USDMF on PharmaCompass.

Lacosamide JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Lacosamide Drug Master File in Japan (Lacosamide JDMF) empowers Lacosamide API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Lacosamide JDMF during the approval evaluation for pharmaceutical products. At the time of Lacosamide JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Lacosamide suppliers with JDMF on PharmaCompass.

Lacosamide KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Lacosamide Drug Master File in Korea (Lacosamide KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Lacosamide. The MFDS reviews the Lacosamide KDMF as part of the drug registration process and uses the information provided in the Lacosamide KDMF to evaluate the safety and efficacy of the drug.

After submitting a Lacosamide KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Lacosamide API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Lacosamide suppliers with KDMF on PharmaCompass.

Lacosamide CEP

A Lacosamide CEP of the European Pharmacopoeia monograph is often referred to as a Lacosamide Certificate of Suitability (COS). The purpose of a Lacosamide CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Lacosamide EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Lacosamide to their clients by showing that a Lacosamide CEP has been issued for it. The manufacturer submits a Lacosamide CEP (COS) as part of the market authorization procedure, and it takes on the role of a Lacosamide CEP holder for the record. Additionally, the data presented in the Lacosamide CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Lacosamide DMF.

A Lacosamide CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Lacosamide CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Lacosamide suppliers with CEP (COS) on PharmaCompass.

Lacosamide WC

A Lacosamide written confirmation (Lacosamide WC) is an official document issued by a regulatory agency to a Lacosamide manufacturer, verifying that the manufacturing facility of a Lacosamide active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Lacosamide APIs or Lacosamide finished pharmaceutical products to another nation, regulatory agencies frequently require a Lacosamide WC (written confirmation) as part of the regulatory process.

click here to find a list of Lacosamide suppliers with Written Confirmation (WC) on PharmaCompass.

Lacosamide NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Lacosamide as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Lacosamide API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Lacosamide as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Lacosamide and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Lacosamide NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Lacosamide suppliers with NDC on PharmaCompass.

Lacosamide GMP

Lacosamide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Lacosamide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Lacosamide GMP manufacturer or Lacosamide GMP API supplier for your needs.

Lacosamide CoA

A Lacosamide CoA (Certificate of Analysis) is a formal document that attests to Lacosamide's compliance with Lacosamide specifications and serves as a tool for batch-level quality control.

Lacosamide CoA mostly includes findings from lab analyses of a specific batch. For each Lacosamide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Lacosamide may be tested according to a variety of international standards, such as European Pharmacopoeia (Lacosamide EP), Lacosamide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Lacosamide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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