Lacosamide

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/204839s000lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/lacosamide.html | http://www.wikidoc.org/index.php/Lacosamide | https://www.ncbi.nlm.nih.gov/pubmed/17461888 | https://www.ncbi.nlm.nih.gov/pubmed/19552484

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 Target	Pharmacology	Potency
Voltage-gated sodium channels 1 Target ID: Voltage-gated sodium channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/17940193 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Blocker 555	164.0 µM [EC50]
Dihydropyrimidinase-related protein 2 4 Target ID: P47942 Gene ID: 25416.0 Gene Symbol: Dpysl2 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20538611 \| http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Binding Agent 1076
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22850102	Substrate 661	1797.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Partial-onset seizures 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Primary		Approved 8583	VIMPAT Approved Use VIMPAT is indicated for: Partial-onset seizures (1.1): Tablets and oral solution are indicated for adjunctive therapy in patients ≥17 years. Injection is indicated as short term replacement when oral administration is not feasible in these patients. 1.1 Partial-Onset Seizures VIMPAT (lacosamide) tablets and oral solution are indicated as adjunctive therapy in the treatment of partial-onset seizures in patients with epilepsy aged 17 years and older. VIMPAT (lacosamide) injection for intravenous use is indicated as adjunctive therapy in the treatment of partial-onset seizures in patients with epilepsy aged 17 years and older when oral administration is temporarily not feasible. Launch Date 2008
Diabetic neuropathy 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19552484 https://www.ncbi.nlm.nih.gov/pubmed/17237664	Palliative		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
13285.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/38513537/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12730.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/38513537/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.13 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22437449/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2935.3 ng/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P2.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
225522.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/38513537/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
230511.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/38513537/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
112.35 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22437449/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
59120 ng × h/mL REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P2.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22437449/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
14.47 h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P2.pdf	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:		LACOSAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Disc. AE: Dizziness, Ataxia... AEs leading to discontinuation/dose reduction: Dizziness (>1) Ataxia (>1) Vomiting (>1) Diplopia (>1) Nausea (>1) Vertigo (>1) Vision blurred (>1) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf
400 mg 1 times / day steady, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Disc. AE: Dizziness, Ataxia... AEs leading to discontinuation/dose reduction: Dizziness (>1) Ataxia (>1) Vomiting (>1) Diplopia (>1) Nausea (>1) Vertigo (>1) Vision blurred (>1) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf
600 mg 1 times / day steady, oral Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Disc. AE: Dizziness, Ataxia... AEs leading to discontinuation/dose reduction: Dizziness (>1) Ataxia (>1) Vomiting (>1) Diplopia (>1) Nausea (>1) Vertigo (>1) Vision blurred (>1) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf
12 mg/kg 1 times / day multiple, oral Studied dose Dose: 12 mg/kg, 1 times / day Route: oral Route: multiple Dose: 12 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/	unhealthy, ≥1 month ≤17 years Health Status: unhealthy Age Group: ≥1 month ≤17 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/	Other AEs: Vomiting, Dizziness... Other AEs: Vomiting (4.8%) Dizziness (4.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/
5.82 mg/kg 1 times / day multiple, oral Dose: 5.82 mg/kg, 1 times / day Route: oral Route: multiple Dose: 5.82 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/	unhealthy, ≥1 month ≤17 years Health Status: unhealthy Age Group: ≥1 month ≤17 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/	Disc. AE: Vomiting, Gait disturbance... AEs leading to discontinuation/dose reduction: Vomiting (8.5%) Gait disturbance (6.4%) Dizziness (6.4%) Somnolence (6.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/31374487/
12 g single, oral Overdose Dose: 12 g Route: oral Route: single Dose: 12 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Other AEs: Coma... Other AEs: Coma Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf
1200 mg 1 times / day multiple, oral Overdose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf
800 mg single, oral Studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/28926353	healthy Health Status: healthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28926353	Other AEs: Dysarthria, Dysphemia... Other AEs: Dysarthria (severe, 1 patient) Dysphemia (severe, 1 patient) Aphasia (severe, 1 patient) Negative thoughts (severe, 1 patient) Coordination abnormal (severe, 1 patient) Muscle weakness (severe, 2 patients) Nausea (severe, 2 patients) Vomiting (severe, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/28926353
100 mg 2 times / day steady, oral Dose: 100 mg, 2 times / day Route: oral Route: steady Dose: 100 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00440518	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00440518	Other AEs: Myocardial infarction, Knee operation... Other AEs: Myocardial infarction (serious, 1 patient) Knee operation (serious, 1 patient) Diarrhoea (below serious, 4 patients) Fatigue (below serious, 5 patients) Nasopharyngitis (below serious, 12 patients) Bronchitis (below serious, 2 patients) Sinusitis (below serious, 4 patients) Upper respiratory tract infection (below serious, 7 patients) Dizziness (below serious, 5 patients) Oropharyngeal pain (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00440518
200 mg 2 times / day steady, oral Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00401830	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00401830	Other AEs: Vision blurred, Constipation... Other AEs: Vision blurred (below serious, 4 patients) Constipation (below serious, 5 patients) Hypoaesthesia oral (below serious, 4 patients) Nausea (below serious, 13 patients) Vomiting (below serious, 5 patients) Back pain (below serious, 4 patients) Pain in extremity (below serious, 4 patients) Balance disorder (below serious, 4 patients) Dizziness (below serious, 18 patients) Somnolence (below serious, 5 patients) Pruritus (below serious, 7 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00401830
300 mg 2 times / day steady, oral Dose: 300 mg, 2 times / day Route: oral Route: steady Dose: 300 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00440518	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00440518	Other AEs: Coronary artery dissection, Vaginal infection... Other AEs: Coronary artery dissection (serious, 1 patient) Vaginal infection (serious, 1 patient) Fatigue (below serious, 11 patient) Nasopharyngitis (below serious, 11 patient) Bronchitis (below serious, 4 patients) Sinusitis (below serious, 3 patients) Oropharyngeal pain (below serious, 4 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00440518
400 mg steady, oral Dose: 400 mg Route: oral Route: steady Dose: 400 mg Sources: https://clinicaltrials.gov/ct2/show/NCT00485472	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00485472	Other AEs: Angina pectoris, Sick sinus syndrome... Other AEs: Angina pectoris (serious, 1 patient) Sick sinus syndrome (serious, 1 patient) Liver disorder (serious, 1 patient) Hypoglycaemic shock (serious, 1 patient) Breast cancer in situ (serious, 1 patient) Vertigo (below serious, 8 patients) Fatigue (below serious, 4 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00485472

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inducer 1087 inhibitor 2252	substrate 1193 inducer 440 inhibitor 2438	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP1A1 132 CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2E1 1060 CYP3A5 136 CYP2C19 2057	CYP2C19 1119 P-gp 2052 CYP1A2 1197 CYP2B6 776 CYP2C8 810	CYP1A2 832 CYP2B6 669 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP1A1 272	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP3A5 201	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive	likely (co-administration study) Comment: POP-PK results showed that lacosamide exposure decreased 20% in the presence of carbamazepine, phenytoin, or phenobarbital Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 10, 46	yes	no (co-administration study) Comment: lacosamide had no effect on omeprazole PK Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 10, 46

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB437062	http://www.abcr.de/shop/en/AB437062
Achemtek	0102-030152	http://www.achemtek.com/175481-36-4
Acorn PharmaTech	ACN-046779	http://www.acornpharmatech.com/
Adooq BioScience	A10510	https://www.adooq.com/lacosamide.html
AEchem Scientific Corp., USA	AE1-014080	http://www.aechemsc.com/info_products/AE1-014080.php
AK Scientific, Inc. (AKSCI)	V0815	http://www.aksci.com/item_detail.php?cat=V0815
Alsachim	2251	http://www.alsachim.com/product-C3292-glo.bal-view.html
Ambinter	Amb13883599	http://www.ambinter.com/reference/13883599
Angene	AGN-PC-0O4YVA	http://www.angenechemical.com/productshow/AGN-PC-0O4YVA.html
Anward	ANW-58547	http://www.anward.com/pro_result/44998
AstaTech, Inc.	86269	http://www.astatechinc.com/CPSResult.php?CRNO=37844
Aurora Fine Chemicals LLC	A13.142.909	http://online.aurorafinechemicals.com/info?ID=A13.142.909
Aurum Pharmatech LLC	M-1600	http://www.Aurumpharmatech.com/Product/ProductDetails/M_1600
AvaChem Scientific	2659	http://www.avachem.com/productSearch.asp?2659
Axon MedChem	1444	https://www.axonmedchem.com/product/1444
BenchChem	B532333	https://www.benchchem.com/product/b532333
BioChemPartner	BCP02197	http://www.biochempartner.com/175481-36-4-BCP02197
Chem Scene	CS-0529	http://www.chemscene.com/Lacosamide.html
Chemenu	CM110363	http://www.chemenu.com/products/CM110363
ChemFish Tokyo co.,ltd	219078	http://www.chemfish.co.jp/index.php?id=2890&project=product
ChemMol	30115908	http://www.chemmol.com/chemmol/30115908.html
ChemMol	44014375	http://www.chemmol.com/chemmol/44014375.html
ChemMol	49400023	http://www.chemmol.com/chemmol/49400023.html
ChemMol	81402572	http://www.chemmol.com/chemmol/81402572.html
ChemMol	96705824	http://www.chemmol.com/chemmol/96705824.html
Clearsynth	CS-O-31324	http://www.clearsynth.com/en/CSO31324.html
Enamine	Z1550648754	https://www.enaminestore.com/catalog/Z1550648754
iChemical	EBD27785	http://www.ichemical.com/chemicals/cas-175481-36-4
Lab Network	LN00220654	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00220654
LGC Standards	LGCAMP3640.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP3640.00-11
LGC Standards	LGCFOR3640.00	https://www.lgcstandards.com/US/en/p/LGCFOR3640.00
LGC Standards	MM3640.00-0250	https://www.lgcstandards.com/US/en/p/MM3640.00-0250
MedChem Express	HY-13015	http://www.medchemexpress.com/Lacosamide.html
MolPort	MolPort-006-170-142	https://www.molport.com/shop/molecule-link/MolPort-006-170-142
OChem	25205	http://www.ocheminc.com/index.php?act=psearch&pid=481L364
Renno Tech	RL02246	http://www.rennotech.com/product_show.asp?id=2495
Sigma-Aldrich	L-029_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/l029?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S046322	http://www.sinfoobiotech.com/product/1049720
Smolecule	S532333	http://www.smolecule.com/products/s532333
Specs	AR-270/11402703	http://www.specs.net/enter.php?specsid=AR-270/11402703
Synblock Inc	SB18905	http://www.synblock.com/product/175481-36-4.html
THE BioTek	bt-272115	https://www.thebiotek.com/product/inhibitors/bt-272115
VladaChem	VL280235-1G	https://www.vladachem.com/product.php?products=175481-36-4
Yuhao Chemical	YH67130	http://www.chemyuhao.com/175481-36-4.html

PubMed

Title	Date	PubMed
Emerging drugs for partial onset seizures.	2010-09	20476851
In silico docking and electrophysiological characterization of lacosamide binding sites on collapsin response mediator protein-2 identifies a pocket important in modulating sodium channel slow inactivation.	2010-08-13	20538611
A high-performance liquid chromatography assay to monitor the new antiepileptic drug lacosamide in patients with epilepsy.	2010-08	20386357
Update on anticonvulsant drugs.	2010-07	20490745
Proteomic searches comparing two (R)-lacosamide affinity baits: An electrophilic arylisothiocyanate and a photoactivated arylazide group.	2010-06-21	20405068
Lacosamide: new adjunctive treatment option for partial-onset seizures.	2010-06	20482307
Lacosamide as treatment of epileptic seizures - cost utility results for Sweden.	2010-06	20199516
Lacosamide as adjunctive therapy for partial-onset seizures: a randomized controlled trial.	2010-06	20132285
Intravenous lacosamide as short-term replacement for oral lacosamide in partial-onset seizures.	2010-06	20041945
[The use of oral lacosamide in a patient with refractory partial epileptic status].	2010-05-16	20473836
Merging the structural motifs of functionalized amino acids and alpha-aminoamides: compounds with significant anticonvulsant activities.	2010-05-13	20394379
[Antiepileptic drugs in North America].	2010-05	20450099
LOCF approach to handling missing data overestimates the pain score improvement of drop-outs.	2010-05	20338823
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs.	2010-04	20502724
Gateways to clinical trials.	2010-04	20448862
Lacosamide intoxication in attempted suicide.	2010-04	20171144
Efficacy and safety of lacosamide in painful diabetic neuropathy.	2010-04	20067958
No pharmacokinetic interaction between lacosamide and carbamazepine in healthy volunteers.	2010-04	19841161
Recommendations for the pharmacological management of neuropathic pain: an overview and literature update.	2010-03	20194146
Epileptic seizures in AD patients.	2010-03	19557550
New Drugs2010, PART 1.	2010-02	20083979
Successful treatment for refractory convulsive status epilepticus by non-parenteral lacosamide.	2010-02	19674050
The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors.	2010-01-28	20028100
Drug interactions involving the new second- and third-generation antiepileptic drugs.	2010-01	20021326
Comparative study of five antiepileptic drugs on a translational cognitive measure in the rat: relationship to antiepileptic property.	2010-01	19841906
The anti-epileptic drug lacosamide (Vimpat) has anxiolytic property in rodents.	2009-12-10	19818346
What is the promise of new antiepileptic drugs in status epilepticus? Focus on brivaracetam, carisbamate, lacosamide, NS-1209, and topiramate.	2009-12	19941524
Lacosamide isothiocyanate-based agents: novel agents to target and identify lacosamide receptors.	2009-11-12	19795888
Gateways to clinical trials.	2009-11	20094643
Painful diabetic neuropathy: advantage of novel drugs over old drugs?	2009-11	19875591
Lacosamide: an adjunctive agent for partial-onset seizures and potential therapy for neuropathic pain.	2009-11	19843834
Six months of postmarketing experience with adjunctive lacosamide in patients with pharmacoresistant focal epilepsy at a tertiary epilepsy center in Germany.	2009-11	19767242
Lacosamide: what can be expected from the next new antiepileptic drug?	2009-10-15	19826503
Lacosamide: new drug. Refractory partial epilepsy: optimise existing combinations.	2009-10	19882781
Pharmacology and treatment of neuropathic pains.	2009-10	19741531
Effects of lacosamide, a novel sodium channel modulator, on dorsal horn neuronal responses in a rat model of neuropathy.	2009-09	19573541
Lacosamide in painful diabetic neuropathy: an 18-week double-blind placebo-controlled trial.	2009-08	19409861
Lacosamide for epilepsy.	2009-06-29	19556941
Minimizing AED adverse effects: improving quality of life in the interictal state in epilepsy care.	2009-06	19949568
Truly "rational" polytherapy: maximizing efficacy and minimizing drug interactions, drug load, and adverse effects.	2009-06	19949567
Transitional polytherapy: tricks of the trade for monotherapy to monotherapy AED conversions.	2009-06	19949566
Antiepileptic drug monotherapy: the initial approach in epilepsy management.	2009-06	19949565
Efficacy and safety of lacosamide in diabetic neuropathic pain: an 18-week double-blind placebo-controlled trial of fixed-dose regimens.	2009-06	19454870
Schedules of controlled substances: placement of lacosamide into schedule V. Final rule.	2009-05-21	19507328
New drugs: Febuxostat, lacosamide, and rufinamide.	2009-05-16	19443330
Clinical perspectives on lacosamide.	2009-04-28	19396339
Gateways to clinical trials.	2009-04	19536362
Lacosamide as treatment for partial epilepsy: mechanisms of action, pharmacology, effects, and safety.	2009	19816574
Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders.	2009	19552484
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.	2008-03-02	19443931

Patents

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 Created by `admin` on `Mon Mar 31 18:22:20 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:20 GMT 2025`
Record UNII	563KS2PQY5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Lacosamide

Official Name

English

MOTPOLY

Preferred Name

English

Lacosamide [WHO-DD]

Common Name

English

LACOSAMIDE [EMA EPAR]

Common Name

English

LACOSAMIDE [VANDF]

Common Name

English

LACOSAMIDE [USP MONOGRAPH]

Common Name

English

SPM927

Code

English

ERLOSAMIDE

Common Name

English

Propanamide, 2-(acetylamino)-3-methoxy-N-(phenylmethyl)-, (2R)-

Systematic Name

English

LACOSAMIDE [USAN]

Common Name

English

(+)-(2R)-2-(ACETYLAMINO)-N-BENZYL-3-METHOXYPROPANAMIDE

Systematic Name

English

(2R)-2-(Acetylamino)-3-methoxy-N-(phenylmethyl)propanamide

Systematic Name

English

VIMPAT

Brand Name

English

LACOSAMIDE [MART.]

Common Name

English

LACOSAMIDE [USP-RS]

Common Name

English

lacosamide [INN]

Common Name

English

ADD243037

Code

English

LACOSAMIDE [MI]

Common Name

English

LACOSAMIDE [EP MONOGRAPH]

Common Name

English

LACOSAMIDE [ORANGE BOOK]

Common Name

English

ADD-243037

Code

English

(R)-LACOSAMIDE 1

Common Name

English

SPM-927

Code

English

LACOSAMIDE [JAN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000008486