Identification
- Summary
Lacosamide is an antiepileptic drug used to treat partial-onset seizures and primary generalized tonic-clonic seizures.
- Brand Names
- Motpoly, Vimpat
- Generic Name
- Lacosamide
- DrugBank Accession Number
- DB06218
- Background
Lacosamide is an antiepileptic drug used to treat seizures. As a chiral functionalized amino acid, it works by blocking slowly inactivating components of voltage-gated sodium currents. Lacosamide exhibits a stereoselective mode of interaction with sodium channels.3 Lacosamide was first approved by the European Commission in August 2008 and was later approved by the FDA in October 2008.3 It was granted approval by Health Canada in September 2010.9
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Lacosamide (DB06218)
- Weight
- Average: 250.2936
Monoisotopic: 250.131742452 - Chemical Formula
- C13H18N2O3
- Synonyms
- (+)-(2R)-2-(ACETYLAMINO)-N-BENZYL-3-METHOXYPROPANAMIDE
- (2R)-2-(Acetylamino)-3-methoxy-N-(phenylmethyl)propanamide
- (R)-2-acetamido-N-benzyl-3- methoxypropionamide
- (R)-LACOSAMIDE 1
- Erlosamide
- Harkoseride
- Lacosamida
- Lacosamide
- Propanamide, 2-(acetylamino)-3-methoxy-N-(phenylmethyl)-, (2R)-
- External IDs
- ADD 243037
- ADD-243037
- ADD243037
- SPM 927
- SPM-927
- SPM927
Pharmacology
- Indication
In the US and Europe, lacosamide is indicated for the treatment of partial-onset seizures in children and adults.6,7,8 In Canada, it is reserved for use in adults.9
It is also used as an adjunctive therapy in the treatment of primary generalized tonic-clonic seizures in patients four years of age and older.6,8
The extended-release capsules of lacosamide are indicated for the treatment of partial-onset seizures in adults and in pediatric patients weighing at least 50 kg.7
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in management of Partial-onset seizures •••••••••••• •••••• Management of Partial-onset seizures •••••••••••• •••••• Management of Partial-onset seizures •••••••••••• ••••• •••••••••• ••••••• •••• •••••• Adjunct therapy in management of Partial-onset seizures •••••••••••• ••••• •••••••••• •••••••• •• •••••••••••• ••••••• •••••••••• ••••••• •••• •••••• Management of Partial-onset seizures •••••••••••• •••••••••• ••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Lacosamide is an antiepileptic drug with high oral potency, stereoselectivity,4 and anticonvulsant effects.2 By blocking sensory neuronal voltage-gated sodium channels that mediate neuropathic pain responses, lacosamide was shown to possess analgesic activity.1,2 Lacosamide is a chiral functionalized amino acid. The S-stereoisomer does not exhibit antiepileptic activity.2
- Mechanism of action
Caused by neuronal hyperexcitability, seizures in epilepsy involve sustained firing of sodium-dependent action potentials. The slow inactivation process, intrinsic to voltage-gated sodium channel functioning, has been implicated in the paroxysmal depolarizing shifts associated with epileptic activity.2 The exact mechanism of action of lacosamide is not fully known; however, in vitro electrophysiological studies have shown that lacosamide selectively enhances the slow inactivation of voltage-gated sodium channels, shifting the slow inactivation curve to more hyperpolarized potentials and augmenting the maximal fraction of channels in the slow inactivated state.4 This results in the stabilization of hyperexcitable neuronal membranes and inhibition of repetitive neuronal firing.2,6 Lacosamide does not affect the fast component of voltage-gated sodium currents, unlike traditional sodium channel blockers.2
Target Actions Organism USodium channel protein type 9 subunit alpha blockerHumans USodium channel protein type 3 subunit alpha blockerHumans USodium channel protein type 10 subunit alpha blockerHumans - Absorption
Lacosamide is completely absorbed after oral administration with negligible first-pass effect. It has a high absolute bioavailability of approximately 100%. Food does not affect the rate and extent of absorption. The Tmax ranges from one to four hours. Steady-state plasma concentrations are achieved after three days of twice-daily repeated administration. The pharmacokinetics of lacosamide are dose-proportional over the dose range between 100 and 800 mg, and time-invariant, with low inter- and intra-subject variability. The major O-desmethyl metabolite of lacosamide has a longer Tmax that ranges from 0.5 to 12 hours.6
After intravenous administration, Cmax is reached at the end of infusion. The 30- and 60-minute intravenous infusions are bioequivalent to the oral tablet. For the 15-minute intravenous infusion, bioequivalence was met for AUC0-tz but not for Cmax. The point estimate of Cmax was 20% higher than Cmax for oral tablet and the 90% CI for Cmax exceeded the upper boundary of the bioequivalence range. In a trial comparing the oral tablet with an oral solution containing 10 mg/mL lacosamide, bioequivalence between both formulations was shown. A single loading dose of 200 mg approximates steady-state concentrations comparable to the 100 mg twice-daily oral administration.6
- Volume of distribution
The volume of distribution is approximately 0.6 L/kg and thus close to the volume of total body water.6
- Protein binding
Lacosamide is less than 15% bound to plasma proteins.6
- Metabolism
Lacosamide is metabolized by CYP3A4, CYP2C9, and CYP2C19 to form O-desmethyl lacosamide, which is a major, pharmacologically inactive metabolite in humans. There is no enantiomeric interconversion of lacosamide.6
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- Route of elimination
Lacosamide is primarily eliminated from the systemic circulation by renal excretion and biotransformation. After oral and intravenous administration of 100 mg radiolabeled lacosamide, approximately 95% of the radioactivity was recovered in the urine and less than 0.5 % in the feces. The major compounds excreted were unchanged lacosamide (approximately 40% of the dose), its O-desmethyl metabolite (approximately 30%), and a structurally unknown polar fraction (~20%).6
- Half-life
The elimination half-life of the unchanged drug is approximately 13 hours and is not altered by different doses, multiple dosing or intravenous administration. The major O-desmethyl metabolite of lacosamide has an elimination half-life ranging from 15 to 23 hours).6
- Clearance
Not Available
- Adverse Effects
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The oral LD50 in rats is 253 mg/kg.5
Dizziness, nausea, and seizures (generalized tonic-clonic seizures, status epilepticus) were observed at doses greater than 800 mg, which is twice the maximum recommended daily dose. Cardiac conduction disorders, confusion, decreased level of consciousness, cardiogenic shock, cardiac arrest, and coma have also been observed.6
Fatal overdoses have occurred with lacosamide. As there is no specific antidote for overdose with lacosamide, standard decontamination procedures should be followed. General supportive care of the patient is indicated including monitoring of vital signs and observation of the clinical status of patient. Standard hemodialysis procedures result in significant clearance of lacosamide (reduction of systemic exposure by 50% in four hours). Hemodialysis may be indicated based on the patient's clinical state or in patients with significant renal impairment.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Reduced O-desmethyl metabolite concentrations in plasma. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Lacosamide can be increased when it is combined with Abametapir. Abatacept The metabolism of Lacosamide can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Lacosamide. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Lacosamide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Lacosamide. - Food Interactions
- Take with or without food. Food does not affect the rate and extent of absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alembic-lacosamide Tablet 150 mg Oral Alembic Pharmaceuticals Limited Not applicable Not applicable Canada 
Alembic-lacosamide Tablet 100 mg Oral Alembic Pharmaceuticals Limited Not applicable Not applicable Canada Alembic-lacosamide Tablet 200 mg Oral Alembic Pharmaceuticals Limited Not applicable Not applicable Canada Alembic-lacosamide Tablet 50 mg Oral Alembic Pharmaceuticals Limited Not applicable Not applicable Canada Lacosamide Tablet 100 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ach-lacosamide Tablet 150 mg Oral Accord Healthcare Inc 2021-04-27 Not applicable Canada Ach-lacosamide Tablet 100 mg Oral Accord Healthcare Inc 2021-04-27 Not applicable Canada Ach-lacosamide Tablet 200 mg Oral Accord Healthcare Inc 2021-04-27 Not applicable Canada Ach-lacosamide Tablet 50 mg Oral Accord Healthcare Inc 2021-04-27 Not applicable Canada Ag-lacosamide Tablet 150 mg Oral Angita Pharma Inc. 2021-12-24 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ELEPSİ 50 MG+100 MG TEDAVİYE BAŞLAMA PAKETİ, 42 ADET Lacosamide (50 mg) + Lacosamide (100 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2018-11-28 Not applicable Turkey 
ELEPSİ 50 MG+100 MG TEDAVİYE BAŞLAMA PAKETİ, 42 ADET Lacosamide (50 mg) + Lacosamide (100 mg) Tablet, film coated Oral SANTA FARMA İLAÇ SAN. A.Ş. 2018-11-28 Not applicable Turkey Lacopat-Filmtabletten Packung zur Behandlungseinleitung Lacosamide (50 mg) + Lacosamide (100 mg) + Lacosamide (150 mg) + Lacosamide (200 mg) Kit; Tablet, film coated Oral G.L. Pharma Gmb H 2018-04-17 Not applicable Austria 
Lacopat-Filmtabletten Packung zur Behandlungseinleitung Lacosamide (50 mg) + Lacosamide (100 mg) + Lacosamide (150 mg) + Lacosamide (200 mg) Kit; Tablet, film coated Oral G.L. Pharma Gmb H 2018-04-17 Not applicable Austria Lacopat-Filmtabletten Packung zur Behandlungseinleitung Lacosamide (50 mg) + Lacosamide (100 mg) + Lacosamide (150 mg) + Lacosamide (200 mg) Kit; Tablet, film coated Oral G.L. Pharma Gmb H 2018-04-17 Not applicable Austria
Categories
- ATC Codes
- N03AX18 — Lacosamide
- Drug Categories
- Acetamides
- Acetates
- Acids, Acyclic
- Alkanes
- Amides
- Anti-epileptic Agent
- Anticonvulsants
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Substrates
- Decreased Central Nervous System Disorganized Electrical Activity
- Hydrocarbons, Acyclic
- Membrane Transport Modulators
- Miscellaneous Anticonvulsants
- Nervous System
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Alpha amino acid amides / Benzene and substituted derivatives / Acetamides / Secondary carboxylic acid amides / Dialkyl ethers / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Acetamide / Alpha-amino acid amide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 563KS2PQY5
- CAS number
- 175481-36-4
- InChI Key
- VPPJLAIAVCUEMN-GFCCVEGCSA-N
- 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
- IUPAC Name
- (2R)-N-benzyl-2-acetamido-3-methoxypropanamide
- SMILES
- COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1
References
- Synthesis Reference
http://www.google.com/patents?id=IIanAAAAEBAJ&pg=PA2&source=gbsselectedpages&cad=3#v=onepage&q&f=false
- General References
- Sheets PL, Heers C, Stoehr T, Cummins TR: Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine. J Pharmacol Exp Ther. 2008 Jul;326(1):89-99. doi: 10.1124/jpet.107.133413. Epub 2008 Mar 31. [Article]
- Curia G, Biagini G, Perucca E, Avoli M: Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders. CNS Drugs. 2009;23(7):555-68. doi: 10.2165/00023210-200923070-00002. [Article]
- Perucca E, Yasothan U, Clincke G, Kirkpatrick P: Lacosamide. Nat Rev Drug Discov. 2008 Dec;7(12):973-4. doi: 10.1038/nrd2764. [Article]
- Rogawski MA, Tofighy A, White HS, Matagne A, Wolff C: Current understanding of the mechanism of action of the antiepileptic drug lacosamide. Epilepsy Res. 2015 Feb;110:189-205. doi: 10.1016/j.eplepsyres.2014.11.021. Epub 2014 Dec 3. [Article]
- European Directorate for the Quality of Medicines & HealthCare: Lacosamide MSDS [Link]
- FDA Approved Drug Products: VIMPAT (lacosamide) intravenous injection or oral solution or tablets (October 2023) [Link]
- FDA Approved Drug Products: MOTPOLY XR (lacosamide) extended-release capsules, for oral use, CV (May 2023) [Link]
- EMA Approved Drug Products: Vimpat (lacosamide) Oral Tablets [Link]
- Health Canada Approved Drug Products: VIMPAT (lacosamide) Oral Tablets or Intavenous Injection [Link]
- External Links
- KEGG Drug
- D07299
- PubChem Compound
- 219078
- PubChem Substance
- 175427063
- ChemSpider
- 189902
- BindingDB
- 50300204
- 623400
- ChEBI
- 135939
- ChEMBL
- CHEMBL58323
- ZINC
- ZINC000000007673
- PharmGKB
- PA166160048
- PDBe Ligand
- LQO
- Wikipedia
- Lacosamide
- PDB Entries
- 8s9b
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Epilepsy 2 4 Completed Treatment Partial Epilepsy 4 4 Recruiting Prevention Opioid-induced Respiratory Depression 1 4 Recruiting Treatment Acute Brain Injury / Brain Ischemia Hypoxia / Cardiac Arrest / Cerebral Ischemia / Comatose / Hypoxia, Brain / Intracranial Hemorrhages / Persistent Vegetative State / Stroke / Traumatic Brain Injury (TBI) 1 4 Recruiting Treatment Alzheimer Disease 3 / Epilepsy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 10 mg/ml Syrup Oral 1 g Syrup Oral Tablet Oral 50.000 mg Tablet, coated Oral 200 mg Tablet, coated Oral 5000000 mg Tablet, coated Oral 20000000 mg Tablet Oral 100.000 mg Solution Intravenous 10 mg Solution Parenteral 10 mg/ml Tablet, film coated Oral Injection, solution Intravenous 10 mg/1mL Solution Oral 10 mg/1mL Solution Oral 100 mg/10mL Solution Oral 150 mg/15mL Solution Oral 200 mg/20mL Solution Oral 50 mg/5mL Tablet Oral 100 mg/1 Tablet Oral 150 mg/1 Tablet Oral 200 mg/1 Tablet Oral 50 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 100 MG Tablet, film coated Oral 150 MG Tablet, film coated Oral 50 MG Syrup Oral 10 mg/ml Tablet, film coated Oral Capsule, extended release Oral 100 mg/1 Capsule, extended release Oral 150 mg/1 Capsule, extended release Oral 200 mg/1 Injection Intravenous 10 mg/1mL Kit; tablet, film coated Oral Solution Intravenous 10 mg / mL Solution Parenteral 10.000 mg Syrup Oral 1.000 g Syrup Oral 15 MG/ML Tablet Oral 100 mg Tablet Oral 150 mg Tablet Oral 200 mg Tablet Oral 200.000 mg Tablet Oral 50 mg Tablet, coated Oral Tablet, film coated Oral 50 mg/1 Solution Oral 1000 mg Tablet, coated Oral 100 mg Tablet, coated Oral 50 mg Syrup Oral 15 mg Syrup Oral 10 mg/1ml Tablet, film coated Oral 200 mg Tablet, coated Oral 150 mg Solution Intravenous 200 mg Injection, solution Intravenous 10 mg/ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5654301 No 1997-08-05 2014-08-05 US 
USRE38551 No 2004-07-06 2022-03-17 US US11337943 No 2020-06-05 2040-06-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 140-146˚C http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500064326.pdf boiling point (°C) 536.447 °C at 760 mmHg ACD/Labs water solubility 10-33.3 g/L https://sds.edqm.eu/pdf/SDS/EDQM_201700391_1.0_SDS_EN.pdf logP 0.728 ACD/Labs - Predicted Properties
Property Value Source Water Solubility 0.465 mg/mL ALOGPS logP 0.18 ALOGPS logP -0.022 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 12.46 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 67.43 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 67.57 m3·mol-1 Chemaxon Polarizability 26.68 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9771 Blood Brain Barrier + 0.7181 Caco-2 permeable - 0.6886 P-glycoprotein substrate Substrate 0.7158 P-glycoprotein inhibitor I Non-inhibitor 0.6904 P-glycoprotein inhibitor II Non-inhibitor 0.8878 Renal organic cation transporter Non-inhibitor 0.8757 CYP450 2C9 substrate Non-substrate 0.8732 CYP450 2D6 substrate Non-substrate 0.7634 CYP450 3A4 substrate Non-substrate 0.6572 CYP450 1A2 substrate Non-inhibitor 0.8084 CYP450 2C9 inhibitor Non-inhibitor 0.8704 CYP450 2D6 inhibitor Non-inhibitor 0.8775 CYP450 2C19 inhibitor Non-inhibitor 0.8201 CYP450 3A4 inhibitor Non-inhibitor 0.837 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9732 Ames test Non AMES toxic 0.7694 Carcinogenicity Non-carcinogens 0.8388 Biodegradation Not ready biodegradable 0.8499 Rat acute toxicity 2.1629 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9678 hERG inhibition (predictor II) Non-inhibitor 0.8489
Spectra
- Mass Spec (NIST)
- Download (18.4 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03dl-5920000000-9d5b2fbeb8e1c5f16b9a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0znc-9400000000-d294c9319650e545b274 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9700000000-dca3475de3ab528d0c9b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0pbc-9600000000-576d9d53a856121b38e6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kc6-9300000000-665c83929139ac8d2366 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-8900000000-73acddbff6c5d745953a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.945654 predictedDarkChem Lite v0.1.0 [M-H]- 159.19606 predictedDeepCCS 1.0 (2019) [M+H]+ 166.126654 predictedDarkChem Lite v0.1.0 [M+H]+ 161.55406 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.523054 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.6472 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
- Gene Name
- SCN9A
- Uniprot ID
- Q15858
- Uniprot Name
- Sodium channel protein type 9 subunit alpha
- Molecular Weight
- 226370.175 Da
References
- Sheets PL, Heers C, Stoehr T, Cummins TR: Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine. J Pharmacol Exp Ther. 2008 Jul;326(1):89-99. doi: 10.1124/jpet.107.133413. Epub 2008 Mar 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...
- Gene Name
- SCN3A
- Uniprot ID
- Q9NY46
- Uniprot Name
- Sodium channel protein type 3 subunit alpha
- Molecular Weight
- 226291.905 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Sheets PL, Heers C, Stoehr T, Cummins TR: Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine. J Pharmacol Exp Ther. 2008 Jul;326(1):89-99. doi: 10.1124/jpet.107.133413. Epub 2008 Mar 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Blocker
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference acro...
- Gene Name
- SCN10A
- Uniprot ID
- Q9Y5Y9
- Uniprot Name
- Sodium channel protein type 10 subunit alpha
- Molecular Weight
- 220623.605 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Sheets PL, Heers C, Stoehr T, Cummins TR: Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine. J Pharmacol Exp Ther. 2008 Jul;326(1):89-99. doi: 10.1124/jpet.107.133413. Epub 2008 Mar 31. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- FDA Approved Drug Products: VIMPAT (lacosamide) for oral or intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- FDA Approved Drug Products: VIMPAT (lacosamide) for oral or intravenous use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Contin M, Albani F, Riva R, Candela C, Mohamed S, Baruzzi A: Lacosamide therapeutic monitoring in patients with epilepsy: effect of concomitant antiepileptic drugs. Ther Drug Monit. 2013 Dec;35(6):849-52. doi: 10.1097/FTD.0b013e318290eacc. [Article]
- Bentue-Ferrer D, Tribut O, Verdier MC: [Therapeutic drug monitoring of lacosamide]. Therapie. 2012 Mar-Apr;67(2):151-5. doi: 10.2515/therapie/2012012. Epub 2012 Aug 2. [Article]
- Chung SS: New treatment option for partial-onset seizures: efficacy and safety of lacosamide. Ther Adv Neurol Disord. 2010 Mar;3(2):77-83. doi: 10.1177/1756285609355850. [Article]
- FDA Approved Drug Products: VIMPAT (lacosamide) for oral or intravenous use [Link]
Drug created at March 19, 2008 16:17 / Updated at February 20, 2024 23:55