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
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 534	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 1059
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22850102	Substrate 656	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 8360	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 1.225152E12
Diabetic neuropathy 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19552484 https://www.ncbi.nlm.nih.gov/pubmed/17237664	Palliative		Phase III 663	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
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	Co-administered	Analyte	Population
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
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 n = 270 Health Status: unhealthy Condition: partial-onset seizures Age Group: adult Population Size: 270 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 n = 471 Health Status: unhealthy Condition: partial-onset seizures Age Group: adult Population Size: 471 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 n = 203 Health Status: unhealthy Condition: partial-onset seizures Age Group: adult Population Size: 203 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 (max) 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 n = 21 Health Status: unhealthy Condition: focal seizures Age Group: ≥1 month ≤17 years Sex: M+F Population Size: 21 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 (mean) 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 n = 47 Health Status: unhealthy Condition: focal seizures Age Group: ≥1 month ≤17 years Sex: M+F Population Size: 47 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 Co-administed with:: zonisamide topiramate gabapentin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022253lbl.pdf	unhealthy n = 1 Health Status: unhealthy Population Size: 1 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 n = 34 Health Status: healthy Sex: M+F Population Size: 34 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 n = 72 Health Status: unhealthy Condition: Migraine Population Size: 72 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 n = 78 Health Status: unhealthy Condition: Fibromyalgia Syndrome Population Size: 78 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 n = 74 Health Status: unhealthy Condition: Migraine Population Size: 74 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 (total daily dose) Dose: 400 mg Route: oral Route: steady Dose: 400 mg Sources: https://clinicaltrials.gov/ct2/show/NCT00485472	unhealthy n = 72 Health Status: unhealthy Condition: Osteoarthritis Population Size: 72 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 1709 inducer 768 inhibitor 1579	substrate 1010 inducer 383 inhibitor 1752	inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1437 CYP1A1 110 CYP1A2 1509 CYP2A6 704 CYP2B6 799 CYP2C8 901 CYP2E1 876 CYP3A5 73 CYP2C19 1463	CYP2C19 985 P-gp 1527 CYP1A2 1032 CYP2B6 660 CYP2C8 688	CYP1A2 689 CYP2B6 538 CYP2C19 290

Drug as perpetrator

Target	Modality	Activity
CYP1A1 218	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP1A2 1673	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2B6 985	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C19 1537	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2C9 1803	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP3A4 1909	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
CYP3A5 130	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	no
P-gp 1626	inhibitor 3240 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 1032	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2B6 660	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2C8 688	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2C9 1010	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 46.0	inconclusive
CYP3A4 1709	substrate 3326 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 1527	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022253s000_022254s000_ClinPharmR_P1.pdf Page: 47.0	no
CYP2C19 985	substrate 3326 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
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
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
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
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
Chemenu	CM110363	http://www.chemenu.com/products/CM110363
Clearsynth	CS-O-31324	http://www.clearsynth.com/en/CSO31324.html
Enamine	Z1550648754	https://www.enaminestore.com/catalog/Z1550648754
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
Lab Network	LN00220654	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00220654
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
abcr GmbH	AB437062	http://www.abcr.de/shop/en/AB437062
iChemical	EBD27785	http://www.ichemical.com/chemicals/cas-175481-36-4

PubMed

Title	Date	PubMed
Management of painful diabetic neuropathy: what is new or in the pipeline for 2007?	2007 Dec	18255001
Pharmacological management of epilepsy: recent advances and future prospects.	2008	18778117
The effectiveness of anticonvulsants in psychiatric disorders.	2008	18472486
Pregabalin for the management of partial epilepsy.	2008 Dec	19337461
Lacosamide.	2008 Dec	19043448
New epilepsy treatment receives FDA approval.	2008 Dec 15	19052267
Lacosamide: an investigational drug for adjunctive treatment of partial-onset seizures.	2008 Jan	18301802
The investigational anticonvulsant lacosamide selectively enhances slow inactivation of voltage-gated sodium channels.	2008 Jan	17940193
Differential block of sensory neuronal voltage-gated sodium channels by lacosamide [(2R)-2-(acetylamino)-N-benzyl-3-methoxypropanamide], lidocaine, and carbamazepine.	2008 Jul	18378801
Lacosamide, the new anticonvulsant, effectively reduces harmaline-induced tremors in rats.	2008 Jul 28	18585381
Gateways to clinical trials.	2008 Mar	18560631
Intravenous lacosamide as replacement for oral lacosamide in patients with partial-onset seizures.	2008 Mar	17888078
Painful diabetic neuropathy: treatment and future aspects.	2008 May-Jun	18395890
Lacosamide for the treatment of diabetic neuropathic pain.	2008 Nov	18986235
[Lacosamide. A new antiepileptic drug as adjunctive therapy in patients with partial-onset seizures].	2008 Oct	18972867
Synthesis and anticonvulsant activities of N-benzyl (2R)-2-acetamido-3-oxysubstituted propionamide derivatives.	2008 Oct 1	18789868
Paroxysmal extreme pain disorder M1627K mutation in human Nav1.7 renders DRG neurons hyperexcitable.	2008 Sep 19	18803825
Lacosamide as treatment for partial epilepsy: mechanisms of action, pharmacology, effects, and safety.	2009	19816574
Lacosamide: in partial-onset seizures.	2009	19323588
Gateways to clinical trials.	2009 Apr	19536362
Lacosamide in painful diabetic neuropathy: an 18-week double-blind placebo-controlled trial.	2009 Aug	19409861
What is the promise of new antiepileptic drugs in status epilepticus? Focus on brivaracetam, carisbamate, lacosamide, NS-1209, and topiramate.	2009 Dec	19941524
The anti-epileptic drug lacosamide (Vimpat) has anxiolytic property in rodents.	2009 Dec 10	19818346
Intravenous lacosamide as successful treatment for nonconvulsive status epilepticus after failure of first-line therapy.	2009 Feb	19130901
Lacosamide: pharmacology, mechanisms of action and pooled efficacy and safety data in partial-onset seizures.	2009 Jan	19102666
Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX).	2009 Jan	19008076
Clinical perspectives on lacosamide.	2009 Jan-Feb	19396339
Efficacy and safety of lacosamide in diabetic neuropathic pain: an 18-week double-blind placebo-controlled trial of fixed-dose regimens.	2009 Jun	19454870
Adjunctive lacosamide for partial-onset seizures: Efficacy and safety results from a randomized controlled trial.	2009 Mar	19183227
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.	2009 Mar-Apr	19443931
Status epilepticus: a critical review.	2009 May	19236943
Long-term oral lacosamide in painful diabetic neuropathy: a two-year open-label extension trial.	2009 May	18619874
New drugs: Febuxostat, lacosamide, and rufinamide.	2009 May-Jun	19443330
Gateways to clinical trials.	2009 Nov	20094643
Painful diabetic neuropathy: advantage of novel drugs over old drugs?	2009 Nov	19875591
Lacosamide: an adjunctive agent for partial-onset seizures and potential therapy for neuropathic pain.	2009 Nov	19843834
Lacosamide isothiocyanate-based agents: novel agents to target and identify lacosamide receptors.	2009 Nov 12	19795888
Lacosamide: new drug. Refractory partial epilepsy: optimise existing combinations.	2009 Oct	19882781
Pharmacology and treatment of neuropathic pains.	2009 Oct	19741531
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs.	2010 Apr	20502724
Lacosamide intoxication in attempted suicide.	2010 Apr	20171144
No pharmacokinetic interaction between lacosamide and carbamazepine in healthy volunteers.	2010 Apr	19841161
A high-performance liquid chromatography assay to monitor the new antiepileptic drug lacosamide in patients with epilepsy.	2010 Aug	20386357
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 Aug 13	20538611
Drug interactions involving the new second- and third-generation antiepileptic drugs.	2010 Jan	20021326
Comparative study of five antiepileptic drugs on a translational cognitive measure in the rat: relationship to antiepileptic property.	2010 Jan	19841906
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 Jan 28	20028100
Lacosamide as treatment of epileptic seizures - cost utility results for Sweden.	2010 Jun	20199516
Intravenous lacosamide as short-term replacement for oral lacosamide in partial-onset seizures.	2010 Jun	20041945
Recommendations for the pharmacological management of neuropathic pain: an overview and literature update.	2010 Mar	20194146

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 `Wed Jul 05 23:40:50 UTC 2023` Edited by `admin` on `Wed Jul 05 23:40:50 UTC 2023`
Record UNII	563KS2PQY5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Lacosamide

Official 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

MOTPOLY

Brand 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