Details of the Drug

General Information of Drug (ID: DMVM6QR)

• Drug Name: Lacosamide
• Synonyms: Erlosamide; Harkoseride; Vimpat; Erlosamide [INN]; Lacosamide [USAN]; ADD 234037; SPM 927; ADD-234037; SPM-927; SPM-929; Erlosamide, Vimpat, Lacosamide; Lacosamide (USAN/INN); (2R)-2-(Acetylamino)-N-benzyl-3-methoxypropanamide; (2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide; (2R)-2-acetamido-N-benzyl-3-methoxypropanamide

Indication

Disease Entry	ICD 11	Status	REF
Convulsion	8A68.Z	Approved	[1]
Epilepsy	8A60-8A68	Approved	[2]
Diabetic neuropathy	8C0Z	Phase 3	[1]

• Therapeutic Class: Analgesics
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 250.29
  Logarithm of the Partition Coefficient (xlogp); 0.3
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 0.57 mL/min/kg [4]
  Elimination: 40% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 13 hours [4]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 22.8297 micromolar/kg/day [5]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [4]
  Vd: The volume of distribution (Vd) of drug is 0.6 L/kg []
  Water Solubility: The ability of drug to dissolve in water is measured as 2 mg/mL [3]
• Chemical Identifiers:
  Formula: C13H18N2O3
  IUPAC Name: (2R)-2-acetamido-N-benzyl-3-methoxypropanamide
  Canonical SMILES: CC(=O)N[C@H](COC)C(=O)NCC1=CC=CC=C1
  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
  InChIKey: VPPJLAIAVCUEMN-GFCCVEGCSA-N
• Cross-matching ID:
  PubChem CID: 219078
  ChEBI ID: CHEBI:135939
  CAS Number: 175481-36-4
  DrugBank ID: DB06218
  TTD ID: D05OFX
  INTEDE ID: DR0911
  ACDINA ID: D00346
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dihydropyrimidinase related protein 2 (DPYSL2)	TTZCW3T	DPYL2_HUMAN	Modulator	[6]
Voltage-gated sodium channel (Nav)	TTIG65Q	NOUNIPROTAC	Inhibitor	[2]
Voltage-gated sodium channel alpha Nav1.9 (SCN11A)	TTN9VTF	SCNBA_HUMAN	Inhibitor	[2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[7]
Mephenytoin 4-hydroxylase (CYP2C19) Main DME	DEGTFWK	CP2CJ_HUMAN	Substrate	[8]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Lacosamide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Lacosamide caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[9]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Lacosamide caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[9]
Levomilnacipran	DMV26S8	Moderate	Antagonize the effect of Lacosamide when combined with Levomilnacipran.	Chronic pain [MG30]	[10]
Pasireotide	DMHM7JS	Moderate	Increased risk of atrioventricular block by the combination of Lacosamide and Pasireotide.	Cushing syndrome [5A70]	[11]
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Lacosamide when combined with Vilazodone.	Depression [6A70-6A7Z]	[10]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Lacosamide when combined with Vortioxetine.	Depression [6A70-6A7Z]	[10]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Lacosamide when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[10]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Lacosamide and Esketamine.	Depression [6A70-6A7Z]	[9]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Lacosamide caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[9]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Lacosamide caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[9]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Lacosamide caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[9]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Lacosamide and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[12]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Lacosamide and Lasmiditan.	Migraine [8A80]	[13]
Siponimod	DM2R86O	Major	Increased risk of bradycardia by the combination of Lacosamide and Siponimod.	Multiple sclerosis [8A40]	[9]
Fingolimod	DM5JVAN	Moderate	Increased risk of bradycardia by the combination of Lacosamide and Fingolimod.	Multiple sclerosis [8A40]	[14]
Ozanimod	DMT6AM2	Moderate	Increased risk of atrioventricular block by the combination of Lacosamide and Ozanimod.	Multiple sclerosis [8A40]	[15]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Lacosamide caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[9]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 2	E00446	2723854	Colorant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Lacosamide 50 mg tablet	50 mg	Oral Tablet	Oral
Lacosamide 200 mg tablet	200 mg	Oral Tablet	Oral
Lacosamide 150 mg tablet	150 mg	Oral Tablet	Oral
Lacosamide 100 mg tablet	100 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7472).
• [2] Antibodies and venom peptides: new modalities for ion channels. Nat Rev Drug Discov. 2019 May;18(5):339-357.
• [3] BDDCS applied to over 900 drugs
• [4] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [5] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [6] 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
• [7] Lacosamide: what can be expected from the next new antiepileptic drug? Epilepsy Curr. 2009 Sep-Oct;9(5):133-4.
• [8] Lacosamide therapeutic monitoring in patients with epilepsy: effect of concomitant antiepileptic drugs. Ther Drug Monit. 2013 Dec;35(6):849-52.
• [9] Cerner Multum, Inc. "Australian Product Information.".
• [10] Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
• [11] Canadian Pharmacists Association.
• [12] Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
• [13] Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
• [14] Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
• [15] Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.