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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18N2O3
Molecular Weight 250.2936
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Lacosamide

SMILES

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

InChI

InChIKey=VPPJLAIAVCUEMN-GFCCVEGCSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H18N2O3
Molecular Weight 250.2936
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lacosamide is an anticonvulsant that is FDA approved for the treatment of partial-onset seizures. The precise mechanism by which lacosamide exerts its antiepileptic effects in humans remains to be fully elucidated. In vitro electrophysiological studies have shown that lacosamide selectively enhances slow inactivation of voltage-gated sodium channels, resulting in stabilization of hyperexcitable neuronal membranes and inhibition of repetitive neuronal firing Common adverse reactions include diplopia, headache, dizziness, nausea. Patients with renal or hepatic impairment who are taking strong inhibitors of CYP3A4 and CYP2C9 may have a significant increase in exposure to Lacosamide tablets.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
164.0 µM [EC50]
1797.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIMPAT
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
2935.3 ng/mL
100 mg 1 times / day multiple, oral
LACOSAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
59120 ng × h/mL
100 mg 1 times / day multiple, oral
LACOSAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.47 h
100 mg 1 times / day multiple, oral
LACOSAMIDE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Initially, give 50 mg twice daily (100 mg/day). The dose may be increased, based on clinical response and tolerability, at weekly intervals by 100 mg/day given as two divided doses to a daily dose of 200 to 400 mg/day.
Route of Administration: Other
In Vitro Use Guide
In recombinant systems the effect of LCM on the potassium current mediated by the human hERG channel was studied. Inhibition of this channel has been associated with fatal arrhythmias. LCM only minimally affected hERG current at concentrations as high as 3000 uM/L.
Substance Class Chemical
Record UNII
563KS2PQY5
Record Status Validated (UNII)
Record Version